How Do I Navigate My New Polyamorous Relationship?

Summary

U Up? Podcast Summary

Episode: “How Do I Navigate My New Polyamorous Relationship?”

Date: November 21, 2025
Host(s): Jordana Abraham & Jared Freid
Guest: Sean Kilby (former producer, current “Picky & Selfish” podcast host)

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Brief Overview

This episode of U Up? centers on Sean Kilby’s transition from a 22-year monogamous relationship into the world of polyamory and modern dating. Sean shares candid reflections about ending his long-term partnership, his journey through singlehood and casual dating in his late 30s, and ultimately, entering a non-monogamous—then monogamous—relationship with a new partner. Together with Jordana and Jared, Sean navigates the emotional challenges of finding happiness, negotiating sexual freedom, and the existential questions that shape modern relationships.

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Key Discussion Points & Insights

1. Sean’s 22-Year Relationship – The Good & The End

• Details
  • Sean was in a relationship from age 17 to 39 (“22 years, not married” [02:36]).
  • The couple agreed on not getting married or having children.
  • The relationship ended primarily due to a gradual emotional disconnect, accelerated by the pandemic.
  • “We just weren’t connected. We weren’t intimate anymore... and stayed together because this is the person you care about most in the world. This is what a quagmire.” (Sean, [06:26])
  • Post-breakup, Sean experienced relief more than grief: “I mourned it while we were in it.” ([08:23])
• Notable Moment:
  • The breakup was so overdue that during a fight, his partner said, “I can’t wait until we’re broken up,” and he replied, “Me too”—yet it still took another two months ([07:37]).

2. Learning to Be Single in His 40s

• Details
  • Sean had to learn what it meant to be alone for the first time as an adult: “Learning how to be single—right? Like, alone. Learn how to be alone.” ([08:23])
  • He avoided dating apps, choosing to meet people through friends, parties, and in-person events ([12:35]).
• Notable Moment:
  • “My last first date was in an Applebee’s in 12th grade.” (Sean, [12:08])

3. From Monogamy to a “Hoe Phase”

• Details
  • Sean reflected on the connection between sex and love: “I always, always, always strongly associated sex with love... I relate more to women now than I ever have.” ([13:14])
  • He challenged himself to get comfortable with casual sex but found it emotionally taxing: “I wanted to get comfortable with casual sex... it was a journey I wanted to go on.” ([14:42])
  • He admits he led with his history (“Out of a 22-year relationship”—often too soon [13:01]), and found he was “good at the relationship-y stuff, not the flirty stuff” ([16:40]).
• Notable Quotes:
  • “I was raised in captivity. I was a zoo animal... then they let me out into the jungle.” (Sean, [17:54])

4. Starting a Podcast and Embracing Self-Discovery

• Sean launched “Picky & Selfish” with Talia Lickstein to document his “hoe phase” and modern dating experiences ([18:29]).
• The podcast served as both catharsis and accountability as he rebuilt his single identity.

5. Entering Polyamorous & Non-Monogamous Dating

• The Mixer
  • A friend invited him to a non-monogamy singles mixer (“for singles or people who are ethically non-monogamous, polyamorous, whatever” [22:38]).
  • Sean approached this world with intentionality, predicting he “might need to be in an open relationship” to make up for lost time ([24:29]).
• Meeting His Current Partner
  • Met a woman in an established open relationship; chemistry was immediate ([25:42]).
  • “We think the same thoughts all the time. She laughs at all my jokes, I laugh at all her jokes... the chemistry is bizarre.” ([25:42])
  • They quickly became emotionally entangled, even saying “I love you” within weeks ([28:14]).
• Polyamorous Dynamics
  • Sean struggled with being the “other partner” and the logistics of sharing time and emotional space ([29:17], [29:53]).
  • “We clearly already have feelings for each other. I even said to her on our second date, ‘I met you too soon.’” ([27:11])
  • Eventually, the partner left her boyfriend, and Sean and she became monogamous ([32:38]).

6. The Tension of Sexual Freedom and Stability

• Sean misses the excitement and attention of being single, even though he loves his current partner.
• “That version of me that for the first time ever was experiencing freedom, was a happier person.” ([36:23])
• The thrill of novelty and the “risk” of new encounters is contrasted with the stability (and “sameness”) of monogamy ([43:00]).
• “What’s the thing I can’t do right now? Have sex with new people. Honestly... even just flirt for fun.” ([57:15])
• Jared contextualizes: “If you aim for nothing, you hit nothing.” ([47:54])

7. Existential Angst: “What Do I Want?”

• Sean is candid about ongoing anxiety and the feeling of holding himself back: “I want to live with this girl in the apartment I live in now… but I have this feeling in my chest.” ([76:03], [76:53])
• The hosts and Sean explore whether happiness is ever sustainable, or if everyone faces a trade-off between passion and security.
• Jordana suggests, “You do seem to be chasing a little bit of, like, a ghost life.” ([60:58])
• Jared: “You can’t have it all.” ([56:01])

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Notable Quotes & Moments

• On Long-Term Relationships:
  • “To me, the most important thing about being in a loving, committed relationship is that you want to be in it actively.” (Sean, [05:17])
• On Polyamory:
  • “Honestly, dating someone with a boyfriend—at first, fine. Kind of nice. It sounds like it would be the best... but the problem is, I fell for her.” (Sean, [28:44]–[29:03])
• On Anxiety & Change:
  • “For the first time in my life since that point where I started being honest about what I want... I’ve experienced anxiety and depression.” (Sean, [33:26])
• On Modern Dating’s Irony:
  • “If you’re a guy who wants to have casual sex and you’re honest that you’re not willing to commit, you’re less likely to get someone to sleep with you.” (Sean, [70:33])
• On Wanting Everything:
  • Jordana: “Is the only way to solve Sean’s problem for his girlfriend to just let him have sex with whoever he wants because he loves her so much?” ([71:37])
  • Sean: “That’s super selfish. Right? That’s not good.” ([71:39])
• On the Limitations & Realities of Relationships:
  • “I don’t think you’re ever going to find the equilibrium… or most people don’t.” (Jared, [60:58])
  • “If you’re looking for a situation that’s going to make you happy 100% of the time, that doesn’t exist.” (Jordana, [75:07])

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Timestamps for Important Segments

• Sean describes his 22-year relationship & its end: [02:36] – [08:23]
• Learning to be single, “hoe phase,” and dating anxieties: [12:08] – [18:29]
• Attending polyamorous mixer, meeting new partner: [22:38] – [27:11]
• Navigating emotional fallout of polyamory: [29:03] – [32:38]
• Transition to monogamy & pursuit of happiness: [32:38] – [36:23]
• Tension between sexual freedom and stability: [40:05] – [44:05]; [57:15] – [58:58]
• Existential conversation: “What do I want?” and relationship goals: [59:09] – [76:53]

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Tone & Takeaways

The episode is raw, self-aware, and frequently both humorous and soul-searching—true to U Up?'s vibe. Sean’s honesty about his confusion and desires is matched by Jordana and Jared’s friendly but challenging commentary. The discussion hits at the heart of modern dating’s paradox: wanting the thrill of newness and the safety of intimacy, and wondering if anyone can ever have both.

Final Thought:
This episode doesn’t deliver easy answers, but it does offer real talk about the complexities of love, sex, and self-understanding in adulthood.

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For more conversations like this, follow @u.up.podcast on Instagram and check out Sean’s podcast “Picky & Selfish.”

Transcript

[Jordana Abraham]

And we can talk about the, like, polyamorous kind of.

[Sean Kilby]

Yeah, for sure. Okay. Yeah, yeah, I'm sure.

[Jordana Abraham]

What the.

[Sean Kilby]

We don't have time for all the sex stuff though. Jared. I learned how to have sex.

[Jordana Abraham]

Sean was a virgin.

[Sean Kilby]

40 year old virgin.

[Jared Freed]

I mean, we're having regular sex.

[Jordana Abraham]

Well, I said, I mean, well. Okay, we'll get into it. Hello and welcome back to the Friday Feels episode of the UF podcast. I'm Jordana Abraham.

[Jared Freed]

And I am Jared Freed. It is so good to be back here with you, Jordana. But it's especially good, good to have a very special guest.

[Jordana Abraham]

Very special.

[Jared Freed]

It is a SOS episode where, where we go and we have someone on who's going through relationship problems to sit on the couch and talk it out with them and try and get some answers and try to figure out what we're gonna do with this whole thing. And today's guest is very special because he's the former producer of this show who moved on to bigger and better.

[Sean Kilby]

Things, smaller and worse things.

[Jared Freed]

Okay. I, I was. Sean Kilby. Thank you for coming.

[Sean Kilby]

Thanks for having me. Thank you so much.

[Jordana Abraham]

Yeah.

[Sean Kilby]

It's so good to come home. I love. I, I decided to come in early to see all my old friends. None of them. None of them.

[Jordana Abraham]

It's Monday, Sean.

[Sean Kilby]

Mondays are barely working.

[Jordana Abraham]

We're a Tuesday, Wednesday, Thursday.

[Jared Freed]

That's. Is that it in the office?

[Sean Kilby]

More.

[Jordana Abraham]

More people in here on Tuesday, Wednesday.

[Sean Kilby]

Do you ever walk into B's Media and go, does anybody work here?

[Jared Freed]

I do have that every day. Every day.

[Jordana Abraham]

Plus it's raining.

[Jared Freed]

You know, it is raining. I mean, I am like, I, I was excited about today to have you on because it's not, it's rare that you get men who are open and honest about their dating life. Like, that's the right. Jordana, you, you kind of met with, you met with Sean and you said you were like, we gotta have mine.

[Jordana Abraham]

Yeah, as soon as we went. We went to coffee last, last week like that.

[Jared Freed]

Beg to come back to Bachelor, Beg for his job back. He's like, I need the health insurance.

[Sean Kilby]

And then Jordan is double pregnant the whole time. No, I, She, I caught up with her.

[Jordana Abraham]

And then you caught up with me.

[Jared Freed]

Yeah, I don't have room for a third child.

[Jordana Abraham]

No, we did.

[Jared Freed]

Out of my face.

[Jordana Abraham]

Sean was like, Sean was like, let's get coffee. And like, we can. I haven't seen you in, like, in a while. We'll do like a full. We'll do a full update and I got an update. On your dating life, which, for the. I mean, you used to produce the show for. For a while. And for as long as I've known you, you had been in the world's longest relation. Like, one of those relationships that's so long that you're like, I don't even understand the math right? How someone could be with this person for this long.

[Jared Freed]

You were with someone how long?

[Sean Kilby]

22 years.

[Jared Freed]

Not married, not married. So 22 years, not married. How did you meet?

[Sean Kilby]

We met. We're in high school. Like, we're, you know, we met.

[Jordana Abraham]

What grade?

[Sean Kilby]

Well, we met in freshman year. We got together the last year of high school and then ended up going to the same college together.

[Jared Freed]

Okay.

[Sean Kilby]

And then no breaks, never broke up. Very healthy relationship. But we were just together along.

[Jared Freed]

You want to move to New York.

[Sean Kilby]

Together, the whole thing.

[Jared Freed]

You understand that someone hears that. 22 years, you're 40, never married, but you guys healthy. It's weird.

[Sean Kilby]

It's. Oh, it's abnormal.

[Jared Freed]

Did you guys decide you never wanted to get married?

[Sean Kilby]

We had, like, a domestic partnership. Like, we were, like, de facto married, but not okay legally.

[Jordana Abraham]

Well, but did it. How did it come up, like, the idea of, we don't want it, we both don't want to get married. And also, like, you didn't.

