The Caller who got the hang up ☎️ on the Phone a Friend Date left our show too soon, but this is your chance to go behind the scenes to get to know this person better. We’ll hear this person’s prediction on which Caller will win 🏆 and lessons from being cheated on not once but twice. 😱


Hey y’all! This is your producer Caitlin. I’m here to take you behind the scenes with one of our Callers who got the hang up.

So if you’re not caught up and aren’t yet ready to hear who got the hang up, this is your chance to pause and go back and listen.

Today I’m here with Kai. Kai got the hang up after the Phone a Friend date, even though he hit it off with Maxine’s big brother.

Marcus: I’ll give you a tip that I haven’t given anybody else. She’s very into comedy.

Kai’s here to share how he got the nickname Loverboy, what he’s learned from being cheated on, and the beauty of monogamy.

Caitlin: Well, hello Kai.

Kai: Hello.

Caitlin: So your hang up was pretty brutal. Maxine's brother Marcus liked you the most, but you were the one who got the hang up. So how does that feel?

Kai: Yeah, I, I was a little bit blindsided, not gonna lie, just from everything, the way we interacted together, the way that went with her brother. I didn't even think there was like a chance when I was like on the call and then I was like very surprised when it happened, honestly. I respect her for having her own opinions on there and not being like swayed by her brother’s thought points, views, whatever it may be. It is what it is, you know. Can't force somebody to like you or uh, you know, pick you over whoever else at the end of the day, it's, uh, all up in the air.

Caitlin: Yeah. What do you think happened?

Kai: I don't know. I think, uh, the charcuterie play was difficult cause I didn't put the whole part together that we were gonna have to be talking over the phone. So it's tough to kind of eat and do that at the same time, but I think maybe she just felt that we had two kind of different personalities. I mean, if if it's something you don't feel from the beginning, then you don't feel it from the beginning. And there's nothing like I said, you can do about it.

Caitlin: Mm-hmm. How were you feeling about her?

Kai: I thought she was really cool. Uh, I wish I had had more time to kind of get to know her.

Caitlin: Yeah. So remaining now are Sasha, Sabo, and Charlie. Do you have an opinion on who you think is gonna win?

Kai: Hmm. They all seemed really cool and it seemed like they all kind of connected with Maxine for different reasons, which is also really cool. I think just from what I could see, obviously, you know, I haven't been on their dates or, you know, been snooping or anything like that.

Caitlin: That's just me. That's what I do.

Kai: Yeah, exactly. I would think the way that her and Sasha would go back and forth, uh, that one seems like the most lively of everything. But again, I could be, I was totally wrong on me, so who knows.

Caitlin: All right, well, we'll find out.

Kai: Yeah.

Caitlin: But enough about the show cuz I wanna learn about you a little more IRL. So to do that we're gonna play Two Truths and a Lie, which is, you tell me three things about yourself. Two are true and one's a lie. And I have to guess which one's a lie. Okay. So are you ready?

Kai: Yes. First one, one of my parents is an Olympian. Second one I was paralyzed waist down. And third one I speak three different languages.

Caitlin: Well, I know you were a paralyzed waist down.

Kai: Ooh yeah. I couldn't remember if we were gonna catch all that one or not. I was trying to see if I could catch you sleeping.

Caitlin: Um, so we're between Olympian and three languages. Um, I think three languages is a lie.

Kai: Got me. Yeah. My mom was a junior Olympiad swimmer. Her and my aunt. Yeah. Yeah. Yeah. So they were, were both really, really good swimmers.

Caitlin: All right. Interesting. Some good family context. I know your family is really important to you.

Kai: Yeah.

Caitlin: Let's talk about your dating life, though.

Kai: Okay.

Caitlin: I am curious about learning a little bit about your exes, like your past relationships.

Kai: Mm-hmm.

Caitlin: To like hear about what you've learned from them, like maybe something that you're like, fuck no, never doing that again. Or a way you've grown personally since then, or something that you like learned that has been really positive for future relationships?

Kai: Yeah, I guess the biggest thing for me is, um, I was cheated on by both my last exes.

Caitlin: Damn.

Kai: And that's why we broke up. Yeah.

Caitlin: So your last two?

Kai: Yes.

Caitlin: Wow.

Kai: So that's why I'm, and they were like long-term, like two, two and a half year long relationships.

Caitlin: Yeah. And you're just, you're not even 30.

Kai: No, I'm 25.

Caitlin: Oh shit. Okay.

Kai: Yeah. So that's what I'm saying. Yeah. Like, this was college, beginning of college and into college basically, and into, you know, here in Richmond. And one of 'em is now like, has a baby with the dude that she cheated on me with. And I'm like, okay, I, I'll take the trade deal. Yeah. I will say that. Um, I'd rather be on this end, but it's made me kind of realize that is a super big thing for me. Like, there's no having to like question or wonder at any time if, you know, they're being faithful or, you know, there's somebody else, or I want somebody who's like a thousand percent down for me. And that's kind of what I took from it.

