Why Won't You Date Me? with Nicole Byer - Dating after a Major Scandal (w/ Monica Lewinsky)

Episode Date: August 1, 2025

Before she was an activist, Monica Lewinsky was the most publicly shamed woman in America. Now, she's reclaiming her story, and her dating life.For the 400th episode of Why Won’t You Date Me?, Monica joins Nicole to talk about dating after a major scandal, being labeled “unmatchable” on eHarmony, and learning to enjoy life when pop culture won’t stop referencing you. She reflects on hosting the wild early-2000s reality show Mr. Personality, shares the worst dates she’s ever had (including ones she walked out on), and even offers up the exact scripts she uses when there’s just no spark.Plus, stick around to the very end as Nicole gets a little reflective on what 400 episodes of the show have meant to her.Check out Monica's podcast, Reclaiming with Monica Lewinsky.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Green Chef: Make this summer your healthiest yet with Green Chef. Head to Greenchef.com/50DATEME and use code 50DATEME to get 50% off your first month, then 20% off for two months with free shipping.» Smalls: Protein packed cat food! For a limited time only, get 60% off your first order PLUS free shipping when you head to Smalls.com and use code DATEME.» Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This is a headgum podcast. Want to watch this episode? Catch the full video on YouTube. Just hit the link in the episode description. Why won't you date me? Why won't you date me? Why won't you date me? Please tell me why.

Ooh, baby, welcome to another episode of Why Won't You Date Me. A podcaster, Meena Cole Byer, was trying to figure out why I was so single, even though you could take me on a hot air balloon and leave me in the sky. It's our 400th episode. Can you believe it? I've been talking for seven and a half years. It's too long. And for a milestone like this, I wanted a guest to embody resilience, reflection, and the power of reclaiming your own story. She's lived through kind of a media, a media firestorm that

it was bad, and I wouldn't want it. And she's come out on the other side as a writer, a speaker, an advocate for change. And she's the host of a new podcast called Reclaiming Unwondry. It's Monica Lewinsky. I want to wake up to that introduction every morning. I think I would have a very, you know, like that's the way to start the day. Right. Isn't it fun? Thank you. someone just like yells nice things about it. Yeah, and congratulations. Thank you. Thank you. That is pretty, it's actually daunting to imagine, but exciting for you. Listen, I get tired, but I just keep talking. Monica, what would you like to reclaim? I know you do this on your podcast. I know, I know. Um, well, having just interviewed Cindy Crawford the other day, and she was talking about her morning

routine, I would like to reclaim my mornings. That's, I sort of left thinking about, wow, she does it right. She does it right. Wait, what does she do? I know people can listen to that episode, but just I'll give you the cliff notes, which is she takes the time in the morning for herself. She, even though she listens to a Bible podcast on her phone, she doesn't check her text or her email. She knows, like, if the kids, it's an emergency, there's whatever that'll happen. Um, And then she dry brushes, uses oil, goes in a jacuzzi, I think has her coffee. That is a morning. And meditates, I think, or meditates with the app.

And, but she's super diligent about it. And she was talking about how it sets her up for a day, like she started the day, super present, super grounded, and kind of in herself. And I was really jealous. I'm also jealous. I woke up today at 9 a.m. Because I was going to do personal training at 10. And I texted him and he was like, oh, I'm stuck on a train because I kept canceling.

So I think he was like not worried about me showing up. And I was like, I'll be there. And he was like, I won't. And I was like, oh, no. And then I just laid in bed for an hour and a half until I was like, well, now you have to get ready. And if you don't get ready, you're going to be late. And I was on time today. I'm never on time.

Well, for the 400th episode. You know. there's so many important things that I've been late to. I'll probably be late to my own wedding. I'm late to everything. It's so bad. Not your funeral, right? I'll probably be late for that too.

They'll be like, you don't know where that casket is. Decades and decades and decades on. Listen, I don't want to be here. You know what? I'm the same. I sort of, I don't want to, I get really anxious seeing people who look really vulnerable out in the world. And I just, I'm like, nip, I'm good.

I'm good. The minute I just, you know, the minute you're worrying too much about walking down the street, carrying your groceries that you're a target for someone to come after you. Yeah, I don't want it. My grandpa's 96 now. All his friends are dead. He doesn't have friends. He'll be like, oh, the lady at the church who used to like go with me to the store? She died. And I'm like, well, who do you go to the store with now? He's like, I got to find a new friend. And that's exhausting. Finding friendship is so hard. And then you're 96. I was like, I guess we'll be friends for a car. couple months before you go. Like, that's kind of depressing. Yeah. Yeah. I guess unless you start to, you know, unless you just begin to embrace, embrace the, I don't know. I don't know. Okay. You can embrace it by being like, all right, I guess all these funerals are social events? I don't know. Maybe. Or just sort of, I'll feel like I'll start to have a bucket list of what do I need to do to make sure I don't come back with the same karma, you know?

Oh, that's good to think about. That's very good to think about. I think we could write a rom-com on that, maybe. We could. Everything you do to, like, try to reverse your karma. Yeah. Wait, Monica, that's a good idea. So you're going to reclaim your morning routine.

I think I should, too. Okay. I know. In fact, it's funny. I was thinking this morning, I was, I mean, Cindy has all these, she's a very successful entrepreneur, too. And I was thinking, I was like, I would pay money to sort of, you know how they say It takes 21 days to form a new habit.

I would pay money to sort of go on a Zoom with Cindy Crawford every day for 21 days and get her to make me do her routine. Yeah, I would do that, too. Right? So maybe I can't come. I have my Zoom with Cindy Crawford. Exactly. I would just love to say that to somebody. Yeah, she's just really amazing.