[Sean Kilby]

You don't.

[Jordana Abraham]

Both didn't want kids.

[Sean Kilby]

Didn't want kids. I mean, I think that used to say. And I stand by it, first we were too young, then we were too poor, then it was kind of too late. It's like, who we getting married for? Everybody else to throw a party for grandparents and parents. I don't care. You don't care. I kind of have this attitude towards relationships in general. You are in it because you want to be in it. Now you aren't in it because you're locked in because you signed a piece of paper or something.

[Jordana Abraham]

Sounds like the classic man who doesn't want to get married.

[Sean Kilby]

No, but I think that's what a healthy relationship is, right? People get divorced because they decide, oh, that doesn't count extra.

[Jared Freed]

I don't know who. Let me give you the feedback as I. You know, as a friend who likes you and. And. But I'm saying, as someone like, you say that. And, like, the problem with dating conversations is that, like, you say that I have a thought in my brain. I go, I don't know if I should say that out loud. And I put it away. When I hear someone say, who needs a marriage? I go, there's bullshit here.

[Sean Kilby]

Like, you hear this Bullshit.

[Jared Freed]

I hear that all. Everything you said.

[Jordana Abraham]

Did you feel validated when they broke up because of that?

[Jared Freed]

That's all. I cheered in the streets when Biden won. I was like, but the thing is.

[Sean Kilby]

Like, somebody can get married and then they get divorced three years later, or they cannot get married and be together 22 years later.

[Jared Freed]

It can happen. But I think the. It can happen. People ruin dating conversations. So, like, we looked like, if you live in the world of normalcy, which is normal doesn't mean good. It just means this is what the thing is right now nowadays. Like, you know, it would be different 100 years ago, a thousand years ago. It might be different a thousand years from now, 100 years from now. But right now, being with someone for 22 years and not getting married and then saying, well, it was too late, too poor to this, do that. There's a point where you go, what are we avoiding here?

[Sean Kilby]

I hear you. Yeah, But I also think, okay, if we'd met 10 years later, if we met at 27 instead of 17, yeah, we probably would have gotten married. But to us, it was like a de facto.

[Jared Freed]

Well, you know, what do you say?

[Sean Kilby]

They don't care. And also, I don't care what my family says. That's, like, kind of important to me. You only are in a relationship for you, maybe your kids sometimes. But, like, to me, I think the most important thing about being in a loving, committed relationship is that you want to be in it actively, not. You're still in it, because it's just what it is.

[Jordana Abraham]

Right. Well, can I ask how the. The kids thing played into this? Like, did you Both at. At 17.

[Sean Kilby]

No.

[Jordana Abraham]

You didn't want kids? Like, how did. How did that. Did that play into the idea that we don't need to get married?

[Sean Kilby]

I think we moved to New York in our mid-20s, and none of our friends had kids. And then when people started having kids, I saw them become less happy. So for me, that's the case now. If I moved to Long Island, I might just pop two out at the same time. You know, like, that's possible.

[Jordana Abraham]

But she had the same view. She had the same view.

[Sean Kilby]

She had the same view. It's like, I. I love kids, and I also love giving them back. Okay, Those are my nieces and nephews. You know, that's. That's who I am. But, you know, so. So. But I do think people will say, like, why did you break up? You know, you're.

[Jared Freed]

Well, so now you're not even here to talk about the 22 year relationship.

[Sean Kilby]

I wanted to breeze right on back.

[Jordana Abraham]

I mean, there's questions about that.

[Jared Freed]

Well, how did that end?

[Sean Kilby]

Honestly, it is one of those things is like, we were just together people. Like, there's no infidelity. There was. We were just together kind of too long. And I think the pandemic put a lot of strain on a lot of us. And there were moments where we almost ended it, and then we got to a point where we just weren't connected. We weren't intimate anymore. And then another year or two went by and I was miserable, but I couldn't say it. I didn't communicate to my friends about it. Our one regret, I think collectively is we hid it from people that we weren't failing as a couple, but stayed together because this is the person you care about most in the world. This is what a quagmire. Someone you care about more than anyone in the world. You have put their life before you, yours. And yet you're supposed to just say goodbye to them forever. So that was really hard for us. Once we did it, the pendulum swung for me in terms of communication. I went from being very locked in talking about these things and very, like, repressed to talking about it constantly. Like my. With my friends with you guys. I mean, I met with Jordana the other day and she we for way too long because I can't shut up about myself. But I found it to be much healthier and I'm much happier now by doing that.

[Jared Freed]

Now you guys break up. How did that. Who brought. Who brings that? Did she come to you and go, I noticed a change. Change in you.

[Sean Kilby]

I. Oh, it was such a long, drawn out thing where we wouldn't let each other go. I think there was one. This is a sad thing. Two months before we broke up, we were in a fight. And she said, I can't wait until we're broken up. And I was like, me too. And it still took us two more months. That's how it.

[Jordana Abraham]

Sometimes. But you're comfortable. Like, everything's kind of. Did you combine finances? Did you combine, like, was there a lot of.

[Sean Kilby]

I just. It was easy for me. I stayed in the apartment. She moved away. Like, basically where that part was not too entangled.

[Jared Freed]

So when does that happen?

[Sean Kilby]

When, like what the day chronologically. This is September of last year. That's about a year ago.

[Jared Freed]

About a year ago.

[Jordana Abraham]

So September of 2024.

[Jared Freed]

So you get out of the relationship. It is hard, but once doesn't sound.

[Jordana Abraham]

Like it was that hard.

[Jared Freed]

Yeah, it sounds like it was A difficult time. And then when you broke up, it kind of like.

[Sean Kilby]

Yeah, it's like, I. I say this, and I think it's true. I mourned it while we were in it, so I didn't have, like, a long, protracted, you know, phase of sadness and whatever. I felt better. It took me a few weeks. I mean, I was sad for a while, and then I had to confront a bunch of new realities. One of them was learning how to be single. Right. Like, alone. Learn how to be alone. Yeah. Spend time, extended periods of time in your own home, alone, when there's not somebody there. You're so used to it. Learning how to be out there in the world and be vulnerable. I never had to face rejection in my entire life because I never tried, you know, so that's at least as an adult. And then learning how to engage with people in, like, a real honest way, physically, emotionally. Dating wise was tough.

[Jared Freed]

So you guys were living together? She moves out.

[Sean Kilby]

Yeah.

[Jared Freed]

Do you talk afterwards?

[Sean Kilby]

We have not spoken since.

[Jared Freed]

You haven't spoken since the break?

[Jordana Abraham]

So you're both, like, over. It sounds like in the same. In the.

[Sean Kilby]

Yeah. And by the way, I have not a bad word to say about this. I mean, she's the best.

[Jordana Abraham]

People always say. I mean, she's not the best.

[Sean Kilby]

No. She's an awesome person.

[Jordana Abraham]

No, no.

[Sean Kilby]

But somebody can be an awesome person. But you grow ap.

[Jordana Abraham]

Second best.

[Sean Kilby]

She's awesome. Fine. Yeah, she was. Yeah, exactly.

[Jordana Abraham]

No, and I think. I mean, like, it's funny because I do feel like when people say it's mutual, it never. It doesn't feel like that's ever really true. Was it. Was it fully, like, even?

[Sean Kilby]

I think so.

[Jordana Abraham]

You wanted it both, like, the same amount?

[Sean Kilby]

I think so, yeah. I mean, like, I don't. I. I've never really even had to grapple with that question because it was just so true for us at the time. It was just too hard to let go. Right.

[Jordana Abraham]

And then it's probably easier to be like, no contact, kind of like cold turkey.

[Sean Kilby]

Yeah. I think that's what she would prefer, and that's what I prefer.

[Jared Freed]

Did she move out of state?

[Sean Kilby]

Yeah, she went. She went. Yeah.

[Jared Freed]

Somewhere. Okay. Out of state. So that makes it a little easier. You can kind of, like, dance around New York.

[Sean Kilby]

Oh, yeah. I got most of the friends. She didn't want anything to do with our friends. So what I did.

[Jared Freed]

So then she didn't want anything to do with your friends?

[Sean Kilby]

Not really, no.

[Jared Freed]

So I got. You would think, like, 22 years, like, you're you know, Bye. Yeah, by her. She was like looking. So she had kind of an extra life.

[Jordana Abraham]

Maybe.

[Sean Kilby]

Maybe. Yeah.

[Jared Freed]

Okay, so that ends. We're out of that 22 year thing now you're a new baby. You're basically reborn. I mean, I will say this.

[Jordana Abraham]

And you're how old?

[Sean Kilby]

I was late, 39 at the time.

[Jared Freed]

You look great. You look like you've lost.

[Sean Kilby]

Well, Jared. Yeah, I did, baby.

[Jared Freed]

Yeah, I did.

[Jordana Abraham]

I got better than an unmarried, childless man.

[Jared Freed]

Yeah, I mean, like, right? You look younger. You look like brighter. I mean, right.

[Jordana Abraham]

A lot of time for grooming.

[Sean Kilby]

Why would go to the gym to play pickleball? Because of that age as well. And people be like, what's going on with you, man? I'm like, oh, I went through a breakup. Oh, got it. I mean, I look totally different a few months afterwards. Just working out all the time. Like trying to make yourself hot for other people. Motivator.

[Jordana Abraham]

Like, is there this thing also? Sorry to interrupt. My, My. My. My husband has had had a 10 year relationship before me that he also started in high school. And I think there's like a little bit of a sense when you get out of that of like, what is my value on the dating market?

[Sean Kilby]

Right?

[Jordana Abraham]

No, I have no idea.

[Jared Freed]

I got going here kind of like.

[Jordana Abraham]

What is like, where, where? Yeah. How well is it? Was there like a little bit of that?

[Sean Kilby]

I was pretty confident that I was gonna do fine. I'm not. But part of the reason I said is because I think that that, that attitude does work the best. I wasn't like. And maybe it's just because I didn't ever have to face rejection before that, but I was like, I'll do fine. But I still was very hesitant to shift. So. So then here's what I did, Jared, and I think that you will probably appreciate this is I went from never having gone on a first date in my life since high school, I guess. I guess my last first date was in an Applebee's and you know, 12th grade.

[Jared Freed]

Okay.

[Sean Kilby]

To having to figure out how to like go on dates, get numbers, do all this stuff. And I chose to speed run my way into becoming a functional.

[Jared Freed]

So how many dates a week?

[Sean Kilby]

Well, at first, a ton. Like the really the I was not. My heart wasn't open. So I had this issue where I didn't want to like, go on a date and act like I was ready to actually date somebody. So I've still never been on the dating apps.

[Jared Freed]

Okay.

[Sean Kilby]

I just would go out with my buddies and get Phone numbers and follow up with people, go to parties, meet people that way. But yeah, maybe like she put on.

[Jared Freed]

The fedora several months in, put on the big sparkly shirt and it was like going out night.

[Sean Kilby]

Yeah. So maybe like a couple a week.

[Jared Freed]

I would say so. But you're meeting these people out at bars.

[Sean Kilby]

Yes.

[Jared Freed]

And you know, I guess what's the. At the beginning, are you telling people I'm out of a 22 year old?

[Sean Kilby]

Too much, too much, too much. Like literally leading with it?

[Jared Freed]

Well, I don't know. I don't know if there's such a thing as to anything, but I would say you're being honest with people. Like, you're not. Are you saying I want to be in a relationship? Are you saying I'm open to a relationship? What's kind of the.

