E980 Ask Nick - I’m In Love With My Boss

Summary

Episode Summary: The Viall Files E980 - "Ask Nick - I’m In Love With My Boss"

Release Date: August 11, 2025
Hosts: Nick Viall, Natalie Joy, and the Household
Description: In this heartfelt episode of The Viall Files, Nick Viall delves deep into complex relationship dilemmas submitted by listeners. This episode features two compelling stories: Victoria's struggle with ending her first serious relationship and Paige's tumultuous feelings for her long-time ex.

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1. Victoria's Dilemma: Ending Her First Serious Relationship ([02:02] - [08:20])

Caller: Victoria, 27 years old
Situation: Victoria is grappling with the decision to break up with her first serious boyfriend of two years. The primary conflict arises from her desire to pursue a 10-month teaching program abroad, which her boyfriend is unsupportive of. This ambition has led her to question the future of their relationship, especially since her boyfriend envisions a "forever relationship," while she is uncertain.

Key Points:

• Healthy Relationship Dynamics: Victoria emphasizes that her relationship has been largely conflict-free, though recent stressors have introduced minor disagreements.

• Career vs. Relationship Goals: Being laid off exacerbated her introspection, leading her to seek opportunities like teaching abroad, which conflicts with her boyfriend's expectations.

• Cultural and Religious Differences: A significant revelation for Victoria is her desire to have a Jewish family—a non-negotiable for her—while her boyfriend is not Jewish. This disparity became more pronounced as she considered long-term commitments.

Notable Quotes:

• "I have just been feeling more recently that I don’t know if this is my forever relationship." ([02:43])
• "I want to raise my kids Jewish first and foremost." ([09:20])
• "He was the only person I had spoken to that hadn’t been excited or supportive of me trying this." ([05:34])

Nick's Advice:

• Be Direct and Kind: Nick emphasizes the importance of honesty without sugarcoating. “If this is how you really feel, then, you know, then, then it’s okay to, like, have your heart change,” ([06:18]).

• Avoid False Hope: He advises against giving mixed signals or hinting at future possibilities that may not materialize.

• Communicate Clearly: Victoria should clearly express her non-negotiable desire for a Jewish family and her inability to settle for less, ensuring her boyfriend understands the gravity of her decision.

• Time the Breakup Appropriately: Given that Victoria is about to embark on her teaching program, Nick suggests she initiate the breakup before she leaves to avoid prolonged emotional turmoil. “You want to do it before you leave, not when you get there,” ([28:05]).

Conclusion for Victoria: Victoria gains clarity on the necessity of prioritizing her personal and cultural goals over maintaining a relationship that may not align with her long-term aspirations. Nick's guidance empowers her to act with integrity and self-respect, ensuring she makes a decision that honors her true self.

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2. Paige's Struggle: Revisiting a High School Ex ([33:58] - [87:25])

Caller: Paige, 22 years old
Situation: Paige is conflicted about rekindling a relationship with her high school ex, whom she has been on and off with since sophomore year. Recently, he reached out expressing remorse and a desire to prove his change, leading Paige to question whether she should give him another chance or break free from the cyclical pattern of their interactions.

Key Points:

• Pattern of On-and-Off Relationships: Paige describes a long history of intermittent connections with her ex, characterized by periods of no contact followed by attempts to reconnect.

• Age and Maturity Gap: Her ex is three years younger, leading to conflicts, such as his parents' ultimatums and his inconsistent commitment.

• Emotional Turmoil: Despite recognizing red flags and having a supportive network advising against the relationship, Paige finds herself emotionally entangled and seeking validation.

Notable Quotes:

• "I can't keep doing this through my 20s. I do want to have a boyfriend." ([81:32])
• "I have become a recent fan of the podcast within the last year. My friend showed it to me, and now me and my mom listen to the reality recaps because we're reality TV fanatics." ([86:32])

Nick's Advice:

• Establish Boundaries: Nick recommends that Paige become less available to her ex, allowing him to recognize the inappropriateness of their interactions without direct confrontation. “You just become less and less available. So much so that he will just organically feel it.” ([44:13])

• Block and Move On: To break the cycle, Nick advises Paige to block her ex on all platforms, making it harder for him to reach out and for her to fall back into old patterns. “I would block him on social media. I’d block his phone. I’d delete his number from your phone.” ([73:08])

• Focus on Self-Growth: Emphasizing the importance of personal development, Nick encourages Paige to invest in her dating life, try new experiences, and seek relationships that respect her boundaries.

• Recognize Toxic Patterns: By acknowledging the manipulative behaviors of her ex and understanding that her support system is guiding her towards healthier choices, Paige can empower herself to make decisions that prioritize her well-being.

Conclusion for Paige: Paige gains valuable insights into the unhealthy dynamics of her relationship with her ex. Nick's actionable advice provides her with strategies to assert her boundaries, seek healthier relationships, and prioritize her personal growth over cyclical emotional entanglements.

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Final Thoughts

In this episode, Nick Viall offers compassionate and practical advice to listeners navigating complex romantic situations. Whether it’s Victoria needing to align her life goals with her relationship or Paige striving to break free from a toxic cycle, Nick’s guidance emphasizes self-respect, clear communication, and the importance of setting healthy boundaries. "You deserve better," encapsulates the underlying message of this episode, encouraging listeners to prioritize their happiness and well-being in their love lives.

Notable Quote from Nick:

• “You have to be as respectful and as kind as possible. Do not sugarcoat things. It’s better to be direct and kind rather than to, like, insert unnecessary hope.” ([06:32])

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This detailed summary encapsulates the essence of Episode E980, providing listeners—both existing fans and newcomers—with a comprehensive overview of the heartfelt discussions and valuable relationship insights shared by Nick Viall.

Transcript

[Nick]

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[Victoria]

You'Re cr.

[Nick]

How's it going?

[Victoria]

Hi, my name is Victoria. I'm 27 years old and I'm wondering how to break up with someone.

[Nick]

Okay. Are you currently in a relationship and trying to figure out how to break up with them? Or are you just like wondering for future reference?

[Victoria]

I guess both. But I am currently in a relationship, yes.

[Nick]

Have you never broken up with someone Before?

[Victoria]

No, this is my first real relationship, my first love, first everything. So not everything, but like first real relationship.

[Nick]

How old are you again?

[Victoria]

27.

[Nick]

Okay, how long, how long is this relationship been going on for?

[Victoria]

Yeah, so we've been dating officially for a year and a half, but we've been together like two years.

[Nick]

Okay. Why do you want to break up?

[Victoria]

You know, it's hard because nobody did anything wrong, so that kind of makes it much more difficult. He's very sure that this is a forever relationship. And I have just been feeling more recently that I don't know if this is my forever relationship. And just a lot of things have been adding up and I've been thinking a lot about it more recently.

[Nick]

Okay, do you want to elaborate at all just for fun?

[Victoria]

Yeah, sure. Absolutely. Yeah. So we have a very healthy relationship. We honestly actually don't even argue that often. We've been getting into a little more recently, but it's. We're able to talk through it, but it's more of like a reflection of where we're at currently. So I was laid off back in February. I cannot, I have not been able to get a job. Like even getting an interview has been a nightmare. And something I've always been interested in actually is going and teaching abroad for a little bit. And so I'm not a teacher, but it's something. There's a program that I've always been interested in. And so I let him know ahead of time I'm applying to this 10 month teaching program. And he wasn't super stoked. But you know, I was also actively applying to jobs, but I got accepted to this and I figured, you know, this is the time to try it. And so he wasn't super happy. We've been working through it. Again, it's nothing we can't work through. But again, since I let him know that I am leaving the country for 10 months, I've just been doing a lot of reflecting and so, yeah, so.

[Nick]

Ultimately you had a bit of like a life crisis, but it's obviously sucks getting laid off.

[Victoria]

Yeah.

[Nick]

You took advantage of that crisis by looking at other opportunities that you've considered doing like this, this teaching thing. My brother did a version of that. Really enjoyed it. Talk. Taught English in Seoul, Korea.

[Victoria]

That's awesome.

[Nick]

You're in a relationship. He obviously wasn't thrilled by the possibility of his girlfriend and what he perceived as his future life partner, like taking a sabbatical from the relationship. But ultimately, I guess it sounds like, I guess where did we go from we're working through it and he didn't love the idea, but we are working through it to like, you know what? Fuck it. I just like, let's break up.

[Victoria]

So actually it kind of was around the time that I had mentioned I was leaving. We took a weekend to kind of think things through. I actually, it worked out perfectly when I let him know that I was actually going to my grandparents house that weekend. So we both kind of just took a weekend apart. We were still texting, but not in person. And when I came back I, I was like, very sure, yes, I want to do this. He was the only person I had spoken to that hadn't been excited or supportive of me trying this, which I understand his significant other is leaving the country for 10 months. So I understand where he was coming from with that.

