Your Worst Dates Ever: With Joel Kim Booster
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From The New York Times, I'm Anna Martin. This is Modern Love. Every week, we've been bringing you stories and conversations inspired by the Modern Love column. We talk about love, lust, heartbreak, and all the messiness of relationships. And mess is how a lot of people would describe the dating world this past year.

I kept seeing headlines all over the place about how bad dating has gotten. Stuff like, "Is dating a total nightmare for you right now?" Or, "How to declutter your dating life."

It's been a year that's felt like people are finally fed up with situationships, with cuffing season, with ghosting, endless swiping. There's just a lot of pent-up frustration. And we wanted to give you all the opportunity to let it out. The worst date I've ever gone on made me feel pretty hopeless about how men think about women. So I open the car door and literally trash just comes spilling out. So basically the rest of the night...

was alone in the stands while Amanda was down on the field with her friend Danny. But it turns out it's not just this past year. Bad dates haunt us.

Some of you had vivid memories of horrible dates from decades ago. It was 1980 and I was a 19-year-old. When I was in high school back in the late 70s, I was crazy about this guy named Joe. It wasn't in 2024 that I had my worst date, but the date was so bad, even though it was 10 years ago, that it just won't leave my memory bank.

So we wanted to turn some of your bad dates into little tidbits of wisdom we can take with us into the new year. And to do that, we brought on an expert, the host of a podcast called Bad Dates, comedian and actor Joel Kim Booster. Joel's got some surprising takes on your bad dates. And talking to him, honestly, I started to feel a little bit optimistic, like maybe all these horror stories are preparing us for something better in 2025. I hope. Stay with us.

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Joel Kim Booster, welcome to Modern Love. Oh my goodness, it's so nice to be here. I am such a big fan.

We are so excited to have you here. For listeners that might not know, you host a podcast called Bad Dates, where your guests share stories about the worst dates they've ever been on. Yeah, real nightmares from the trenches. Oh my God, real nightmares. Is that the tagline, official tagline? Yeah, it should be, it should be. Literally, okay, well, you can put it on the merch. Do it. And today, we're going to do a kind of special Bad Dates edition of Modern Love. We asked our listeners to send in your worst dating stories.

And we're going to listen to them. We're going to weigh in on them. We're going to hopefully solve some dating problems. Does that sound good to you, Joel? Oh, that sounds perfect. That sounds like exactly why I got into this business. Okay, we really booked the right guest. So first of all, I want to know from sort of an anthropological perspective, what is it about bad dates that interests you so much?

I want to specify that on our show, dates is an umbrella term that we use to encompass everything from actual first dates or dates where you're meeting for dinner, etc. But also hookups. For me, the thing that's fascinating about all of these stories is the vulnerability that goes into sitting down with a stranger and trying to dig deep to find a connection. And it is like, there's nothing quite...

similar to it. And it is like something that we're told from the time that we are very young, that it is something that we should be seeking and finding. And the struggle to be seen, and more often than not, the struggle to see someone else for who they actually are, underneath all of the layers of performance that they're putting on for you in the beginning stages of a date, it's fascinating. It's theater. And I love it.

I mean, I love what you're saying. You're saying that there's a real bravery in dating to sort of go on these dates and to not know, you know, how you'll fare and whether it will be great or horrible. And then when it goes so poorly to sort of dust yourself off and go back out on a date again, like that's brave, too. That's very brave. And I think the difference between dates with a potential romantic partner and like meeting a new friend or something different.

or a business relationship is the stakes feel so much higher than any other social interaction that you have because this could be your future. You know, your future is on the line with every first date.

And people feel that. People feel that in their bones. And that's what makes so many dates so bad is the stakes feel high. And then because of that, you act in ways that are often so out of pocket and crazy. Wow. Yeah.

