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Nick
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Amber
You're crazy.
Jesse
How's it going?
Amber
Good.
Abby
I'm abby and I'm 36 years old. And I'm curious. How do I date? Like, it's 2025.
Jesse
What do you mean by that?
Abby
Well, I have been recently single again, and I'm used to dating as being more of a serial monogamist. So I usually date one person at a time. I usually fall pretty fast, and I'm usually just right off to the races. But I'm trying to slow down a little bit, not chase the spark as much and date multiple people at once. And that's getting kind of messy. I've actually started to like a couple different men at once, and it feels a little bit icky to me to be dating two people at once.
Jesse
So just hearing your quick synopsis of, like, your. Your dating life, it was, you know, I'm a serial monogamist. I'm used to, like, being in committed relationships. I fall fast, you know?
Abby
Yeah.
Jesse
And now I'm trying something different. And the different you're trying is to date multiple people at once. And. Yeah, again, I'm oversimplifying, but I'm just using your words. The only thing that you've done differently is to be open to meeting multiple people at once in the hopes that that would slow you down. But there was no intentionality around slowing down. So all that's happened is now you've fallen from multiple guys quickly.
Abby
Yeah, I guess that's true. I mean, I have been trying to be intentionally a little bit slower, so definitely trying to slow down the pace with each of them. Keep, like, physical intimacy off the table for longer, pay more attention to how I'm feeling and, you know, evaluate that against, like, my values and what I'm actually looking for now. And so I've been trying to do that at the same time. It just so happens that I somehow have enjoyed the company of two people at once, which I really wasn't expecting.
Jesse
But I mean, you know. Well, how does it feel like? Do you. Is it fun?
Abby
It's very fun. I'm enjoying it a lot. And they're extremely different people, so I think that's why it's so challenging. We connect for very different reasons.
Jesse
What are you enjoying about them?
Abby
Well, one of them, I think he's a little bit older than me. He's divorced, he's got kids. He's more of that stable presence. I tend to kind of go for more adventurous, fun, off the beaten path kind of people. And so he's a little bit different in that way. And I think that's really grounding for me and forcing me to grow up a little bit. And he asks a lot of questions. He's very emotionally available. Yeah, he's just interesting and like, tickles that side of my dating life. And then the other guy is a little bit more classically what I'm interested in. He's a little bit more, I don't want to say it like masculine, but he's a little bit more take charge, take the lead. I feel like we have better banter, we have more fun together. And then he is also just like, asks a lot of questions, makes me feel really good about myself. So they're similar in that way, but just very different logistically.
Jesse
What do you mean by logistically?
Abby
I guess just in lifestyle.
Jesse
Okay. How do they compare to your people you've dated in the past?
Abby
That's a good question. The one who's older and a bit more stable is very, very different. He's a lot more stable, A lot more.
Jesse
Are you stable a lot? Like, do you. Are you attracted to instability?
Abby
Yeah, I think that might be something I'm challenged with. I think I really like independent people, and I'm someone who likes a lot of adventure in my life and likes to take paths that are like, I'm not a follow the traditional path kind of person necessari. So that tends to lead to a lot of guys who are maybe less stable and stable in the traditional sense, just like not following a career ladder, not necessarily intent on marriage and kids, but this guy is more like that. And I think that balance is nice, but maybe a little too far away from what I'm maybe after.
Jesse
What are you looking for in your life at this point?
Abby
I'm looking really for a partner and companionship. I don't have specifics about wanting to. To get married or have kids. I'd like to have a family presence in my life. But that to me, doesn't need to be like the classic nuclear family.
Jesse
Okay.
Abby
So, yeah, I'm really more looking for someone who wants to be a partner and build something together. But what that looks like is not necessarily, like, predetermined for me.
Jesse
And is that how you always been, or is that based off of, like, your. How life has worked out for you as an adult?
Abby
That's how I've always been. I've never been really certain about kids, and I've been an entrepreneur and been kind of not necessarily interested in following standard protocol.
Jesse
Well, I mean, in terms of, like, answering your immediate question, you know, like, I mean, specifically, how to date in 2025 is honestly just requires a lot more, I think, discipline than maybe in the past. Mostly because if you want to, you can have an abundance of options. Like you kind of pointed out, I've kind of been more monogamous. I've decided to open it up a little bit. And wouldn't you know it now you're attracted to. You have two things going on, which is fun and certainly might be good practice for you to kind of compare and contrast, especially if you are dating men who are pretty different, you know, and it's a good way to, like, see the difference. But there needs to be some kind of end game, right? And I guess in 2025, there's just like, if you want to, there's just an abundance of options. And again, with not necessarily good options. By good options, I just mean, like, you know, it's easy to connect with people via social media, via the dating apps. Now, is it easy to meet people? Harder to say, you know, is it easy to really make connections with people? But, like, the connecting part, you know, just, you know, who's. Who's single, who's available. It's a lot easier than it used to be, you know, 25 years ago, you know?
Abby
Yeah, I guess it's also, for me, I'm just wondering for your perspective on, like, how long is too long to be in a multiple dating situation or how do you navigate. Like, do you tell.
Jesse
Are you sleeping with any of them?
Abby
No. So I have. It's only been like six or eight weeks or something, and I haven't slept with either of them.
Jesse
Well, that's good. And, you know, I mean, it's just like I get, you know, once you are physically intimate, then. Then the, like do. How the line. I think that's a pretty big line, you know, because it's kind of like, I think most people would want to know man or woman, you know, in 2025. I don't know if that's the line. You know what I'm saying? I think in 2025, you know, people might have different opinions with hookup culture being so prevalent. But I think if people are being pretty honest, I think it's hard to find people who wouldn't want to know if you were dating.
Nick
Also, you should be able to tell, right?
Jesse
You should be able to tell how much of a connection you are feeling with either of these men. And on some level, you should be able to tell how much a connection you might think they're building with you. Do you get the idea that either of them feel like this is really moving in a good direction for them and they're excited about what they're building with you?
Abby
Yeah, I think both of them. And I tried to be honest and upfront early on and say, like, I'm trying to take things very slowly. I'm not trying to rush into anything just so that I can better understand what I'm looking for. We can really get to know each other before we kind of go down a more traditional path. But that is my ultimate goal, to find a partner.
Jesse
So why do you feel like things haven't worked out for you in that department? Or maybe they have and you just like, this is exactly how you wanted your life to be?
Abby
No, I mean, I think I was with someone for 10 years through all my 20s and early 30s, and I think we just picked each other when we were like 21 and realized in our early 30s, oh, we were wrong. So that was just compatibility of what we wanted out of life was not aligned. But since that the couple of guys that I have had shorter term, couple year long relationships with, I think it's been this challenge of finding somebody who is independent enough to have their own life, but who still wants and craves partnership. So I think I've really fallen for people who are charismatic and independent and have interesting things going on in their life, and then they are not really great at prioritizing partnership once it gets past that honeymoon phase.
Jesse
Yeah, that makes sense. I mean, it's. How old are these guys?
Abby
In their 30s or the current guys?
Jesse
No, I mean, the ones that didn't work out, give or take.
Amber
Yeah.
Abby
It was, like, early to mid-30s.
Nick
Yeah.
Jesse
I mean, that is the. I think you are probably a perfect example of many of us. I mean, I would include myself in this, you know, before I met Natalie. It's just today's dating culture, I think. You know, I guess to go back to your. How you framed your question, I think it's harder to navigate because I think we are allowed and we have the option or at least the perception of, I guess, being really selective and picky and the opportunity to want to have our cake and eat it, too. That inherently makes our lives a little bit more complicated, you know, when we get a little more choosier.
Nick
Also, it's hard to meet a goal.
Jesse
Without a specific plan.
Abby
Yeah.
Jesse
And on some levels, you know, we lose anything in life. We need to be the more intentional we are, the better chances that we have at accomplishing whatever you want to accomplish. You know, like, things happen when we make things happen a lot more quickly than when we let things happen. Now when it comes to dating, you.
Nick
Know, we're always like, don't force it.
Jesse
Let's think. Let it play out. Be open. But the reality is, is that, you know, like, for example, when I met Natalie, right. Like, we've told the story a bunch of different ways, but, like, you know, when it got to the point where she was like, you know, like, either we're gonna do this or we're not, you know, And I. I finally was just, like, kind of really thinking about, like, you know, my choices in the past, and. And, you know, I had. I had had similar flings, you know, by similar, I mean, like, there were. Over the years, I was pretty much single for a long time, you know, but here or there, I had a couple situations where I was dating women for a period of time. I liked them. I enjoyed their company. It was nice. I was like. But there was something that stopped me from really moving forward, probably is that again, I was comparing it to all these relationships had in my 20s, probably on some level, my time on TV, the feeling of falling in love. I had a hard time replicating that, you know, and so I was just all very unsure. And then when it came back to, like, Natalie, I really had to, like, Consciously make. I had to. I had this thought process of I had been single for eight years, you know, Eight years. You know, it's just like, you know, I'm like, I could have had, like, three girlfriends or, you know, four. Girl. I don't know.
Nick
I could have had a few girlfriends that have.
Jesse
Could have come and gone, and I could still be in this place today. And I'm not saying I wish I would have dated any of these women, but my point is, like, I didn't try with any of them either, you know? And so here I was kind of like, am I just going to not try again, you know, with this person who I've been hanging out with a long time, I clearly really care about? I certainly have a lot of reservations, but am I just going to not try? You know? And I had to kind of be intentional, and I had to, like, make a. I had a chain. I had to make a different decision than I had in the past. Because in the. In the past, in my 30s, I just got really good at convincing myself why things wouldn't work. I think as we get older, especially if we're. We have all these relationships in our 20s. In our 20s, we're not sure. We're a little bit more explorative. We try things out, you know, then we fall in love. It's really based off of emotions, reactions. We just really. It's just all feelings. Right. And then we get older, and if we're in our. If we're single in our 30s, then we become a little bit more pragmatic. We're in our heads a little bit more. You know, we're. We are better at reading situations. But then that kind of flips where we're constantly in our heads. We overthink a lot of things, you know?
Kristen
Yeah.
Abby
This is resonating.
Jesse
Yeah. And so. Yeah.
Nick
And I listen there.
Jesse
I don't want to. I know. Like, I think it was maybe last week's episode, and I talked about. I don't know, someone called about their job, and I was like, you know, your profession doesn't make you happy. And I. I knew it would, but, like. And obviously, I. I know my audience from my perspective. I'm not trying to tell people, like, to get married or have a family or, like, do the whole. I mean, obviously, that's been great for me. My whole point is, it's like, listen, no one's meant to be alone. I don't care what your family looks like. Right. Like, just be.
Nick
Have it.
Jesse
Be friends. People you can invest In. Right. I just think sometimes that, like. And I. I've been you, right? When I met Natalie, I was like, I still want to have kids. I'm not getting married.