[Nick]

Did you understand but also like resent him a little bit for not supporting you or did you just kind of totally understand?

[Victoria]

A little bit of both, I guess. A little bit of both. But there's, I don't feel any resentment. If anything, I'm worried that he will resent that I leave just based on conversations. I am concerned he will, I don't want to say, hold it over me over my head when I come back and if we stay together, I am a little worried.

[Nick]

But what makes you worried about that?

[Victoria]

He's very concerned. The conversation was very eye centric when it came to him. There were a lot of I statements like I can't believe you would leave me. What if you find someone and break up with me while you're there? I. What am I supposed to do when I'm home here? What about what Everything we've worked through over for the past two years, building this foundation, etc.

[Nick]

Which is, I imagine, in the heat of the moment when I imagine all this is coming from at a time where he was first just processing the news that you were incredibly serious about this.

[Victoria]

Yeah, yes, absolutely.

[Nick]

Okay. And so the fear that he might resent you is that again, just based off of just common sense and these I statements that he mentioned recently or is there something more about his personality that he's also that you've gotten to know that makes you like think he, you know, is a little resentful and kind of has a side to him that would ultimately not see the bigger picture when you got back and assuming like, let's say you went over there whether he loved it or not, but he was just like, you know what, obviously I don't like this, I don't love that my girlfriend's leaving. But I want to support you. Obviously I have a lot of fears and anxiety about this, but I want to support you. And let's say you go and you choose to work. You guys work through it as a couple and you're faithful and he's faithful and you come back. What makes you think at that moment he would be like, you know what? You got to do this. And I'm going to start, you know, like, and just kind of always bringing it up as like the thing that, like pissed him off that he feels like you owe him for. Like if someone was unfaithful and that person forgave them, but they never let it go in the relationship and things like that. What. What makes you think that he might do that?

[Victoria]

I mean, I think it is a little bit personality, but also just who he just kind of like who he is. I think also just my personal fears about it. It's. I also, I think part of it is I, I'm. I might also be projecting kind of what I am worried about as well, just because I've been thinking a lot more about if this relationship is for me. And so it's just that whole. It's just all of it, I guess, together.

[Nick]

Okay. And then I guess, what part outside of this scenario, what part of the relationship is this? Are you also wondering, like, is this relationship for me?

[Victoria]

He's been very certain since the very beginning. I, again, this is my first relationship. I love him so much. But I've been doing a lot more thinking recently. There has been. There was a time when I was like, yeah, I could see a future, but as time has gone on, I just see less and less. Okay, that sounds bad. I just don't know if I picture him in my future as much as he pictures me in his. I did go against some non negotiables that I didn't think were important in the past. And you used to talk a lot about this. You used to talk about how important non negotiables were. And I've thought about it a lot more recently and I've realized how important they are. I should have listened to you a long time ago. I apologize.

[Nick]

Whatever. I don't listen to me often. You know, what are some of those things you're referring to?

[Victoria]

Well, so I'm Jewish and something important to me is I do want to have a Jewish family. I want to, ideally would love to marry someone who's Jewish and he's not.

[Nick]

Okay.

[Victoria]

And for a while that was fine. Um, but Again, more recently, I've been thinking more and more about it as more of my friends get married, have kids. It's been more of a topic on the top of my mind, I guess. Okay.

[Nick]

Yeah, that makes sense. Yeah, I think, you know, usually when with those types of things, I mean, we're younger, we might be a little more rebellious, and then we definitely get out of that rebellious phase and realize, no, that maybe this does matter to me more than I thought. Well, okay. Anyways, I just. Thanks for sharing all that. I'm not trying to. Like, you're not even asking whether you should break up or not. I just. I always want to hear your thought process, it being your first relationship. I also just want to make sure you're making decision with, like, a clear head. It kind of raised a bit of alarm bells for me when it's this whole story started by, like, so I lost my job. And usually those types of, like, pivotal moments, like will. Will. Will affect us in ways that we don't realize. And then kind of a snow. Snowball effect. And maybe sometimes all for the pos. Maybe, maybe, maybe this period, Will, is a wake up call for you that you've been kind of, you know, sitting on and not doing anything about making meaningful changes in your life. And you've been kind of going with the status quo and living in a more of a state of comfort rather than like, hey, I'm only 27. Like, now's the time of my life to be a little riskier. I won't get many opportunities to do what I even have an opportunity to do. So now, Now's the time. I mean, how do you break up with someone? There's no good way, right? Like, and, you know, so couple of things is to remember, I'm sure you've heard me say this before, you want to be direct and kind at the same time. All right, you also, your. Your goal is not to be friends with him, and your goal is not to make sure he likes you when you walk out the door, so to speak. You know, you have to allow him to think of you as the villain in his story. You're gonna break his heart. He's going to be like, why are you quitting on us? I'm willing to. Like, it's gonna feel like it's not good enough for, you know, it's like, first he presented him with this thing that you wanted to do, and he's like, he hated it. Like, and then he was like, well, I guess fine, if I don't want to like, stop you from chasing your dreams. So, like, I guess go, I have my concerns, but, like, big picture, if we end up together, like, this is a blip on the radar. So, like, I guess I'll support you. And now you're gonna be like, well, actually, just kidding, I don't want your support. I just, I want, I don't want you. And that's gonna hurt, you know, and so he might be angry and sad. And although all those things, it's gonna be a process. So, like, I think the, the nicest way is to be as kind as possible. Do not sugarcoat things. It's better to be direct and kind rather than to, like, insert unnecessary hope that he is going to be looking for. He's going to look. Be looking for you to say things like, maybe in the future, or, I don't know how I'm going to feel when I get back. And that might all be true because you're also going to be operating from a place of fear as well, right? Like, you don't know for sure. Maybe this is a mistake. I don't. Who knows? I don't know. Like, but if this is how you really feel, then, you know, then, then it's okay to, like, have your heart change, so to speak. And so people in your position are going to want to hedge the bet, right? You're going to want to be like, fuck, well, if I do, like, I do want him to not be mad at me. I don't want to be a bad guy. I don't want to break his heart. And, oh, by the way, if I change my mind, I want to make sure I can get back in. But I don't think you should, that should be your priority in the moment. I think it is one of those things. You have to be as respectful and as kind as. And then allow him to be angry, to hate you in the short run, knowing that you ultimately didn't do anything mean or cruel. And he will eventually get over it and see it for the big, big picture that it is. But, like, don't fill him with false hope. Don't ask to be friends. Don't. You know, and he's gonna figure out, you know, he will try and he will really try, most likely, to figure out ways to stay connected to you. And it's gonna feel mean to turn him down because it's going to feel so reasonable. And it's also going to feel like something honestly that you want, right? There's a good chance he'll. He'll be angry he'll be sad, whatever. And then, like, maybe a week later, before you go, he's like, I totally get it. I'm sorry if I handle it this way. But, like, I just want you to know that, like, I'm still here for you and I, you know, I'll still be a friend to you. And like. And in the back of my mind, what he's hoping is to just have access to you. He just wants to stay close to you. Right. Because, like, the, there's so many phases of breaking up, right? Like, there's the initial breakup of like, hey, just bad news, don't want to do this anymore. Right. And then, and then you both grow this for this emotional process, right? Like, he being on the receiving end of. Of heartbreak. He, he, he's. He's going to have a relationship with you in his head for a period of time. Well past that, Right. He's going to be talking to friends and having conversations in his head and things like that. And that's where, like, the hope can be very dangerous. You know, that's where it's just like, you don't want him ruminating over your maybes in the will sees and like, the possibilities in the future, and it's all, you know, and it will be something that also you probably would benefit from. But it would be ultimately selfish of you to take him up on that offer. For him to be available to you.

[Victoria]

Yeah.

[Nick]

When you want. While he essentially puts himself on hold and he's gonna say that he wants that and you're gonna turn him down for that, and he's gonna take that as. You don't even want me. Why? You really fucking hate me. You don't even want me in your life. That is, in my opinion, the right, most mature way to approach this very. It's hard to do, you know?

[Victoria]

Yeah, it's hard to think about. It's been difficult. There, There have been other times that I've questioned the relationship throughout, and I just. I mean, things have been fine, they've been good. And yeah, you did mention comfortability and everything as well, which is definitely. I know. A part of it.

[Nick]

I think you didn't ask. But I do think in your breakup, you should communicate to him and it will feel, I'm sure you. Because I'm sure somehow he's aware of this and it's going to feel like you misled him and you changed your mind. But I would communicate to him your desire to marry a Jewish man.

[Victoria]

Yeah, we. We've had that conversation before, actually. It actually came up kind of recently too.

[Nick]

Yeah. How did it go?