And oftentimes out of character, sometimes deeply in character. It's actually sometimes you're revealing parts of your character that you've been trying to hide for so long. But the crazy comes out because you feel the heaviness of what is at stake. You know, you're sending a shiver down my spine when you said this could be your future. You know, but it's so true. It's like as much as we can or I

I'll personalize like as much as I can tell myself to take it lightly. Like the thing I am seeking is a long-term partnership. And so you're so right. Like that pressure we put upon ourselves to perform can, as you said, make us act in absolutely out of punctuality.

pocket ways. Now I just have to ask you, because you are clearly such an expert, and this must come from some amount of lived experience, what is your worst date story? Can you share like a bad date that you've been on? Yeah, no, I can definitely share a bad date story. So I will set up a little context about me is that I gave up on dating, like pretty much in my 20s. How old are you now? I am about to turn 37. So it's been I would say it's been a decade almost since I went on

But previous to meeting my partner who I met when I was like four years ago, so like 34, 33. But the problem was with for me and that I realized really quickly into adulthood is that if I can't picture myself spending the rest of my life with you within the first 15 minutes of meeting you, then I'm out.

I'm sorry. For that reason, I am out. You know, I will not be making an investment today. Like it just didn't seem tenable to me. So I say all this to say is that on my show, like the reason hookups count is because I would have nothing to talk about.

if I didn't include simple hookups and less like romantic dates. And so the story I'm about to tell you is a hookup story. And it is the third day that I moved to New York City from Chicago, getting my bearings. How old are you? At this point, I am 20. I must be 27.

And I was excited. I was on the apps. I was like, let's get this going. Like, I'm new to this city. Like, I want to, you know, make a new friend, so to say. And so I talked to this guy on an app and we're going back and forth. And like, you know, I knew he was in an open marriage and that was fine. I wasn't looking for anything serious. That was totally cool with me. So I show up to his house on the Lower East Side.

And he greets me. Everything feels normal. The chemistry feels right. And then he sits me down in the living room and he says, oh, by the way, we will have to hook up in here in the living room today because my husband's home and he's a little bit of a racist. What? What?

And he goes on, and I was like, wait, excuse me? And he goes on to explain that, like, you know, we're open, and he doesn't care that I'm hooking up, but, like, if he saw me with you, he'd be sort of upset. What? I know! Did you get the... Can I... Did you get the hell out of there? I left saying it was because of the couch, and not because of the racist in the other room. I was going to point that out. And...

And he, I think he knew obviously what the real reason was. And even if he didn't, like he was very like, yeah, I figured. And I just have to say, like, if this is your situation, you got to disclose. Like, you know, there's like, that's that, that seems to be the problem I find with so many of the bad date stories that we receive on my podcast is that there's just not enough context before you get there, you know?

And people really disagree on the kinds of contexts that are important to lay out for the person before the first date or the first meeting. And, you know, this was a big one. This is a big one. That is OK. That's really bad. Yeah. No, he really level set for me what New York dating and hookups would be like.

And that was helpful. I feel like we should hear from our listeners because they too have been on some very bad dates. Let's queue up this first one. This first one, this first one is kind of like a bait and switch from a good first date to a horrible second date. I'm Michelle Monroe. My pronouns are she, her, and I live in Los Angeles.

It was our second date. We'd actually known each other for a couple months after we met playing soccer, and I eventually asked him out. Our first date, I got all dolled up, and we went to go watch stand-up comedy. After the show, we went to a bar, and he held my hand. He asked me questions. He listened to my answers. Actually asked follow-up questions to the things I said.

And I remember feeling so heard and seen and respected. I had so much hope for him. For our second date, he asked me out for lunch after morning soccer. As we left the field, I had made cookies and I gave them to him as a little gift. And he told me he was actually fasting to lose weight. So he probably wouldn't eat them. And he also wasn't going to eat at lunch, but he was super happy to watch me eat. Very weird, but I was super hungry. So we went.

He talked at me for 28 minutes about how much he loved ChatGPT. So just to get a word in, I asked him if he'd ever used ChatGPT to research fasting. He assured me that he had, and then he proceeded to talk about how impressive he is because he can fast for days, still be surrounded by everything he loves to eat, and

and it doesn't shatter his willpower. And then he said something that almost made me lose my appetite. He said he struggles to empathize with women who are trying to lose weight because why don't they just fast for four days and drop 10 pounds? So I was pretty offended by his comment, and I interjected again and said, actually, men and women lose weight differently. And he called bullshit.