Abby
Right?
Jesse
You know, and I. And I think it was this, you know, I be. I was so, like, independent and single for so long, I was able to be like, I don't need the traditional shit. And I'm not saying people need it, but I guess my point is when I talk about intentionality and people talk about wanting to have a partner and wanting to have a family, I think in 2025, society has allowed us to, like, break down some of those traditional norms, right? We don't need them and that. I think there's truth. We don't need them. I think there's a lot of ways to do things. And then you can get into the whole, like, argument about how, like, silly marriage laws are and. And how outdated, antiquated they can be, and yada, yada, yada. But I guess what I'm saying is, like, there's no, like, clear alternative.
Nick
Like, what's the alternate?
Jesse
You know?
Nick
And so when people go into the.
Jesse
Dating life and kind of be like, well, I'm looking for a life partner, but, like, whatever that it looks like, I'm fine with, I think people just.
Nick
You know what I'm saying?
Jesse
Like, it's hard to be intentional, you know?
Abby
And I think I do see the value in marriage. I'm not anti traditional milestones, and I'm.
Jesse
Not selling you on marriage. That's a lot of flaws.
Abby
I mean, I think ultimately, I think I would want to get married in the end if I find the right person. I think I'm just not, obviously. I'm 36, I'm single. I'm not interested in getting married just to check that box. I want to make sure the person is right.
Nick
And people can get married and divorce.
Jesse
And be miserable and all those things.
Nick
It's just.
Jesse
I just think it's. You gotta be intentional. You gotta put yourself out there. You know, Back to, like, the example I gave with Natalie. I had to be like, I have to like, listen, this could blow up in my face, and I had to take a risk, right? And so I just think as we get older, we become more like, when we're 20s, it's like, YOLO, whatever. And then you get your heart broken a couple times, and you're like, I don't want to deal with this shit again. I'll just date kind of more casual, you know, And I'm going to Be slower. And, you know, it's just we. I just think sometimes we don't appreciate the guard we put up.
Abby
Yeah, no, I think that's fair. I think I am trying to find the balance of moving slow enough that I don't overlook red flags while still choosing someone that I have the right chemistry with. And yeah, I think dating these two guys at the same time has been really challenging for me because I would prefer to just pick one and invest in that one relationship and see where it goes.
Jesse
How old are these men?
Abby
Late 30s, early 40s.
Jesse
What questions are you asking them about their past relationships?
Abby
Oh, that's a good question about their past relationships. I think I delved into it more with the slightly older divorced guy because I wanted to understand the divorce and the reasons, what he'd learned from that relationship, what he's looking for differently this time, what he thinks he needs out of a partner in the future, and what he wants since he already has done marriage and kids. The other guy I've been a little bit more loose with because he presents as more of a free spirit, energy. So to me, I haven't probed as deeply to him on what he's looking for or what he's learned from his past relationships as much as.
Jesse
Okay, what's his relationship with his ex wife?
Abby
Civil. Now they share kids, so they have to.
Jesse
How many kids?
Abby
Two.
Jesse
Have you learned anything from that?
Abby
Yes, I've learned a lot. I think he seems to have done a lot of post divorce soul searching to understand why the relationship devolved. And he's learned a lot from his kids. He's actually sat around being more emotionally present for them because he wasn't necessarily that way for his wife. So, yeah, I think he's. For me, he has said all of the right things and done all of the right things, and I'm just maybe doing what you said around, like putting up my own guard around. Okay, well, he's already had the marriage. He has kids. He's probably less interested in having more kids if that was something I wanted. He's a lot more buttoned down than I am. So is that the kind of.
Jesse
You haven't asked about his interest in kids?
Abby
We've talked about it a little bit. He said he's open, but he didn't expect that he would want to have more kids.
Jesse
I think it's typical. Right. I mean, I think in those cases it really comes down to when you meet someone that you fall in love with, that conversation kind of takes care of itself usually. Right. You Know, it's interesting, like if we wanted to like, nitpick and pick holes, right. Like, on the one side, the married guy who seems to be more open and connected emotionally is showing some green flags, checking those boxes, as you say, saying the right things. But he also, it seems like, has acknowledged this is because he's done the wrong things.
Abby
Yeah.
Jesse
And the question is, has he really changed or has he learned at least what he's done wrong and talk about what he should do wrong, but in practice, will he do that? You know?
Abby
Yeah, that, that resonates because I think like, part of my concern or hold back with him has been like, how authentic, like how genuine is this versus just. Are you saying all the. The right things?
Jesse
He might not know. I mean, you're right. Like a lot of us are just like. Yeah, I don't know even like with. When it comes to like how we speak to each other, like, especially in relationships, you know. You ever been like, someone's like, hey, don't talk to me that way. And you're like, what? I'm just talking. And you're in person's like, no, you're kind of raising your voice at me and you're like, no, I'm not, I'm.
Nick
Just, I'm just talking.
Jesse
I mean, like, I'm a little. I mean, I'm a. You know, but then when someone's doing it to you, you know, it's like we don't see it when we're doing it. You know, we see it when other people are doing it. So it could be something like that. Then the other guy, right, he's the, he's in his late 30s. Up into this point, his resume hasn't demonstrated like any kind of ability to commit or sustain anything long term. So what's going to be different about this relationship? Is a fair question you'd want to ask.
Abby
Yeah, no, no, I think I need to delve more into that with him because I think at the beginning I had kind of written him off as like, he's this free spirit, creative, like, never been married, never been in a. Well, he's been A like 7 year relationship, but never been in 7 year relationship. A super.
Jesse
That's a long time.
Abby
So he's been in a long term relationship, but never done the more committed thing. So I kind of wrote it off as this is gonna be a little bit of a fun for now thing. But he started to show up more seriously and I've noticed in the way that he approaches me that it seems to Be very intentional. It seems to be very intent on actually getting to know me and build a potential relationship. So now I'm starting to question, okay, did I maybe write him off too quickly as this free spirited, not gonna be a partner person?
Jesse
If you had to, like, if you don't have to, but if someone's like, you gotta pick today, time's up, like, who would you pick?
Abby
Oh, God, I don't know. I think I'm more drawn to the free spirited guy and I'm maybe stopping myself because I assume, like I'm worried that I'm maybe doing the same thing again and pursuing the person who's less stable.
Jesse
Well, like, so tell me more about your dating. Like, again, I don't, I don't want to imply that you're not in a happy place right now, but I just like, what, why do you feel like when it comes to at least your relationships, you're still looking?
Abby
Yeah, I think when I started dating again in my early 30s, I hadn't dated since I was like 20. And so I was not being intentional about it. I was still probably dating, like you said, dating as if I was in my 20s and being like, oh, where's the spark? Where's the chemistry? And I followed that a couple of times. So I had two, I've had two relationships since my decade long one ended. And yeah, both of those, I just was like, oh, the chemistry is immediately there. I immediately am very, very interested in them. And I think I probably overlooked some flags early on by just like jumping straight into it.
Jesse
What would like, if you had to nitpick, like, what would your exes say about you? Oh, you know, where it's like, yeah, you're great, but like, you do this thing and honestly you should work on it.
Amber
Probably a few things.
Abby
Like, I think they would say that I. That's a good question. I think they would say that I'm probably, I go from being very independent to being a little bit too needy. I'm like, I'm a anxiously attached person. So I think I'm drawn to like the independence at the beginning. And I like, like having our own careers. I like having our own space. But then it hits a certain point and I start to be like, well, why aren't we doing the partnership thing more? Why am I not becoming a priority? And I think that can probably be challenging for them.
Jesse
That's an interesting answer.
Amber
Yeah.
Jesse
Again, I'm not a therapist and I'm only guessing here, but I do think the reason why I'm somewhat Good at doing this. Right. Because I don't think we as humans, you know, you mentioned attachment styles, right. Everyone loves talking about attachment disorders. And it's not like there's 30 of them or 100 of them. There's like, there's like six we all fall into. Right. And I, and I just think as humans we have various patterns and, you know, we do. You know, we're kind of predictable. I don't think it's a coincidence that, like, you are drawn to this. Kind of very free spirited, independent, you know, in your story, there's an element of chase and validation and feeling special. Right. There's an element of like, the wild guy, I can tame him. And then once he's tamed, then you have the expectations. You tell yourself you don't necessarily want or need, but once you're in the relationship, you default, you know, into the relationship mentality. So you know what happens, right? Like, maybe you're. You're not setting up for expectations as the relationship. The people you are dating get a little caught off guard. They see it as needy, you know?
Abby
Right.
Jesse
They see it as, oh, she changed.
Abby
Right.
Jesse
You know?
Abby
Yeah.
Jesse
You might feel it as like always pulling back, you know, because you're thinking, I didn't change, I progressed. You know, like we met, you know, and now I just like you more. And now I have more expectations of you. Right. In that scenario, no one's really doing anything wrong. But I think it is interesting.
Abby
Yeah. I don't think that my ex has necessarily did anything wrong either. I think it's just like we've figured out a mismatch in style. So the reverse is happening now with the stable, emotionally present guy where he's very much pursuing me and very much showing me the relationship potential. And it's making me like. I don't know if I just don't trust it or.
Jesse
Yeah, I don't know. I don't think it's trust. I mean, I don't maybe. I mean, again, because he. Based off your history, it seems more likely that it's a you problem than a him problem.
Abby
Yes. Yeah, probably.
Jesse
I get the sense in a lot of ways, and I'm oversimplifying, but your dating path has a lot of similarities to how mine was. And if you have any similarities, then you would be someone who kind of got good at convincing themselves of what you don't want or need. And there's some truth in what you're saying because, you know, you seem, like, generally happy. I don't know much about You. Your house looks nice, you know, like, it sounds like you're doing fine in life. Right. You're like. So despite, you know, not finding your person in your life partner, you've carved out a nice little life for yourself. And you've been also, I'm guessing, been able to, like, be happy as a single woman. Right. You are. You. You probably can be a good third.
Nick
Wheel or fifth wheel.
Jesse
You can, you know, like, you're. You're totally fine. You're totally fine. Right. And so I think that's allowed you to. Yeah. Tell yourself of things you do and don't need. And I'm just wondering if, at the end of the day, you just got more good at convincing yourself than the opposite. I don't know if that really answers your question either. These guys, I would.
Amber
Yeah.
Abby
Which one do I pick?
Jesse
I don't know.
Nick
I mean, listen, I don't think you.
Jesse
Have to pick anyone now. You're not sleeping with them, so, like, you might have some time. But I would.
Nick
I think with the free spirit guy.
Jesse
You need to maybe. Maybe test out. You coming across is a little more interested in traditional things, whether it's true or not. Right. Just. I, you know, I think there is some truth into it, but I think again, in 2025, I think all of us, men and women on different sides, are trying to, like, water down. It's like, well, I don't need that. You know, I'm not traditional. I'm progressive, you know, and you can be progressive, but, like, you can. You still want traditional things if you want traditional things.