[Victoria]

Well, I, at the time, he was like, I appreciate you accepting me, like, for me, because it was brought up. I was like, you know, something important to me. We had one of those conversations, like, what's important to us in the future if we do want to make this work? And I said, you know, I want to raise my kids Jewish first and foremost. Like, that is very important to me. And I asked him how he felt about that, and he was like, yeah, I'm all for it. I'm 100 on board with that. I will support that. And I juice, you can't really ask people to convert. We don't do that. And so I said, would you ever consider the idea of converting? And he actually hit me with the. I actually always thought I would get baptized when I was older. I was like, that wasn't answering my question, but definitely answered the question. And so I've been thinking about it a lot since then. And then he was like, thank you for accepting me for me. And I was like, I.

[Nick]

What did he mean by that?

[Victoria]

That I. That he wasn't interested in converting? That I. I was like, I. I love you. I love you for you. But I've been thinking about that conversation a lot more recently.

[Nick]

So you're going to be basically telling him, I, I don't love you. That's how he'll tell you. I mean, listen, I'm giving it a hard time, but yeah, yeah, these are very difficult conversations to have. And he, he heard what he wanted to hear. And you. Sounds like you, it. You didn't get the response that you're hoping for and you didn't really know how to say anything.

[Victoria]

I, I kind of had to ruminate.

[Nick]

On it as a follow up. And he was like, thanks for accepting me. And you're like, I guess for now, circle back.

[Victoria]

Well, in the moment I was like, of course. I love you so much. And then I thought a lot. I'm home alone by myself a lot. I have a lot of time with myself in my brain. It's been tough recently. But I guess another question is like, do I bring up any other things? Like, there are other things that have bothered me throughout the relationship. Do I bring them up?

[Nick]

No.

[Victoria]

Okay.

[Nick]

Because that, that to me is just like piling on unnecessarily. And you might get into like, semantical arguments and things like that. And then like, there's no point giving. It's like in giving him notes about essentially something that just might be Preference based.

[Victoria]

Yeah.

[Nick]

On your part. And this is not like an exit interview from a job where you're just like, hey, in the future, like, in case you care, you know, that's just not the role that someone breaking up with someone needs to play. And. But I, I just, I do think the exception to that is the non negotiable that you're realizing is important to you about your faith, that he can, he can't do anything about it. And I mean that in a good way. Where it's just like, that is part of your upbringing, your heritage, whatever you want to call it. Right. And yeah, like, you might owe him an apology for having to like, learn that about yourself in real time while having a relationship with him. Because from his point of view, it might feel a little misleading. Hey, she told me it wasn't that important to her. Now she's telling me it's important to her. That seems unfair. Had I known that a year and a half ago, I never would have like, allowed myself to fall in love with someone who ultimately told me, like, I'll never marry you because you're not Jewish, so he's allowed.

[Victoria]

I wouldn't have let myself get into the relationship if I had known.

[Nick]

Yeah, of course. And he, that's just like how he's like, I'm just anticipating how he might feel.

[Victoria]

Yeah.

[Nick]

But I just, it's something that I think he can eventually accept that. Right. Like, and that's why I think you should communicate that, which is like, you know, these are difficult conversations to have and I don't honestly don't know the right way to have them. And I'm apologize. I apologize for if you feel mess, feel misled. I didn't really know. But the more I'm reflecting and, you know, I'm realizing it is of great importance to me and I don't want someone to, I don't want to force someone to convert. I obviously, like, it's a very, you know, you can be honest about that. Like, you know, there is no wrong answer, but the answer you did give me is not something that I'm comfortable with. But you gave me the right answer, which is your answer, which is true. It's just like he doesn't want to and you don't want to. Like, will you do this for me? Like, like, that's just a weird. You want to share your religion with someone. You want to share in your faith so that when you raise your children, it's a, it's something you're sharing, not be like all right, kids and husband. This is how we're. Let's talk about Judaism. You know. Yeah, you don't want to do that. Right? So, you know, he didn't give the wrong answer. He gave the, you know, and so. But I. I just think, personally, just an opinion that that would be something that will allow him, when he's ready, to get over you.

[Victoria]

Okay, that makes sense. Yeah.

[Nick]

He won't want to accept it right now. It will feel like you misled him. He'll be angry about it. He'll ask questions, he'll say things. Eventually he'll be able to be like, I'm not Jewish. I didn't want to be Jewish. And as much because he, like, he might say things like, is it about converting? I'll convert. I mean, if this is what you really want, just tell me. I'll. I'll do it. And you're gonna be like, that's not what I. That's not what I want. And.

[Victoria]

Yeah.

[Nick]

And eventually when he gets over it, he'll be like, yeah, I'm glad I didn't do that, because I didn't want to do that. And I was only doing that for her. And that's just not help. Like, that's not why people should be doing those types of things. But we've all made 100% exceptions in very vulnerable moments, Right? I think maybe you should. That's the one thing you should be honest about, because it is in the best possible way. He can't do anything about it. And he should eventually be able to accept that reality so that it won't allow his ego to just be like, well, why couldn't you be Jewish? You know, like, you know.

[Victoria]

Yeah, I really appreciate you. I appreciate hearing this and you saying this, because I, at my core, am a people pleaser. And I. I mean, we. There was a long time in our relationship even where we just didn't bring up any frustrations because neither of us wanted to rock the boat. I didn't want to ever hurt his feelings. I he similar. And so I'm so scared to hurt him. Like, genuinely. That's kind of like, at the core of this too, is I love him. I don't want to hurt him. And so I appreciate you saying that. That, of course I'm gonna hurt him like that. That's inevitable, but it'll be okay. I appreciate hearing that from your perspective, just because I also, again, I've only ever been in situationships. I've never been in an actual relationship. And so I've Never been on the receiving end of a breakup either. Like on either end of it. I should say so.

[Nick]

Yeah, yeah, it's tough, it's tough to know if you're doing the right thing, especially if ultimately, like so many people, it's just like even me, I, maybe my third relationship was somewhat. Even then there was some toxicity and we were arguing a lot, but a lot of it. Most people just like only break up after they've exhausted. Like, it's just like, oh my God, Honestly, like, why are we together? This is so, so exhausting. But doesn't sound like that's the position that you're in, but for different reasons. There's something inside you that's telling you that there's more out there. But yeah, I think if you, if you're kind and respectful, if you know, like it's true, like if there's, if there's really a future for you guys, you, you will, you will find your way back to each other. I'm not saying that as someone who believes in fate or destiny, but if you both mutually realize that you guys threw something really great away, then you will find your way back together on the, you know, otherwise. The alternative is, is one of you comes to regret it and the other one does it. But that's only because the person who regrets it in that moment has just gotten impatient with their reality or decision. Right. So.

[Paige]

Right. That makes sense.

[Nick]

And so like you being the breaker upper, I know he's wonderful, yada, yada, yada, but the reality is that you think there's something better for you. Not that he, you could. It's not about you doing better than him or anything like that, but there's something inside you that says there's something better out there for me based off of my wants and my needs, my non negotiables, whatever. Right. And you're now going to make a decision to do that, which includes you going abroad and teaching. And when we make those decisions in the back, we always are kind of like when we're feeling adventurous, when we're betting on ourselves, we, you know, kind of in that mindset of like, things are going to happen for us, but the next person you connect with, it might not happen when you expect it. Right. And so then you might become impatient. Maybe you'll feel lonely abroad, you'll want to reach out. You know, you're going to be looking for comfort. He pops up on your explorer page and he's looking good and you're like, man, like. And then you convince yourself that maybe you made a mistake and that you miss him. And like, you know, you start missing, you start only memory remembering, like all like the cute little moments and wonderful moments. And then all of a sudden, like, you find out he has a girlfriend. And then that hits you that you find that out when you're feeling the most loneliness in abroad, like right after, like, you made a friend, but you had a friend breakup or whatever, and you're feeling really vulnerable right now. And then all of a sudden you're just like, I made a terrible mistake. And in reality, that's not you making a mistake. That is you just like becoming really impatient with your decision, things not working out quite the way you wanted to, and then operating from a place of fear because the person you rejected that you like, right now you're up. As much as you care about them, you don't want to hurt them. You are in a position of power right now and you're in control of your destiny. And that, that is a feel good thing. And if that scenario which I just painted, like, happens, you will feel powerless and he will feel in control and yada, yada, yada. And that is not like the world telling you fucked up. That's just like, that's just life saying, you know, you don't get to dictate terms and you have to be a little patient and that's all that's happening, you know, and he's gonna be impatient because he's, you know, right now he wants to be with you. But like, I guess what I'm saying is maybe you go there for 10 months and you find your way back to each other and you realize, and he's like, you know what? I, in the, in the meantime, I looked into Judaism. I don't, you know, whatever. And like, maybe you'll find your way back, but it really comes down to being mutual, right? And if you both want it, the same reason why you'd want him to convert would be the same reason why you guys fell on your way back to each other. Because it just, it worked out and no one had to convince the other person and no one begged the other person. And no one sat around and waited for 10 months, like, while the other person lived their life, only to, like, have that person resent that person for sitting around even though they didn't get asked to sit around and yada, yada, yada.