[Sean Kilby]

No, it's always. I'm looking for something casual. So here's the big thing. This is like the big headline of my. Like what? I'm still working on my transformation. Whatever is always, always, always strongly associated sex with love. Kind of in a way. Like I relate more to women now than I ever have in my entire life. And I worked at Betch's Media for years. And part of the reason why like I, I fit in here is because I'm kind of, kind of a girl in some ways emotionally, which is fine.

[Jared Freed]

You can own that as something that's.

[Jordana Abraham]

A little bit why you fit in here. You're, you're, you guys are more communicative than you are for sure, Jared.

[Jared Freed]

Absolutely. And I think we're. You and I probably are more up for the conversation than I went from.

[Sean Kilby]

Having a core group of close friends. I have like a dozen best friends now. Half of them are women and the reason they love hanging out with me is because I like doing this shit about their relationship. So fit in greatly, but are really well. But then I had this issue where it's like, okay, associate sex with love. I need to get comfortable with casual sex. Why do you have to?

[Jordana Abraham]

Well, can I ask you also just as fat as a. Just a fact checking thing. You had only had sex with one person?

[Sean Kilby]

No, two people. Okay. My whole life I had a girlfriend before that.

[Jordana Abraham]

You had a girlfriend before the 22 year.

[Sean Kilby]

Yeah, before the 22 year old.

[Jared Freed]

Okay. So that's all.

[Jordana Abraham]

So you had sex with two people?

[Sean Kilby]

Yeah, that was my number.

[Jared Freed]

Okay, that's. But I, I think the idea that you have to get comfortable with casual sex, I, I don't know.

[Sean Kilby]

I, I think it would like, I.

[Jordana Abraham]

Think it's because that's what you wanted to do.

[Sean Kilby]

Yeah, yeah, right. That's what I was looking for.

[Jared Freed]

Well, why can I, you know, I don't know. I, I, I'm thinking, I'm like thinking out loud a little bit here, but like that idea, like, like, I don't know, it doesn't have to be, I don't think it has to be that way.

[Sean Kilby]

I'm saying it was like a journey. I wanted, you wanted to go on to do it. I think it is healthy to split the difference. Like you'll get in a relationship.

[Jordana Abraham]

His whole face.

[Sean Kilby]

Yeah, I'm looking.

[Jordana Abraham]

I always say men don't have a whole face.

[Jared Freed]

Men do not have a whole face.

[Sean Kilby]

I was looking for a whole face. I was kind of getting into. It took me a couple months to get to, to get comfortable with going from just like getting the phone number, you know, whatever the case may be, to getting physical to actually going from nothing. And I actually had a few moments with different people where I talked myself out of it my way out of sex, basically, or, you know, making out, whatever the case may be. And a lot of it was because of what you said you lead with. I was in a 22 year relationship and nothing ever lasts. Like, okay, that's not hot.

[Jared Freed]

Jordana, I have to ask you, is it hot to you, to a woman? Is there like some, like, I can teach him. Like, is there a little bit like.

[Jordana Abraham]

The sexual and experience?

[Jared Freed]

Yeah, like, well, yeah. Sean's coming up to people going, it's been 22 years. And being super honest as you're saying, like, I'm looking for casual, but it's been so long, I don't know if I can really do it anymore. I don't know if I'll be able to. Are you looking at this, like, shivering naked mole rat thinking I can form him into a wolf that he needs to be like, all right, Is there any of that to that?

[Jordana Abraham]

I think it depends what I'm looking looking for. If I'm looking for like a long term monogamous relationship, I might be like, and this, I don't, this is, I'm not looking. He's also say you're saying outright I'm looking for casual, but if I'm looking for casual, I could see this being like, again, like a, why not? Like, let's, you know, I'm not saying it never worked.

[Sean Kilby]

I'm saying it took me a couple of months for me to emotionally be prepared to, to initiate, to go from one phase to the next.

[Jared Freed]

Okay.

[Sean Kilby]

You know, like that. I think that's the thing that most people get used to in their 20s and. Or perhaps 30s. And so I was here in my late 30s, experiencing what everybody else experienced in their maybe early 20s and through their 20s, perhaps with the wisdom and emotional maturity of a grown man who worked at Betches for years, but also without the level of experience where I, like it, was comfortable with it. So I actually have said this to people, too, is if I'd be in those situations and I could have just done. Acted how I can act now, you know, just like, go be the kind of flirty person that you need to be. But I didn't really know how to do that. I'm really good at the relationshipy stuff. And I realized, like, okay, I was trying to come up with an analogy for this. Like, what was up with me? And it was kind of like I was like in a spaceship. And I knew it was going back on back down at Earth. And I worked on the U UP podcast. I know exactly how dating works for everyone else, but until your feet are on the ground, you don't know. I don't even think that that's a good enough analogy. I realized what it really was, Jared. I was raised in captivity. I was a zoo animal. I was the king of the zoo. And then all of a sudden, they let me out into the jungle. And you're like, oh, this is crazy.

[Jared Freed]

So much of what we say here, we always say. We say me so many times that it becomes annoying. Advice is easier to give than it is to take, you know, and once you're in it and you have to, like, deal with the, you know, the turn of your stomach, you know, it's a lot harder to say the right thing, do the right thing. You. You know, that's all that. That's all where all ethical conversations come up, like, you know, and where you land on it. That's where the. You know, the. And that's where, like, the vilification comes in. Well, they didn't do the right thing, but you're trying to do the right thing, so.

[Jordana Abraham]

But it seems like you. You figured it out, right? Like, to. To.

[Sean Kilby]

Oh, yeah. So then I started this podcast. Actually, part of the whole thing is like, you remember our old friend Tali Lichstein?

[Jared Freed]

Yes.

[Sean Kilby]

He used to host a show here at Betches Media. She's one of my best friends, and we're like, let's do a podcast together. So we started this show Picking Selfish, and we're going to chronicle our Hodom Together, you know, and like me, she is a counterpart. She's Gen Z, but it's like we're kind, I'm kind of like a Gen Z girl in a lot of ways in terms of like what I'm going through, you know, And I'm also trying to become this like, you know, my hoe phase, an ethical boy or whatever the thing would be. Right. And so that was kind of my process. And that's what we're doing on the podcast and that, you know, I, I hadn't even gotten on the dating apps yet, like that sort of thing. So. Yeah, that, that was kind of like a whole process for me. And I will be honest with you, I started figuring it out. That was good.

[Jared Freed]

So you're meeting a few months.

[Sean Kilby]

Yeah.

[Jordana Abraham]

You're having lots of casual sex Enough.

[Sean Kilby]

Yeah, a good amount.

[Jared Freed]

Okay. And it's then I guess what this SOS episode is about is that you meet someone that you get into something more serious with.

[Sean Kilby]

Oh yeah. So all my friends are like, you know, what are you, are you gonna like what's going on? Dating anybody? Seriously, etc. I'm like, I'm gonna be single for one to five years. I think I'll be single for five years. Which I think, Jared, you've, it's probably been, it's been years since you were in a long term committed relationship as well. I kind of wanted to live the Jared path. I'm not kidding.

[Jordana Abraham]

Does it look fun?

[Sean Kilby]

Kinda. Well. But I will tell you, I, I.

[Jared Freed]

It'S a blast over here.

[Sean Kilby]

I will say that.

[Jared Freed]

Yeah. Just trying to live this lifestyle of martinis.

[Jordana Abraham]

But yeah, you're like, it's okay. I think you're, Jared is like, I want a relationship more like you're saying that more to people. You wouldn't say?

[Jared Freed]

No, I would say I'm looking for a relationship. I, I don't think, but I've, I've toyed recently with the idea of like just saying I'm looking for casual.

[Jordana Abraham]

Sounds like get you in a relationship.

[Jared Freed]

It would get me in a relationship a little bit quicker.

[Jordana Abraham]

Yeah.

[Jared Freed]

So I, but I do, you know, I was, you know, in a long term relationship and then I've been in a series of like three months with this, like kind of, and then being on the doorstep and then kind of backing out of it.

[Jordana Abraham]

Well, it sounds like the difference between your two breakups though are that like, Sean seemed to be like pretty mutual and like very clean cut and maybe like yours left you with a little bit more of a, A Little more of I've gotta be if I, I can't date anyone, I'm not gonna marry.

[Jared Freed]

Right, right, right, right. Which is like, you know, feeling like I don't want to like make someone's. I, I really don't want to be in someone's book about their lives. Well, I know, like I don't want to make such a mark on someone where I'm like that they're like traumatized by you. Right.

[Sean Kilby]

I do have a couple rules. And one of my things is like the number one headline. If you're going to try and be casual or whatever, don't be reckless with anyone's heart. That I think is important. And I made some mistakes. I mean, there was a girl from out of town who came in to stay with me. That blew up. I hooked up with my childhood crush on a whole thing and it turns out that was way more emotionally weighted than I thought it was gonna start.

[Jared Freed]

Having crushes like a 5 years old childhood crush?

[Jordana Abraham]

No, but I mean, you know, they're in California.

[Sean Kilby]

Oh yeah. New Year's Eve was.

[Jared Freed]

Hey, I've been thinking about fifth grade a lot.

[Jordana Abraham]

Yeah.

[Sean Kilby]

So I'm like going through all that stuff and I was like. And honestly it's been the most, it's been the, the happiest year of my life.

[Jared Freed]

So when do you meet this person? So you meet someone new.

[Sean Kilby]

So then all my friends are like, look, you need to stay single. Don't like get anything serious. I'm like, great, I'm not going to five years. But one of my buddies, he's very Jared Freed, he's wise beyond his years, is like, yeah, but it's gonna happen. I see it six to, six to 12 months. You're just gonna like meet somebody. It's gonna happen. So I go to this mixer with and this is about to get juicy. Jared, I don't think you've heard these details.

[Jordana Abraham]

Okay, this is where, this is where, this is where it takes a turn.

[Jared Freed]

Let's start a break right here.

[Sean Kilby]

And when we get back, I will. I totally changed my life. Okay, so my friend throws these mixers for people who are non monogamous relationships.

[Jared Freed]

Okay.

[Sean Kilby]

Yeah, so it's like, it's for singles or people who are like ethically non monogamous, polyamorous, whatever.

[Jared Freed]

So where in Brooklyn are these going?

[Sean Kilby]

Jackson, I'll invite you. No, I went to one. Like I went on a date with somebody after she was also single.

[Jared Freed]

Like it's kind of like weirdos get together.

[Jordana Abraham]

Is it for people in Relationships?

[Sean Kilby]

Not necessarily. No, no, no, no.

[Jordana Abraham]

Or you could just be like interested in hooking up with someone who's in a relationship.

[Jared Freed]

It's a bunch of couples that are about to break up that get together to see what's out.

[Jordana Abraham]

Well, I guess kinda based on Sean's story, right?

[Sean Kilby]

Yeah, I guess so. I don't know.

[Jared Freed]

So I buy it, but I don't buy it. Okay.

[Jordana Abraham]

I know it exists. It exists like factually.

[Sean Kilby]

I mean, how much time do we have?

[Jared Freed]

But like, but go ahead.

[Sean Kilby]

There's so much to the whole. All the questions that go into, like, what makes us want to be monogamous or not monogamous? Etc.

[Jared Freed]

I, I've. I've had a running, you know, policy on this show. The non monogamous thing, it exists. I believe it can happen. I think it takes up a lot of space in the relationship conversation because we're all trying to be nice. I think to do it you have to be so communicative, so on board with it. Like, you know, so you and your partner have to be so on the same page. So I'm assuming that's why I'm saying a bunch of weirdos, you got to be a little weird. Like you go to that party, it's a lot of people, not non traditional, but also that's just. You're living outside the kind of the, the functions of society at that point. But that's okay. Yeah. So you go to these parties, your friend puts them together.