Nick
And I think if there's any part.
Jesse
Of you that wants some stability and commitment, I would lay it out on and see how he responds. I would explore more questions about his past and see if he's remotely interested in having that conversation.
Nick
And he's got to give you more.
Jesse
Than, like, well, sure, if I, you know, if at all. If I meet the right person, then anything's possible. Like, that's not an answer.
Abby
Yeah.
Jesse
You want to see if this guy really wants to invest in someone and wants to settle down at all.
Abby
So would you just probe him around, what does he actually want out of life and partnership and everything? Or would you just, like, put forward what I want and see how he reacts to it? Or both.
Jesse
Maybe both. I mean, you know, I don't think you're totally 100% sure what you want. Or maybe you are and you're willing to kind of be honest with yourself. I don't know.
Abby
No. Yeah, I'm not sure what I want, but I do know that I want, like, commitment. Whether that's like, I'm not looking to go, yeah, I do know that I want commitment. Long term.
Jesse
Yeah. If I were you, I, I would give it some thought about what you want and what commitment looks like. And I would be. I, I think you, you would do well by being able to answer that question for yourself. That's gonna require a level of vulnerability and a level of like, no.
Nick
Okay.
Jesse
Cause it's scary to say I want this. Because once you want it, then there's like, what if I don't get it? If I want it, then if I don't get it, I'm not going to be happy. It's easier mentally psychology to be like, I don't need anything. I'm flexible, I'm adaptable, I'm good. And to say, you know what? Deep down, this is the thing I want immediately, it's a vulnerable moment. And I think in the long run you might want to put some thought and what a long term commitment looks like for you. And deep down, whether you need it or not, what do you want? Like, this isn't about what you need. I want you to learn about telling yourself what you want. And how do you, how do you go about chasing that and going and get it?
Abby
Yeah, fair. I think it's just changed so much over the years that I struggle to believe. Yeah. Yeah. I struggle to articulate obviously what it is that I want because it has changed so much.
Jesse
I don't know if it's changed that much. I think you've changed, you know, you've become way more multidimensional. And again, I don't know you, but again, I changed a lot from like being a 22 year old. Right.
Abby
Yeah.
Jesse
But once I found Natalie, that the things I wanted for myself when I was 22, big picture wise were the same. And ultimately they were the things that when I thought would make me really happy did make me unhappy. Now how I, how much I've changed, I feel like I'm a better father and a better husband and a better person just because I've matured and I feel like I've become more empathetic and yada, yada, yada. But like. Yeah, I mean, I hope this was helpful. I don't know if it is, but.
Abby
Yeah, no, it is, it is.
Jesse
You're the common variable. Right. So. And I think that's important for all of us to remember. Right. And I, I'm sure you're a catch. You Obviously don't have a problem like meeting men, but. Yeah, just try to be more intentional about what you want and have the guts to tell the people you're dating what you want and know that they might not accept that or want that. But you're gonna save yourself a lot of time by being specific and expecting specificity from the people you're dating, especially the people who come across as a little bit more free spirited. And with the married guy. Yeah. I think you also can ask more probing questions and just be like, how long has he been divorced for 5ish years. 5 years. All right.
Abby
Yeah.
Jesse
Has he had any serious relationships between his divorce and you?
Abby
Yes, he had one. That was a couple years.
Jesse
What happened there?
Abby
Yeah, I haven't gotten enough detail on that. They were long distance.
Jesse
Okay, Well, I don't know. If you listen to a recent episode. Don't, don't let him blame long distance.
Abby
Yeah, no, I, Yeah, I definitely.
Jesse
But that would be interesting, right? Because like, well, I thought he healed. And again, I'm not saying like, people break up all the time. Just because they break up doesn't mean he's like a bad guy. But I just want to know, he invested into this person for two years. That's a long time. So he at one point was very serious about this person. And this was a person that he was like, this was the person that, you know, he got divorced. Sounds like he did some work on himself. Right. And then picked this woman and was like, this is the person that, like, after all the work I've done and I got divorced, I'm going to pick her. And then he didn't pick her anymore. And I just be curious as to why, you know, maybe she was a nightmare. And I'm sure distance had something to do with it, but like you, you might discover something in those questions.
Abby
Yeah, that is a very good piece of advice.
Jesse
All right, well, anything else I can help you out with?
Abby
No, I think I have some figuring out to do, but thank you.
Jesse
Keep me posted. Love to know where you get.
Abby
Yeah, for sure.
Jesse
Will do.
Abby
Thank you.
Jesse
But yeah, I, I think the biggest takeaway is I think you need to be a little bit more intentional and don't let dating in 2025 give you excuses to be non. Non committal year. And I think slowing down isn't dating multiple men. It's just asking more questions and thinking about their answers and being able to learn, you know, it's not just quality time and hanging out and doing things and having banter. You know, it's it's learning about each other.
Abby
Yep. Very good points.
Jesse
All right. All right.
Abby
Thank you.
Nick
Take care.
Abby
Bye.
Jesse
Bye. Bye.
Nick
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Jesse
How's it going?
Abby
Good.
Amber
How are you?
Jesse
Good. What's your Name?
Amber
Amber. I'm 35. How can I help Did I just up my perfect life?
Jesse
Oh, my God. Well, what did you do?
Amber
Well, I fell in love with somebody outside of my marriage, which.
Jesse
Are you still married?
Amber
I'm still married. Separated, but getting divorced and have three children with this person. Been married for nine years and living in what seemed to be like the perfect life. We lived in the perfect neighborhood, had the biggest house. I have a fantastic job, our kids are great. And met somebody who, the moment that I met them felt as if I had like been with them my whole life before. And it sort of reminded me or kind of made me realize what was broken sort of inside of my marriage. And I had been for a long time trying to get my marriage to be different and trying to get my husband to, you know, be more motivated or do things that were better for our marriage. And nothing would happen for years. And after we had our third kid, it was really, it went downhill. And so I think I just kind of became emotionally ambivalent in terms of indifferent to what he was doing and didn't air anymore. And so when I met this person who was our contractor, we had just bought a new house and we were remodeling it. We bought it in January. So I met him once in January and it was an immediate, like, there's something here. I don't know what that is, but it was a 30 minute conversation. And then I didn't see him again until June. And then in June, the same thing happened all over again and it was a mutual thing.
Jesse
And so how did you find out it was mutual?
Amber
It progressed. You know, when he was in our house and he was doing, doing all the construction, like, we just couldn't not be around each other. It was like you could feel the chemistry in the air.
Jesse
Well, how does your husband feel about all this?
Amber
Well, I mean, he's devastated.
Jesse
He is. Okay. I don't know, like, I mean, he may be, but, but, but what's his point of view? You know, this is such a, obviously a fascinating. I don't mean fascinating like I'm like enjoying your challenges. But, you know, listen, you've, I'm assuming you listen to the show. I don't think anyone is surprised to hear me. Like, obviously I'm in my, like only been married for less than two years. We have a young daughter living the dream. Right. And obviously I am projecting that. Obviously I'm assuming a lot onto my audience and talking about all the things I'm enjoying for the people especially literally. The last caller, right. Was someone who's, she's in her mid-30s. She's has everything she's got going for her, but she's kind of like, I don't need a guy, and blah, blah, blah. I'm just kind of like, listen, I'm not saying I don't know what you need, but just be open to, like. Like, fallen for, like, you know, finding love, whatever.
Amber
Yeah.
Jesse
It takes two to make a marriage successful. Right? Like you. You have to wake up every day and choose each other. Right. What happens when someone stops choosing themselves or stoops choosing you? You know, I've talked to enough of people on this show to really feel for, you know, it's mostly women I'm talking to, to the people who really feel stuck, you know, who really feel like, what the fuck am I supposed to do here? You know, it's like I'm. I want.
Amber
Yeah.
Jesse
I am curious about a couple things on your end. It's like, all right, so, one, what made you call in and. And with the question, am I blowing up my life? What makes you worry that you're blowing up your life? Two, for the part of your husband that's devastated. Like, what's the part of him that recognizes how it got to this point?
Amber
So, first, after we had our third kid, he did not want three kids. I wanted more kids. So we sort of compromised at 3, and he completely checked out. So that was three years ago. Our kids are 7, 5, and 3.
Jesse
He checked out on being a dad.
Amber
Yeah. And, I mean, I can go into. After our first kid, he left for a month to go on a surf trip two weeks after he was born.
Jesse
So I can't. I can't.
Amber
Yeah. So did it again with our third or our second was during COVID so I guess it wasn't an option to go anywhere. But.
Jesse
So wait, he just. Oh, my God. That's the crazy thing I've heard.
Amber
Yeah. And it just became my responsibility. Right. And in terms of handling not just only the kids, but our entire life. And so I sort of, like, say my job, you know, I run a technology company in AI and we do really, really cool things. I talked to some really, really cool people.
Jesse
And so you're the. You're the. You're the boss both in life and in your marriage.
Amber
Yes, 100. 100%. And I think.
Jesse
And he's just, like, a surfer dude.
Amber
Yes. And a golfer. Yeah.
Jesse
What's he do? Nothing interesting. So is he more devastated? Well, I'm assuming if he gets divorced, he will probably benefit financially from this.
Amber
I come from families of lawyers and so it's pretty airtight. But I think that he.
Jesse
Oh, so he. Is he. So what do you think he's more.
Amber
Sad about your exact thoughts? That's sort of where. That's what happened. And sort of where we led. Got to. Where we are is like, there's a lifestyle that I was able to provide that he was able to live, and he got very comfortable in it. And I think that. I do think that he loves me. I. I know that, but I think that he's. Yeah. I mean, we bought the biggest house in the neighborhood, and he was excited to have that, and I sort of blew all that up. And I think that now everyone around us. Right. Is losing it.
Jesse
And I sort of like, who's everyone around us? And what do you mean by losing it?
Amber
I mean, everybody, family, friends, community.
Jesse
How are your kids, first of all? I guess let's start there.
Amber
Perfect. Fantastic. They are the best ever. They probably. My oldest is the most aware. I guess he's 7, and so he's sort of the most aware, but they're great.
Jesse
All right. Well, that's all it really matters as far as. Okay. So friends and family. I mean, I'm sorry. I just. I. I can't get past the fact that you. He. You had a. Two of your children.
Amber
Yeah.
Jesse
He went on a surfing trip. He left you? He left you. He left you? Oh, yeah.
Amber
I mean, I would talk to him in the middle. He was in Australia, so I would talk to him while I was breastfeeding.
Kristen
In the middle of the night.
Amber
That was when I would talk to him.
Jesse
What's his story? That, like, there was a specific wave coming and he just, like, once in.
Amber
A lifetime, he got to surf the coast of Australia and he. You know, I don't know.