[Victoria]

No, I, I'm also kind of a believer of, like, everything happens for a reason. If it's meant to be, it's meant to Be. So I'm. I've also told myself that. Told myself that more just to help me feel better about the situation as a whole more than anything else. But I agree with everything you just said. I appreciate it. It's. Yeah, it's been hard. And I know it sounds like it was maybe like a split second decision that I made, especially because I'm in this weird place in my life after being laid off and everything, but I think it's been. It's been growing for a while, and I think this is just really kind of. It's brought it to a T. Like, I have to figure out my life more and I don't have to have my life figured out, but you know what I mean?

[Nick]

Yeah, for sure. When do you. When do you leave? Have you already said yes to this opportunity?

[Victoria]

Yes. Yeah, I have. I leave end of August coming up. Yeah.

[Nick]

Yeah, just go ahead and rip the band aid off.

[Victoria]

Okay. Yeah, okay, I will. Thank you. I appreciate it.

[Nick]

I really don't want. You want whatever grieving and emotional, like, just energy you're gonna have to spend on this breakup because you care about his feelings. Do it before you leave, not when you get there, you know?

[Paige]

Yeah.

[Victoria]

Yeah.

[Nick]

You don't want to be dealing with, like, calls from him. Can we just talk? Can we just talk? While you're supposed to be. Your energy should be focused on your new adventure, Teaching, making friends.

[Victoria]

Yeah.

[Nick]

You know, clean your house, so to speak, before you go. So, like, I would. I would do it sooner than later.

[Victoria]

Okay, I will. Yeah. It's a ten hour time difference too, so it's. It's a huge time difference, so.

[Nick]

Sure. But that's not why we're breaking up with them.

[Victoria]

No, no, no. Not. No, no, no, no. I'm just saying, like, if we were to try and do it, try and make it work, which is like the mindset at the moment, it would be really difficult, so.

[Nick]

No, I know, but I'm saying, like, all those thoughts of you trying to convince yourself you're making the right decision, it sounds like you know what you want to do deep down and you have your reasons in either way. Like, that's how you feel right now. And I think you got to. I think you got to follow through. And.

[Victoria]

Yeah.

[Nick]

As long as you're respectful and, you know, direct, if you will, you will have an opportunity if, if, if. If life wants you to have one with him.

[Victoria]

Yeah. Thank you. Yeah. I appreciate it. I really do. And it's more than just this one non negotiable that's been building up. But I think that's the biggest reason of it all, I guess.

[Nick]

Yeah. When he starts asking questions other than, you want to marry a Jewish man. And I would just be really direct about that. Just because I would say, like, listen, I. I just. Something I feel and I need to do this for myself. I don't want to sit there and, like, give you a bunch of, like. I don't want to have to come up with reasons. Like, it's not going to sound good. Is it another guy? It's just like. Like. No. I mean, you know.

[Victoria]

Yeah. I won't. I won't bring up the fact that he forgot my birthday two years in a row.

[Nick]

I'll.

[Victoria]

I'll leave that.

[Nick]

Yeah.

[Victoria]

In the past, but.

[Nick]

Yeah. I just wouldn't sugarcoat anything. Okay. I just. If he asks questions, you should. If he wants. If he asks you direct questions, give him direct answers.

[Victoria]

Okay. Sounds good. I appreciate it. Thank you. Thank you.

[Nick]

Well, good luck. Congratulations on the new adventure and. Yeah, it's never fun or easy.

[Victoria]

Yeah. It's that everything in the near future is a new experience, big or small.

[Nick]

Well, you'll be glad that you bet on yourself.

[Victoria]

Thank you. I appreciate it.

[Nick]

All right, take care.

[Victoria]

Thank you. Bye.

[Nick]

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[Angeline]

My name is Paige. I'm 37 years old and I am in love with my boss. Help.

[Nick]

Okay, tell me more about this situation. Let's start with like your relationship and his relationship status.

[Victoria]

Okay?

[Angeline]

Great. So this is a new boss of one year. I have been working at my current job for over a decade, but this is a new boss and we. He's my direct boss, and we work together every single day. All the time, see him all the time. And it basically is just something that's grown over this past year. And it's not great because of course, he's my boss, but he also happens to be taken.

[Nick]

Okay, yeah. So he's in a relationship.

[Angeline]

He is in a relationship.

[Nick]

And is this. And these feelings from your point of view, are these just you falling in love from afar, or do you feel like he reciprocates those feelings despite his relationship status?

[Angeline]

I feel he reciprocates those feelings despite the relationship, which is why I definitely wanted to call in, because it feels like I'm not the one initiating things, but I absolutely am feeling the same way.

[Nick]

All right, so as much as you possibly can and as much detail as you can, tell me the first moment that you thought of, is there something here? And then give me as many examples as possible that were him doing something that you took as him taking the initiative or flirting with you or showing an interest in you that you thought was unique and special.

[Angeline]

So I would say the easiest kind of example and kind of list of examples is we work together on a lot of different events and projects that actually take place over long periods of time. So they're not necessarily one off events. And so we spend all that time working together. But then what would happen is the minute we would head back to our respective households, it would then turn into another phone call to basically go over what just happened. And then that phone call somehow turns into like two hours of conversation that has to do nothing with work. Or after we finish the event, we're going to dinner, we're grabbing drinks, just him and I. And I'm part of a larger team. But those team members are never invited to those scenarios. And one in particular, I think good example would definitely be where we were out of town traveling for an event. We were staying in the same hotel, and the whole team basically went back to their hotel rooms and was like, okay, I guess we're in for the night. And then the minute I got back to the hotel, I got a phone call from him and he just said, dinner, question mark. And so it was like this moment of, okay, team, good night, see you tomorrow. But then calling me immediately after and taking me to dinner, basically. And so that's, I think, one of the main ones. But to answer Your question about dinner.

[Nick]

Is dinner like what are you guys talking about?

[Angeline]

Like a four hour dinner, drinks, he pays situation.

[Nick]

He pays or the company pays?

[Angeline]

He pays.

[Nick]

Okay. Is he, does he have a girlfriend? Is he married? Does he have a fiance? What's his relationship status?

[Angeline]

Girlfriend, but it's long term and they live together currently. Okay, so they've been together for about six years.

[Nick]

How much does he talk about her to you?

[Angeline]

To me, never. So I've heard him have conversations about her with my co workers or like other people I'm around, but he never brings her up with me.

[Nick]

And this is ongoing?

[Angeline]

Yes. And I feel like it's getting more and more as we have more and more time and events together. And so it just. For example, just last night we communicated on the phone for like two hours and it was about like our personal traits and where we get them from and our humor style and like it just starts to get more, less and less about work and more and more about like personal.

[Nick]

Has there been any, outside of like dinners that all, everything you described, has there been any like physical moments or moments of like things got a, a little out of hand or do you guys cross any boundaries that way?

[Angeline]

Haven't. I will say, like, we're both incredibly professional in this situation. Like the first anything physical that's happened has been like a hug or like, you know, nothing. We haven't cross those boundaries.

[Nick]

Well, I wouldn't accuse him of being incredibly professional, but he, you know, that's, you know, he hasn't done the egregiously unprofessional things because keep him like. And how big is this organization you guys work at?

[Angeline]

It's not super big. I would say it's like my, like.

[Nick]

Do they have an official hr, HR department and do they have like a policy around like what you guys are, what you think is going on?

[Angeline]

Well, I would say, I mean, I would say it wouldn't be ideal. We do have an hr, an HR department. I would say it probably wouldn't be ideal to date someone within the organization.

[Nick]

Certainly someone that you work directly below.

[Victoria]

Exactly.

[Nick]

Right. Yeah. Okay. How old is he?

[Angeline]

37. He's my age.

[Nick]

So what do you want to do about it and what can I help out with?

[Angeline]

My initial question, honestly? Well, I think I have a few. I think like why I wanted to call in is one, get some advice on kind of like especially because I'm below him and this is my boss kind of. I'm trying to be very cautious with like how I respond when he initiates things like this. But also it's like he kind of like leaves me with like a sense of hope. It almost seems like we have so much in common and we have so much chemistry and we're not acting on it in a physical way, but feels very mental and emotional at this point. And I just, I feel like I want some advice to either be like go for it and like hold out for hope, which is not the way I want to go but or two, to just be like this has to stop, like stop responding, you know, those types of things.

[Nick]

So I think it's kind of what I'm looking for advice in the grand scheme of things. Where do your priorities lie as it relates to the like your career, this specific job, and your love life as it relates to him?

[Angeline]

I would say my career has always taken precedence, like my priority definitely lives there. I haven't been in a serious relationship for a few years now and this is the first time I've kind of had such intense feelings for a while. So it's, it's like this toss up of like oh wow, this feels really great and I have this connection with someone but XYZ and just out of.