[Sean Kilby]

Yeah.

[Jared Freed]

And are you going like, hey, I'll be the third? Is that like.

[Sean Kilby]

No, no, no, it's. It honestly is just a way to like go and get phone numbers.

[Jared Freed]

Okay.

[Sean Kilby]

And like Annie Mixer it honestly. And again, I went to one and I want to date with one girl and we made out and it was. She's a normal person, but she used to be in an omnivorous relationship and she's looking for people who don't want to be exclusive.

[Jared Freed]

Also like minded people that like, to me, a non mon party can be the same as, hey, it's a bunch of you up listeners. Like people are on the same page.

[Sean Kilby]

And honestly I was coming into it partly with an open mind because I did say to people, and really I think was true, is my next relationship might need to be an open relationship. Okay. Because I haven't sewn my wild oats. I haven't gone out there and like explored all the things that I want to and get used to casual sex and have meaning. I remember talking to one of my friends at a party and I'm like, guys, I figured it out. Here's how you make out with somebody. And honestly, I did. There's six steps to it. I'll tell you later, Jared. Okay. And they're like, okay, it seems like you're coming at this with a lot of emotional weight when I was describing this thing. And she says to me, I hope you get to have a meaningless one night stand soon, because I think that would be good for you. And I'm like, okay. I think that there's probably some truth to that, that that's a healthy thing for me. Somebody who was a caged animal out in the jungle needs to learn to be wild. So I go to this thing and I'm like, this is a place where I can hook up with people and not be reckless with their hearts because they know what the score is, and you can be communicative and whatever.

[Jared Freed]

It's a little bit easier, right?

[Sean Kilby]

So I met this. I'll tell you the long version. I met this thing for a while hanging out with my buddy. Like, this is not working out, you know? Like, this is not. There's nobody here that I'm interested in, et cetera. We're about to go and this girl walks in, and to me, she's the hottest girl I've ever seen.

[Jared Freed]

Okay?

[Sean Kilby]

And she is like. I'm like, who is that? And he's like, well, you should go talk to her. She's friends with our friends, et cetera. So I go and meet her and. And I've never been more in sync with anybody in my entire life. Like, we think the same thoughts all the time. She laughs at all my jokes, I laugh at all her jokes. We're so into each other. Like, the chemistry is bizarre. Great. Yeah. Is it great? Because now I know it's great. So now I'm like, okay. So, you know, we go dancing at this party, continue the night, make out, whatever. This girl, though, has a boyfriend, okay? And she lives with him, and they've been non monogamous for years. So I'm like, okay, this is.

[Jared Freed]

So this is perfect for you because she's a. A pro at lifestyle. She can kind of lead you through it. You're being open and honest. Hey, I'm looking for casual. This is something that I'm new to. She can. She can, like, show you the ropes a little bit.

[Sean Kilby]

Okay, Right? So then we go, we have our first, like, real date a week later or something. And it was. I mean, it was awesome. It was great. It was too perfect. I'll Describe it to you in two sentences. It was eight hours long, and it was bookended with sex, Lord of the Rings and more sex. Like, what a perfect night, Jerry. You know what I mean? Like, we're perfectly in sync, but also we're just getting along. Yeah, exactly. Yeah. But you know the sort of thing where it was like, this is awesome. And then we were like, on our second date, and we're clearly already have feelings for each other. And even then, I did say to her, I met you too. Sim. Like, that was a real. On our second date, I said, I met you too.

[Jared Freed]

These are all mistakes that someone doesn't make if they've been dating, you know, at this age. This is a very. That's. This is a very 20s.

[Jordana Abraham]

In your 20s, right?

[Jared Freed]

Saying I met you too soon is something that if you have been dating around for a bit, you can't say to someone.

[Sean Kilby]

Why can't you?

[Jared Freed]

It's too romantic. It's too much. It's. I mean, you have to be in. Yeah, I mean, like, you know, that's again, to say, be reckless with someone else's heart. Like, I think that to me is being reckless. It makes you feel good to say, and it makes you feel good to hear back. I feel the same way. Or I feel the same. I'm on the same page as you, but you also have to own that. Like, you have to kind of like pay the tab on that, you know?

[Sean Kilby]

And this was all in the context of talking about the fact that my heart was not open. It's like, just so you know, I want.

[Jared Freed]

But even giving that. That's like a little taste.

[Sean Kilby]

Yeah, you're right. Like, you're right. Right.

[Jordana Abraham]

Of romance.

[Jared Freed]

Yeah.

[Sean Kilby]

Okay, so fast forward about.

[Jared Freed]

We can't. But we should. We shouldn't, but we can't.

[Jordana Abraham]

How long does this go on where you're dating?

[Sean Kilby]

When she's more like a month and a half and we say, I love you already. I mean, like, I gave.

[Jordana Abraham]

Even though she's my.

[Sean Kilby]

Oh, yeah, I gave her. No, we never met. And that was like.

[Jared Freed]

Is that her rule? Does she have a rule for the boyfriend?

[Sean Kilby]

No, I didn't want to meet. I. I kind of didn't. I have this. This is a whole team. Oh, yes. She wanted me to meet him. This is like how it usually works in the poly community. It's like you kind of do that sort of thing. I feel like that's, to me, not right for me. Let's just put it that way. I don't want to be super Critical about it.

[Jordana Abraham]

Yeah. But I think like dating someone with a boyfriend, honestly, at first, fine.

[Sean Kilby]

Like, kind of nice. It's like, it sounds like it would be the best.

[Jordana Abraham]

You don't have to do nightmare, right?

[Sean Kilby]

Well, no, and this was. This was the thing for a while with all my friends. I know, I know, I know. But people are like, aren't you bothered by it? I'm like, honestly, I think it's fine. Like I came in with open eyes and like I can see other people and this will be great. Great. But the problems. I fell for her and I was.

[Jordana Abraham]

Obsessed with her and she only dating you and her boyfriend, so like three.

[Sean Kilby]

Weeks, then she goes, just so you know, I don't want to see anybody else.

[Jordana Abraham]

And I'm like, besides you and my boyfriend? Yeah.

[Sean Kilby]

No, I mean, honestly. Yeah, yeah, I know, it's hilarious.

[Jared Freed]

Did you find yourself fighting for time with the boyfriend?

[Sean Kilby]

No, I found myself spending her spending five nights a week with me. Like, with you? Yeah. So like that sort of thing.

[Jared Freed]

Do you look for any explanation as to what that that other relationship is.

[Sean Kilby]

Doing for her for a while? No. It's like, don't meddle. It was like the sort of thing. So you know what I actually do.

[Jordana Abraham]

What are the rules of like. Of like the non monogamous community there? You're like, don't ask, don't tell kind of thing.

[Sean Kilby]

No, no, no. Ask, tell, talk. I mean, I think that a lot of people try and do the don't ask, don't tell thing when they open up is a really common thing. And that is usually the biggest mistake that people do.

[Jared Freed]

But I mean, five nights a week.

[Sean Kilby]

Yeah.

[Jared Freed]

I would tell my friends about you.

[Sean Kilby]

I would tell my friends that and they would go, oh, it sounds like they're gonna break up. I'm like, I don't think so. I think they're fine. But we're spending a lot of time together and we're like crazy about each other and in love and. Etc. So, yeah, that all was going. So in the meantime, I started reading a book about non monogamy to try and get.

[Jared Freed]

You're figuring it out.

[Sean Kilby]

Yeah, figuring out. I'm like, I'm approaching all this stuff with tons of intentionality. I will tell. I told Jordana this the other day. It is the most emotional work I've ever done in my entire life.

[Jared Freed]

Okay.

[Sean Kilby]

It was like you'd read two pages of this book about how to like sh. Share someone or be shared, and you just stop and like, think about what matters to you and the emotional weight of like committing to somebody and how it feels to like, do all these, like, you know, separate sex from love in a lot of ways, in order to be non monogamous, you kind of have to separate sex from love. Right? Like, you have to be able to have it. Be somewhat casual.

[Jordana Abraham]

The kind of person who can do that. Yeah, yeah.

[Sean Kilby]

And I don't know if I can. That's the problem. I'm. It's still struggling with it.

[Jared Freed]

So when does this kind of go bad?

[Sean Kilby]

It finally hits. It comes to a head two, three months ago. Where.

[Jordana Abraham]

So how long were you dating her while she had a boyfriend?

[Sean Kilby]

This is like four or five months in.

[Jared Freed]

So four or five months in. What happens? That makes.

[Sean Kilby]

I think maybe I go away for a weekend. She can't go because she has an obligation to go something with him. And I'm just like, you should be here. Like, I'm, I'm sad. Like, this is. It's not great. We. And we, we even had. This one's pretty funny. I mean, we, we. At one point she said to me, you're one of my favorite people. That was something that she said. I will say she said it during sex. And afterwards I was like, you both.

[Jared Freed]

Saying, I love you at this point.

[Sean Kilby]

No, we were saying, I love you. Oh, for sure. Yeah, we were, we were very in love. But at one point she's like, you're one of my favorite people. And after sex I was like, don't do that. And she was like, well, why not? That's a nice thing to say. I'm like, no, I can read between the lines. You want to say you're my favorite person, but you can't. Like, we're in this weird thing.

[Jared Freed]

So you're not doing well with it.

[Sean Kilby]

No, at that point it's like, well, in some ways.

[Jordana Abraham]

Does it add to the excitement?

[Sean Kilby]

Not really. I think the big issue is that I didn't want to see other people. And it felt like she didn't actually want me to see anybody else either. So I started to really get comfortable with it just being me and her. And like, the idea of like going on dates with other people wasn't exciting to me. It's like, I want you to be my person. You want to be my person. So I finally. We're having a conversation one night and I'm like, I'm struggling with this and this, but I can't finish my sentence because I don't want to meddle in your life. She's like, well, I think you got To. And so I basically said, I don't really want to repeat the mistakes that you've made, the things that haven't worked for you in the past. I want to do this in whatever way that makes us both happy. And that kind of opened the floodgates of like, what are we doing here? Fast forward a few months. We are a monogamous couple together.

[Jared Freed]

You guys are together now.

[Jordana Abraham]

How was her breakup?

[Sean Kilby]

What do you. How was it?

[Jordana Abraham]

How did it go? Like, easy.

[Sean Kilby]

I thought it was going to be easy. It. It's never easy. So. Yeah, that was not easy. Yeah. So what's that? Except for mine. No, but mine was just so long. Mine sucked too. It's just that, like the breakup all took place during the relationship and then there was like, not a lot of after effects. But no, it was not an easy process. It was like, honestly, during it. It was the first time in my life from that point where I started being honest about what I want is the first time my entire life that I've experienced anxiety and depression. I was like, it was tough for. I still feel those emotions, like, there's still lingering of it of like, this is taking an emotional toll on me because what is sharing somebody who doesn't want to share you and being in limbo and being. And I mean, to put your needs on a shelf for a while.

[Jared Freed]

Well, then you put your needs out there and they made a move based on that.

[Sean Kilby]

Yeah.

[Jared Freed]

So now they've broken up with this other guy.

[Sean Kilby]

Yeah. And it makes me very happy.

[Jordana Abraham]

Now you're in a monogamous relationship.

[Sean Kilby]

We're in a monogamous relationship.

[Jared Freed]

So to me, I don't know. One of the things you said in the beginning of this is that you never felt like you tried, like, and you never felt like you made an effort.

[Sean Kilby]

Effort to what?

[Jared Freed]

In a relationship? Like, to meet someone, to put. Isn't that something you said in the beginning?