Caitlin: So how has that affected how you are looking for relationships now?

Kai: Um, I'm definitely waiting for the right thing. So it's like, do I 100% want to be with this person for the next however long or no? It's not like a in between like median range of like, here, let's see how it plays out the next three months, or something like that.

Caitlin: Yeah. Yeah. It sounds like you're strongly like a monogamous person. Would you ever be in like a poly situation?

Kai: I don't think so. Just cause I would get too jealous. And it's not even anything about like, uh, who it would be or whatever. I'm just like, I'm, I get very selfish when it comes to people I feel like, like that. Um, not in a bad way. Like obviously like I'm not one of those guys that’s like, “you can't go out with your friends, blah, blah, blah.” I'm, that's one of the reasons why I want somebody that is extremely monogamous, cause I wanna be able to trust them. And not have to worry at all. Be like, yeah, go hang out with whoever. Doesn't matter. Just like, come home.

Caitlin: It's good to know yourself, whatever it is, you know?

Kai: Yeah. Yeah.

Caitlin: How have, uh, what's been like the best part of past relationships or something, even people you've dated, not necessarily people that you've been with for a long time, that you feel like has like really positively affected yourself or like what you're looking for?

Kai: Yeah, I would say, hmm. Calming me down. That's one thing relationships definitely do for me. I feel like I'm a very live in the moment type of person most of the time. And having somebody around really kind of does help you plan a little bit more.

Caitlin: So like planning and like future thinking has helped a lot. I feel like though, like I know, you know, on the show, you talk a lot about what you want for your future, you're switching jobs, like all of that. So do you think that was, kind of came out of past relationships? Is that an example of that?

Kai: Yeah, definitely. And I definitely get, uh, concerned, like, not concerned, but like worried, I have like, I wouldn't call it like a fear of commitment, but a fear of just like being tied down to things. Like when somebody makes plans with me for two weeks ahead, it like, it gives me anxiety cause I'm like, I have to be there. Like I'm also somebody that doesn't flake, like if I say I'm gonna be there, I'm gonna be there. And it's just like, it gives me anxiety though, having to know that I have like this commitment and it like, it pulls this like freedom away from me. I love like the freedom that I have. Like one question, me and my friends always talk about whenever we're all together, we came up with to figure out, measure how much freedom you have in your life right now is if you, if I gave you a ticket to Australia, how many phone calls would you have to make before you could go get on that plane? And like half of them are like, “oh, I, I couldn't go. like, it's just, it's not gonna happen. Like, they're like, I have kids.” I have, they're like, it's just, it's impossible. Like I mm-hmm. I could never go. I'm like, I could make two and be gone. Yeah. Like, that's about it. And, uh, That's kind of…

Caitlin: I like that. y'all made that up.

Kai: Yeah. And that's what I love about it. I'm like, I would love that. Like I love maintaining that sense of freedom. And that's kind of where sense of, fear of commitment comes too. Cause it's like all of a sudden you're tied to something you kind of. You lose a little bit of freedom when you're with somebody, but hopefully not like in a bad way.

Caitlin: Yeah. I, I really would be interested in digging in that in a little more because I really identify with that of like, I identify both as a planner, and I do like my own freedom too. So, but there is something in there, and I think particularly with young men, there is this idea around relationships that it limits, it's limiting of your freedom. So how do you think about that? Especially as someone who wants a monogamous relationship?

Kai: Yeah. Like I said, I, you hope it's not the bad parts that's like limiting your freedom. Even though it's, you know, taking away some freedom you have because I also like to be considerate of the people that I'm like dating, I'm not one of those guys that just like drop off the face of the earth, give no heads up, it's just you, you live a different life once you're with somebody, cause you have to give and take and, you both give up a little bit of your own freedom to kind of be together. You give up a lot of things for each other.

Caitlin: Yeah. I think too, like our culture kind of doesn't want us to see how you gain a lot of freedoms too when you're in those relationships, like just sharing your life with someone, even just like, you know, from a pure financial lens, you're, you know, then sharing your rent or your mortgage or you, like, I wouldn't have been able to buy a house without my husband, you know? And so there's all these kind of like other ways I'm free and when I do go out of town, I have a dog and somebody, you know, my husband's here taking care of it, so that's interesting too.

Kai: That's definitely true. And like, I like that because like I will say, one of the things I miss the most about having a relationship or living with somebody like my last ex, we basically lived together through Covid. She, but it was just nice having somebody to make dinner with. Like helping you to make dinner so you're not doing it all, all alone and you don't have to do the dishes at the end.

Caitlin: Yeah. That's freedom.

Kai: That's, yeah. And like those little things, like I'm a big acts of service person, so like The little things like that are like huge to me.

Caitlin: Yeah.