Wait, Monica, are you single right now? Are you dating? Are you married or do you not want to say? I am dating. So I'm not in a relationship, but I'm dating. Okay. Yeah. I was on a really nice date last night.

Oh, that's nice. I like that. Yeah. Oh, that's why you're glowing. So it was nice to you. Have you ever been on the dating apps or is that just like a no-go? Okay. So I've not been on the dating apps that I did make a profile.

Like I started to make a profile on one and then I chickened out. and I also couldn't figure out how to do it. But what I did have was a really horrific experience. Sorry, E-Harmony, but this was in... I hate E-Harmony. You know, it was like 2007 or eight or something. And so I took the 40-minute fucking long test and then you should finally finish.

And then you're waiting for them to show you their matches. And it said, we're sorry, at this time we have no matches for you. I was part of the 5% of undatable people. Yeah. They were like, we can't accept you, but also I answered the question. Well, okay, but then I learned from somebody. I didn't realize that it was all religious-based. Yeah.

So I was like, oh, yeah, no, I'm not religious. I'm spiritual, but I'm not religious. I don't love Jesus like that. I don't know. And then I retook the test at some point, answered the questions, I guess, a little better. And then I had matched with some. somebody, but I hadn't used my real name. And then it got to a point where I had to sort of do the thing.

And it didn't go well. It was, he, like, you know, wanted to get on the phone. He thought it was, he thought his friends were pranking. I mean, it was just bad. It was really, it was bad enough that I felt so mortified and terrified. You were like, this is it. I can't do this. So it's just set-ups for me.

And on occasion, I meet somebody organically. I never, ever really met people organically, except when I lived in New York. Yeah. Do you find dating easier? Because you lived in New York and you lived in London and L.A. Right. I think dating in New York is easier than dating in L.A. I think so, too.

I think L.A. is really hard. Although I've had some, I've, you know, had relationships with men who are from L.A. who are wonderful. I've gone on some, you know, probably. like weirdly best date, I would say, was in L.A. So, yeah, but New York, how about you? What do you? I think New York, hands down, is so much better because, I don't know, you're, like, waiting for a show to start

or, like, whatever, and you're like, I'll just pop in this bar for a second. And there's always somebody at a bar in New York who's like, hey, I have something to say. Would you like to listen? And I'm like, well, okay. Yeah, I love New York. I feel like L.A. people are like, mm-hmm. I don't have anything to say because I'm going to go on a hike in a morning. Right, exactly.

Or they're looking over your shoulder to see if there's, you know. If somebody better is over there for them to talk to. What was, do you have like a first crush? I had so many crushes in high school. Yes. Well, okay, here's what's funny is I recit. I had my first crush was in nursery school. Oh.

And we reconnected on Instagram. Wait, like recently? Yeah, in the last year. I randomly awakened one morning thinking, like, I was like, I wonder what happened to so-and-so. And so I was like, oh, I wonder if he's on Instagram and he was. And so we've been, you know, friendly, which is so nice. So, but I think that was, I started early.

Nursery school, first grade. I mean. I mean, that's when I started. I was like, oh, my goodness, boys are cute. I like that. I want to talk to them. Oh, I still love men. I wish I didn't.

Some of them are bad. But whenever I see a cute man, I'm like, oh, my God. Like, I fell in love at the airport. It was like a couple weeks ago. He was wearing sunglasses. I have no idea what this man looks like. Yeah, 100%. Also, you know the sunglass thing, right?

Everybody looks 10 points hotter with sunglasses. And he was so hot. I think, sure, I had bad deaf perception. I don't know. We could have been the same height. But we were getting in the elevator. Have I told this story, Mars? We were getting on the elevator and because the escalator was broken.

And we get in, and then there was a family. It was a mom, a dad, and a baby in a stroller. And he was like, oh, we'll just wait for the next one. And then the door is closed. And then they immediately opened. And he went, oh, I'm sorry because he, like, hit the button too soon. And we were both, I guess, tired from our flights. And then the door is closed.

And I was like, if he presses that button again, and then this hot man goes, I'm going to kill his baby. Yeah. And I said, and I'll hold that baby down. And then we laughed so hard. Wait, this is a lost connection, right? I know. It's a misconnection. You, sunglasses, threatening to kill a baby.

Exactly. You're accomplice. But I have a boyfriend, so nothing happened. All right. Do you get recognized at the airport, like a situation like that? Does someone, do you feel like someone's going, oh, I listen to your podcast? No. Sometimes.

I shouldn't just say a blanket, no. Sometimes people do recognize me. Usually it's my voice. But it's never weird or anything. It's usually just someone being like, oh, I really like your podcast. The weirdest interaction I had was, I know I talked about this, but I was in, I was doing shows. And I don't really talk about my relationship and my act because I'm happy. Yeah.

So I don't know how to write a joke about happiness. It's not really, like. It's not funny. No, it really isn't. Right. I smoke. And this person was like, you got to stay true to who you are. You'll find somebody one day.

And I was like, I'm just going to let them have this moment because I'm, I don't want to be like, I did find someone. I just don't talk about it yet. So, you know, sometimes, I mean, yes, I got recognized because it was my show. Right. But, yeah, sometimes at like a restaurant or something, do you get recognized often? Yeah, yeah. Not as much as I used to, thank goodness.

So it's, and what's been really surprising and really lovely for me is I've had people stopping me about the podcast now, which I sort of, I feel I get really surprised every time I've. realize it's not just someone in my family listening. Like, oh, there are real people or my friends, you know, so it's funny. I don't know if you felt this. I now feel a pressure before I'm going to see one of my friends to say, I don't expect you to have listened, like, you know, because they feel like they'll come and go, oh, I really like, blah, blah, blah. And I just, do you have you know?