[Nick]

Here, outside of this relationship or whatever, whatever this relationship is just like what is your dating life look like? Or what do you.

[Angeline]

You know, I would say my dating life currently is pretty light. I absolutely like, I try hinge dating, I try online dating. I sometimes meet up with people, but in general, like I'm not dating that much and a lot of that is because I've been so busy with work. So it's just kind of interesting that now the person I like is like a part of the work.

[Nick]

Yeah. I don't if that's less interesting and more of a, a result of, of where you're investing your time and energy.

[Angeline]

Right. Okay.

[Nick]

Yeah. Less than, of like oh my God, fate, like coincidence.

[Paige]

Yeah.

[Nick]

Okay, so just a couple things. I think it's important for you to consider, to try to think of this for more an objective approach. It's like if you are, for one, if you're right about his potential feelings, then you have to acknowledge he's doing something wrong.

[Angeline]

Yeah.

[Nick]

And I think that's something for you to note about his professionalism, his character, his potential as a partner. All of the above. Two, like I agree with you. Like the picture you painted is, is goes beyond the like I don't know if this guy's flirting with you, you know, type of thing. Right. But a guy in a long term relationship who's been dating the same person for six years. Like, whether it's a, you know, girlfriend or a wife, there's, you know, I guess, I guess things become routine and stale and whatever. And this could be very easily his way of, of threading a needle, which is to not really do anything wrong. None of your conversations really have, like, broached topics of, of true inappropriateness other than, like, I don't know, we were just two colleagues who had dinner and we talked about life, but I don't know, I didn't say anything. I didn't hit on her and touch her and say anything inappropriate. We just, like, we're being friends. I don't know. We're just two adults, like co workers. I don't know. Like, but he, you, you know, he could be enjoying your company as a woman and he could find you attractive and, and, and this is an outlet for him that makes him feel, you know, test the waters of whatever it is he's looking for that. But he's not actually seriously considering you at all. Right. Like, he could easily be like, oh, what are you talking about? Like, I, like, right. I just, we're just. What are you. I'm sorry I led you on, but like, I, we're, we're just friends. Like, I'm in a relationship, you know, he could easily say that. So that's something you should consider. I, I think what you should do based off of that, if this is someone you really want to pursue and you're going to give him the benefit of the doubt that like, if you are right, like, despite like the low car character moment he is having by pursuing you while being in a relationship and kind of like going about in a way that's like, not very professional and, and potentially puts both of your careers at risk. If you want to forgive all that and still like, like, cross your fingers and like, see if there's something there. I definitely don't think shooting your shot is the way to go about it. I think it's more the opposite. I think you pull away a little bit. I think you kind of become unavailable, take away the thing that he's benefiting that goes outside the scope of your job. Right? Like, you going to dinner with him is not part of your job requirements. You know what I'm saying? Like, that is something that you are both, as adults agreeing to do because you find it fun. Now you are getting something out of it that you're not sure he's getting out of it. You're wondering if he is. But have Developed these feelings. So, like, you just need to stop giving that access to him and see how he responds.

[Angeline]

Right. And that's. Well, no, and I think. And that's why I wanted to call in and kind of hear your thoughts. Because there's also the other part of me that like, hates the fact that I'm even a part of it because he's in the relationship, the long term relationship, obviously. And again, like you said, it very well could be we're friends. Like, what are you talking about? Like, I actually really feel that. But I also don't want to be like this, this girl that he's hanging out with while he's in a long term relationship. Like, that doesn't stop that.

[Nick]

Right. And again. Yeah, you exactly. All you. What your move is to just change something up, right? You don't have to put yourself out there. You just become more unavailable. You don't need it. And like, you don't sit them down and be like, just, you know, I think we need to stop doing this. He's like, well, what are we doing? I think you just become less and less available. So much so that he will just organically feel it. He's like, wow, she's. She's just been busy. Every time I ask her to have dinner, she's just. I'm only. She. I only have access to her. Like, I have access the rest of my employees, you just switch up without any explanation because you don't owe him an explanation. And see if that rat, like, see if how he responds, right? Like, he might just leave it, let it go. And if he's just like, hey, just like, wow, just did I do anything? You know, like, which would be kind of. If he says something like that. But if he starts asking you more questions, then, you know, then depending on how he asked, then you can kind of change your decision tree about how you approach it. But I would make him bring up the topic, whatever that is. So you know what I'm saying? Like, I would make him call out the thing that you think might be.

[Angeline]

There might be happening. Right?

[Nick]

You know, even if it's just, oh, I really miss our friendship. And then you could just be like, you know, if he says something like that, then I would, I would say that would open the door for you to say, I'm just not entirely sure our friendship is appropriate given, like, situation art, you know, like that I work for you and the fact that you're, you know, even if it is just platonic. I don't, I've never met Your girlfriend. If I were her, I would want to know who I am. You don't say any of those things to him. He has to, like, ask you a question and he's got to call it out. That makes you the only. The only response is to then call out the thing that he is tiptoeing around. Does that make sense?

[Angeline]

Yeah, that makes total sense. And, and honestly, like, so I'm, I mean, I'm a huge listener to your podcast. I think you have, like, such good advice. And like I said in my email, I was like, even if it's tough love, give it to me. But I find it interesting to think about the idea of, like, men and women friendships and like, can they be. Can men and women just be friends with each other? And I grew up with, with a lot of male friends, but, like, in this situation. And I also think about a lot of your podcasts where you're like, sure, like, men and women can be friends, but when they're finally like, in a long term relationship or a relationship at all, you gotta, like, let up from that. And I feel like that's what he's not doing.

[Nick]

Yeah. Or re. Engaging with you. Like, I don't think any peop. Any people in a heterosexual relationship are having regular dinners with people with the opposite sex that aren't, like, filling some sort of void that they're not getting in their relationship. So, yeah, I think for the most part, people of the opposite sex who are in committed relationships can't or really shouldn't be in, quote unquote friendships. I had a lot of, and I've said this before, but I had a lot of very platonic friendships with women when I was a single guy. And I'm still friends with a lot of those people, but the dynamic of those friendships have drastically dated, even though we were very platonic friends. And there was never any, like, awkward tension or like, weird moment. But like, me going to dinner with them, like, still, like, played a role in my life. You know, I had the, the company of a woman at dinner, and even though we were platonic friends, it was not the same as going to dinner with the bros, Right? Like, going to a movie with a girlfriend who was just a platonic friend, like, still filled it, like, filled that role of woman companion. When I was a single guy, right. There was nothing physical going on. But there was. And then when I got a relationship, I wanted to invest that energy into that relationship and that person. And so, like, nothing against my platonic girlfriends. It wasn't like, oh, There was something going on there. It was more like, I don't need a woman to go out to dinner with, so to speak, because I got my partner, I got my girlfriend, you know, And I really think that's generally how it, how it works. Always, always exceptions to rules. But I think for the most part, like, him investing time in you and having dinner with you, you're doing something for him outside of your job requirement, right?

[Angeline]

Yeah. And I always, I kind of felt that way too, because it's like, with past bosses or other people, it's like, that wasn't like, work ends and that's it.

[Nick]

Yeah.

[Angeline]

Like, we're not, like, doing any further hangouts.

[Nick]

Also, there's the whole, like, again, like, power dynamic. That's, it's like, he's your boss and he is being very sloppy with the fact that, like, he should IGN these, these long, intimate conversations and dinners. He should be like, with, with a woman that works under him, that's in his same age group and he has a relationship. He should be worried about optics and he's not, you know, he should be worried about. I mean, I, I. Does his girlfriend know that you guys have dinners? I don't know. Maybe yes, maybe no. Maybe he's always selling it as like, a work call. I don't know. Maybe this have. But, like, the fact that you feel the way you do and you are unclear about how he feels. This is not like, I'm obsessed with my boss and he, like, he, I'm delusional and he's in a happy relationship. I just love him. I don't know. What do you want me to do? That's not what this is. Right. Like, you're giving me some, like, very solid examples of like, I don't know, like, why does he fucking want dinner with me? You know, why is he always calling me?

[Angeline]

Yeah, that's another thing. I'm always like, at the end of an event or whatever. I'm like, why is he calling me and not, like, talking about that event with his girlfriend? Like, it's just so bizarre.

[Nick]

Yeah, I mean, yeah, that's a good question. Yeah.

[Angeline]

And then just the kind of, the other one example I did want to give you that I thought was really kind of wild was I overheard him talking with another person, not colleague, but person that we contract out for these certain events. And that person was talking to him about, like, just his personal life and like, you know, Are you married?

[Paige]

No.

[Angeline]

Do you have a girlfriend? Yes. Do you want to have kids? Like, and his response that I overheard was like, well, yeah, that's kind of the issue. Like, I've. I've always kind of wanted kids, but my current partner doesn't. And then, like a week later, when we had dinner, he was like, do you want kids? So it was like a very. Yeah, it's just all those things together.