And I said, you should ask ChatGPT. So he did. He took out his phone. He asked ChatGPT and holy shit, I was right. He'd never known that, never even considered that genetics might play a role or hormones. He just always assumed that women were weak-willed. It was like going out with Dr. Jekyll and then second date was Mr. Hyde.

Okay, what do you think happened here? How does a guy go from Jekyll to Hyde like that? Like, was he just on his best behavior for the first date and then he let the sort of curtain fall for the second? What do you think happened? Well, first of all,

When she dropped the tidbit about how he was obsessed with ChatGBT, I immediately looked off into the middle distance. And it was, that's where I thought it was going to end, honestly. I was like, that's bad enough. That's simply terrible. But I think what happened on the first date is actually quite clear based on the information that we've gotten from the first date, which is he asked ChatGBT, how do I perform well on a first date?

And ChatGBT spat out, listen, ask questions, ask follow-up questions, hold their hand, go to, you know, like, and then I think he simply thought, I got it. That is such a plausible theory that never occurred to me whatsoever. That is so true. He was like, hi, ChatGBT, there's a cute girl from soccer, like, what do I do? I think most...

Most of us can probably relate to trying to be in our best behavior for the first few dates with someone and then we sort of slowly start to show our real selves. Hopefully, you know, our real selves are not like what this guy was revealing. When do you think is the best time to start revealing these sort of parts of yourself that maybe aren't your best qualities to a new person you're dating? Do you have a theory or a thought about that? Well, I think it's like...

It's a balance, right? Because you don't want to get too far into the relationship without peeling back enough layers that they, you know, it's like a sharp left turn suddenly three years in and you reveal that you are a huge Jordan Peterson fan, you know, which is, it sounds like, you know, there he's, he's a fan of the Rogan sphere. Uh,

I can guarantee you just from the pseudoscience of it all, the fasting of it all, the not believing women of it all. That seems like me. But I do think it's like it's a gradual laying out. It's sort of like a three for them, one for me sort of situation is like you balance everything out with like as you're revealing all of these amazing like sort of nuanced layered –

vulnerable parts of yourself, you then sort of, once you're at that point of comfortability, then you can sort of start dropping sort of the more unsavory parts of your personality, I think, is fair. Yeah, that's great advice that I feel like the guy in our next date should follow. And I feel like the guy in the first date and the guy in this date are

would really get along. Hi, my name is Laura Faye Tenenbaum. My pronouns are she, her, and I live in Burbank, California. The worst date I've ever been on was fixed up with this guy by one of my girlfriends. The problem was he talked endlessly about himself.

And he'd just gotten his scuba dive certification. And he was acting like the king of the sea, bragging on and on and on about how awesome he was as a scuba diver. And he never asked me anything about the ocean. Turns out I have a master's degree in marine science. I have over 3,000 dives.

I taught scuba diving. And I just sat there not saying anything about any of that because he continued to brag about himself.

and never asked me a thing about anything about myself. Wow, very thematically connected. Truly. I mean, I was going to say, like, maybe also the takeaway for this is just always assume that the person sitting across from you has a PhD in the thing you're talking about, and maybe that would really put you in your place. You know what I mean? Like, that could be a good way to operate in the world. Again, I have to say two things, though, that may...

You are really standing up for the guys. I know, this sounds terrible. And listen, I want to preface this by saying this guy is a shithead. She's completely right. No second date for him. Obviously, he's in the wrong here. But two things I will say, and this first one is not a defense. Right. People who scuba dive. God, do they love to talk about it. And it's because... It's because...

It's because they have to go through that certification process. And boy, do they love to talk about it while they're going through the certification process. They can't shut up about it. And it's because they have to leave every Friday night activity by saying, I'm so sorry. I have to be up at seven because I'm getting my scuba certification. And, you know, I got to get out there. I will say so that.