Jesse
It's crazy. It's crazy.
Kristen
And.
Amber
Yeah.
Jesse
And I mean, how was he as a dad when he got back?
Amber
He's a great dad. He's a. He's a really good dad. So, like, he's very involved. He's like a camp counselor. He's a great dad. Like, he does all the fun things, but he doesn't do. Doesn't know when they have doctor's appointments. He doesn't know. He doesn't even know that they need doctor's appointments when they turn a certain age. So, like, I handle all of that emotionally.
Jesse
Like, when did you feel like. I don't know. Did it. I must have felt like some huge betrayal when he left you, or were you kind of like. Or. I don't know, maybe you knew who this guy was when you married him?
Amber
No, I'd say by the third, I was kind of like, go, it's a little easy. It's more easier when. When you're not there. And, you know, he, I think, fell into a depression that I think it takes a lot to be with somebody like me, who I am very strong and like, I do run things, not only just like work wise, but household wise. And like, I think it takes a particular type of person to be able to handle that. And I think he started to feel, particularly after our third, that he just fell into a depression. And so I would try to get. Pull him out of it and be like, let's go see somebody. Let's get you out of this. And he's had a very hard life. He lost his brother and his dad and lots of trauma that he just has never dealt with and refused to deal with it. And so I think it all just kind of comes together. And I think I got to a point where it was just like, I don't know what I'm supposed to do anymore.
Jesse
Yeah, it sucks. I don't know. I mean, I can see why a guy like. I mean, like, we've, you know, we've had plenty of people call in women, specifically successful women, and it's like, you know, it's a stereotype of the trope for a reason. Because, like, I think, well, people find successful people intimidating, Right. I think there's an extra layer of it when it's a very successful woman and a guy who hasn't found his foot wedding yet. Right. And so here you are. Your husband is like one.
Nick
I think it helps that he's a.
Jesse
Free spirit for him. And maybe he just, like, he's less career motivated maybe than other people or yourself, but whatever part of him that is in, like, biology or just, you know, as a guy that needs to feel that purpose, he doesn't have it. Right. And he hasn't dealt with this. And so it's like the most exciting thing he has in his life is leaving his wife who just had a baby, to go surf, you know, and like, he's trying to find some spiritual fucking moment or whatever. What's a real bummer for him, what makes me sad for him, is that even if he didn't find his thing, right, whatever that thing is, that thing that, like, from a career standpoint, that made him, like, really proud of himself and really gave him some purpose, that he didn't embrace fatherhood to the point of that's enough. Like, hey, I didn't know what life was gonna bring me, but when I take a step back, I got a beautiful wife, she's a kind of a fucking boss. We're rich. I mean, it's kind of her money, but whatever. I got a big house. I got three beautiful kids. I get to go surfing now and then, but I'm just gonna be the fucking. And again, I know you said he's a good dad, but, like, I don't know, he sounds like he's a fine dad. He doesn't sound like he's a bad dad, but, like, is he a great dad? I don't know. Like, he left and he doesn't seem to be all that present, you know? And I think. And maybe, fine, maybe your personality is a little overbearing. I don't know, maybe. Whatever. But, like, I just. I feel like part of your personality might be overbearing because, like, you know, it's like.
Nick
It's like it's kind of a balance, right? When you're a strong personality.
Jesse
Yeah. I think sometimes strong personalities can be attracted to people who are a little.
Nick
Not strong.
Jesse
Whatever.
Nick
It works out.
Jesse
And then you have a tendency of, like, always taking control of situations, and then he has a tendency of just letting you take control. But I don't know, I think that's probably a little bit of excuse on his part to a certain extent. And it just makes me sad that he could have chosen fatherhood and embraced that and got an incredible amount of purpose from that and just said, you know, all I need to do right now is this focus on my wife and my family, and I'm going to get an incredible amount of purpose from this and, like, happiness and let's build. And he didn't want to do that. And that makes me sad.
Amber
I mean, I'm sure I am overbearing. I have to be in a lot of ways to make things run normally. But I guess in terms of my question, there's so much noise, right? So we had a very tight group of friends. They're all up in arms. My family's up in arms, I think. So when I met this person, it's a feeling that I didn't have when I met my husband, which, well, is also alarming. And, you know, I don't. I don't know if that. And I met my husband when I was very young, when I was 21, and it was a quick little meeting. And then again, we. When we met again, it was the same thing, and it was really like this feeling Like, I know this person in and out. Like, this person is, like, for some reason connected to me in some way.
Jesse
What, what is your relationship with this person at this point? Like, how evolved has this relationship gotten?
Amber
It's evolved. I mean, we, like, can't help it.
Jesse
It's hooking up.
Amber
I would say, like, I'm separated. So, like, I'm not married. I've been separated.
Jesse
Yeah. I'm not trying this, but, like, are you dating?
Amber
When this all came out? We're like, together.
Jesse
Yeah, together. Listen, I, I don't want to discount what seemed like euphoric feelings. I just, I think feelings and chemistry and that's kind of what you're describing are just, you know, but unpredictable, temporary, hard to trust. Again, I'm not a psychologist, I'm not a therapist. That being said, you were in this marriage for a long time, clearly feeling unfulfilled and not getting your needs met for a long period of time at very pivotal times in your life. Right. So it's not shocking that you met a guy who is a business owner as a contractor, he's a doer. That alone, when you're like, oh, I knew him forever, like, I don't know, you recognize a lot of yourself in him at a time where you were just so tired of feeling more and more disconnected from your husband. So I just, like, it's just, Just be careful. How serendipitous.
Abby
Yeah.
Nick
Listen, if you want to be with.
Jesse
This guy, be with this guy. And whatever drama that your friend group, the fallout, deal with it, whatever. Just don't, don't dilute yourself into like you're making choices because fate has taken over your life. You know, like, make choices, own your choices. You know, you're, listen, you're making a very difficult choice. And I, I, I, I really empathize with you because, like, and again, like, when, when you tell me this, when you first called, the story, my, my, you know, new married, new dad energy is like, you gotta make that marriage work. You know, you gotta do what you can.
Nick
Right.
Jesse
But, like, I don't know what it's like to be married for nine years. And again, I'm just blown away that your husband went on a surfing trip after you had K. I can't compute that. Like, it, that is, I, I just think that says so much about, you know, him being a partner and him being a father. And I'm sorry, like, I just, I can't wrap my brain around that. And as far as the friend group drama, like, that should be the least of your concerns. You know, it'll work itself out. You're gonna lose some friends out of this. Probably. Try to be open to listening to your friends. What? I mean, my question is, like, it took me five minutes to go from, you gotta make this work to being like, oh, man, leave his ass. Who of your friends, like, understand your plight.
Amber
The girlfriends, too. Like, it's the husband group that he's. And he has gone around talking very poorly about me in our community to the point where I was like, live in the house. I don't care. I will continue to pay for it. I'm gonna go find somewhere safe for our kids to, like. Like, have a safe space. He's rallied, like, the dad. Like, the. The husbands. Like, you would think that I did whatever I did to all of them as well. And it's just very.
Jesse
You're just like, what?
Amber
A stupid.
Jesse
A dirty. Or something in their mind, basically.
Amber
Like, it's so stupid. And they don't talk to me. And these are people that were, like, very close to me, and they won't speak. I mean, it's almost laughable. Like, that part of it is, like, so stupid. But. But there are days, of course, where I'm just like, ugh. Like, do I just go back and, like, it all falls back together and it's like, I just deal with it and figure it out, and then I think about it and I'm like, I don't think that I could ever just go back and do that. But, you know, I mean, I don't know.
Jesse
Do you. What does it. What part of you still loves your husband?
Amber
I mean, I love my husband. I will love him forever, but am I in love with my husband? Like, mad.
Jesse
But is there a world where he could have swept. Like, I don't. What could he be? What could he have done differently?
Amber
I don't know. I mean, I said. Always said to him, too, like, the moment I become indifferent about you and, like, what you're doing, I'm done. Like, I'm out. Like, I don't know that I come back from that. And I gave him so many options and opportunities to pull himself out that I just. I don't know that there's a world where he wants to.
Jesse
Has he been trying?
Amber
No, he wants to. Look, he's like, I am gonna make you fall back in love with me. And I don't really know, like, how much weight do I give? Like, you know, I was alone in my marriage for so long for. And, like, do I just say, like, we're just supposed to be parents. And, like, maybe that's like, our relationship and I can love you. It doesn't mean you're my person. You know what I mean? It doesn't mean, like, I have to be with you. But some days that feels like it would just be easier. It would just shut everyone up. And on other days, it would be sacrificing myself.
Jesse
That's tough. What do you believe? What do you believe? Like, I guess. What do you believe in. In terms of what he's saying? Because you're right. Like, you know, so it's like, you know, my wife and I were talking about this yesterday on the show for a completely different. Different reasons. But. But, yeah, like, she was referencing, like, you know, I think once you're. It's like, once you're. You're. You reach a breaking point. It's like forgetting about, like, oh, once I'm indifferent, like, yeah, it's almost. You draw a line. But I think it's more comes down to you've tried, and he's only reacting to you leaving now.
Amber
Yeah. And that's my biggest problem is. And he'll always say, there's not one person that wouldn't think that we were in love a year ago. And I was like, well, yeah, I made it seem that way. Like, I held it all together. Like, I made this picture perfect.
Jesse
But does he think that. I guess my quite. You know. You know, it's just like, again, the thing that makes me most secure about my relationship today is that I feel like both of us when we're like, hey, I'm a little disappointed, frustrated, upset, irritated, whatever it is, the other person's like, oh, well, you know, and we might get defensive.
Nick
There might be some bickering, but at.
Jesse
The end of the day, we care about how we're making the other person feel. Feel. So if we're disappointing our partner, we both feel like the other person's like, oh, shoot, I don't want to disappoint you. Let me try not to do that. Or I should do more of that. Or, like, I want to like, oh, I'm leaving. I'm gonna send my wife flower. You know, like, clearly, he wasn't doing that. He stopped giving a shit about. He stopped responding to your frustrations. Right.
Abby
He.
Jesse
I'm assuming you felt an indifference from him about your needs not being met.
Nick
And to your point, when you feel.
Jesse
Like that person doesn't care that you're sad, mad, irritated, it's hard to keep going.
Amber
Yeah. I mean, we were like that in the beginning. And then we had a lot of kids in a short period of time, and it just became to no fault of really his. It was both of us. Like, I'm not going to say that I was like a perfect person in this marriage at all, but became transactional. You know, it was logistics. It was, you know, we have these three kids. I already was, like, kind of checked out with how he was feeling, and I know he was checked out with how I was feeling. So it was just sort of like. And he would be. And he was very angry all the time, and our kids would notice, and so I would, like, try to.
Jesse
Angry about what?