No. All my friends are like, they're comedians or actors. so, like, it's hard to consume everybody's stuff. So I don't expect any. Like, I'm always surprised when our friend's like, oh, I listen to the podcast. I'm like, you did? Right.

Well, that's, I mean, that's sort of how I feel. But I feel that they're somehow, maybe just because it's new, that they're feeling of pressure. Ah. That they, you know, that I'd be offended or something. I'm always like, I don't care. Maybe I'm more anal than you are that people think I'm, that I would be fussy if they didn't listen, my friends.

I don't know. I almost don't want my friends to listen because I feel like it, like, creates a parissocial relationship where it's like, oh, just call me. Just like call me. We'll hang out. We'll do something like my sister was listening for a while. And I was like, you have got to stop listening because we'll just be in the car and she'll just say something from the podcast.

And I'm like, wait, were we talking about? Wait, oh, are you talking about the podcast? And she's like, oh, yeah. And I'm like, no, girl, don't do that. Just call me. And I'll tell you, I'll tell you everything I say on the podcast. but it just feels a little uneven to me because it's like I can't respond to the things that you're thinking are saying back to me.

Right. Yeah, 100%. I had a, not quite with the podcast, but I had a really funny thing happen. It was probably maybe a year two after I did my TED talk and I was living in New York. My mom lives here and I called her and she's so funny. She's like a kindergarten teacher whenever my brother or I call. It's like, hi! You know, literally I might have spoken to her 20 minutes.

Hi, hi, you know. But I was like, there was all this chatter in the background, and all of a sudden I recognized my own voice. Oh, that's so funny. I said, are you listening to my TED Talk? She was like, well, I missed you. So I was like, oh, that's pretty cute, but also weird. You know, so.

What was it like prepping for a TED talk? Oh, my God. It was so terrifying. It was so, I worked harder on that talk than my mom. master's thesis. That's really wild. That's truly so funny. Of course, got opinions and helped from other people of, I think that was a really, that

was an interesting experience for me, too, of having to manage my ego and my drama of people having thought I was dumb for such a long time. So this feeling of I have to do everything myself and then the sort of like a higher version, you know, the more pleasant version of myself, being able to step back and, and, Talk to myself. Mm-hmm. That one does, right? Talk to myself all the time.

And sort of say, like, okay, no, this is actually about what's the best talk to put out there. Okay, my cousin went to Wharton. So I'm going to ask him to look at this section and can he make suggestions. And I'm going to ask this person to look at that section. And this person, you know, said this, that, and the other. And so it was hard for me to do that. Mm-hmm. And then I practiced and practiced.

and then you have one dress rehearsal. And I had been really clear, want to do the talk, cannot memorize. Like, cannot memorize it. I just, I can't handle that level of stress. So they said, okay, just, you know, do the best you can, but you can have a confidence monitor. Is that like a teleprompter? Yes, but no, right? So it's sort of, if there's a screen in the back, like, okay, that TV, well, if it were farther away,

and you had your script there. So it's sort of, you're not reading it like a teleprompter right in front of you, right? So it was supposed to be just a little bit of a crutch. But the font wasn't big enough. And so I was kind of straining. And so Chris Anderson, who owns and runs Ted, was like, listen, we're going to have to get you a podium. And you're just going to have to have your talk there because, like, you're not connecting with the audience. You're not present.

Because I was like, but it's the font, the whole thing. So then I did a whole number on myself about what a loser I was and how everybody was going to laugh at me and the whole thing. And ultimately, I had this travel music stand with me to practice in my hotel room. And I ended up using the travel music stand because the podium was really big and hulking. And I thought, this sends a message of hiding, you know. And the one thing I am not doing with this TED Talk is hiding anymore. And so I use the music stand, and now they have a music stand that they use instead of, like, a big podium. I love that.

You incited a change. Yes. That's wild that you couldn't have a teleprompter. Even Beyonce has a teleprompter with her lyrics on it, just in case she gets lost. Well, hopefully, you know, we know she remembers lyric in partition, but, you know, I could help with that one. Wait, speaking about that, I think you're in, you're mentioned in a hundred and ninety three rap songs. Oh, it's up to 193 now. You said it's up to 190. Yeah. Well, it's like the first time we counted it was in the 40s and then it was over 125. So I'll have to update my, it's

wild. It's bonkers. I mean, how amazing though, if I, if I got residuals, that would be cool. It would be so incredible if you got like any sort of compensation from people mentioning your name. you would never have to work again. Or if late night hosts had to, you know, do something every time people laugh, they tell a joke. Listen, that shit was so wild. Did you ever, like, hear Jay Leno say your name and then be like, well, fuck this. I should just go to sleep. No, because I didn't, I knew enough to not even watch.

That is very, very smart. So I think I knew enough. But there were times that I would come across, you know, they would post David Letterman's top ten list after, you know, sort of the next day. And so there were times they came across that or cartoons, all sorts of things. But Jay Leno was the worst. He was the worst of the late night. He's getting his.

He got beat up by a hill. Do you see that? It was my favorite new story. I was like, what do you mean? You fell down a hill. And that's what you look like. Sir, that was more than a hill. Anyway, I feel like the 90s was, everyone was very complicit and okay with terrorizing young women.

Because it wasn't just you. It was like, Lindsay Lowe. Well, I guess that's like the cheese. Yeah, it bled into the 2000s. It was just like, how can we make women feel less than and feel like shit? And it's it's so wild that like a bunch of writers in that writer's room was like, yeah, say that about that woman. Yeah. Say it.