[Nick]

A lot of red flags here, for sure. On the off chance that you two are destined to be lovers and have a family together, then I think it's really important for you to go about this in a very tactful, in a very deliberate way to protect both of you. Because if you are seeing this the right way, and let's say he actually has some feelings for you, he's not going about it the best way. And one of you two need to step up for the both of you. And again, I think to protect yourself, since you don't know, change the variables in this equation, change your actions, see how he responds. And the first thing you again call out is that. Like this. I just don't know, you know, make him call it. He's. Because, you know, like, oh, did I do something wrong? And, like, no, you know, it's just. I would play dumb at first until he really calls it out. Yeah, I've just been busy. Whatever. Oh, I miss. I just miss our friend, you know? I don't know what he's gonna say. Like, I just missed. I miss having dinners with you. And that's where you could be like, I'm just not, you know, to be honest, like, that's kind of why I'm not available, because that. That doesn't feel like something. I'm confused by what that means. And the fact, you know, the fact that you are unavailable and my boss is why I. I'm not available.

[Angeline]

Right. Okay. I think that's. Yeah, No, I think that's great advice.

[Nick]

Something like that, you know?

[Angeline]

Yeah.

[Nick]

But if he wants to shoot his shot, you don't make it easy on him. He's got to deal with his shit. Step one would be maybe ending the relationship rather than, like, you know, he's doing the very low character thing, which is he's out there window shopping and he's like, test driving cars while thinking his current automobile isn't, like, actually right for him.

[Angeline]

Well, and the other thing is that the current partner, I think he met through work.

[Nick]

So it's like a. Yeah, well, that would just be another red flag now. Yeah.

[Angeline]

Well, then again, that's why I called in, because I'm like, obviously, like, these are all Very much red flags on his end. But I also was like, yeah, but I kind of want to know, like, what's my problem if I'm like, interested, you know what I mean? If I'm like, you know, what's happening here? But I mean, I don't know if.

[Nick]

It'S a problem, but like, you know, listen, you're. Everyone nowadays out there and dating is feeling a little bit of loneliness. It's hard for. People are having a harder and harder time connecting, regardless if you're 21 or 37. And when we get lonely, we, you know, we make exceptions to our rules and boundaries and things like that. And, you know, he. You're enjoying the conversation. You're, you know, like, it's ultimately like harmless, but, like, you at least have the self awareness that, like, you know what, you've let this go on a little too far. But before things get really inappropriate or you really do something that you regret or, you know, you're at least asking yourself the right questions and wondering what you should do about it, which is, I think, positive, you know, I don't think anything that's going on right now is something you really need to, like, beat yourself. I don't think it means anything other than like, yeah, like, you know, like everyone else, you're looking for connection. You found it with this guy. Unfortunately, he's not available. He's also your boss and he hasn't really been direct with you about what his expectations are or why he's inviting you to these dinners. And he's kind of playing dumb and having his cake and eat it too, and. And now you're finally kind of calling it up.

[Angeline]

Yeah, no, exactly. Well, I appreciate you saying that and feel like I'm not crazy. It's definitely is the connection thing and just trying to understand what the best move is. But yeah, I like your. I like your advice about just kind of taking a step back from the extra things, you know, outside of what. What our work responsibilities are.

[Nick]

Yeah. So next time it's like, sorry, no she at work.

[Angeline]

Interestingly enough, next week we're actually traveling for another event so I can test it.

[Nick]

That would be very professional and very unavailable to him outside of very specific work obligations.

[Angeline]

Yeah, okay, I will do that.

[Nick]

Oh, keep us posted. We'd love to know how that all goes.

[Angeline]

Yeah, I will. No, I will for sure. Now that I have like a game plan and tell you what happens from there.

[Nick]

Well, appreciate the call. Good luck. Keep us posted on how things play out.

[Angeline]

Well, thank you so much for your advice and I love the show and we'll probably be listening forever. So thank you.

[Nick]

I appreciate you saying that. And as always, thanks for tuning in.

[Angeline]

All right.

[Nick]

All right.

[Angeline]

Thanks, Nick.

[Nick]

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[Paige]

Hi, I'm Angeline. I'm 22 years old. And am I the idiot for giving my high school ex another chance?

[Nick]

Okay, are you guys like, like, are you still considering this? You guys like officially back together?

[Paige]

So there's like a little bit of background if you don't mind like me diving into it a little bit. I'll make it brief because it's, it's kind of like a years long thing. So me and my ex started dating when we were in high school, like our sophomore year of high school. And then we broke up because, you know, high school relationships are whatever. And so we broke up within like six months. And then from there we were like on and off friends with benefits, like hooking up, that kind of thing until like our senior year of high school. And then he got a girlfriend and then they broke up and then we started on and off again until like our sophomore year of college.

[Nick]

Okay.

[Paige]

And I haven't seen him since then.

[Nick]

So what made you stop seeing him then?

[Paige]

He just like would put an end to it. Like he would just be like, I can't have a relationship right now. Or he would just like stop answering like texts or anything. So then I just was like, okay, then I'm not gonna message him anymore because I don't want to.

[Nick]

Look, most part it sounds like he has been the one to decided when things started and stop and like for the most part you've gone along with it.

[Paige]

Yeah.

[Nick]

And a few times maybe you kind of like said, well, if you, I'm not going to keep doing this. So you kind of stopped and then he would disappear for a while and then some time would pass and then he would reach back out and kind of convince you to like pick back up whatever it is that you guys were doing.

[Paige]

Right.

[Nick]

So again, back to like, are you guys back together? Or he's just now reached out again and has been pursuing you in similar ways as the past.

[Paige]

He messaged me, like, a while ago in, like, April, and we started talking again. And then we hung out once in, like, like, June. And then after that, I didn't. I haven't seen him since we hung out. But when he messaged me originally in April, it was this whole big thing of, like, an apology. Like, I'm so sorry. Like, I treated you like shit for all. Sorry. Treated you like, for all these years. And, like, I want to prove to you that I've changed since then. And, like, I. You don't have to give me another chance, but if you're willing to, like, I'd like to show you how different of a person I am. And. And I told him I was like, well, actions speak louder than words, so I'm willing to see what happens, but I'm not pro. I can't promise anything. And then we kept talking and talking, and I, like, he, like, slowly started, like, proving things to me and like.

[Nick]

Like, what do you mean? Whatever. Is this, like, before and is this prior to you guys meeting up in June?

[Paige]

Yeah. So he was, like, being, like, more considerate in his mess. Like, when he was texting me, he would be more considerate than I ever knew him to be. And, like, like, opening up.

[Nick]

What do you mean?

[Paige]

Instead of just, like, short one word sentences, he's like, actually, like, asking me, like, how's your day? How's this? Like, I was in a sorority in school. He's like, how's the sorority stuff? Like, actually, like, wanting to know about me and then rather like just being like, send me a picture of your ass. Like, it's. It was better than that.

[Nick]

Okay.

[Paige]

And I know that sounds like bare minimum, but, like, I had been used to something from him for so long.

[Nick]

That it was like, oh, it felt like progress, maybe.

[Angeline]

Yeah, yeah, yeah.

[Paige]

So then we hung out in June, and then I haven't seen him since then. And I made.

[Nick]

And I tried in June. Like, what'd you guys do?

[Paige]

We went and saw a movie. And then after the movie, we hooked up in his car. And I felt like we were in high school again, which is stupid, but, like, we both live with our parents, so we couldn't go anywhere else.

[Nick]

And then you haven't heard from him since?

[Paige]

I've heard from him. Like, we've talked and, like. But I actually haven't. Like, we didn't make any other plans to hang out again. And I tried.

[Nick]

Like, has he been pursuing you, not pursuing you? Like, who's dictating terms right now?

[Paige]

So there's no. There's no terms right now because last week he messaged me and was like, I have no time for a relationship. Like, I'm so sorry I led you on and promised you these things again, but the next year of my life or so is going to be insanely busy and I have no time to be in a relationship. And I was like, wow, okay, so.

[Nick]

Then what are you considering at this point?

[Paige]

Well, I'm just considering, like, I want to know how to not fall back into that cycle and, like, just for once, actually just not answer him back and not concede and not be like, oh, well, now you're back and you're saying all these nice things. How can I not forgive you for the umpteenth time?

[Nick]

Yeah, well, there's no magic pill. I think you first need to give yourself a little bit of grace, right? This is like, I guess for all intensive purposes, like, your first love, you know, he's been the first guy in your life. Those are always motherfuckers to get over your first love. Doesn't matter, guy or girl, whatever. Like, your first love just. It really messes with you also because, like, you don't really know how to get over them. Right. You have no playbook in terms of, like, someone emotionally breaking your heart and disappointing you and then knowing that, like, I can get over this, or just knowing that there is life in love outside of this, of the only real romantic relationship you've only really known. How much dating have you been? Have you done in between this guy?