What he should have done immediately when he brought it up is been like, oh, do you scuba? Like, do you know, like, you know, as he's talking about it, like that's obvious. That's the right answer. But I will say that she could have. Yes. Given him a little test, a little like she could have interjected and given him the information. I think she's right that the real test that he failed immediately was not doing.

doing that work himself. And I don't want to put labor on women to do this work himself, but it would have been an interesting thing. I wonder how he would have, if he would have course corrected, you know, because this, so many adult men are little boys and they're just so excited. They're just so excited to talk about their scuba certification. They cannot help themselves or like, I just can't believe that scuba

He never said anything that like it would come up. It would seem natural for her to be like, oh, as someone who is an expert in this field, like you're wrong about that or you're right about that or a lot of people don't know about this and like things like that. But again, completely theoretical. I think she's in the right. I just I would I'm always interested to see how little thing little changes like that might change their behavior as well. After the break, we'll hear about a date with parental supervision.

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Okay, Joel, we're on to our next string of bad dates here. And for this next one, there is a surprise guest. Let's do it. This is Mindy Bell. It was 1980, and I was a 19-year-old outgoing, friendly bar waitress who was serving a table of rowdy college boys. And they were celebrating that one of them was turning 21 that night.

He was attractive, painfully shy because he couldn't even make eye contact with me. One of the other guys said to me, don't you think Jeff's cute? I did, but I really only played along hoping for a bigger tip. He'd like your phone number to call you for a date, but would you go?

Would you give him your number? He actually did seem okay and kind of different from the others. And so I said, yeah, sure, let's go. So I chose a small pizza place around the corner and I arrived early the next day and he was already in a booth and I slid into the booth across from him and had barely broken the ice when this slightly older woman walked in and came over to our table and started taking off her coat and

Jeff said, hi, mom, we haven't ordered yet. What kind of pizza do you want? I was speechless. So really my date was with both of them. And although I had much more to say to mom than the mama's boy,

I felt kind of obligated to tell him after we parted. You must be pretty new at this whole thing, but for future reference, don't invite your mom along on the first date. It's so cute. It's so, okay. What I love about this story, and Dan Savage, I don't know if he coined the term or the idea, but like campsite rules apply, where you want to leave the person alone.

In better shape or as good a shape as you found them. And I love that she did this work with this man. Again, not something that she's not the labor, not labor that she should have had to do or was obligated to do by any means, but very kind of her to have that conversation with him. Because oftentimes I feel like we just cut and run, cut our losses and run and don't give the note.

It's a hard thing to do. It's a hard thing to do because it's an extra layer of investment in someone you have no interest in seeing again. But I am a huge proponent of the campsite rules. Like, I'm constantly giving the note. Like, you've given feedback to people after, like, a bad date. You've been like...

Like, wait, can you give me an example of when you did that? Not always bad. It depends on the bad date. Like, I didn't tell the guy who had a racist husband. You know, I was younger at that point. But I am, especially in sexual situations and especially when I'm having sex with someone who's maybe a little more inexperienced than I am, I'm always saying, like, hey, just so you know, like...

Lube is important. And the fact that you didn't have any is a problem. I've told people straight up, you need to remove X picture from your profile because you don't look like this. And always, always, always in the context of you look better than this photo suggests.

And I have told men straight up post-coitaly like, hey, just so you know, like you are so much more attractive than this photo. And I want to let you know. That is a real service. She saved this man maybe a lot of grief. And like, I think she's a hero for that. And I think it's a brave thing to do. I think it's, again, like labor that she did not need to take on. And the fact that she did speaks volumes about her. You and this woman share a lot. You and this woman share a lot. We're heroes.

We don't all wear capes. Yeah.

Okay, our last one is a, it speaks for itself. It's a doozy. The worst date I ever went on, I was in my mid to late 20s and I had an on and off relationship, mostly off, but sometimes on with a guy who I knew was just bad news. And I came home from work one day and I was just gonna, my plan was just to shampoo my carpets and watch Frasier and everything was gonna be fine.