Say it multiple times, too. Well, I think what's interesting, too, that I've been thinking about a lot, whether it's comedians or news anchors is sort of what women's experience was in the workplace. right, of sort of having to be complicit in telling news stories a certain way or writing jokes a certain way because that's what they had to do at that time in order to sort of, I think women were still moving their way into, we're like finding our way into different industries and higher levels of jobs, whatever. Yeah, I mean, it's just improv, but I remember starting improv where it was teams of eight and there would always be no more than two women per team.

And in my brain, I was like, well, that makes sense because, like, women aren't that funny. And then I was like, wait, some of these women are some of the funniest people at this theater. And then I just started thinking I was like, oh, no, more women is better. And I stopped seeing women as competition and started being like, oh, there's just room at the table for all of us. You just have to, like, scoot over a little bit and create a seat for somebody else. And that was a hard thing to wrap my head around because I feel like we're just so, socialized. Well, and our kind of our reptilian brain, right? Like, I mean, it's sort of, it all goes back to resources and then the resources and reproduction and how many grandchildren do, you know,

all this stuff. So just to bring Darwin into the conversation a little, Nicole, you know. I never think about Darwin. Enough. Real quick, we have to take a break. They say the way to someone's heart is three. their stomach and baby, I believe it. Cooking together is love and Green Chef just makes it easier. This summer, if you're trying to eat better and trying to impress someone, whether it's your partner, your situation ship, or just yourself, Green Chef has your back. They're the number one meal kit for eating clean. And it shows. Green Chef makes it easy to build healthy habits that stick with real organic ingredients, responsibly sourced proteins, and meals that come together

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Give your cat the food they deserve for a limited time only. Why won't you date me listeners get 60% off their first order plus free shipping when you head to smalls.com slash date me. That's smalls.com slash date me. Bebop, boop, we're back. Okay, you hosted a show for one season called Mr. Personality. Oh my gosh, yep. It was in my notes, and I was like, wait, I don't remember this show.

And then I looked up. There's a reason why. And I was like, those masks are scary. Okay, the premise of the show was really great. Yes. It was really about trying to, you know, know, try. Now, I was not the contestant. Let's just be clear. Right. I was the host. And it was, the premise was, you know, don't judge a book by its cover, right? The execution needed some work.

And, you know, I said yes. It was like a year's salary with three weeks of work. And that's great. You know, mama's got to support herself. So at least try. But the masks. Did you see the mask and be like, hey, I have some notes? Or are you like, hey, listen, it's fine? I had notes, but I kept them to myself. I was not a producer on the show, so it was, yeah. But you know what's so funny is I got to keep the clothes from that shoot, and I just had one of the outfits altered.

Like, I've had it for 20 years. So. I love that. Yeah. I have things from like H&M from 20 years ago, and I'm like, they didn't mean for this to last like this. No, but probably it was probably better made back then. Yes. Everything now is just garbage. And I hate it because I love buying furniture and sometimes you'll buy furniture and you're like, this is just plywood.

Right. And I have to put it together. I'm not Bob the builder. Please send it fully made. So on that, did you find hosting hard? Was that like a hard transition to make? Yes. Yeah. I think it was hard on many levels. One, I think just like, like. for me at that point was hard and trying to find different ways to move forward and to figure out who I was as a young, I was still in my 20s. So trying to figure out who was I, who was I post scandal, who was I, you know, all those things. And yeah, it was, you know, it's sort of one of those things where it was an experience, you know. Well, I'll just say, I hosting for me, because I hosted the show on Netflix called Nailed It for a little bit, hosting for me was so interesting and like a little hard because I was like, oh, the onus is on me to keep the show rolling when there's dead air. I just have to start talking and do something. Also, do you remember your first date?

My first date, solo, I don't know, because it was like group dates, right? So I remember the group dates. And I think that was in Westwood, seeing a movie in a group. And we went to the patio that no longer exists. You're too young probably to know. Yeah, I simply don't know. I'm so young. And I remember he bought me a bracelet. But that guy actually turned out to then be my first French kiss, too.

Oh. I didn't date until, like, I didn't go on any real date. dates till like my mid-20s, it was a lot of just like hanging out and like not knowing if this person liked me or not. And then like getting kissed and being like, so it was a date. Okay. I see. I still sometimes have those. Do you ever get confused when a man hits on you and you're like, are you nice or are you hitting on me? Well, or the other is when you're recognizable, it can be very hard to tell the difference between someone being interested and what behavior.

looks like when someone's meeting a recognizable person. So that can be confusing. But I know I had an experience, I don't know, a couple months ago where someone had, you know, asked a mutual friend to introduce us. He asked me to dinner. I thought it, you know, I was like, okay, I think this is a date. And then, you know, paid for dinner and my parking and the whole thing. And then I didn't hear from him.

So the next day I was like, oh, thank you. I was like, I had a great time. He's like, I had a great time, too, and then never heard anything. So he's like, okay, was that a date and he's not interested? But is this not a date? I don't know. I'm really bad at all these things. But he was bad.

That's weird. Well, I don't know. He's a really lovely person. So, like, yeah. I just feel like if you go out with someone and you do chivalrous things, like pay for dinner and parking and stuff, I think you could at least go, hey, well, I'm feeling it. or had a nice time. I don't think this is going to continue. That's what I do.

I don't like ghosting people. I feel like it's really, really mean, but I've been ghosted so many times. Really? Oh, my God, so many times. I went out with this Australian man who was so handsome and we went on like two dates

and I had texted him. I was like, hey, are you here or are you in Australia? And he said, here. And I said, do you want to go out again? And then I never heard from him again. Wow. Oh. Interesting that he would even respond to the first. I think he was hit by a bus. I think that's what happened. That's like. One can only hope. That would be lovely if I just like, not lovely, but like, you know, validating if like I was just perusing the internet. And I'm like, oh, that Australian man was hit by a bus. That's why he didn't reach out.