[Paige]

My senior year of college, I. So, like, very recently, I had a boyfriend for, let's see, a couple months, I would say from like September to March, I had a boyfriend.

[Nick]

Okay.

[Paige]

And. And, yeah.

[Nick]

What was that?

[Paige]

And then. But he. It was nice. We met on a dating app and he. We broke up. Not because. And it sounds so stupid, the reason we broke up, he was. He's significantly younger than me. Not significantly, but, like, he's three years younger than me.

[Nick]

Okay.

[Paige]

And when he told his parents about me, they gave him an ultimatum of you either stay in college and finish it and we pay for it, or you can drop out and you can stay with this girl.

[Nick]

Okay. I mean, yeah, he's 18.

[Paige]

Yeah, he's.

[Angeline]

He.

[Paige]

Yeah, he. 18, 19. Yeah.

[Nick]

How did you end up meeting and dating at 8, someone who. Years younger than you?

[Paige]

It was just my settings on the dating app, I guess. He came up and I accidentally swiped right and we matched and we started talking and. Yeah, he was a freshman at my college so like I was a senior, he's a freshman.

[Nick]

Yeah, yeah. Back to the original guy. Yeah, I mean listen, there's no magic pill. I think it's just really holding yourself accountable. Right. Like one, I think. I don't know if you hear, you know, this would be interesting, you listening to this back and hearing it out loud when you're listening to yourself tell me this story about this relationship. But you paint a very clear picture that throughout this relationship he has dictated terms, he has come in and out of your life. You've always just accepted his words and he's always this kind of saying the right thing, never really delivering. Every time you meet up, you hook up. He ultimately gets what he wants. Most likely, you know, he's not to cliche, but like, you know, he's a young horny guy. I think even young, young men, like they might think they have the best intentions. They don't even realize all they want is sex kind of thing. And then you guys go to a movie, you hook up in the car and it's like ultimately he's like, yes, that's. I guess that's what I wanted. And then you start following up on some of the promises he made and he gives the like, oh, I'm so sorry, I can't do this right now. And he's really nice and apologetic about it and it sounds sincere and. And then he will reach out again. You know, like these types of like relationships, especially the ones that are like early in your life, have a way of just like going on forever and ever and ever unless you something about it like most likely he won't be the one. Either you will find the strength to enforce the boundaries necessary or he's going to meet another girl and she will make him do it, but he won't ever do it on his own. And then if they break up, he'll obviously circle back as long as he keeps getting the consistent sex. And it's just like, you know, he's very comfortable. He knows he's very comfortable with getting you to do what he wants. He's known you very long.

[Paige]

Since we were like 16. Yeah, yeah.

[Nick]

So it's just very easy for both of you to kind of get back into that kind of cycle. And so just being aware that that cycle exists and then holding yourself accountable, knowing that like you have to have these conversations with yourself in these moments. Right. And you have to anticipate the fact that he is coming back. In the past, I'm sure you've talked to the girl, your Girlfriends or yourself and be like, do you think he'll call me again? Like, do you think he'll do that kind of hope? Like, your ego just, like, making you feel like you weren't good enough. And then you.

[Paige]

All my friends and family hate him, by the way.

[Nick]

Okay, that's good. But at some point there was maybe those conversations, right? But you were trying. You were wondering if he was going to call back. And then that was. And so that when he did, he already had you. Right now it's like acknowledging he. He's never going to really go away until I enforce that boundary because, like, he. I keep giving him ultimately what he wants. You have to kind of mentally prepare yourself in these moments right now when you're seeing things a little clearer, because when he does reach out, I. It. You're vulnerable, right? Like, you kind of go back into that romanticizing the relationship. You're caught off guard by him sounding different and doing things a little bit differently. And that's usually followed by, like, periods of, like, gaps in the relationship. So, like, I don't know, you're thinking, like, maybe he has grown up this time. He's always like, it's a. Whether it's deliberate or calculator or whatever. It's like a perfect recipe to trick yourself into thinking there's hope with a guy you've always wished the best for but never really got what you wanted. And so the fact that you never really got what you wanted from this relationship will always give you that hope that ultimately convinces you to make exceptions for someone you shouldn't make exceptions for.

[Paige]

Yeah, I guess it's like when you said in the beginning you were like your first love. They're always like a motherfucker. And that's. That, like, has been the thought in my head, like, every single time. Because I do want him to be happy. And I wish it was. I wish he could just make up his mind one day and be like.

[Nick]

You don't care if he's happy. You want him to be happy with you. We don't give a fuck if he's happy. And I pro. Like, I think when you really accept that he's not your guy, you will be. Honestly say, I don't. Honestly don't. I don't give a. If he's happy. Like, other, like, human to human. Sure, you want everyone to be happy, but yeah, you don't give a. So, like, that is like, you saying that out loud. I think you. You need to recognize that's you still kind of lying to Yourself a little bit. Right. Like, we do these. We have these narratives in our head where we try to, like, sugarcoat what we really want. Like, oh, I just want him to be happy, you know, and me checking in with him is making sure he's happy. And it has really nothing to do with that. Right. You want. You want to hear that you can make him happy, that he makes you. That you make him happy, that you're enough, that he is willing whatever is going on in his life, you want to be enough for him also to make you a priority, which he's never really done. And. Yeah. And that makes you feel a certain kind of way about it.

[Paige]

So if he reaches back out again, what should I say to him?

[Nick]

Why are you answering that call? Call. But just to.

[Paige]

That's a good question.

[Nick]

What is that?

[Paige]

I don't know.

[Nick]

So you don't have to answer the call.

[Paige]

I just naturally do.

[Nick]

Yeah, no, I know. I get it. Like, and that's what I'm saying. It's like. This is. You kind of have to almost, like, practice in your head, and when you right now say it. So if he calls again, there is that part of you that wants me to say, oh, he will call. Because, like, you're coming. Like, there's like. Like. And I. I'm guess, you know that he's got your number. And that's, you know, we. Everyone. There's always someone who's kind of had our number. You know, I certainly. People have had my number, so to speak. Right? Where it was just like, despite what my family thought and everyone telling me, like, I deserved better, like, I. All I wanted was for her to, like, want me. And so when you're like. So if he calls again, you want me to validate that and. And confirm that he will call. I think he definitely will call, but I think that's definitely. You should see as a warning, as a negative, not a good thing, not a, like. Got it. But, yeah, if he calls again, the first thing you should do is nothing. I wouldn't answer the call if I were you. I would just block him right now. I would block him on social media. I'd block his phone. I would delete his number from your phone, you know, after you block it, of course, so then you could forget it. And I would just, like, try to do those, like, very simple things that hold yourself accountable, that make it difficult for him to, like. Like, check back in at his convenience and then kind of just, mind you again, that being said, if you don't take my Advice, which I suspect you probably won't at first, but that's fine. And he does call. I mean, again, already, like, just you. You need to recognize that if you're not doing those easy, obvious steps, then there's a part of you that's not just your. That is not ready to do what you need to do to move on. On. Right. And ultimately you will move on when you're ready. Right. When it's really enough. When you're. When you're really tired of how he treats you. Because you clearly have the, like, the awareness that, like, you deserve better. Sounds like you have a good support system of friends and family who are saying, hey, you're better than this.

[Paige]

Yeah, they're great.

[Nick]

And those are good, you know. Right. So you have, you know, it's not like you're on an island and there's this is some incredibly toxic. And you don't realize what's going on. And. And you were, you know, but, like, you're just not ready. And when you're ready, you will block him and make it difficult for him. And you won't answer because, like, he's just not. He's not going to change, not at any time soon. And also, like, you're. You're. You're so young. Go out there and date other people and, and try things out. And the more you date, the. The more you will realize how much energy you gave this person who didn't deserve it. But you just need to. To. You need to see it by seeing other options. And now. And that's why it's like, you have to date a lot. Right? Because if you only date in small sample sizes, then you have a better chance of really hating the dates that you went on or your last boyfriend who was like, three years younger. And then it's just like, all right, you dated the guy who was three years younger who's got weird. His parents saw you as like, this older person.

[Paige]

Yeah. It was so weird. They literally were like, basically, in a sense, called me a creep and told me it was. That I was weird.

[Nick]

Yeah. I mean, then from their perspective, I kind of get it. You know, Whatever. You know what I'm saying? Like, I'm sure you had nothing but good intentions, but, like, you know. Yeah, whatever. But. But that situation didn't make you feel good about yourself, so what do you know? Right. So then that makes you more susceptible to, like, when he enters in the scenario. Scenario, because in the short run, he's good at making you feel good about yourself at the Cost of how you feel about yourself in the long run. But you just need to go out there. You need more. At bats. You're only 22. I would just more. Meet people, get out there, meet other men, meet other people.