And then he calls and says, hey, I have tickets to go see Mariah Carey. He was in pharmaceutical sales and would often get freebies. And he says, why don't you meet me down at the arena and we can go. And I said, okay. And I hung up the phone and I was thinking, okay.

I don't know. This guy is super cheap. Nothing is free. I'm going to end up regretting it at the end of the night. But then I thought, I love Mariah Carey. I'm going to go. So I quickly got myself together and we meet at this restaurant that is adjacent to the arena. When I walk into the restaurant, he was in there holding court. He had bought people rounds of drinks and was just being a real showman. Didn't offer me so much as a glass of water. And

And he was just, okay, you ready to go? Let's go. So we walk a block to the arena and he goes into a concession stand, buys himself something to drink. Again, offers me nothing. And immediately I started thinking, this is why I stopped messing with him because he was super cheap and just always wanted to get something for nothing and just really didn't care. So I ignore it. And finally we're sitting down. I'm like, great. I love Mariah Carey. Let's get into this music. He then starts chatting me up.

Oh, you look like a swimmer. Did you swim in high school? And he's just chatting with me as if we're over dinner. And so I look at him and I'm just like, oh, you know, we can talk about it later. You know, I just want to enjoy the show. And so he's like, he kind of shrugs. He's like, okay. And I could just feel him just staring at me the whole time. I did my best to enjoy the show. Eventually the show ends.

And what he says is, you know, I'll drive you to your car. You come to my car and I'll drive you to your car. And we get to his car. And then I look inside and it looks like he had been living in his car the whole time. And I'm reminded, okay, he's a pharmaceutical sales. He does spend a great deal of time in his car. So I opened the car door and literally trash just comes spilling out. And so I said, don't worry about it. You know, I'll just, I'll just walk to my car. No, no, no, no, no, no, no. Don't worry about it. I'm going to take, I'm going to take you. I'm going to take you.

And I'm like, "No, seriously, it's fine." He does not bother to pick up the trash. He says, "I just wanna use the bathroom first." I said, "I'm not sure there's a bathroom in the parking structure."

He unzips his pants and is now peeing on the same trash that falls out of his car. I look at him and I was completely horrified. People can see him peeing on this trash like a savage. And I was just humiliated. And I could not wait for the day to be over. I was glad that it was. I cried all the way home because I did not follow my own instincts about this guy not being like worth me coming down. I had a perfectly fine plan for the night.

And it was like, one of those things you learn in your 20s, like, you know, by listening to your gut. Like, it was the worst. I don't think I even spoke to him again after that. Wow. That is so tough to hear because, like, Frasier is such a good show. You know? Like...

To think about what she could have had. She could have been shampooing her carpets. I love that detail. And there was no DVR. There was no streaming. There was no way to... She missed a perfect three-act farce. Perfect. To live out her own. And that is such a bummer.

The thing is, like, at the beginning of this story, she says, like, she didn't even really want to go out with him in the first place. Like, she had a bad feeling about it. She just loved Mariah Carey's music so much. And that's a testament to Mariah Carey right there. Just a testament to Mariah Carey. The Mariah Carey tickets...

Aside, Adrienne, the woman who told us this story, was still giving this guy who she knew was not the best for her another chance. Do you think a lot of people end up having bad dates because they're giving someone like one more opportunity to prove themselves?

I just, that's the huge, the biggest reason why is that I refuse to give people the second chance because it's a gut check thing and you gotta listen to your gut. And I will say this too, and I think this worked out slightly in her favor.

But like I find movies and concerts and any sort of performance first date to be a mistake unless there is some component on either side of it where you actually can communicate. Now this worked out in her favor because she was just able to enjoy the concert and then just had to, you know, suffer through some pee on trash.

But I think it would have been a much more painful experience for her if she was sitting across from him at a table and had to like actually engage with him. And sometimes people reveal themselves early on in a way that is like, thank God. Thank God she saw him pee on that trash. Right. Thank God she saw him pee on the trash. I mean, she said she cried on the way home, which I...