[Sean Kilby]

Well, I. What I did not do. You're saying I didn't try to.

[Jared Freed]

I'm saying the reason that you were breaking up with your original 22 year relationship is you felt like you weren't making an effort. And then you get out, right, right into the world. And I mean, to me, this is the ultimate effort you put. You, you meet someone, you, you decide on them whether they, you know, to me, like the differences between you and someone on hinge is not that much except yours is more honest. Like, yeah, you know, about the other guy. You go, I've tried this out. I've tried this thing of Us dating other people, knowing the person is a little different, more intimate and more honest. But honestly, you go, I. This has to end now. And then they made a decision. You know, you took a chance. They could have said, no, I'm not going to do that. And they did that. I. So what's the issue?

[Sean Kilby]

Here's the issue. I was really happy, really, really happy when I was single. Then I found somebody who is perfect, second best. Well, the new person is honestly my favorite person in the world. Like, she is. She is awesome.

[Jordana Abraham]

The last person was the best.

[Jared Freed]

Right.

[Sean Kilby]

No, I'm sure. I'm saying she was a wonderful person. I don't know.

[Jared Freed]

We're not leaving here without a woman hating you. Okay.

[Sean Kilby]

No, but then it's like, okay, so then you, you have this. I know. Jordan, tell me.

[Jordana Abraham]

Sorry.

[Sean Kilby]

No, I, I get, I get. Get into this old path. My friends were all like, look, you're doing. You're. You're. You're going back to something that's comfortable. And I'm like, yeah, but, like, I'm really enjoying this. And then I get into a monogamous relationship. And I think the big thing that I've always focused on when having these kinds of conversations is this idea that, that there's a balance between stability and comfort, stability, whatever, security and passion, and having, like, those passionate experiences that make you motivated and make sex, whatever, like all kinds of things like that, versus, like, when you have, you know, a home life where it's so. You're so sure that they love you and will never leave you and blah, blah, blah, that it just overshadows all the passion.

[Jordana Abraham]

Right. Well, also now you've, like, you've shifted the relationship from being in this anxiety, which is kind of often mistaken for, like, like passion. Anxiety and passion go hand in hand. And now you're more. And now you have the stability.

[Sean Kilby]

Yes.

[Jordana Abraham]

Right. Where you're like, in the monogamous thing, there's no other guy, and now you can decide if you really want it. In a way.

[Sean Kilby]

Yes. And the problem is that I'm not happier, like, emotionally, like, mentally, I have everything that I want. Like, I know she is perfect. I. I love spending time with her on the couch. I love having sex with her, I love going out with her with our friends. All these things, things. But that version of me that for the first time ever was experiencing freedom, was a happier person. And that is a mind, the idea that you get what you want.

[Jordana Abraham]

What does happiness mean?

[Jared Freed]

Right.

[Sean Kilby]

I.

[Jared Freed]

Do you think you. Yeah, go ahead. I'm sorry. I.

[Jordana Abraham]

No, I mean, I just think. I think, like, happiness is something you feel for, like, 10 minutes. Content is like. Is like, are you happy with the state of your life?

[Sean Kilby]

Agreed.

[Jordana Abraham]

Right.

[Sean Kilby]

Well, it's also, like, what is your ongoing. When you wake up in the morning, are you excited about the day? Are you feeling negative emotions in your body? Like, I went a solid less content. Yeah. Well, not just contentment, but it's, like, excited about life and not really struggling with anything emotionally. I think is like a good, contented, happy space. Sure. And having a lot of fun, exciting experiences. I mean, also just deepening friendships. Like, pouring my love into a bunch of things, filling my life with a bunch of different. Different things that were making me happy. Then I get into a relationship and I'm so obsessed with somebody that it's hard to. And I feel like I kind of. Not by any fault of hers, lost a little bit of myself. Right. You, like, kind of get into a relationship, and now you're like, a pair. And I'm like, man, for some reason, this is not making me as happy as I was when we were new or before I met you. So I'm trying to find my way towards that.

[Jordana Abraham]

That.

[Sean Kilby]

What's gonna. How do you have both? How do I have both? Somebody who didn't sew.

[Jared Freed]

Does she know about this right now?

[Sean Kilby]

Oh, yeah. Oh, she's. She's fine with me talking about it, and we talk about this all the time.

[Jared Freed]

Are you living together?

[Sean Kilby]

De facto. She stays with me most of the time. Yeah.

[Jared Freed]

Does she have a job?

[Sean Kilby]

She has a job. Yeah.

[Jared Freed]

I mean, I'm. To me, like, it sounds like you're bored.

[Sean Kilby]

Oh, no, I'm not bored at all.

[Jared Freed]

So then what's the problem? I don't know.

[Sean Kilby]

I don't know, you guys.

[Jared Freed]

I go to therapy.

[Sean Kilby]

I started therapy.

[Jordana Abraham]

What does your therapist think?

[Sean Kilby]

Think? Yeah. My therapist doesn't say a whole lot. I need to talk to Dr. Naomi Bernstein. Well, no, he did say this. This, I think was really interesting. It took him a while to, like, pipe up. Yeah, no, I actually like him. Okay. But he was like, look, it seems like you do this thing that we call a compromise formation where, like, you're willing to. You have this one thing that you want, so you have to hide this other thing that you want from yourself. And the other thing that I want is to get to experience what everybody else seems to have experienced in their life. And it's, like, apparently pretty fun.

[Jordana Abraham]

Do you want an open relationship?

[Sean Kilby]

Yeah.

[Jared Freed]

What do you think people are experiencing?

[Sean Kilby]

I think what they're experiencing is a version of what I experienced for six months for an extended period of time. Like, I, I assume over the last five years, you've had a lot of fun being a single person.

[Jared Freed]

Yeah, but it goes up and down.

[Sean Kilby]

Like, I know it goes up and down.

[Jared Freed]

It goes up and down. But I, I, My priority was something else and probably still is. And it's like, this show, my career has been, like, the priority. And I think, like, that keeps my mind busy. That keeps, like, the puzzle of it, like, is, like, such an exciting puzzle to me that sometimes, like, the relationship stuff, all of a sudden I'm with someone and I'm like, I get three months in. I'm like, this wasn't a priority. It just happened to get here.

[Sean Kilby]

Yeah.

[Jared Freed]

And that's why I feel the need to, like, back out of it, because I feel like I kind of eased into it and it wasn't something that I, like, worked for. You're working for it, and you got it. So, like, I don't. I, I kind of. I don't know.

[Sean Kilby]

What.

[Jordana Abraham]

Is it, the set? Is it the sexual freedom that you.

[Sean Kilby]

I think so. Yeah. I think so.

[Jordana Abraham]

And I mean, like, you want. Aren't you on? It sounds like you want her previous relationship almost with, like, not exactly, but.

[Sean Kilby]

Like, to some degree, there is this thing, and we talk about it where it's like, you know, part of the reason I. Maybe the whole reason I was willing to open my heart to her rather than say, like, look, this just has to remain casual, is because there was an understanding that I wouldn't have to start to hold myself back. And I think this is, like, my biggest lesson that I had from the breakup. Probably should have led with this, is that nobody holds you back but yourself. You make a choice to hold your back. For example, I never literally in my entire life ever did drugs. My entire life. I'm 39 years old, right. Never smoked weed. I went to, like, the biggest weed college.

[Jared Freed]

You are right.

[Sean Kilby]

Like, crazy. Oh, I'm outing myself constantly, Jared. Don't worry.

[Jared Freed]

Well, no, I'm just saying you're. You're like. You're like, out of a rom com.

[Sean Kilby]

I am like, you're doing Billy Madison, where he goes to, like, from kindergarten to 12th grade in two weeks. I did that with dating, in sex.

[Jared Freed]

But also the drugs thing. So what drugs did you do?

[Sean Kilby]

All of them.

[Jordana Abraham]

All of them.

[Sean Kilby]

Were like, I was afraid to. Right. And part of the reason is like, I, I. Coke. Oh, baby. Yeah.

[Jared Freed]

Okay.

[Sean Kilby]

Yeah.

[Jordana Abraham]

It's like, Five minutes ago.

[Sean Kilby]

Yeah.

[Jared Freed]

Mushrooms.

[Sean Kilby]

Oh, yeah, mushrooms.

[Jared Freed]

Weed?

[Sean Kilby]

A little bit. I hate weed.

[Jared Freed]

But Molly.

[Sean Kilby]

Molly's the best one.

[Jared Freed]

That's okay. Smart person's coke.

[Sean Kilby]

Yeah. Ketamine. That's really big. Now. I heard about ketamine from Jordana's oversharing podcast. We had somebody on who talked about, like, ketamine therapy, and I was like, oh, that's interesting.

[Jared Freed]

So why is this. So why is this part of it?

[Sean Kilby]

Why is this important that I point this out?

[Jared Freed]

Yeah, that's what I was thinking.

[Sean Kilby]

Yeah. We do drugs together all the time. But. No, no, I'm kidding.

[Jared Freed]

But are you guys being adventurous sexually?

[Sean Kilby]

Yes.

[Jared Freed]

So then I, like. I don't know.

[Sean Kilby]

The drug thing. Here's the reason I bring it up. It's like. Like my ex didn't care if I was doing drugs or not. She wasn't approved about these things. I was holding myself back for myself. And then all of a sudden, I'm like, this stuff isn't so scary. You, like, you hold yourself back. Right? Okay. And then I got into this new relationship, and I'm like, am I holding myself back again now? Because I'm not hooking up with anybody else. She's not asking me not to, but, you know, that sort of thing.

[Jordana Abraham]

What is so appealing about having sex with a bunch of different women?

[Sean Kilby]

I don't know. I think it's like, you know how you feel. No, no, but think about it this way, okay? Think about it this way. This is dead serious. Like, you know, there is a feeling that you have when you're attracted to somebody. Like in the first few dates when people talk about there's, like, some passion there. That's. That it's the new.

[Jordana Abraham]

The novelty.

[Sean Kilby]

The novelty and the newness. The novelty and the newness. Excitement, novelty and newness. That I think is a thing that, like, she and I still actually have it. Like. Like, I mean, our sex life, right?

[Jared Freed]

That's right.

[Sean Kilby]

But it's still like there's. There's like a. A churn to it where you're like, okay, that makes you still feel something in your body that can't be stirred by the same person forever.

[Jordana Abraham]

Do you almost feel like you want it because you can't have it anymore? Like, let's say. Let's say it was open and you could go do it. Would you. Would you want it? Would you, like, go do it?

[Sean Kilby]

Yeah, but I would be afraid to do it, I think, because it's, like, a risk.

[Jordana Abraham]

But if you. With someone who was just previously in a Non monogamous relationship. Couldn't, Wouldn't you? Couldn't you say this to her? And she'd be like, all right, let's, like, try that again.

[Sean Kilby]

Yeah, it's a conversation that we've had, right? But then you're like, well, what do I actually need? What do I actually want? I mean, it's. It's a challenge. By the way, Jordana's asking a question, like, what's so appealing about that?

[Jared Freed]

Right?

[Sean Kilby]

I don't know. But, like, when you're making out with somebody for the first time, it's fun. You know what?

[Jordana Abraham]

I think this is the difference between being, like, 40 and being single for a very. For a long time versus, like, being single, like, feeling like you're in your 20s. If someone in your 20s was like, to you, you found the perfect person and everything's great, but, like, you're not gonna sleep with anyone again, you might think differently than you did, Than you would now.