Amber
He would wake up angry, and that would be the whole. I'd be like, what did the kids do? Like, they. You just woke up. I don't know. He came downstairs pissed off. I have no idea. And that was just our life. And I just hit a breaking point where I was like, you know, I'm not gonna live like this for 40 years. Like, I just am not going to. And there were so many times that I was like, try. You need to fix this. And so many times that we would even, like, we started a business where he had plenty of money to go do this, and just like, nothing ever happened, he didn't go do it. And I was always like, I don't care if you bring money and, like, go open a crystal shop. I. I don't care about something. Yeah, just go. Have a purpose. Like, go leave. And that's not just hanging with your friends and.
Kristen
Or whatever.
Amber
Do I believe him? I do. I mean, I think his world is, like, flipped upside down. I think he had this very, like, idea of what the net. What his life was going to be like. And I think I ripped that away. But I don't believe that if I were to go back tomorrow, it would be different. I think it would probably fall back into the same pattern, mainly because of me. Not even necessarily because of him. Just, like, I don't know how I get over some of those things.
Jesse
Well, I mean, you do. You just get over it, right? Like, yeah, this, you know, construction guy aside, despite the hurt, the frustration. Yeah. I'm sure he caused some pain and some scars by, like, dismissing you ultimately. Right. You know, and you're right. It's a big lift. It's a big ask. And it's unlikely because people don't just change for. They only need to change for themselves. And right now he's changing for his marriage in you. And, like, that wasn't enough. In the marriage and it's only right, but let's just crystal ball it and fantasize about a world where, you know, he went and got some therapy. He was like, you know what? I need to be a better dad and I'm gonna start there and I'm gonna need to be a better husband, and I'm gonna start there and I'm gonna find purpose in that. And like, you know, as far as the other stuff, I'm just gonna appreciate the fact that I'm married to a boss ass woman and my needs are met. I'm gonna be a dad. I'm gonna take them to practice, I'm gonna give a shit. I'm gonna be involved. I'm gonna alleviate some of my wife's stresses because she is making the money. And I'm gonna, like, we're gonna be a team and I'm gonna, I'm gonna focus on being a good teammate. And then, you know, he romances you and things like that. Like, if that were to happen. Yeah, you let go of the past. You know, a marriage is like you said, 40 years like this. You. I don't want to tell you what to do. You're going to figure it out for yourself. And again, I've heard enough of stories for people who feel stuck and I feel for them. And you have the benefit of being an independent person who, like, you know, you're going to be okay. Like, you know how to take care of yourself. And a lot of people don't have that freedom and that confidence. And so you, you're going to be okay. It's just that, like, listen. Yeah, yeah, this is your family. It's a family. You made a lifetime with someone is really hard. And you're gonna have to be able to forgive this construction guy if, let's say you guys, you get divorced, you start a life with him, he's gonna hurt you. I don't know how something's gonna happen five years from now. I don't know what his flaw is. I don't know what his things are, but he's got things. And the big question is, at some point, every marriage, I feel like that I've heard the ones that, you know, it's just like the old people who are like, you know, there's always a period where they talk about a dark point in their marriage, you know, where it really, there was a lot hurt. So there's that. And if you want a marriage that lasts a lifetime or most your life, you will have to figure out how to get through it with someone. And I think that's something to consider. But you know, your husband the best. You know, your situation is much different than, you know, especially in my relationships in my 20s. But there is a part of me, you know, I have a. I always think our strengths and our flaws are often the same. I feel confident whether it's my relation. I see things through. I don't like being a quitter. And not being a quitter has caused me on a negative side of staying in things a little too long, holding on to people a little too long, whether it's relationships, whether it's friends, could be employees. But I don't have any regrets because I definitely saw it through. I definitely tried. I felt like, you know what? I did my part, I tried. And I. I don't. I didn't leave a situation being like.
Nick
Should I have tried a little bit harder?
Jesse
What if I would have done X, Y, or Z, I saw it through. And if you can feel that way, then put it this way. With three kids in a. In a marriage of nine years, I. If I'm in your shoes, and this is just me, and this is my opinion, and I could be wrong, like, I would have rather. Too many times, too many times. So that, like, when it's done, it's like, no, I have no regrets. I. Fuck it. You're like, no. Like, almost to the point where, like, like, are you kidding me? I tried. Rather than wondering, you know, if I. You know, if I didn't there. And then you just have to ask yourself, how much is this new guy clouding your judgment? Right? And when I mean by that is like, I would like to see you make this decision without being attracted to anyone else. Right? I'd like to see you make this decision solely based off of your husband's lack of meeting your needs and expectations as a husband and a father and not being able to compare it to someone who is showing is. You know, my very first girlfriend, I was pretty religious back then, you know, and so. And she wasn't. And we fought a lot about church. Seems silly at this stage in my life, but we did. And, like, I just wanted someone who was just like, willing to go with me, right? And like, she.
Amber
What?
Jesse
We fought, right? And then we broke up. And then again, I met an. Oh, I met another girl. It was a very much over. You know, it's like. And I was just like, obsessed with her because she was. She was willing to go to church. And like that. It's just like, at that time, it Was such a, like a frustrating point in our relationship that for her to be willing to go was this like, just. I mean, it was the best thing ever. It was the best thing ever. And yeah, he is, he is no doubt giving you some of the this is the best thing ever feelings because he is doing things that you begged your husband to do and he wouldn't. And, and, and, and, and this guy, I'm guessing you don't have to ask. It's just like second, it's just who he. It's like he's, he wants to, it's easy for, you know, like, and, and so you're, it's just like, it is the contrast to like your husband is so fucking steep that you do want to be careful there because that other girl that ended up being worse wasn't great, you know, like.
Amber
Yeah, no, I mean, I think it's a really valid point. It's exactly what I'm struggling with now. I mean, I think what's so difficult too is I've tried for so long silently, like with myself and with my husband, sort of behind closed doors in the sense of like we have two very different versions of history. Like, his version is never didn't take me seriously. Right when I would bring these things up. And I think it's part of being like dismissive of sort of what I'm saying and how serious I am. And I think he. Maybe at the end of the day this is just a wake up call. And he does. I mean, he is going to therapy.
Jesse
Have you guys gone to couples therapy?
Amber
Oh my gosh, I'm therapy.
Kristen
Like out.
Amber
I go to therapy.
Jesse
No, but have you guys con. You guys have gone to couples therapy?
Amber
Oh yeah, we're in couples therapy currently. Yeah. Mainly like to help co parent. But yeah, therapy.
Jesse
Yeah. But like, I'm assuming you guys talked about this stuff.
Amber
Oh yeah, we've talked about all of it.
Jesse
Has it gone anywhere?
Ad Host
No.
Jesse
You don't feel more heard? No, no. Common ground has been like discovered between the two of you?
Amber
I mean, maybe a little in the sense that he. Well, he won't take accountability for why we got where we got. And that's my biggest frustration is like, yes, I made the mistake. I can own that I will lay in my bed and I made that bed.
Jesse
Like in the sense that you want, you stepped out and you explored this guy. Okay, yeah.
Amber
Yes. Like, that is totally on me. And you can call me whatever you want. I don't care. That didn't happen in a vacuum. Like, it didn't happen.
Jesse
I'm with you.
Nick
I don't know.
Jesse
I don't know if you're watching Secret Lives of Mormon Wives, but you should listen to that episode with Jesse that we just had. Everyone. This. Infidelity is such a. Like a hot button topic in relationships, period, and happens all the time. And there are situations where people just do it, you know, and they. And then, you know, and. And it's a Into them problem because they're. You know, they got some issue. I don't know, whatever. And. And there are people who are victims of infidelity who didn't do anything wrong. They're just like, I don't know, their partner. Just like. I don't know, just figure some shit out. Whatever. People can feel stuck in a relationship. People can feel helpless in a relationship. People can be begging their partner to see them and hear them. And I'm not a therapist, but I wish I was your guys's couple therapists so I could be like, dude, you left her when she had a baby. Like, what? This wrapped my brain around that. Like, what? Per. Like what. How can anyone feel safe in a relationship when in their most vulnerable moment, you chose to leave because of weather patterns? Yeah, you know, I just. I don't.
Amber
And not once, but twice. That's like, what.
Jesse
Like, why should she bet on you? I want to know. I want to ask him why she should bet on you.
Amber
You don't want to be our couple's therapist because he rage texts the three of us constantly. He'll only communicate with me sometimes via text. So.
Jesse
It sounds like you've kind of done what you've tried to do. I mean, like, if you're already in therapy, it's, you know. You know, I don't know.
Amber
I keep asking for, like, I'm. And then he will demand something from me, like, an answer about something the next. The next day or a few days later. So I don't ever feel like, to your point, I get to sort of sit with a decision that I make and, like, feel regardless of this other person, regardless of my husband, but, like, with myself, and I'm in therapy by myself, and I just am never given that opportunity. Like, he's always sort of, like, demanding these things from me, and I keep saying, like, you need to just give me a minute. Like, I know.
Abby
I.
Jesse
What's he, like, what's he demanding?
Amber
Are we gonna move forward with mediation? Are we gonna move forward with a divorce? Like, he demands an answer, like, immediately about these big, heavy things, and I'm Just kind of like, give me, like a day to, you know, I need longer than that.
Jesse
And then what was his relationship with his dad?
Amber
You know, not great. I mean, his dad passed from als, and his dad's lovely and a fantastic person, but they didn't have. He left home when he was 18 and never went back.
Jesse
Why?
Abby
He.
Jesse
I left when I was 18 and never went back. In a way, he grew up in.
Amber
Like, parents did the best they could, but his brother was a very, very kind of intense drug addict. Would like, steal and just he was the younger brother. And so he was always sort of in the shadow of like, this really dark stuff. And he left. And you would have a heyday with just all the things that have happened with this. When we had our daughter, his brother passed like a few days before we had her, and she was a scheduled C section. And he got the phone call and then just went back to sleep, like, fell back asleep, and it was three in the morning. And I was like, well, what am I supposed to do? Like, he never let me meet his brother. Like, just a very dark sort of like, tumultuous thing. His mother is fantastic. Like, she's amazing. But he had a lot. He's had a lot of. Of bad things. And I would push him. I was like, you need to go to therapy. You need to figure this stuff out. Like, I can't hold this for you.
Jesse
Yeah. I don't know. It's. I mean, back to like, this Jordan and Jesse episode. I asked just because, like, I'm just curious his relationship, who are his role models, you know, and things like that. And you can have a bad role model and be a good person because it's like, you've chose to be like, I don't want to be like that. Right, sure. But, like the Jesse and Jordan from Secret Lives, you know, here's a guy, you know, it's like, yeah, I'm sure she had her part in their relationship problems, and I think she did emasculate him at times. But, like, how he apparently has spoken to her is so nasty. And then, you know, she eventually, like, kissed a guy or whatever. And it's just like, he. He just can't wrap his brain around his actions. And it blows my mind. I am sometimes floored. And I'm not trying to pat myself on the back about, like, I'm a great, you know, but, like, it's just like, I just blown away. Like, I just. I'm shocked that, you know, a lot of guys don't hold themselves to A certain standard. And I understand that men have feelings too, and men, we need our needs met as well too. But like again, there's just so much he could have done. You know, there's just so many things that were in his control that he had. He was set up, you know, like the fact that he had this very successful wife. I mean he had like, he had more options than most guys in this position because he could have just. All he had to do was try things out.