It's like dating can be so... Traumatic. Traumatic and demoralizing. It's just this pileup. I mean, that was a really extreme case. Like, it's just, it's very exhausting. Well, because it's an investment. It's an investment of time, energy, money, vulnerability, all of these things. It's why, no matter what the situation is around a breakup, if you've been with someone for three years and you break up, even if it's amicable, it is sad. Because that is...

so much investment in someone else.

And to what end at this point? Okay, wait. Well, that's my question to you is like, I want you to continue that thought and give us a little light at the end of the tunnel. Like, what advice can you give to people to sort of get through the slog or the exhaustion that dating can sometimes be? Like, I'm looking to you to inspire those of us who are not engaged, I'm happy for you, who are not engaged, who are still out here, like, trying to put ourselves out there. Like, inspire us. Why should we keep doing this? Well, I think, like...

uh,

my biggest advice is to protect your peace and trust your gut. Life is so short. The world is ending. Watch Frasier. Stay at home and watch Frasier. That is a huge thing. Don't force yourself. Don't force a square peg into a round hole. And do not kill yourself trying to do that. And I think the other thing for me is that understand what you're actually looking for.

I think a lot of people are sort of like, this could work without really understanding. And I had a really specific list of qualities that I was looking for. And if you go into dating with that intentionality, and it can be a list of 100 qualities. In my case, it was three. I wanted someone who...

Who could keep up with me energetically, who I could take anywhere and would fit into any social situation without me having to worry about them either being bored or needing me to sort of hold up the social end of the obligation or embarrass me.

Yeah.

And so I literally just had those three things in mind. And I met this guy and he also happened to be incredibly fucking attractive and kind. But the thing is, I had those three things to fall back on. And it was like, check, check, check. I know I can at least pursue this a little bit more. And so I think dating is only worth it.

If you set the intention and this person is meeting that intention, like if it's just too much investment to not have something specific on your mind that you are looking for. And of course, sometimes it takes some trial and error to figure that out. But knowing yourself is a huge part of it. Like so many people go on dates and they don't know themselves well enough. They have not taken the time to get to know themselves and their needs and their wants properly.

To even be in the position to be dating. And so, you know, I think that's why people end up on bad dates. I think that's why a lot of people are bad at dating on the other side. But I also think that's why a lot of people find themselves on bad dates with people that are just fundamentally not right for them. And they know that or they should know that, but they just haven't done enough solo work to get there.

I'm like nodding. I'm thinking about these dates I have scheduled and if I have to cancel them based on what you're saying. Joel Kim Booster, thank you so much for this. I came in thinking we were just going to gab, but you really gave me so much wisdom. You gave me a lot to chew on. Honestly, I'm feeling more optimistic now

So thank you. Thank you so much for today. I mean, take it all with a grain of salt. Look at my life and look, you know, I am engaged, but like there's a lot else that led me to this place and not all great decisions. So, you know, take it all with a grain of salt and everybody's different and everybody's story is different.

Thank you so much to everyone who sent in your bad date stories. They were so fun to listen to. In some cases, they were very hard to listen to. You all, you're troopers. Here's to better dates in 2025. Modern Love is produced by Reva Goldberg, Davis Land, Emily Lang, and Amy Pearl. It's edited by Lynn Levy and our executive producer, Jen Poyant. Production management by Christina Josa.

The Modern Love theme music is by Dan Powell. Original music by Marion Lozano. This episode was mixed by Daniel Ramirez and Afim Shapiro. Studio support from Maddie Macielo and Nick Pittman. Special thanks to Mahima Chablani, Nelka Lokely, Jeffrey Miranda, and Paula Schumann. The Modern Love column is edited by Daniel Jones. Mia Lee is the editor of Modern Love Projects. If you want to submit an essay or a tiny love story to the New York Times, we've got the instructions in our show notes.

I'm Anna Martin. Thanks for listening.