But also it makes a little bit no sense, right? If he's going to ghost you, why tell you he's here? Yes. Just don't ever respond to me again. But hey, maybe he was like, I need her to know that I'm here and ignoring her. Right. Which is hateful. We do not like you, Australian man. No. Have you ever been to Australia? Oh, yeah. Yeah, several times. That's not my favorite. No. No, it's too far for what you're getting. I love it there. My only difficulty is there's something, I don't know what it is. There's something for me about being upside down. I, like, the first several days there, I just want to die. Like, literally just want to die.

And, I mean, I really have to watch for suicidal ideation kind of a thing that strong. Do they have a different altitude there? I have no idea. I don't know what it is, but I, like, in a hotel room, staring at a wall for three hours. That happens to me in Denver. Oh, okay. When I get altitude sickness, it manifests in, should I walk into traffic? Mm-hmm.

Or should I sleep for the rest of my life? and never live again. It's tough. Yeah, it's a weird. So, but it's so beautiful there. And I think they have such a great kind of work-life balance there, too. I went on a budget tour of Europe when I was 19. A budget tour. Yeah, but it was because you're on a bus. Uh-huh. Ooh, a bus. Yeah, you're on a bus. You're staying in like not the greatest places. Like hostels? I've never stayed in a I have not stayed in a hostel. So it was not that budget. But it was not bougie.

It was a slightly elevated budget. It was not bougie. And there were a bunch of Australians on that. And that was sort of my, maybe my first exposure. And a lot of them had work jobs. Then they took a severance package and then traveled the world. And then they go back and get a new job and start working again. And when you compare that or contrasting.

Right? To the American way of life. It's sort of that work, work, work, work until you retire. And then you're going to live your best life. Which is unhinged. At 65 years old, that's when I have to live my best life. No, thank you. But also, I'm the, I can't quit a job. I like, this is the 400th episode. I can't. I will do it till the wheels come off. But I also do take time for myself. I do like to take, like, you know, a vacation here or there or just, like, go away for the weekend. I love doing that. Yeah. I'm, I like a staycation even. I do like a staycation at the beach. Oh, that's so nice. Except the beaches here are so cold. The water's so cold. Yeah, I don't go in the water. Me either. I like to be by the water. See, I like to be in the

water. One with the ocean. I like to be by the ocean. My best friend is like that. She likes to be by the water, but not in the water. Exactly. But that's not me. I can spend all day in the water. I'm a real water baby. Are you an Aquarius?

No, a Virgo. Oh, okay. What are you? Well, I'm Leo, but I'm right on the cusp of cancer in Leo. And I am very much a combination. I don't know anything about the signs. Oh, okay. Virgo is very organized, usually.

No. No, okay. No, she's got the ADHD. So it's, I'm a particular person. Okay, well, yes. My mess is particular just around the house. Mm-hmm. Well, I say I'm messy, not dirty.

Yes. So, yeah. And there's a really big difference between that. There really is. And sometimes I go to people's homes and I'm like, sometimes I'll clean. Like, if I'm in the bathroom and I see some like dirt on the baseboard, I'll just clean the baseboard for them. Wow.

Do you want to come over? Sure. I'll clean your baseboards. And I won't even tell you. It'll just have. Happened. Yeah. But that's, do you like to entertain?

Do you entertain a lot? Okay. I love to entertain and I don't entertain at all. So, in fact, I was just having this discussion with someone the other day of I work from home and I work in my dining room, but my dining room is set up as a dining room. And I was kind of going back and forth of maybe I really just need to make this more a functional office that can be a dining room if I really need it to be. Because I've now lived in the place I'm in for two years. And aside from children, my niece and nephew or family, I have not

entertained once. Or maybe I have, but we sat on the sofa. Yes. You know, so eating on the sofa. So there's that. But when I lived in New York the first time, I used to have these, you know, the game taboo? Yes, I've never played though. Oh, it's really fun. So I used to have taboo parties. Oh. And so it was, that was a, yeah, it was, you know, really fun, especially when the edition

came out and I turned out to be an answer. That was, that was a fun, you know, like, okay, all right, how are we going to do this one? Does that put a damper on the mood when you appear in something that you're not anticipating? Well, it was, let's say this. It wasn't offensive, so it was funny. But I have had plenty of experiences where I'm either sitting in a movie, like sitting in a theater, watching a movie, and there's a reference, and that's weird, or reading a book.

That's all. Somehow the book is the weirdest to me of all. I don't know why. I think I know why. I think it's because when you're reading a book, you're imagining things. Yeah. And then when you see your own, like, legal name in it, it takes you out of the imagination of things because you're like, well, now it's very real.

I'm in here? Why? Just it's such a weird, it's just, I don't know, it feels like you're kind of crossing a whole other Rubicon of, you know, to have that happen. So that's, um... Especially if it happens in like a fantasy novel, you're reading like Harry Potter and they're like, Shazam, Monica Lewinsky, and you're like, wait, well? That I would totally welcome.

Are you kidding? That would make me really cool. But, no, it's sort of, well, it was interesting. Did you read that book? It was out a few years ago, three women. Mm-mm. Lisa Toledo, I think, or Toledo, I don't know how you say her last name. And I'd so many people telling me to read it, and I started reading it.