[Jared Freed]

Absolutely. And I. I think I. It is. I definitely would think differently in my 20s than I would now. But I. I understand exactly what you're saying. I mean, the idea of meeting someone, like, having that moment, the spark, all that stuff. I think there's a couple things from my perspective that I, like, hear here, and it's a couple things that, like, I mean, I told you, like, I was like, I met. I was like, I was on. I was like, I met someone. I was like, we had this great back and forth. It was exciting. I understand that. And then I found out they were married. I was like, maybe we only spoke that way to each other because they were married. And, you know, I didn't think of them as someone that, like, I was gonna, like, hook up with. And we just had this, like, really good back and forth. I'm like, you wonder about those variables when you're single. You're like, if I pulled this one out. And especially as you're attach. Attempting to get into a relationship or maybe being on the brink of it, you're like, well, if you get a little precious, is there a piece of you that this is about? Like, the attention you got as a.

[Sean Kilby]

Single guy, like, the validation that you get from that attention, I believe.

[Jared Freed]

Attention. You're someone I know that's done. Stand up. You have a podcast that you're starting based on, you know, being single and being new to this world.

[Sean Kilby]

World.

[Jared Freed]

There's a lot of, like, attention you get from just having this conversation, being in the conversation. That. And I think for a lot of men, too, when you become the boyfriend, get to the background. You know, you're the fuddy duddy dad. You're. It's, you know, relationship content is, you know, not as fun, you know, just not something that hits in the same way as like, single guy out there, there who can talk to women and be compassionate about it. Look, I. This is something I deal with. I'm not just putting this on you.

[Sean Kilby]

I will tell you, it's funny because I don't think it's like, attention thing. I don't think so. There's a validation thing that you get from like, hooking up with different people. I think that's a thing, especially when you're single. Like, if you have a dry spell for a little while and then you hook up with somebody, like, oh, that was validating. I still got it right. There's that feeling. I think the thrill of the chase is more the thing than the. And the motivation that comes with that. That, like, I think that a lot of what men are driven by, especially women too, is like, okay, I want to be successful. My career, I want to have a nice place. I want to be in good shape. All so that I'm appealing to people when I chase after them.

[Jared Freed]

Well, then that, that goes back to another thing, which is this, like, lifestyle you're choosing. Like, you know, there's a line from I. I love the Marvel. Marvel movies. This is going to be like a funny movie to reference, but Shang Chi, do you watch the Marvel movies? So Shang Chi. There's a whole thing. There's a whole arc.

[Sean Kilby]

Yeah.

[Jared Freed]

Story arc with awkwafina where it says where the grandma's like, no, no, no goal, no aim. What is it? Do you remember what I'm talking about? It's if you don't have any. If you aim big, aim small, you hit small. If you aim for nothing, you're doing nothing.

[Sean Kilby]

Yeah, yeah.

[Jared Freed]

So, like, if you're in this lifestyle where you're like, I don't want to be married, I don't want to have kids. I like giving people their kids back. Like, I'm not here to be like the old. Like, I sound like I'm like, here from the church.

[Sean Kilby]

Yeah.

[Jared Freed]

But I, I do think, like, what are your goals personally and outside of achieving the rush of meeting a woman? And I'm. I could be talking to myself too. So I, I hope this doesn't sound like I'm, like, being hard because I have this thought about myself a lot. Like, what are my goals that someone being in my life would Help me get to, like. That would help me achieve those goals. If there are no goals, then of course, this is just another person that you have fun with that you like. But where am I trying to get to?

[Sean Kilby]

I've said I've never seen relationships that way. I don't really think that it's like, there's a goal.

[Jared Freed]

If your aim is nothing, you'll hit nothing. Aim at the sky. Win or die. I don't know. If you aim in the sky part, I think that takes us off of it. But if you aim at nothing, you hit nothing.

[Sean Kilby]

So you're saying if I was more goals oriented.

[Jared Freed]

I don't know what your goals are.

[Sean Kilby]

I honestly, I think there's no marriage.

[Jared Freed]

If it's. If it's. Meet the most wonderful person that can fit me perfectly. You did it.

[Sean Kilby]

No, I honestly think my goal up to. Up to the moment I met her was get comfortable with casual sex, get good at initiating, and fill your life with a bunch of things, including dating, but not exclusively, and, like, do those things alone.

[Jordana Abraham]

And you wanted to do that, like, sort of just forever?

[Sean Kilby]

For exactly as long as Jared has been doing it for the last five years. I joke about this, but I also kind of mean it. I was like. At a certain point, I was like, I'm kind of mad at you from. For. For showing up because I love you so much and you're so perfect. Like, the girl is perfect.

[Jared Freed]

Well, do you feel indebted to her now that you've said those things to her? And now you might have to, like, end it and. And she's left, but it's just like.

[Sean Kilby]

It's figuring out how to, like, make it work where I'm not holding myself back or doing so we've talked about having threesomes. Like, this is a whole thing. Like, how. Like, maybe I just. That's, like, something I would want to do together.

[Jared Freed]

I'm like, stay with this woman as.

[Sean Kilby]

Long as I know Jared, she's perfect. But, like, that. That kind of thing, it's like, okay, so how do you make that be happy?

[Jared Freed]

I got too many chicks. I'm at the same time.

[Sean Kilby]

I know, but I mean, that is the sort of thing where it's like everybody else had their kind of wrong spring. Right. Like, at some point in the 20s.

[Jordana Abraham]

So it's not. This is all like, a big case of fomo.

[Jared Freed]

Yeah.

[Sean Kilby]

Yeah. Honestly, it's a big case.

[Jared Freed]

Yeah. But I don't know what you think you're missing out on.

[Jordana Abraham]

Yeah, I think that's the Thing built up a gross.

[Sean Kilby]

I know, guys, but here's the thing. There's two things that, that prove to me that you're a little bit wrong about building with. Number one, those six months are the happiest ever.

[Jordana Abraham]

But that's because they're new.

[Sean Kilby]

I agree. Right.

[Jordana Abraham]

If you were on Hinge for like six years, you wouldn't be like, best six, best six years of my life, Jordan.

[Sean Kilby]

That's, that's, that's point number two that I was about to make, which is like, everybody tells me that, like it get shitty at a certain point. You. There's certain lessons you can't be told. Some of them you got to experience yourself.

[Jared Freed]

Well, I mean, here's the.

[Sean Kilby]

You can't like feel. It's like literally being like, oh, guys, I already ate that meal, like, and it was good for a while and I ate too much of it and then I don't want to eat anymore. Don't eat any.

[Jared Freed]

The feedback from women is like that, you know, the, the, the, the female complaint, right. Is that like these men are using. Are draining your resources as a girlfriend to then move on to the next woman to suck the girlfriend out of. Okay, so like, do you have any, like, when. If you're saying, I'll do this for six years, I won't go on the apps. I'll be totally upfront. I'm just casual guy. You're still entering into something that is a relationship. Ish. Most guys who go into long relationships. Most guys who got out of long relationships start looking for someone, act like a boyfriend in those initial, like hitting on girls phases and then.

[Jordana Abraham]

Sounds like it's what you did. Kind of.

[Sean Kilby]

It is. But I was very upfront about not wanting.

[Jordana Abraham]

Right. But so are those guys. They're always like, everyone, I just got out of something. But you're still like in boyfriend mode.

[Sean Kilby]

Yeah. Because that's what you're good at.

[Jordana Abraham]

Right?

[Jared Freed]

Right. You're good at like being compassionate, you know, doing the right thing and being that kind of boyfriend. Acting as boyfriend. But not really. But also you're saying it turns out, no, it's like I'm doing this with my left and I'm. I'm you over with my right. It's a little magician.

[Sean Kilby]

Well, a little bit. But I've talked about this with my friends and it is true. No matter how forthright you are, no matter how much you repeat to somebody like this needs to remain casual and non committal. It doesn't matter how much you tell them people if they develop Feelings, then you have to be like, okay, this isn't going to work. So that happened a few times. That'll be a few times.

[Jordana Abraham]

Practically. I think there's a solution that requires a risk, is that you could, say, met the right person at the wrong time. I'm not ready to be in a relationship right now, but, like, call you when I am if you're around. Right. And then, like, you have to take the risk that when you are ready, that person is not available, but maybe they will be and it could work out.

[Jared Freed]

And let me say, add on to that, because as someone who has said that to people that I, you know, that I've been with for, you know, the three months, the calling them back and thinking about them later on can happen. But the thing that I run into, and this is like the hardest part, is not knowing what will happen after that call to me.

[Sean Kilby]

So, like, what even happened to you?

[Jared Freed]

So if you say to this, and I think Jordana's advice, I'd be like, I agree with it as far as, like, like figuring out your feelings. But if you get six months away and you have a tough day and you're like, I really miss this one person. And then you're going to have to deal with, should I text them to let them know I'm all in. And then it's almost scariest that they go, thank God you're back, because now.

[Jordana Abraham]

Now you're in for life.

[Jared Freed]

You're in for life.

[Sean Kilby]

I know. I get it, guys. And.

[Jared Freed]

And maybe you don't know what it's going to feel like. Like after that, maybe you're back here sitting with us.

[Sean Kilby]

No, I.

[Jared Freed]

So that's. I mean, I'm saying I've had that thought go through my mind, and that's like kind of a curse I wouldn't put on someone. Like, I. I actually think it's like, for me, it's been like, a little bit annoying going to.

[Sean Kilby]

What? Which part?

[Jared Freed]

What's that?

[Sean Kilby]

What's annoying to me?

[Jared Freed]

The feeling of, like, trying to do the right thing by not texting these people.

[Sean Kilby]

Yeah.

[Jared Freed]

And going, well, I made this promise that I would only come back if I was ready. And then you go, man, everyone I date, I kind of think of these people and maybe I should do this. But then again, I can't. I don't want to be disrespectful. So, like, this idea of, like, hey, wrong time. I'll come back to you if I feel that. And I hope that you're here, still available. It sounds Easier than it's is in reality.

[Sean Kilby]

No, I. I mean, I've obviously talked to her about that and my other people have brought it up too. Like, this is the solution. It's really easy, again, as you said, to prescribe that to somebody else when you're not in it.

[Jordana Abraham]

Right.

[Sean Kilby]

You know, and it is not the outcome that I want. I want to be with this person. But it's also, I don't. I didn't do the. All the stuff that you guys said where it's like, you get so comfortable with it that you're tired of being single. I didn't get. Get to that point yet. So, like, how do I split the difference? I don't know. I'm going to therapy to help with it. Like, the feedback that you've given me is similar to what other people have given me, but it's not really a solution. Right. Because, like, I also want to be with the love of my life.

[Jordana Abraham]

Well, what's her take?

[Sean Kilby]

Well, what's her.

[Jordana Abraham]

What's her take is her take, like, oh, like, I'm with this guy who just kind of like, is constantly telling me that he's like, was happier before we were together.

[Sean Kilby]

Like, constantly telling her that. But I hear.

[Jordana Abraham]

But if I were her, I'd be. I'd almost be like, all right, why don't I break up with him? And then he can come back when he's like, when I. That's not his frame of mind.

[Sean Kilby]

And I want to be clear, like, when I say, like, happier, it's not like I'm complaining about the situation or something. Like, I'm very happy with the situation, but, like, why am I still anxious? Right. That's one of the things. Like, why is it still giving me.

[Jordana Abraham]

You're anxious when you were. When she was. When you were in an open relationship also. So maybe you just have anxiety.

[Sean Kilby]

Yeah, but I never. But this is my point. I never had anxiety in my entire life.

[Jared Freed]

What are you anxious about?

[Sean Kilby]

I don't know. I gotta keep talking to my therapist about it. But, like, I. I think part of what it is is that. That I'm holding myself back again. That it's like, I got to this point where we ostensibly could have been in an open relationship, but neither of us wanted it. And then once I have all the security that I thought I wanted, I still feel like I'm holding myself back.

