How Do I Navigate My New Polyamorous Relationship? - U Up?

Transcript

Jordana Abraham (0:00)

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

Sean Kilby (0:02)

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

Jordana Abraham (0:04)

What the.

Sean Kilby (0:05)

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

Jordana Abraham (0:12)

Sean was a virgin.

Sean Kilby (0:12)

40 year old virgin.

Jared Freed (0:14)

I mean, we're having regular sex.

Jordana Abraham (0:17)

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 (0:26)

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 (0:34)

Very special.

Jared Freed (0:35)

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 (0:58)

Things, smaller and worse things.

Jared Freed (1:00)

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

Sean Kilby (1:04)

Thanks for having me. Thank you so much.

Jordana Abraham (1:06)

Yeah.

Sean Kilby (1:07)

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 (1:12)

It's Monday, Sean.

Sean Kilby (1:15)

Mondays are barely working.

Jordana Abraham (1:17)

We're a Tuesday, Wednesday, Thursday.

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)

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.

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])

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])

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]

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.

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