And then there was as a complimentary reference. Did you go back to your friends and be like, hey? No. What the fuck? I did to somebody. I remember because then someone asked me, and I was like, no, I started to read it. And they hadn't remembered that, which I totally get that they would, because it wasn't something that threaded throughout the book either, you know, but yeah. So it's just,

it's a strange, it's so, it's such a strange existence. So strange. But it's taken me to places good and bad that I never, I never could have imagined. I couldn't have imagined having my own, you know, podcast and getting to sit and talk with people. And I couldn't have imagined that my worst moments and experiences could be shared in ways that would help other people feel less alone, you know? So that's... And it is a specific experience, but, like, I feel like everybody has that, like, one moment in their life that they're like, well, this is the worst thing in the world and I fucking hate it. And maybe I don't... Maybe I just don't live anymore. Maybe I, or whatever.

So, like, I do think your experience is incredibly relatable to people, just not the specificity of it. Right. And I do appreciate you talking. about it. And I love that your podcast is called reclaiming because you basically had to reclaim your whole life. Like, it's wild. Yeah, I did. And I think what's really, you know, the idea first started for me, I actually thought about it as of writing a book myself. And so I kept taking notes in the notes app, you know, as we all do, list of invention. I have so many notes that like I haven't touched in years. Yeah. I think I look at the notes more than I look at the things I saved on Instagram because that's a whole other. Oh, I never look at it. I'm like, ooh,

$8.00. Save. I'm never cooking it. Yeah, no. But so I was like had these notes and then I started working with managers and they were like, you know, this is much better as a podcast idea. And it started to really appeal to me this idea of talking to other people, you know, about their other experiences. And the more and more I thought about reclaiming and as I was working. working on the pitch for the podcast, I just kept seeing how elastic it was and actually seeing how it was this thing that threads through our life in the same way, mindfulness. Like I think we're moving towards that of understanding all the different ways that we lose something and we either replace it with something else or we get it back in a different

way. I mean, just today reading, you know, my reclaiming icon of Taylor Swift and Taylor's versions. You know, so that it's, and now today she completed her, she bought her full catalog back. You love to see that. So. I wonder how much that was. Yeah. That was a pretty pricey purchase.

She probably didn't pay and pass. Probably not. Probably not. But maybe she did. Right. But imagine if she put it on her, on her Amex and got all the points. Right? Oh, that would be incredible.

That would be a baller move. Oh, my God. Then you would definitely be Delta 360. Yeah. I'm obsessed with status on airlines. Okay. I'm a Delta Diamond Diva. What's your preferred airline? You know, it changes.

Oh. So when I was living in New York before the pandemic, I lived downtown. And so Newark was my airport of choice. And therefore, airline at that time was United. Oh. Why do you JFK? I said JFK. Well, so if you're on the west side, downtown.

you can get to, at the right time of day, you can get to Newark in 20 minutes. Oh. So that's, you know, if I flew in on a red eye, I would be home in 20 minutes. So that's like, and. Okay. Fair. If you're on the east side of the city, you know, or uptown, it's a little different. And JFK or LaGuardia makes more sense.

I'm a JFK gal. But I am a JFK gal now. I'm also an LAX gal. I do not like Burbank. Oh, I don't like regional airports. I know I've said this, but like people, like, just being in an airport without, like, people with, like, people with people with, like, people with people with someone going to Paris, okay?

Like, I just, I don't, I simply, I've just learned, like, a lot about you in the last 60 seconds, so. It's, I have unhinged thoughts. I was on the phone with my partner last night, and I said something, and I was like, you don't have an opinion about it? And he was like, I'm pretty neutral. about a lot of things, Nicole. And I was like, you don't have a hard opinion about everything. I have a hard opinion about every single thing in the world. Balloons? Love them.

Yeah, I love balloons. Billas, ooh, can't get enough. Do you think you're neutral about a lot of things, or do you have strong opinions? I think I am really good at having strong opinions about things I actually know nothing about. So I will find myself at a dinner party and I'll realize, wow, you are spouting out an opinion from having read a headline. I'm like that with things that like I've seen and how I remember it. I'm like, no, no, that's right. I know I'm right. Like I got into an argument with my partner because the doorway to his sister's living room,

I was like, there's no door there. And he was like, yes, there is. And I was like, no, there's not. And he's like, I've been there so many more times than you. And I was like, and you're wrong. Turns out I was very wrong. Couldn't see that one coming. No, but also, I still stand by.

I don't think there's a door there. Even though now I know and I've seen a picture of it, I'm like, eh, it doesn't exist. Maybe in a previous lifetime, you were in the house in a different incarnation and there was no door. You know, maybe. And then I got bad karma for being wrong now in this life. Yeah. Monica, we have to take another break. Wait, will you tell me about the worst date you've been on?

Sure. There is, I'd say that there's like probably a tie among several. Uh-huh. Probably, okay, one where about 20 minutes in, it was a setup with a lawyer, and 20 minutes in, and this was a few years after 98. Mm-hmm. And he told me he didn't think Ken Star was a real. really bad guy, such a bad guy. And so that was, that was kind of like, I left after appetizers that I just, this is.

How did you leave? Are you like, I got to go? Yeah. Yeah. I love it. And we were in a nice restaurant, too. So it was just. You're better than me.

I would have stayed for dinner. No, well. I love a fruit dinner. Then another time that I left in the middle of a date was we had gone to a Yankees game. And we're sitting on the front row. on the third baseline, which also means you might get caught by cameras, right? Okay. And halfway through, he told me that he was married for a green card.

And I was like, okay, I am not going to sit on third base, front row on a date with a guy who's married. This is just not a good plan for me. Yes. Not a good PR plan. No, I get that. So there is that. And then I'd probably say, you know, I was on a date where it was so bad I didn't want to have dessert.

And then the guy was like, no, come on. Order dessert. He's like, I like, I like women who are bigger than I am. Like, go ahead and eat the dessert. And I just, you know, yeah, that was. Go ahead. Keep eating. That's wild.