[Paige]

I'm on the apps. I'm on all the apps.

[Nick]

You know, you're only 22. You're only 22.

[Paige]

Yeah.

[Nick]

And even whether it's just saying yes to things, I mean, I think just try to. It also just takes time. You just have to give yourself some grace. It took me seven years to get over my first girlfriend.

[Paige]

Yeah. The saying yes part is also kind of hard for me. Not because I'm like, I mean, yeah, okay, I'm gonna be honest. There's part of me in the back of my mind that's like, well, he's gonna find out that I did this and this. But then. But another part of me is like, I always like to stay in my comfort zone, and, like, I just need to get out of it. When it comes to dating.

[Nick]

Yeah. For sure. 100.

[Paige]

Yeah.

[Nick]

Because, you know, you. It's like the saying goes, you. You're gonna have to kiss more frogs before you find your prince. And when it comes to dating, dating is like exercise. It's a means to an end. You're. You're. You're gonna go on more bad dates than good ones, and that's a good thing. And if all your dates are great dates, then you don't have enough of expectations for yourself or standards for yourself because, like, most people aren't your guy. And so you just have to be willing to be patient. And in the meantime, get better at, like, the only problem with this guy, right? The. The risk you're at with this guy is that he's so ingrained into your dating life, he is a consequence of some other mistakes you're making. Right. Like, he makes you feel bad about yourself. And so you're searching for validation in other, more toxic places because, like, you want to scratch that itch. And, like, you know, you're looking for a quick way of feeling better about yourself. So you need to make just. You need to get good at making, like, healthier choices for yourself that, in the long run, in the short run, make you feel generally pretty good about yourself. And, like, you surround yourself with people who, like, lead with their words and not with their actions. And, like, if people have to apologize more than one time, then that's a pattern. And if there's a pattern of them having to apologize for you, the chances are they're not going to learn on the job, so to speak. You know, you're not there to like, teach people and things like that. Like, but that's really up for you to set for yourself, right? And I think it's just recognizing it in that moment. And you just have to get to a place where you talking about him is more than just like something to do or kind of fun, fun gossip. You kind of have to be offended, truly by how he's gone about this. I don't think you're angry enough about.

[Paige]

Yeah.

[Nick]

How he's treated you. And I think, you know, you want to see it how your friends and family see it.

[Paige]

Yeah, I was, I think I'm not like, as angry this time. This time because, like, I didn't even cry in the past. I would've cried, but like, I didn't cry at all. He texted me like in the morning, I answered him back and I went back to sleep. And then like, so you're right, I definitely wasn't angry, but I think it was just. Cause I'm, I'm kind of used to him being that way. But a little part of me hoped that it would have been different. Like, he would have like, made the effort, made the time, and not actually said all those things to me.

[Nick]

That's a good sign, right? Like, you know, you're, you're taking the long approach, which I did too, right. Which is like these, like, these kind of baby steps of progress which you first decry. Now you're just kind of, now you're just kind of getting numb to the disappointment. And so, yeah, the big question for you is I'm not worried about your ability to get over this guy. Right. He will keep making it easy for you because I doubt he's going to change. And eventually you will find someone worth your time and you will just get tired of it. But the big question for you is, are you gonna let this, like, play out over time and go on much longer than it needs to, or are you gonna take control of your dating life and actually, like, put a stop to it before he just like, really exhausts you and really, like, you have a couple more like, moments of like, feeling like you hit rock bottom because you, you know that you let a guy like, convince you to do something you ultimately knew you shouldn't have let him do, but you didn't anyways for like the short term thriller and you got exactly what you expected to get, which is just more disappointment. And like, are you going to save yourself from that? Is the Big question. Because I'm really not worried about you eventually doing what you need to do. The big question is how much longer is it going to take you and are you going to spare yourself from unnecessary moments of just disappointment that will cause you to like, like make short term decisions that you wouldn't otherwise make and have it just be like a tougher lesson than it needs to be? That's kind of the question, right?

[Paige]

Yeah, I just, I can't keep doing this through my 20s. Like, I can't because I do want, I do want to have a boyfriend. Like all my best friend has a boyfriend and a lot of people in my life have a boyfriend or they're getting engaged. Not that I want to get engaged, but like, it'd be nice to have somebody that actually wants to.

[Nick]

And who knows, maybe you dating a younger guy was the consequence of you feeling like you didn't know how to have control in your own relationship with someone your age. And like the last thing you did that he constantly like always dictated terms and like controlled a relationship and came and, and like having a three year age difference between you and your other boyfriend just kind of gave you a little, little confidence boost that you needed because you're just so used to like chasing and following and waiting for permission to do things and, and you were able to dictate terms with this guy, you know?

[Paige]

Yeah, that's a good way of looking at it. I didn't look at it like that before.

[Nick]

Again, dating is this like, it's exercise. You're just kind of learning. You're three or four years removed from like not being an adult and kind of learning the ropes of like relationships. So give yourself some grace. This shit's hard, but like, you will learn faster the heart the more you hold yourself accountable. And you clearly know the difference, right? Like outside of the emotional being emotionally triggered, you know, versus right or wrong. Right. Like you, you know when you're being taken advantage of, you have again, a solid support system who's calling it out and saying, hey, you deserve better, you deserve better. So now you just need to like, like do something about it and execute and hold yourself accountable in those vulnerable moments and say no. And again, the easiest way to start is just block them.

[Paige]

Yeah, I had him blocked for I don't know how long and then block.

[Nick]

Him and then delete his number and then forget it exists and then block him on social media half blocking someone and not. Is this like, it's just you just playing games with yourself.

[Paige]

I know, I know too Old. I can't. I'm too old to play games. I feel like I keep. I mean, I'm so young.

[Nick]

I mean, like, you are young, and sadly, we're never too old to play games.

[Paige]

Yeah. Yeah. But I don't. I don't want to play games, and I feel like if I'm not playing games, then that'll maybe lead me to somebody who does. Also doesn't play games. I don't know. That's just how I look at it.

[Nick]

Yeah. I mean, that's a good approach, but, you know, again, the part of it is just like, yeah, this guy has dominated your entire adult dating life and then some.

[Angeline]

Yeah.

[Paige]

Yeah.

[Nick]

And so much of all your decisions you made about your own personal life has been centered around him. But you want to change that, and you can, and you're. You're pretty close.

[Victoria]

Yeah.

[Paige]

I just need to take, like, the final step and block him.

[Nick]

Yep. And. And keep it blocked again. Delete him from your life.

[Paige]

Delete it. Yeah. Okay. Wow.

[Nick]

But he will definitely keep coming back. And you. That is a warning, not something for you to look forward to, Right?

[Paige]

Yeah.

[Nick]

And will be based off of him being bored, wanting to know he can.

[Paige]

Right?

[Nick]

Yeah.

[Paige]

Yeah. I don't want to be part of his boredom anymore because I get bored, too, but it's not like I reach out to him, so I don't. Yeah, he can be bored by. He can be bored by himself.

[Nick]

This is helpful. Okay.

[Paige]

Yeah, very. You're. I really wanted to get an outside perspective on it because I've had my. My parents have seen me through every stage with him because we were at high school together, so. And my best friend, who she's never even met him, feels the same way. So, like, I kind of just wanted to get a perspective of somebody who's not so attached to it.

[Nick]

All right, well, no problem. I mean, like, again, give yourself grace. This is pretty normal stuff that many people before you have experienced, and it just comes down to knowing what's going on is not okay and just, like, putting a stop to it and then being patient while you try to, like, discover and learn other people, knowing that, like, there's more disappointment when it comes to dating than. Than excitement, and it's just all part of a thing. And Also, you're only 22 and. And enjoy your friends right now and invest in relationships outside of your romantic ones. It's like I always say, like, keep the doors and windows open to the rooms that you want to fill, but, like, you don't need to constantly Be, like, advertising and, like, making it a mission to, like, put your love life atop of, like, friendships and other relationships. If you just make good, healthy decisions when it comes to your love life and not waste your time and give people who make it very clear that they're not worthy of your time and you just set boundaries with them, you'll be in a really good spot.

[Paige]

Yeah, that's.

[Victoria]

That's really good advice.

[Paige]

Better than I've ever gotten from anybody. So I appreciate it.

[Nick]

Glad I could help. All right, well, keep us posted on how things progress. If there's an update and just. Yeah, just. You're in good shape. Just do the. Do the little things that, you know, work. Start there.

[Paige]

Right. All right, well, thank you. And I just wanted to say I. I have become a recent fan of the podcast within, like, the last year. My friend showed it to me, and now me and my mom listen to the reality recaps because we're reality TV fanatics.

[Nick]

So we love it. Love to hear it. I appreciate you listening. Tell your mom I said hello and thank you as well. And I appreciate the call.

[Paige]

All right, thank you so much, Nick.

[Nick]

Take care.

[Paige]

Bye.

[Nick]

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