[Jared Freed]

I. I mean, I'm going to say something very annoying.

[Sean Kilby]

Go ahead.

[Jared Freed]

You can't have it all.

[Sean Kilby]

I know.

[Jared Freed]

I mean, but then also, people do.

[Sean Kilby]

This is why people do open relationships, right? Because they want to have it all.

[Jordana Abraham]

All right. But even those people don't have it all.

[Sean Kilby]

I mean, I don't know.

[Jared Freed]

But also what do you want? Like I don't even know where this relationship with her goes. It goes towards moving in. And then what are you guys going to do together? Like do you have plans together? Do you want to travel together? Do you want to, like we already.

[Sean Kilby]

I mean this thing, like we went on a two week trip to Europe a few weeks ago and it was the best vacation I've ever been on.

[Jared Freed]

Okay, so is there an idea of like let's plan the next trip. Let's, you know. You know, I don't know. Like I, I, I'm sitting here single. Like I should be like saying, you know, man, get out here, get out of that thing. Start other chicks.

[Jordana Abraham]

Yeah.

[Jared Freed]

I mean it sounds like you found it. Like I, I, I don't really believe in that.

[Sean Kilby]

Well, when you say like what are the goals? Like neither of us want children. We're not trying to like, you know, but we have entwined our lives a ton. We spend a ton of times time with my friend. Like, like everybody loves her. Like our lives are very much enmeshed now.

[Jordana Abraham]

Sure.

[Sean Kilby]

Like I, and my therapist asked me, what is your goal? I kind of do want what I have right now, but I also don't want to feel like I'm holding myself back.

[Jared Freed]

What do you, what do you, like, name one thing that you can't do right now. Yeah.

[Sean Kilby]

Have sex with new people. Honestly, Honestly, forget about, forget about the threesome. You just don't want working on it. No, no, no, I don't. That could be a solution. Don't get me wrong. That's why I said could we could talk about this today, but maybe it'll change tomorrow. Like there is that kind of thing. But I honestly, I'll give you the, the number. Like here's the best example. It's not even like sleep with other people. It really isn't. Is that like there was a thing where I would like when I was newly single and I go with my buddies and we go to like this thing. You can just go and flirt with somebody. Right. And when I used to flirt with people when I was in a relationship, but I would never have cheated on my ex. Like you just flirt for fun, right? It's totally different when they're sticking. Sure. There is like a thing that happens in your body that, that mo. That just changes how you feel.

[Jared Freed]

I gotta start Going out with Sean alone in the corner, I don't even talk to him.

[Sean Kilby]

But honestly, just like the act, like it's only happening for three days.

[Jared Freed]

I didn't talk to one woman.

[Sean Kilby]

But the idea literally going out and like bringing some someone home like that night is a different kind of risk. It's scary, like that kind of thing. And when you have security with somebody, you don't experience that kind of risk. Risk, right. So like she and I have, we have a very spicy sex life and we do role play and we do whatever and it's like what we have is very good and healthy. But what's the thing I can't do when I go out? I can hit on someone. She won't care if I hit on someone cuz she's like, feels secure with me. But I can't actually. There's no stakes. So I decided to put all that on a shelf. Like I put that part of myself away. And that has made me go to the gym less. It has made me like feel kind of weird at certain times where I'm like, what am I, I, what am I looking for in life? It, that's a challenge. I don't know. That's the thing I can't do.

[Jordana Abraham]

I think that question wouldn't go away either way. The what am I looking for in life thing I think is almost like separate from the relationship, the answer to your problems. Like if you can figure that out.

[Sean Kilby]

What do, what do I want? Can you tell me?

[Jared Freed]

Well.

[Jordana Abraham]

I mean only you can know what you want. I think it's like I agree with Jared in that sense of like, I think it's a bigger, like, I think that anxiety, you're kind of like putting it on being in a relationship too, too soon. But it sounds like you, the relationship's great and has like all these components of things you want. To me, it's not like you're almost like using that as like a, someplace to channel that anxiety about like who do I want to be as a whole.

[Jared Freed]

Right. And you're putting, I think the one thing I'm hearing too is like I want to have this thing that everyone else has.

[Sean Kilby]

Yeah.

[Jared Freed]

And then you're saying, jordana, what do I want? Like you're kind of looking towards everything else as like where you should or shouldn't be. I don't know. I, I, I know. And listen, I, I, you know, I think a lot about this stuff, you know. Absolutely. I think you get into, you know, like I, I'm forced to think about you Know, Jordan's asking me hard questions when you're not here every week, so I hear where you're at. I don't know. I. I don't know if I've said recently. I used to say it all the time, and it was a thing. 20s, early 30s. Thing of me to say was, if you're in a relationship, I envy you on a Sunday morning, and I pity you on a Saturday night. And that's a very male thought.

[Jordana Abraham]

Like, I.

[Jared Freed]

You know, Sundays you want to be hugged and you want to be in a relationship, and on Saturdays, you want to go out and have this chase. And I kind of want that Saturday a lot less now than I've wanted it before. But maybe because I'm single and have been single a while, maybe I'm saying that because I am single. And I wouldn't be saying that if I was in a relationship, I'd be yearning for a little bit of that. I'd see that my married friends, they. They get a little jealous of me. I get a little jealous, and then that's the cruelty of life. I don't think you're gonna ever find the equilibrium, you know, or most people don't.

[Jordana Abraham]

That's true. You do seem to be chasing a little bit of, like, a ghost life. Of, like, you know, the security of being with someone that you really like, that's there, that you like hanging out with all the time, but also the, like, excitement. Like, it's all a trade off everything.

[Sean Kilby]

Here's the thing I will say to you guys, like, to. To widen the scope. Thank you so much for letting me make it all about me, which is what I do with all my friends.

[Jared Freed]

This is why we're here, you know.

[Sean Kilby]

This is the best.

[Jared Freed]

Yeah. This is what the episode is.

[Sean Kilby]

But to, like, pull it to a wider.

[Jared Freed]

I've tried to make it about me a few times. We keep coming back to you.

[Sean Kilby]

I started reading the book Many in Captivity recently by Esther Perel. Well, Jordan, have you read this book?

[Jordana Abraham]

Of course.

[Sean Kilby]

Of course. Okay, Jared, you're aware of it?

[Jared Freed]

Not for me, but it addresses this out June 2026.

[Sean Kilby]

I think it addresses man captivity, addresses this question that I think kind of haunts us all a little bit as animals. Like, we're human beings. We're just animals. And we're built on our DNA to have certain urges. Right. And we simultaneously want to find somebody who is our person. I think that's like a really natural human urge to have somebody you feel comfortable nesting with and building a life with. But there's also this other element where you have a drive to like chase and be chased. And over time in a long term committed relationship you that other feeling starts to creep back in. And that's a really sad thought. It bums people out when they're like it doesn't last forever. Can it not last forever? That feeling of excitement for your partner not lasts forever. Amy the thing that I was grappling with with my ex up until the end and Esper wrote this book about this, like there's ways that you can do it through strategies and some of the strategies include infusing some versions of insecurity into your relate not insecurity but like excitement in different ways. And I've tried to do that with her. I've tried to do it for myself. I'm still grappling with that question. But I think that's part of the reason why some people try non monogamy or I think that's one of the reasons like the, that there may be a chance that our lives just follow this kind of undulation of tons of happiness and security followed by dissatisfaction and insecurity.

[Jared Freed]

It's just so interesting to me that you like you're going to end up like. It's like almost like a sci fi movie where you're becoming the guy that she had before.

[Sean Kilby]

Oh, I, I desperately want to not be that guy 100%. I think that's her big fear is like say we did the open relationship thing. Like what I don't want to do and not bespurging him or anything.

[Jared Freed]

Right.

[Sean Kilby]

I don't want to get into a situation where we are disconnected. I'm desperately afraid of losing our connection. Like I'm, I, I feel so much intimacy with.

[Jordana Abraham]

What are you more afraid of? Losing your connection or not being able to have sex with new people?

[Sean Kilby]

Honestly, I think this is the problem is they both like are creating attention to me that's making my chest hurt right now. Like does that make sense?

[Jared Freed]

Yeah.

[Jordana Abraham]

One that matters more. No. I think there's got to be one that matters more.

[Sean Kilby]

More.

[Jordana Abraham]

I think that's like.

[Jared Freed]

But I think without goals that's where you can't judge it because now it's in a vacuum. What matters more to him doesn't. It means nothing. Where if you don't have your whole.

[Jordana Abraham]

General life goal right in your.

[Jared Freed]

And I listen that is something I can understand. You know, like what's the greater picture here? If the greater picture here is like I want to live this life where, where I'm having all the experiences, then it's probably not with a. Another in. In a relationship.

[Sean Kilby]

Right, right.

[Jordana Abraham]

Or the relation or not with someone not in a relationship where the other person doesn't also want to do that.

[Sean Kilby]

To do that. I think one of the issues, of course, is like, here's me on this trajectory towards like, getting used to casual sex and then her meeting me and like getting really in love with the idea of. Of having her favorite person be her person and that's enough. And like, I gave that to her and then I. And it's why we're monogamous together now. And I do enjoy being monogamous with her. But then it's like, why do I still feel like I'm left out of a club that the rest of you. Maybe I'm not smartching anybody, but like most people that we are friends with have experience.

[Jordana Abraham]

I mean, you could give it up for the chance to try that club and then realize that it's not that fun. Or like, you could.

[Sean Kilby]

Right.

[Jordana Abraham]

That's an option.

[Jared Freed]

I've never done ketamine, so I don't know.

[Sean Kilby]

Come on over. I gotta find.

[Jordana Abraham]

Yeah, there's a lot of things you haven't done that you know are fun but probably are not that great in the long term. Right?

[Sean Kilby]

Yeah, sure. But it turns out that, that, that I can know it. You can know the thing, but still feel the tension inside.

[Jared Freed]

It's going to be tough for people. I think there's going to be a lot of, like, angry women.

[Sean Kilby]

I know I've been worried about this. I should have led with this. Can we insert this at the beginning of the episode? I just want to be clear that because people really hate when somebody is this honest and honest.

[Jared Freed]

I mean, like, I appreciate the honesty.

[Jordana Abraham]

It's just frustrating.

[Sean Kilby]

I think as a woman, I think.

[Jared Freed]

It'S going to be frustrating to hear there's a single guy who's out there having his cake and eating it too, and then going, what else could you possibly want? Right. I'm. You have a sexually adventurous woman that you're attracted to and with no thoughts of future college payments for kids or retirement, and you don't care what your families think. Yeah, like, in my mind, I'm like, I got it, got.

[Sean Kilby]

I got it all. But I think part one other thing that I. I'm skirting around is like, that she, she got. One of the things I'm resentful of is that she doesn't really want that with me, which is great. It makes me feel good. But at the same time, it makes me feel like she doesn't really want for me to have that exploration that she had for herself.

[Jordana Abraham]

Well, you've said this a little bit before where it's like, men don't want to be like the guy after you had all the fun, crazy sexual times with. And then like now you're with. With. With me and it's like, like great and safe.

[Sean Kilby]

Right.

[Jared Freed]

Well, I don't want it said about me the way sometimes women will say, no, I had my fun. They. They go into this, like, long. Oh, when I was out there and then I found Sean.

[Sean Kilby]

Yeah.

[Jared Freed]

You know, and you're like, what the. You know, I'm not part of the, the tale as well.

[Sean Kilby]

I feel very validated by her in that.