Amber
Yeah, I don't care. I didn't care at all. It's interesting too because my girlfriends when we got married, so like my college girlfriends had a lot to say about us getting married. And then when this sort of happened, they all were like, it's about time. Like they watched from the outside sort of this me hold everything together. And that reaction was actually incredibly eye opening that like, you know, because you can't really see it when you're in it, even though I was feeling it. And so I feel stuck between, like I have committed so much time. I have a beautiful family. My kids are, are the greatest gift on this planet. Like I'm obsessed with them and I would do anything for them and trying to keep everything together for them. Do I do that? I don't want my daughter to like see that this is like at least what our marriage was like, that's not an example that I want.
Jesse
Like, I'm not in a position to answer that question. And as a new dad, I just, just before I was a dad, it was easy for me to say, listen, like if it's a shitty marriage, like, you know, when my brother had two kids, you know, and we, you know, with this high school sweetheart, I was like, yeah, listen, you guys are better off. And I think they are better off. And they both found happiness and I think you can get divorced and co parent and, and, and it could be better off for the kids as now that I'm a dad, it is harder for me to be like, go do that, you know, because I just couldn't imagine sharing custody for my kid. I just like, I don't want to ever to be put in that position. I don't want to do that. It's horrible. I don't. This is hard for me to like flippantly be like, yeah, I mean, whatever, you know, like it's a tough decision, but it really feels like you. I said this before different ways, but like I think when it comes to men, I bring up that Jordan episode, your husband, whatever. Men are really simple, right? They Are all golden retrievers, right? And you maybe have already done this, and it sounds like you kind of articulated that you did, but, like, it's just really. I think it's just really important that men are believed in and they need cheerleaders. And you can call it what you want, you can call them soft or whatever, but men need that, right? And they need someone to believe in them for them to do things. Now, I think a lot of women can be supportive and believe in them, and their husbands are just deadbeats. I don't know. They're just like. I don't know, they go to surfing in Australia. But just make sure that for whatever part, like, if you want to get a guy to do something, believing in him and making. In making him feel like he is the king of his castle, so to speak, is I. That might make some women listening cringe because it sounds patriarchal or whatever. I can't even say the word. But that is how all men respond. It's just. You gotta believe in them. They need to feel like they are. They are capable of being that king of their castle. And your problem is probably, is that you are the king, queen of the castle. It sounds like you've been more than willing to let your husband be the king sometimes, but he hasn't taken you up on that. But all I'm saying.
Amber
I'll hand it over in a second. Yeah.
Jesse
Just remember, when you're frustrated to still want to believe in this next guy too, you know, but. Yeah, I don't know. It sounds like you've really tried everything with your husband. And I feel for you. If he can't listen, if your husband's anything like Jordan, get divorced. Because I. I listen to that. I kind of wish I was harder on him, but it's like he taught, you know, it's like he's like, I'm in therapy and it's like, okay, you know? But like, it was like, you know, to him, that was the answer to all his problems. He seemed more focused on Jesse's mistakes. And I'm like, I don't know. Like, maybe. Yeah, I kind of. I don't blame her, you know, like, it's. You know, and I. He. He kind of treated like her mistake absolved all of his. And I don't think they remotely do.
Amber
Very similar.
Jesse
He just doesn't see it. He just doesn't. I don't know. I just. Again, I don't know what it's like to be in their relationship behind closed doors, but I'm So tired right now. River, whatever reason, didn't want to sleep last night. She wanted a part, you know, and we both, at different times, were up there for two and a half hours. It's like, you know, we share in the responsibility of parenting, of helping around the house, of doing things. At times. I'm sure we both feel underappreciated and overworked, but we check in with each other.
Amber
I like that perspective. I feel like that's a perspective. Men in relationship to me.
Jesse
Yeah. And I'm talking about just being there every day, being present, you know, helping out little things, just being there. And that just goes so fucking far, you know, making your partner feel like you're proud of them, believing in them. Like, you know, it's just. It's hard to find. I don't know if this was remotely helpful, but.
Amber
No, it is. I mean, perspective. Your perspective as you're sort of where we were years ago. And. And it's nice to hear that. Your mind, mindset then. I think that. I feel like I have tried in so many ways. And to your point about Jordan, like, until there's any accountability on, like, why this happened, I just don't see how.
Jesse
The problem is believable. The problem is, is that, like, you finding this new guy. Yeah, he's. He's scapegoating, probably. Now he's. Now your husband's the victim 100.
Amber
And that's what every conversation is about is like that. And I keep articulating and trying to. Again, I didn't wake up one day and say, I'm gonna blow everything up. Like, I didn't. That didn't happen. It happened. If I was happy and fulfilled in our marriage, like, this would never have happened. So, like, how did we get there? And can that be repaired? Or maybe it just can't be repaired. And maybe that's just the answer. And we need to, like, move on, because our kids are better not in this limbo. So we have to figure out one way or another.
Jesse
Yeah. Well, what is your timeline?
Amber
I don't have a timeline. Like, I want to. I don't want to rush into anything. So, like, I don't want to rush to get divorced. I don't want to rush to get, like. I just want to, like, sit. And that's what I've been asking for is, like, sitting with everything that's happening and not rushing. He wants to rush for an answer one way or another, and I just can't give him that. And so that's sort of the source of a lot of our conflict right.
Jesse
Now is, like, have you said to him point blank, you probably have. I recognize that what I've done recently in me stepping out of our marriage was wrong and I'm sure very painful. And you have every right to be angry and mad and you can call me names, but it didn't happen in a vacuum. And you scapegoating your actions that led to this moment. And I have begged you and given examples and, like, I'm not justifying my decision, but it's why I made my decision. And I was just unhappy and miserable and alone. And I want someone who is by my side, who doesn't go up and go, you know, who works on their shit, doesn't wake up angry, take it out on me and the kids. Like, everyone's allowed to have bad days, but, like, do something about it. And you never were willing to do anything about it. And you just. You pushed me to this limit. And if you can't recognize that, if you can't own that and you can't focus on that, I don't need to. I know I made a bad decision. I don't need to be reminded of it. I don't need to be lectured. I'm owning that decision. I made a mistake. I'm not perfect. It is what it is. And I'm sorry you're hurt, but, like, if you can't own, you can't just scapegoat me and. Because you feel like a victim, and sure, you're a victim of my choices, but, like, we are a victims of our choices in this marriage. And if you don't want to, like, own the problem of our marriage is you never wanted to own the responsibility. I needed a partner, and so often you weren't willing to be one. And even in this moment, you are not being a partner in the problems of our marriage. You are just, like, expecting me to solve the problems, which is, like, to decide to work on it, decide to be together. Have you ever said that?
Amber
Yeah, all the time. I mean, and then his answer is that I'm mentally ill and I need help because nobody does what. You know, so. Yeah, I mean, the more we talk.
Jesse
This out, I feel like. I don't know. I just. I don't want to tell you what to do, but he went surfing. I just. I feel like that says so much. And if he's literally gaslighting you into, like, calling you crazy and mentally ill and he's refusing to see the obvious, Jordan's answer just, you know, spoiler it was like my family talk. We're harsh with each other and I'm. I, you know, just like, that's okay. Sure, whatever.
Amber
Yeah.
Jesse
That's why you.
Amber
I think there's a. We come from very different backgrounds and. And in therapy, like, I'm. And I'm not trying to, like, pat my own back or anything. I'm incredibly high functioning and like, I just get things done. And like, I think a big part of the disconnect is like, his version of doing things is just so low. Like, it's very. Just like he. He thinks that he did. Like, I think there. I think he genuinely thinks that time, like, he did act as a partner. And in my head, I'm like, just because you, like what, you know, held the baby for an hour, that's not like a partner. Like, you know, so those things. And I've used the analogy with him too. Like, I'm the pilot of a plane and I'm responsible for the mechanics of the plane, the flight crew, the passengers on the plane. I'm responsible for the entire plane in the air, making sure that it stays in the air and it doesn't crash. And like, you were supposed to be my co pilot and you're surfing or like you're. He.
Jesse
He makes sure that the garbage gets emptied out.
Amber
Right? Exactly. Yeah, he does like, something. And that's. And that's what he does. And then he thinks that that is enough. And.
Jesse
Yeah.
Amber
What I'm trying to determine is like, will that ever. Maybe we're just two. We're on two different frequencies as people.
Jesse
And I think you're gonna figure it out. It sounds like you're. It's a difficult decision, but it sounds to me like the only thing that's really holding you back is the idea of the family and the nucleus and the kids. And you have. You're trying. You are in therapy. You guys are in couples therapy. I think you're actively doing the thing I did, which is like, I'm just doing all the things I need to, like, internally make sure I have no regrets.
Amber
Like, check. Block this. Yeah, yeah, yeah.
Jesse
I'm sorry. It sucks. It's. It's sucks.
Amber
Yeah, it's shitty, but it's fine. It's okay. We'll be fine. Have beautiful kids.
Jesse
Does the other guy have kids?
Amber
No, but he loves my kids. Like, he's around that. I mean, he was in our house for so long. Like, the kids know him.
Jesse
Yeah.
Amber
Before it was a very. I'd probably do it a little different had I go. I go back. But yeah, no, he doesn't have kids. But I would have more kids. Like that's what the other thing I was like, I wanted more. And then he got my husband got a vasectomy and didn't tell me.
Jesse
It's crazy. That's crazy. Your husband does some shit. That is crazy. Well, I'm sorry you're going through this. It sucks.
Amber
No, I appreciate it. Thanks for helping me.
Jesse
All right, well, keep us posted. I want you to decide. Good.
Amber
I will.
Abby
For sure.
Amber
All right, I will.
Jesse
Take care.
Amber
Thank you.
Jesse
Happy holidays.
Amber
You too. Bye.
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Kristen
Hi Nick.
Amber
I'm good.
Kristen
My name's Kristen, 31 and my question is how do I get over a guy I really liked who might be gay?
Jesse
Okay. Are you guys currently dating?
Kristen
No, we're not currently dating, just kind of a drawn out situation. But no, not currently dating him. No.
Jesse
Why do you Think he might be gay.
Kristen
Things that he had said to me that I did some research and, you know, it. It might be that he actually is, so I can share that. But there's things that he had told me that based on the places he's been going or things that he said that leads me to believe that might be the case.
Jesse
Why did it. Why did it end?