Yeah. I once had a man say to me, he was like, just because I'm into fitness doesn't mean I don't like your body type. And this is as I was leaving his apartment. And then the door closed. And I remember staring at the door being like, what? Yeah. What?

And then walked to my car, got in the car, and was like, what? Yeah. Got home. I was like, what? It was so strange. What was your worst date? My worst date. I mean, it could have been that one.

I think my absolute worst date was, I've talked about this, but it was a man who had long fingernails, like he was in interview with the vampire, like long ovals. And he was by me. drinks. We were at Good Luck Bar, which doesn't exist anymore. And maybe an hour and a half in, I was like, oh, I don't really like him. But he was like, all right, do you want to go back to my place? And I was like, oh, no, I have to be up really early in the morning. He was like, but I bought all your drinks. And I was like, oh, wow. And like, kind of got aggressive in a way. And then he's like, let me walk you to your car. And I was like, no, thank you. I don't want that.

And then I went on a date with the man. This was at club. Well, I don't have to say the name of places, what am I doing? But I went on a date with the man. It was going so poorly. He was just, we just didn't vibe. It was, and I don't know, I think I could talk to anyone, really. Yes. You know, you just find something to connect on, but we just really couldn't connect. He was giving me one word answers. And then I was like, I think I'm going to, oh, and then I ran into a friend. And she was like, oh, you're on a date. And I was trying to make eyes at her to be like, save me. Tell me somebody's dead. You need me to come with you. But, and then later I told her that. She was like, you were looking at me funny.

But anyway, as I was leaving, he walked me to my car. And he was like, hey, my apartment's right over there. And I was like, that's nice. You'll get home real quick. And he was like, oh, okay. And I was like, yeah, okay. And then I got home and I was like, ugh. And then he did text and was like, hey, do you want to go out again?

And I was like, oh, I don't, I didn't feel a spark. And then he went, good luck. And the good luck didn't feel sincere. No. And it felt kind of kind of like he was mad. Yeah, I'm not great at dating, and I find myself constantly needing to get, like, scripts from friends. What do I, how do I do this? What do I say, you know, my therapist gave me a really good one, which was, I think, that I can only offer you friendship.

Oh, right? That's good. That is good. But then sometimes they try to be your friend. And you're like, I didn't want that. I was trying to be nice and congenial in Jamil. Right. Or the, let me think if I know somebody who's a good match for you. That's good, right? That's kind. Right. But there's also that element too, right? If you kind of, if you push all the, you know, fear of abandonment stuff aside, either someone thought we might have some sort of a connection, right? So there's something there. Or you have these nice qualities. There's a reason I said yes to go out with you. And it's just not a match. But I might know someone. know, but...

I've never thought of that. That's so nice. Well, you know. I'm just trying to think of my single friends that, like, I would, like, hook up with somebody. No. None of them are good. No, I'm kidding.

So you said that you're bad at dating. I feel like I was also very bad at dating because I'm not very good at a... I guess putting my best foot forward. I read somewhere that it's like people are on their best behavior for, like, the first couple months and then like the real them comes out. The real mate just comes out. I'm just a strange little gal. And I'll talk about anything. Like, I think it was my second date with my partner. I just droned on and on about cars. And then he was like, I really like that you know a lot about cars. And I was like, oh, okay. So you want to hear more thoughts about cars? She's like,

sure, whatever. But that's, I think it's great that you're authentic. I think I have gotten, I have to say that having turned 50, there was just a level of acceptance that happened in my life on many levels. And one of the things that totally went away was the whole, I'm going to try to figure out what you're looking for and be that. And pretend I know that music or that artist or, you know,

so that, and that is very freeing, you know. Because I think there's nothing more interesting than being like, oh, I don't know what that is. Can you tell me about it? Yeah. Because then that person gets to tell you about the thing that they're interested in. Yeah, that's a great point.

But it's funny because I think the dating I've done in the last few months has also made me realize that this year I'm actually dating my podcast. So this is sort of like you want to be on the side a bit more or whatever. Yeah, I get that. I've been standing a show up is a lot of work. It is a lot of work. It's like having another job. You're like, oh, I got to like go on a date.

I got to respond to this person. I've got to be interested in them. It's just, I just think, I think there's just a level of where a lot of my energy and a lot of my focus is. And I'm also EPing a show. So that's been a whole other. You're just busy. You're a busy booked diva. Have you ever been on a date where you felt like it was an interview where you're like, I don't think you're here to date me.

I think you just want to know things about me. I don't think so. That's nice. I don't think so, yeah. But, I mean, I have said on dates before, you know, because this is my policy, not just dates, but anybody of a version of, I hate the idea of someone sitting, having a conversation with me, wondering about something, wanting to ask a question, and but they don't ask it. And so my policy, not when I'm doing podcast, but my policy in real life, in real life, is like, yeah, is, you know, you can ask me anything. I may just choose not to answer. Oh, I like that.