Kai: When somebody like, can do those for you, and I like do the same thing, like she, this is my ex, it was snowing, we were up in Harrisonburg. And, uh, woke up, she had a flat tire and I changed it before she even like woke up and had to go And leave for work. So yeah, it's like doing things like that that, yeah. You don't have when you're alone. Or single.

Caitlin: So I guess all that being said, eventually, do you have like an ultimate goal of dating?

Kai: I. I have like a, How I Met Your Mother, like one, like I'm definitely my, all my friends call me Loverboy. I'm like a hopeless romantic. They call me, uh, Smoocher or Loverboy cause I like kissing and then that, so yeah, it's, uh…

Caitlin: That should have been your name instead of Kai, you know? Just gone as Loverboy.

Kai: Yeah, I wish I had gone with that one. But, uh, so I'm very like, hopeless romantic like that. I love the way that things transpired in that show with him and the actual woman. You have this relationship where they met and it was immediately like, “Yes.” Like you immediately knew what was going on here. They were like engaged within like a couple months, I think like three or six months or something like that, and then found out she was pregnant and never got married. Like I'd be totally fine never getting married, but just like knowing that I'm with that person, you know, I'm getting into that age bracket now where it's like everybody's, you know, getting married, about to have kids, things like that. You're always getting asked, and I know a lot of girls out there especially that are like, I got hit, you know, planning and they wanna like hit this mark. I wanna be married before I'm 30, have kids before I'm 33. And things like that. And I hate that mentality where it's just like, I'm more concerned about hitting these milestones than like finding the right person and letting life progress like the way that should.

Caitlin: Got it. Okay. So you just are like, I want it to just like, soon after I meet this person, it's just so natural and we both just know and we're just locked in and like that is the goal rather than… it's just like finding a solid partner.

Kai: Yeah, I want something where that is the most important thing, not all the other extra side stuff. And it's like, other people can see it too. Like my brother, my brother, he's uh, married to this woman. She has the same name as my mom. They're both named Angie. Yeah. They're both named Angie. And even before I met her, he told me about her, and then after like 10 minutes of telling me about her, he told me her name and then I was like, “Oh. They're gonna get married.” Like I knew immediately. And then I met her and I was like, yeah, no.

Caitlin: Like it's obvious to everyone. So what are you still working on in yourself? Um, especially in like the context of dating or like looking for your partner, like where are you still, what's your like, kind of growth areas that you're focused on right now?

Kai: I think the same thing that like any other mid twenties guy is trying to be more open and like talk about things that are going on. I'm very, I'd never had conflict really in my family. My family life growing up was so easy. And like my parents got in one fight in the entire time they've been together and they've been together for 35 years. I didn't grow up around a lot conflict, and I think because of that I didn't have to face it or approach it as much. And so now I just get very, I like kinda lock up when there is conflict at times and I'm like, I have no idea what to do, like even my best friend, like I said, he's married, I'll be in the car and they're fighting, I'm I, they literally now quote me every time when I'm there and they're like, because I would just look out the window, I'll go, “Dang, these, uh, these clouds are crazy.” Just to like break up them fighting so I don't like have to hear about it or whatever, them arguing or whatever. So I am trying to work on that, like, uh, facing those types of things. Not just like blissful ignorance type of thing or, um, avoiding it until it becomes an issue. So, It's very, very tough for me. So I'm trying to get better at like those kinds of things.

Caitlin: Hmm. Yeah, that makes sense. Well, since you're looking for someone, I did wanna give you the opportunity here if you want to say what your real name is and/or plug any socials where people can hit you up.

Kai: What??

Caitlin: But it's totally your choice.

Kai: Yeah. No, I'm totally down with this. Okay. Um, God, I don't even know how to go about this. Can I give out like a PO box? Geez. Okay, so my name. my real name is Nate Poole. My Instagram is @thepoole. I mean maybe from me on Facebook, but otherwise I'm probably gonna think you're a fake Russian person or something like that. This is why I wanted to come to this and do this was just the opportunity and experience to try new things, meet new people. So even though this might be a horrible idea, it's worth a shot. You might as well go after it and see you know who you're gonna meet. You never know. Like I said, it's like How I Met Your Mother. You're constantly just missing somebody. It might cross paths with somebody just by making more opportunities for yourself.

Caitlin: Beautiful. Thank you Nate, then.

Kai: Of course thank you, so much. This was awesome.

Hang Up is created and produced by me, Caitlin Pierce.

Our host and story editor is Zakiya Gibbons.

This episode was mixed and sound designed by Ben Montoya. Ben is also our story editor.

Music by Jeff Carter and Stephen Pathe of Sandy. Hear more at

Art by Alex Teschel.

Studio recording by the ICA Community Media Center.

Our sounding board is Allison Behringer, Karla Corrales, Chioke I’Anson, and Grayum Vickers.

Hang Up is a proud member of Radiotopia from PRX, a network of independent, creator-owned, listener-supported podcasts. Discover audio with vision at

S1 Caller Exit Interview: Phone a Friend Date