Kristen
I mean, it's a situation where it's like, on and off communication. We'll chat, we'll talk, then it trails off and it's kind of where he hasn't taken it further. That also, like, gives me an indication that, you know, my thoughts of him being potentially gay could be true.
Jesse
So how long you were hanging out with him?
Kristen
So I met him more under, like, a professional setting, and then it kind of turned more personal once that was done.
Amber
Okay.
Kristen
But I. I had known him like, over the course of like, a year, so. But yeah, it is like an. It was an on and off thing where we would connect, disconnect, connect, disconnect. So.
Jesse
Well, I honestly think, like, his sexuality is kind of irrelevant. I only say that because, like, whatever the reason, it sounds like he's not pursuing this relationship in a way that you kind of want to correct. Right?
Amber
Yeah.
Jesse
Maybe he's bisexual. I don't know. You know, which is why maybe he's shown some interest in you and also maybe talked about some other things that he's kind of breadcrumbed some information that suggests that he might be also into men. I don't know. But that's really neither here nor there in the sense that, like, that it's like, honestly, from your perspective on some levels, it's like saying, like, I don't know, I think he's into blondes.
Kristen
Right.
Jesse
You know, like, whatever the reason is that stopped him from pursuing something with you at the end of the day needs to be enough for you to accept that and move on. Right. Like, we all like people who sometimes don't like us. We will make connections with people and value their time and enjoy their company. And sometimes we will shoot our shot with those people or want to explore something deeper with those people. Only for them to be like, I don't. I don't know. I'm not. You know, I made a lot of friends with women when I was single that I feel like maybe they might have felt connected to me emotionally. I only saw them as friends, and there probably was a world where they would have dated me if I would have wanted to date. Ultimately, I just saw them as friends. And I don't want to date. You guys never really dated. So you clearly. So you probably romanticized thing moments that you really enjoyed with him. And I'm sure if he is gay on some levels, he probably is better at being more empathetic and connecting with you than, say, your traditional straight man. But I guess the question is, why do you have a hard time accepting this and moving it on?
Kristen
Yeah, I guess because I think I, like, did build it up in my head, too. And, you know, I kind of had this hope and this what if, like, what if he decides he does want to continue and go out with me again? What if he wants to maybe, like, pursue something more, like, casual with me? It's always like a what if? Like, maybe he wants this, maybe he wants that. And that's what keeps me kind of, like, circling back and thinking about it. And it's like, I have tried to, you know, know, go out with other people and, you know, pursue other connections. And sometimes I do compare, but I feel like it's something I think about. But I don't feel like I would reach out at this point because I feel like I've given him many opportunities, and he hasn't really taken the bait on anything. And the only scenario in which I would speak to him again is if I ran into him somewhere. And thinking about it now, like, yeah, I would probably, like, move with caution, but would still probably entertain it as, like, okay, what if he's, like, ready now to date me? Or, what if he's ready to actually, like, be serious now? But then it also weighs on me that, like, how can I even think of pursuing something with someone who maybe exhibited behaviors that I necessarily wouldn't even, like, agree with or view as, like, a red flag?
Jesse
Like, did you think he's potentially closeted where it's like, he hasn't?
Kristen
Yeah, because it's like, the. The main thing that. The main red flag about it is when I had went out with him and I asked what he did the previous night, he mentioned he went to this bar and then another place. And I'm not familiar with the area because I had just moved here, so I didn't question it. I just thought, oh, he went to these bars. And then I ended up looking up the place, like, the name of the place. And it has a reputation where men will go to either engage with other men or experiment with other men. And, I mean, I was shocked to see that, but part of me is like, okay, maybe he went there with, like, a friend.
Jesse
Yeah, I mean, I was just gonna say, like, I have a lot of gay friends. I've been to gay bars.
Kristen
Yeah.
Jesse
Is there any other than, like, he frequented a couple gay bars?
Kristen
Yeah, I mean, it's. I don't know if it would be considered like, a gay bar. It seems like more underground. Yeah. It has, like, a. Not a very, like, good reputation from what I read. And it's not like, a place where, like, yeah, we can all go out to this gay bar and, like, have a good time.
Jesse
Sounds like you're partying in West Hollywood.
Kristen
Yeah, it's not like. Not like that, but yeah, some. If I was actually going to, like, date a person who went there, I mean, I would have probably concern and would want to know, like, the context in which they were there. But that's what I also questioned myself. Like, I feel like I'm trying to believe he was just there under, you know, innocent, like, pretenses.
Jesse
I mean, the reality is, is you don't need a bot. You don't need to concern yourself, you know, because I think for whatever reason, he rejected you in the sense that, like, there's you like him, and you kind of just said, I mean, if he were to call you up today, you'd probably accept an invitation to dinner with the idea of exploring, you know, having a good night. Right? Yeah. And he hasn't taken you up on that. And so there's a level of rejection that you feel right now. You're into the weeds, wondering about his sexuality. And there may be, like, legitimate, like, reasons why you have the right to wonder, but it's a moot point, you know, but, like, I think you're investing your energy in it because, like, you know, listen, you were rejected, and it's probably a little easier to discover that you never had a chance than maybe just, you know, you're not as cup of tea. Regardless, I think at this point, you just need to, like, be like, when it comes to dating, it's really difficult, but you have to just try to, like, remember what you liked about the interactions you had had. And those are the moments you want to replicate. You want to remember the conversations that you enjoyed and the ways, like, the men that you dated opened up and were vulnerable, that made you feel connected to them, and those are the things you want to replicate. You want to remember the things you didn't like. So, you know, to avoid them in the future with things. Try not to romanticize, you know, and just accept that, like, this situation didn't work out. You know, let's let's assume he's just tell you he's not going to reach out.
Amber
Yeah.
Jesse
And if he does, I think a better question is, like, why would you go out to dinner with him at this point? When I started giving this relationship advice back in the day, when I was doing questions with Nick on my Instagram, like, the number one theme that I would, like, want to remind people is like, he's not. He's just bored. You know, at this stage of the game, for him to reach back out isn't like. It's just more. He forgot why he said no to you. Time has passed. He's gotten a little lonely. He looks back, sees a picture, and it's like. It's like almost like resetting. You know, the dating app algorithm, where it's just like, oh, wait, she is cute.
Kristen
Right?
Jesse
You know, and time pass and reach back out, and they're like, hey, what's up? Haven't seen you in a while. You've been good, and you're like, you start all over, but nothing's really changed.
Kristen
And I think that's what was hard. It's like when that happens and then he reaches out and. Or you reach out and then there's, like, back and forth. It's kind of like you get hopeful again, and then it crashes back down.
Jesse
But in those moments, you. At a minimum, at a minimum, you have to recognize that pattern. Pattern. And you can't be so accommodating, you know?
Kristen
Yeah.
Jesse
If a guy who you had an interest in got a little flaky with you and got a little inconsistent, or quote, unquote, the ghosting ish kind of stuff, for them to re engage you, whether it's a week later, a month later, you got to make them beg, right. You got to give them a hard time. You know, it's just like, I don't know, you kind of seem unserious and uninterested and, like, I'm looking for things that are a little bit more intentional and a little more deliberate and, like, I, you know, listen, I think you think I'm cute, but, like, you know, whatever. Stop you from reaching on the past. I think you just need to, like, sit with that, you know, and, like, be really direct with these guys. Because, like, some guys might, you know.
Nick
I think a lot of guys in.
Jesse
Those moments be like, yeah, you're right. Honestly, like, you know, if a guy who's, like, flaky. Because we all could be flaky, right? And we forget that we're bored. We forget that we are each. But I think in those moments, you will save yourself a lot of energy and time with the guys who, like, are well intentioned and maybe are just bored. And then you kind of call them out and they're kind of like, yeah, no, she's right, she's right. I don't know why. Why am I reaching out?
Kristen
Okay.
Jesse
You know.
Kristen
Yeah, yeah.
Jesse
And then you want to find the guys who, like, No, I mean, honestly, like, I really want to see you. And listen, you might catch a, you know, the. The guy who just wants the chase and then our, you know, kind of narcissistic personality. I don't know. But like, you know, I think most. Most of the decent ones will just, like, hear that and be like, you're right. And then maybe you'll find a guy who is like, no, I. You're right and I'm sorry. And I. I still want a second chance. And really, you make them beg it. It can't be that easy.
Kristen
Okay.
Jesse
Because I think when we meet people who are good at setting their boundaries, it. You know, no one likes to have difficult conversations and uncomfortable conversations. And if you show that you're good at standing up for yourself, you'll. People will be a lot less likely to waste your time. You know, they're not gonna want to deal with that.
Kristen
Yeah, I feel like I could definitely be more direct.
Jesse
You seem very sweet and very accommodating.
Kristen
Yeah.
Jesse
And I think you open yourself up to, like, yeah, bored men.
Kristen
Yeah. And, yeah, I know part of it was me. Like, I built it up in my head. And also, like, taking all those, like, moments when we were together or we're talking, like, taking it as like, again, this could be something, but it's, again, just breadcrumbs. And I feel like I'm at that point where I've decided there's nothing left for me to do. Like, I've exhausted this with him and I do think about it. But again, I feel like you're right. Like, if I ever do hear from him again or see him again, I have to be a little bit more direct because it's.
Jesse
I think right now you need to catch yourself from thinking about it. The thing that, you know, like, how do I get over it? Like, you gotta. You got to actively be like, stop, stop. You're thinking about it. You're ruminating about something that is over. And your conscious brain has accepted it's over, but your subconscious brain is a little resistant to that. And your ego or whatever it is that's causing you to ruminate or wonder if he's gay or whatever. This is kind of a waste of your time, but also keeps you emotionally invested in that relationship because you have something to figure out. His sexuality. You're invested in what, figuring out whether he is or he isn't. And you spend your time thinking about that and breaking it down and maybe talking with some of your girlfriends, friends about it. And all that does, at the end of the day, doesn't get you anywhere. It just keeps you stuck thinking about him. Right. So if you want to stop thinking about him, stop figuring it out. You know, it's like, listen, it didn't work out. He didn't call me back. He didn't, like, accept my invitation to do things more. I feel a certain way about that. I'm a little sad, but he did it. And I want people who do. And I'm gonna move forward.
Kristen
Yeah.
Jesse
I mean, it's kind of that simple. We all ruminate. You just gotta catch yourself and not go down those rabbit holes that it seems like you're going down. And that's why you feel stuck.
Amber
Yeah, for sure. And.
Kristen
Yeah. I mean, it's like. Yeah. Then you kind of go out with people after that. And then I find myself, like, sometimes I would be, like, comparing.
Jesse
Sure.