You know, and that's, and I don't, I think I've only one time not been like yet that I'm not answering that question. I've been on dates with like other comedians where they're just like, well, how did you do this? How did you do that? And I'm like, oh, no, this is, no, I don't want. this. Right. I want to get slammed through a mattress. Anyway, Monica, do you have any advice for single people? Yeah, don't take dating advice for me. Fair. I get that. I also don't really have dating advice because it just, my therapist was like, you should start going to dates or think about going to dates where you have no expectations. So if there are no expectations,

you either have a nice time or a bad time, but you didn't have any expectations, and that's the only advice I have. You know what? I have just, whenever someone says a version of that, no offense to your therapist, but like, or they'll say, well, you know, you'll, you'll meet someone when you least expect it, when you, well, okay, show me how to not have expectations. Once they come in, they're there, right? They're not going to, they're kind of not going to go anywhere. So you could, you could pretend like, okay, I'm going to, I'm not waiting for the phone to ring in the old days before we had cell phones. You're like, no, you're right. Sit by the phone. And I've told my partner, I'm like, you took too long to ask me out on a

second date. He was like, it was three days. And I was like, too long. But, you know, can't go, can't go back in the past. And now it's fine. How long have you two been together? A little over a year. Oh, what'd you do for your, if it's not too personal? It's not. What do you do for your first one year? Vegas. And gambled. And I won $3,000. Wow. And have you ever won money in Vegas where they give you a handpay? No. So that means they take taxes out. And then a lady comes from the back. And then you have to hold your hand out. And then they count it. So I guess you can't dispute it later. And it's like, no, no. We have the footage of you getting paid.

Wow. Okay. It was all the way in the corner. So nobody saw nobody was cheering. And I was really upset about that. Oh, my gosh. Yeah. I like when people cheer and clap for me. I just, oh my God, thank you. I just really like being special. I went to a restaurant the other day, and I was like, it's not my birthday, but can I have a candle on this dessert? And they said short. Well, my friends and I, when we were younger in high school,

we would, particularly Bob's Big Boy, would give you a free dessert on your birthday. So we would always pretend it was someone's birthday, so to get free dessert, you know. See, I love that. I used to do that at Chili's all the time in high school. I love a lava cake. It's great if you're ever dating someone who has kids.

It's a great, like, first meal with the kids in a restaurant is to sort of sidebar them of, you know, or do it for the dad. And then everybody's laughing. Yeah, exactly. That's smart. I love that. It's a good. It's a good icebreaker. If I'm ever single again, I'm going to borrow it.

Well, Monica, we've come to the end. Do you have anything you want to promote? My podcast. Yeah. Please listen to Reclaiming with Monica Lewinsky. And when do new episodes come out? Every Tuesday. Uh, love it.

Ooh, would you date me? That's the question I always forget. Um, if I dated women, of course. Oohie. That's the response I like, because if you had said no, I would have cried. If you like this episode of Why Won't You Date Me, you can like it, you can rate it, you can subscribe. You can give me five stars on Apple Podcasts. And if you write me something nasty hitting on me, I will read it.

This person writes, a day one listener here. I know you usually ask for something filthy, but I'm built more for soft intimacy. Since you've given me so many years of joy, I tracked down the chef at Little Dom's, bribe him with a mysterious envelope, and a firm handshake and secure that legendary lasagna recipe for you.

That's nice. I love lasagna. I once ate lasagna every Friday for a year. Call me Garfield. Yeah. Then I build you a lasagna. one layer for every episode you've made. That's a big lasagna.

That's nearly 400 sheets of love and cheese. It would be so tall we'd need scaffolding. That's funny. I'd hoist you onto my shoulders so you could eat your way down like a victorious pasta goddess descending a tower of her own greatness. When you're full and slightly cross-eyed from carbs,

I'd run a bubble bath with extensive oils and soft Beyonce and hand you a freshly charged iPad so you can scroll Zillow listings of all of your friends' homes so you can softly judge them. Honestly, that's nice. Thank you.

Bye-bye. It's episode 400. Can you believe that I've made it all the way to 400 episodes? Each episode's like an hour long. That's 400 hours, over 400 hours of talking, because some of them go long. I started November 30th, 2017. That was a whole world that was different back then. But honestly, thank you for going on this journey with me.

Thank you for listening. Thank you for coming to my shows and telling me that you listen and like telling me stories that I simply don't remember that I've told on the podcast. That's been fun. One of my favorite moments on the podcast has truly happened in within the last year. It was Lou Wilson's episode where I didn't remember we went on a date. But now I remember all the details. I've also loved having my friends on.

I've done multiple episodes with Sashir. The live episode in Arizona was a really fun one where I offered to buy vibrators for women and 200 people emailed me and then I had to recruit my friend to help me fulfill those orders and then a lovely person on Twitter was like, I work. I know someone who works for the company

and they helped me fulfill the orders, which was like wild and insane. Truly, it has been really massive. and I bounce between networks and you followed me and that's really been wonderful. For the future of the show, I hope to continue doing it. I hope that I get to continue talking about love and relationships because it is a comedy podcast, but I do fucking love love. And I love relationships and I love hearing about people's struggles and I love hearing

about people's triumphs. I think it's just really special. Love is something that is, you know, in all of our lives, whether you have it or not. you're looking for it or you have it, and I think that's special. If you want to tell me what your favorite moments of the podcast are, let me know in the dang comments. And then I won't look, but Mar is my producer who's wonderful, who's been with me this whole time, who is so wonderful and she works so hard and she's so dedicated, she'll read them

and she'll let me know, and it'll be nice to hear. Also, my assistant Lindsay has been incredibly helpful, so I just want to thank her. I want to thank HeadGum. I also do want to thank Team Coco, the network I was on prior. I was HeadGum, Team Coco, back to HeadGum. They were really great. HeadGum is really great. And I'm really thankful that you guys listen.

Okay, goodbye for now. I'll see you next week. Oh, you've been listening to Why Won't You Date Me with me, Nicole Beyer. This show is produced and edited by Mars with executive producer Anya Kennef Skiya. It's engineered by Casey Donahue. with guest research by Lindsay Kempth. Our VP of content at HeadGum is Katie Moose. And our Thieve music is arranged by Mike Cometeg.

Ah, thanks for listening. We'll be back next week with a brand new episode. See you then. Okay, bye-bye. That was a HeadGum podcast.