[Jared Freed]

I think it sounds like you are like, I. It doesn't sound.

[Jordana Abraham]

It sounds like she's a lot more open than I would ever be.

[Jared Freed]

Right.

[Sean Kilby]

Sleep.

[Jordana Abraham]

You found your. Now you found. There you go.

[Sean Kilby]

No, I mean, there's this whole thing was like we, we started hooking up and like, the sex is just like, I, I feel very validated by the sex with her. And it's also just like I was figuring out how to have sex.

[Jordana Abraham]

Let's say she was like, john, go out there, have sex with five women and then we'll be done.

[Sean Kilby]

Yeah. I think even that if, like, say we did that. Not enough. No, no, no, no. I think that would be one of those.

[Jordana Abraham]

An animal.

[Sean Kilby]

No, no, no. But I think that's one of those things where it's like, like. And this is part of what, when I read this book about that sort of thing is like making promises like that, like knowing, oh, five people is enough, or whatever the case may be, might seem like it's good for you in the moment, but then once you've done it, you're like, yeah, but I still feel like now I'm holding myself back again from what I want. Like, making those kind of promises is.

[Jordana Abraham]

A little bit of the difference between us and animals. Right. Is that we're able to like, have a little bit of a trade off off or like, be in a little discomfort where you're like, there's a little bit of a. I mean, and I think that happens in any monogamous relationship where there's like, even someone who's like, desperately wants a monogamous relationship. Like, I was. You still have, like, if you're like a person who thinks critically about things, there's always going to be like a little bit in the thing in the Back of your mind of like. And this is, like, this is it. But, like, I don't know if, like, the right solution to that is to be like, I need to make sure that this is never it. Instead, maybe it's just to, like. Like, as Dr. Naomi would probably say, like, sit with that. Let it, like, move through you, and then, like, be a little uncomfortable. But then you realize, like, that's not worth the trade off. If it's not.

[Sean Kilby]

If it's not. I know. I mean, I. I'm trying. I want to win back the female audience a little bit first.

[Jared Freed]

I think they're going to be upset with this no matter what.

[Sean Kilby]

All right. Damn it. No, I know.

[Jared Freed]

No, I think.

[Jordana Abraham]

I think the honesty is refreshing.

[Jared Freed]

I know, but this straight guy talking about relationships is a very tough, tough.

[Jordana Abraham]

You can share the.

[Jared Freed]

Yeah, I'm sharing the Bronx.

[Sean Kilby]

Come back and take the shots for anytime you want.

[Jared Freed]

When I see anger with me as a dater, I can feel that they're like, m. There's an anger with, like, it's societal. It's not me. Like, it's like. Like the fact that I even. Cuz everything you're saying, like, you know, that they come at you with like, oh, well, who do you think you are?

[Sean Kilby]

Right.

[Jared Freed]

I'm just a person who's allowed to live sharing your own personal experience, and the world allows me. I'm sorry. Life is unfair.

[Sean Kilby]

There's a huge cat 22 that happens. And I learned very quickly in dating, and I think you guys are probably aware of it, which is if you're a woman who's looking to have. Let's. How do I put this? If you're a guy who wants to have casual sex and you're honest that you're not willing to commit, you're less likely to get someone to sleep with you. If you're deceptive and you just go, oh, my heart is open. Anything could happen. I think you're so hot. This is great. Okay, great. Can start hooking up and he breaks. Break up with them two weeks later. Meanwhile, if women want to, like, we'll do the opposite. Where, like, they. If they are not willing to, like, be honest about what their casual versus, like, relationshipiness is, people will approach them differently. When you sit down in a chair, like Jared and I, and you're super honest about what you want, people kind of get mad at you for telling them how you really feel.

[Jordana Abraham]

Well, I think it's more.

[Sean Kilby]

It's a real feel.

[Jordana Abraham]

I don't know if it's like, Mad about Tell. I'm trying to think of, like, put myself in the position of hearing this.

[Sean Kilby]

I'm trying to give the ladies the information.

[Jordana Abraham]

I. I don't think it's, like, mad at you for telling me how you really feel. I think it's like an. An anger at, like, well, what do you. What do you even. What do you want? Like, like, what is the. Yeah, almost like, how can I win here? Like, what is. Like, what do you. Like, you want. You don't want to break up, but you don't want to, like, be with, like. So you're not only going to be happy in your perfect situation, which is, like, you have me, you're the love of your life, but also have ability to have sex with anyone you want. Like, is that the only way we can solve this is by giving you whatever you want?

[Sean Kilby]

Or we're talking about me again? Or are we talking about men?

[Jared Freed]

Well, you.

[Jordana Abraham]

I mean, we're talking about you. That's what I'm talking about. I'm talking about why someone would hear a Sean episode. I'm talking about why someone might be frustrated listening to this. Like, I might be listening to this and be like, is the only way to solve Sean's problem for his girlfriend to just let him have sex with whoever he wants because he loves her so much and he doesn't want to be with her?

[Sean Kilby]

That's super selfish. Right? That's not good.

[Jordana Abraham]

Right?

[Sean Kilby]

I know.

[Jordana Abraham]

Or for Sean to break up with her, which he does. He doesn't want to do.

[Sean Kilby]

Well, neither of us want to break.

[Jordana Abraham]

Up, so I'm kind of like, that. I guess that would be my frustration as a listener of, like, what is Mad? What is Sean, really? No, I'm just thinking, like, like, what does Sean want?

[Sean Kilby]

No, I know. I. I know. And I. But I think, okay, again, I have to, like, broaden the scope a little bit to what my experience is as well. And I think there is some wisdom that I have that a lot of listeners haven't, like, gotten to this point. So I'll give you, like, the. The framework, and we can move on from. But there's, like, these movies called the. You've ever heard, like, the before series, Before Sunrise, Before Sunset, whatever. It's three movies. They're the most beautiful movies you've ever watched in your entire life. I'm single for, like, three, four months, and I'm like, guys, I'm never going to be in a relationship again. And then I watched the first one where they walk around for a European City all night and fall in love. And the movie ends. And I'm like, ball in my eyes. I'm like, guys, I'm gonna fall in love again. Like, it's. This is the stuff. This is the stuff. The, like, chase part. The part where, like, you're starting to feel new feelings. Like, this is where it's at. And the second movie rolls around. It takes place 10 years later. It's like, they reconnect, and you're like, oh, my God, the heartache. Like, don't let somebody go. When you have the opportunity to find your person. I can't believe you would let that happen. And then the third, and I'm like, but, guys, it always kind of fizzles for people at some point. It always fizzles. And they're like. My friends are like, you're crazy. No, it doesn't. It doesn't have to be that way. You can still be madly in love with each other 50 years later. I'm like, I don't know. Not in my experience. It's a feeling in your body. And then the third. We watch the third movie together. It happens 10 years later, and like an old married couple who kind of is fighting all the time, and they're struggling with all the things that I'm telling you about. My friends finish watching the movie, they go, oh, I get it now. Fuck does that happen to all of us? And it happened to me, and I don't want to do it again.

[Jordana Abraham]

Again.

[Sean Kilby]

But I also have found my person in that first movie, and I don't want to let her go. It's like, it's such a mind to be a person in love and also seeking passion.

[Jared Freed]

Yeah, but this is how everything you talked about is like a hypothetical, you know, like, you're not in it.

[Sean Kilby]

No, but I'm saying I've done it all.

[Jared Freed]

No, but you've. You haven't done it all.

[Sean Kilby]

You.

[Jared Freed]

22 years with someone you met in high school, you've had that relationship. And then when it didn't work out and when you felt a little dead inside from it, you're thinking, well, I guess there's a little PTSD of, like, you know, I don't want to be dead inside next to someone that I really like and have to, like, move on from it, whatever age. I don't know, I. I think it's like, that's stuff you say from the outside, looking in, you know, Like, I. I do this too. I don't know. I. You know, the idea. Like. Like, you know, that's more of a high level conversation about whether monogamy is worth it or not. Like, I, I tend to think it's worth it.

[Sean Kilby]

I don't do I love love.

[Jordana Abraham]

I think we, Yeah, I mean, I think we, we need, we, we need to, to wrap generally. But I'm going to, But I, I would leave it just on saying, like, I think that there's no. Even those people who are in love for 50 years or whatever don't all have their moments of feeling some type of way. And so I think if you're looking for a situation that's gonna make you happy 100% of the time, that doesn't exist. And only you can know what would make you happier. So, like, and I, and I get like the, the existential crisis of not really knowing or not knowing which way to go. And that's something you should probably work out, like, over time with a therapist. But if I were her, I would be like, why don't you come back when you, like, know what you want?

[Sean Kilby]

Want?

[Jordana Abraham]

That's what I would say if, if I were dating you.

[Jared Freed]

Right. And maybe she hears this and, you know, hears this podcast and she's like, okay, like, what does she want from life? You know, that's another thing.

[Sean Kilby]

Yeah, no, she knows what I mean. I, I know that I make her really happy. We're starting couples therapy this week. Look, we're working on these things together.

[Jared Freed]

I mean, what does she have, like, a goal? Like, I mean, I, I just, I.

[Sean Kilby]

Don'T really, I don't think either of us approach relationships.

[Jared Freed]

Goals or relationships, Life, you know, like, what is.

[Jordana Abraham]

Where are we heading?

[Jared Freed]

Goals.

[Sean Kilby]

Right.

[Jared Freed]

Does she have like, I want to be retired and how do the both.

[Jordana Abraham]

Of you fit into that? Right.

[Sean Kilby]

Career isn't really, like, a driving force for us in our relationship.

[Jared Freed]

That's fine. But I'm saying it kind of all those things matter.

[Jordana Abraham]

Yeah.

[Jared Freed]

You know, that's like saying, like, oh, we're not very political. Everything.

[Jordana Abraham]

What's the life you want to build together? I think is what you're saying.

[Sean Kilby]

Yeah, no, I mean, my therapist asked me the other day. I'm like, I want to live with this girl in the apartment I live in now.

[Jordana Abraham]

Take her out of it. What's the life you want to build overall? Like, what do you want to be in 20 years?

[Sean Kilby]

I could be right where I'm at right now, just like, without these struggles, like, emotionally, but, like, the world I've built. You know, What I always want in life is friends apartment. I want to be either Ross, Chandler or Joey, whichever one. And I. I found myself in that this year. I have so many close friends who all live right here in lower Manhattan.

[Jared Freed]

Sure.

[Sean Kilby]

And we go out all the time and have a great time together. And I am doing all the stuff that I want to do. And I have a hot girlfriend who is good at sex with me. And we go out with our friends and have a blast.

[Jared Freed]

Come here to brag.

[Sean Kilby]

I know, but I also don't want the coke talking. Not right now.

[Jared Freed]

I hear you.

[Sean Kilby]

That's the thing. I know I want.

[Jordana Abraham]

Why don't you just keep doing that?

[Jared Freed]

You want time to stand still?

[Sean Kilby]

Because I have this feeling in my chest.

[Jordana Abraham]

Maybe you need like a. A ain prescription.

[Jared Freed]

Listen, Sean, thank you for coming on Drugs.

[Sean Kilby]

Thank you.

[Jared Freed]

New podcast. You can hear more about his dating life and what's going on. Picky and selfish. It's with Talia Lickstein. Listen, we. We tried to solve.

[Jordana Abraham]

We tried to solve it. John, I. I think you need to come back with an update when there's. When, when, when the dust come back.

[Jared Freed]

When you guys break up.

[Jordana Abraham]

We'll be back next week.

[Sean Kilby]

Week.

[Jordana Abraham]

Thanks for listening, guys.

[Jared Freed]

Boom.