Kristen
But, you know, that's the thing too. Like, going out with a guy who might seem like he has all these green flags and, you know, seems so good on paper. And then I'm like, I don't feel that, like, spark or immediate connection and not ending it, but kind of closing that door or opportunity. But yeah, I don't want to force anything either, so. And I guess the same could be said about him, Whatever his reason is, like, he didn't want to force things with me. And, I mean, I feel the same way with other people, too, so.
Nick
Yeah.
Kristen
But, yeah, I feel guilty sometimes. Like, why did I like a guy who clearly has some, you know, either personal dilemmas or challenges, and then there's guys who might seem more.
Nick
Because it's exciting.
Kristen
Yeah. Yeah. So, yeah, I think I just have to more consciously, like, stop myself from ruminating, like you said, because I feel like that is a trait of mine, liking to. I like to overanalyze and dwell on things, so.
Jesse
Same. Try not to do that. I mean, again, it's. It doesn't just. It's not just a switch that goes on and off. You have to actively kind of check in with yourself. But.
Abby
Yeah.
Jesse
Yeah. As long as you're. But again, I. I think it's really important for you to understand his. His sexuality is irrelevant to you.
Amber
Okay.
Kristen
Yeah.
Jesse
I think that's step one.
Kristen
Okay.
Jesse
It's a conversation. You can talk about your friends, you can break it down, you can analyze it, you know, and if you're someone who likes to ruminate and. And has a habit of doing that, it's just a. It's a topic you. You can get really stuck on.
Kristen
Yeah. And I guess I felt a little bit too, like, if someone is going through that or dealing with it, like, why I was thrown into the situation, like, why they weren't thrown into it. No, I mean, like, he pursued me, like, after the.
Jesse
Well, again, like, we don't know and we honestly don't care. But just to play this game again, maybe he's bisexual. Maybe he is closeted. I don't know. Like, you know, I think a lot of gay men have a lot of meaningful, close connections with women, right? So it's maybe just easy for him to make emotional connections with women. Right. And then he kind of gets to a point where it's like he feels like a woman is attracted to him and he doesn't have any of those romantic feelings towards her because he's gay or whatever. And, yeah, he's having a hard time doing that and he's navigating, you know, and, you know, he's closeted, so, like, it must be very difficult for him, you know, but, like, you're not a victim in this relationship. He just, like, enjoyed having a connection with you, you know, like, it's. You had a good time and like, like, you know, you were forming a friendship and, you know, you probably found him attractive or whatever. And like, you know, with the assumption that he was straight, you were allowing yourself to be like, oh, I'm having a nice time with a man who's treating me well, and I'm enjoying his company. I think I might like him. Right. You know, and so there's nothing to analyze there, you know?
Kristen
Yeah.
Jesse
We don't know what a sexuality is. There's your bits of information. You learned that. Oh, maybe, but it really. I think it's. It's. It's irrelevant. It really is irrelevant.
Kristen
Yeah.
Jesse
It's no different than finding out, you know, you're a brunette, right. Like, you went on a date with a guy, let's say everything was the same except for his. The questions about his sexuality. You know, you had a couple good dates. It felt like meaningful. And then he kind of flaked, kind of just. Yeah, fizzled out. And then, like, you ran into someone he knew, and you're like, really? You guys dated? He's like, I've only ever seen him date blonde. And. And then you spend the next months being like, well, why did he date me? Like, what was it about me? Like, why did he date? I'm the only.
Nick
Why.
Jesse
Why did he do that? Why did he waste my. You know what?
Nick
I'm like, you could do the same.
Jesse
It's the same thing that you're doing. Right. You're just like. You know, the fact that it's about his sexuality feels, I don't know, more.
Nick
Serious to you or something.
Jesse
I don't know. But it really is no different than if. If.
Kristen
Right.
Jesse
You know, if his preferences were blonde.
Kristen
Yeah.
Jesse
You know, he tried to mix it up.
Kristen
Right. That's.
Jesse
You know.
Kristen
Yeah, that's true.
Jesse
The point is, he just. He lost interest.
Kristen
Yeah.
Jesse
And your ego's a little upset about that, a little sad. And rather than accepting it, you're trying to figure it out, and that is what's keeping you stuck.
Amber
Yes.
Jesse
And that's why you have to.
Kristen
Yeah.
Jesse
Challenge yourself to stop doing.
Kristen
Yeah. It's like you're looking from. For some type of, like, final. Like. Okay. And this is the reason why. But you're not gonna get that million reasons why. Yeah.
Jesse
You know, you have a bad day. I don't know. Doesn't matter.
Kristen
Okay. Yeah, no, that's. That's a better way to reframe it and look at it. So. Can I ask you one more question?
Jesse
Shoot.
Kristen
So this is a different subject now. I had met this guy while I was out during, like, Halloween weekend. And, you know, we connected. We vibed. He's like 10 years younger than me. We. He ended up, like, texting me after we went out last week, like, on a date, and then we're going out again tonight. I guess, like, I like him, but I know, like, given the age gap and where I'm at, where he's at the expectation that there will be something, like, serious. I mean, I don't. I don't expect that, but it's like. I don't know. I guess just, like, advice on, like, navigating.
Jesse
Go have fun. I mean, he's probably gonna. He'll probably be fun, and there's probably an excitement, and there's probably, like, I don't know, a little bit of an ego boost to be, like, you know, a guy who's 10 years younger than me is interested in me. I think you can go and enjoy it and. Yeah. Proceed with caution. How Old are you again?
Kristen
I'm 31 now, so he's 21. Yes.
Jesse
I mean. I mean, listen, I think there's exceptions to every rule. Rules. My wife was 21 when I met her. Men and women are different emotionally. Anything's possible, but there's a more likely chance than not that he is way less emotionally mature than you. And this is very exciting for him. And I think a lot of young men. It's fun. It's exciting. So I would. I would just see this as a fun and exciting thing.
Kristen
Yeah.
Jesse
You know, and. And I would.
Kristen
Okay. Yeah. Because that's the thing, like, long term, like. Yeah, I want to meet someone and, you know, be in a serious relationship with them.
Jesse
If you have no other plans tonight.
Abby
Right.
Kristen
Yeah. So that's the thing.
Jesse
I'm like, you're allowed to go.
Nick
Yeah.
Kristen
Yeah. So. And it's like, of course, if someone else came into the picture, I would prioritize that if they're, you know, more in the same, like, age group as me and, you know, same stage, what.
Jesse
You don't want to do is don't have so much fun and have it, like, turn into something. And then all of a sudden, you know, you might. You could easily just be like, this is run its course. Or he could say, it's run its course. What you don't want to happen is that you keep hanging out with them, you have some fun, you let your guard down, and then he, like, it's run its course for him, and then you are emotionally hung up on a guy you really shouldn't be emotionally hung up on, but you feel rejected, he beats you to it, so to speak. And then you get a little crushed over something that you honestly were never serious about or shouldn't be serious about. But it was a good time, and he was a gentleman, and he made you feel hot and sexy, and you're gonna miss that, but you're not gonna miss him. Like, just be careful. You don't allow that.
Kristen
Yeah. Yeah. I feel like I'm proceeding with caution with it, but I'm not trying to set an expectation, allow him to make.
Jesse
You feel good about yourself, but, like, just be aware of the situation.
Kristen
Yeah, for sure.
Jesse
All right, cool. A lot of fun.
Kristen
Thank you. Yeah, maybe I'll give an update, so.
Jesse
I would love one.
Kristen
Awesome.
Jesse
All right, well, hopefully this was helpful.
Kristen
Yes, it was. I'm glad I got, like, a. A male perspective just because, like, I just talk about it with my girlfriend. So it's good to get.
Jesse
Stop talking about the other guy with your girlfriends.
Kristen
Oh, yeah, yeah, yeah. I know. Yeah.
Abby
All right.
Kristen
For sure.
Jesse
Okay, take care.
Kristen
All right. Thank you. Bye.
Release Date: December 15, 2025
Host: Nick Viall
Panel: Jesse, Amber, Abby, Kristen
This "Ask Nick" episode invites listeners into real-life relationship dilemmas, gently dissected by Nick Viall and his co-hosts. Three callers—Abby, Amber, and Kristen—seek guidance on dating intentionally in 2025, navigating marital breakdown after emotional infidelity, and letting go of an unavailable crush. The tone is supportive, pragmatic, and at times candidly raw, with Nick and Jesse blending empathy with hard-won advice. The episode unpacks modern romance, the pitfalls of overthinking, the challenge of setting boundaries, and the struggle to honor one’s needs without guilt.
Caller: Abby (36)
Timestamps: [03:36 – 36:22]
Dating in a New Era:
Intentionality & Abundance of Options:
Physical Intimacy & Transparency:
Reflecting on Past Patterns:
Advice for Clarity:
Memorable Quote:
"Slowing down isn't dating multiple men. It's just asking more questions and thinking about their answers... It's learning about each other."
— Jesse [36:13]
Caller: Amber (35)
Timestamps: [40:14 – 85:41]
The Situation:
Amber is separated and heading for divorce after falling in love with another man. Married nine years with three young kids, she felt emotionally abandoned by her husband long before the affair: "He completely checked out... It just became my responsibility, not just the kids, but our entire life." [44:08]
Community Fallout & Internal Guilt:
Nick and Jesse’s Perspective:
"He left you when you had a baby to go surf? That is—I just think that says so much about him being a partner and father."
— Jesse [47:03]
On Guilt & New Love:
"Don’t dilute yourself into thinking you're making choices because fate has taken over your life. Make choices, own your choices."
[54:00]
Marital Autopsy & Moving Forward:
"He gaslights you, calls you mentally ill. He’s refusing to see the obvious."
— Jesse [82:12]
Big Takeaway:
Memorable Quote:
"I’m the pilot of a plane... You were supposed to be my co-pilot, and you’re surfing."
— Amber [83:54]
Caller: Kristen (31)
Timestamps: [88:58 – 109:20]
The Crush:
Kristen had an on-and-off, emotionally charged friendship/connection with a man she suspects is gay or possibly bisexual, based on social clues and his pattern of engagement. He has not pursued anything further.
Letting Go & Moving On:
"It's really that simple. We all ruminate... But your ego's a little upset about that, a little sad. And rather than accepting it, you're trying to figure it out—and that is what's keeping you stuck."
— Jesse [105:25]
Boundaries & Self-Protection:
Bonus Dilemma—Younger Man:
Memorable Quote:
"His sexuality is irrelevant to you. That’s step one."
— Jesse [102:28]
| Time | Segment | |-------------|----------------------| | 03:36–36:22 | Abby: Intentional dating, attachment, slowing down, choosing between two men | | 40:14–85:41 | Amber: Infidelity, marital breakdown, self-forgiveness, motherhood, co-parenting | | 88:58–109:20 | Kristen: Letting go, ambiguity, rejection, boundaries, casual dating |
For those navigating the muddy waters of love, loss, and new beginnings, this episode offers both comfort and a challenge: know yourself, ask the tough questions, and don’t settle for less than true partnership.