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Jenna Ashkowitz
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Kevin McHale
Call it what It Is with Jessica.
Jessica Capshaw
Capshaw and Camille Ludington, an iHeartRadio podcast.
Kevin McHale
Hello, hello, hello, hello, Call it crew. And welcome to another episode of Call it what It Is. Tink style.
Jessica Capshaw
I'm just coming out with it.
Kevin McHale
I love it. No, I mean, seriously, I, I, when we teased out the Tinks was coming, overwhelming response. Yes. And I even got text through, like, oh, my God.
Jenna Ashkowitz
Oh, my God.
Kevin McHale
Can you ask her this?
Jessica Capshaw
I know she, it's like, she's the oracle.
Kevin McHale
I want to ask her.
Jessica Capshaw
And I feel like we, we. We represent ourselves as though we know a thing about a thing or two.
Kevin McHale
But maybe she more. No, because I was on her tik tok, like, all last night, and I was like. And I was learning. I was like, I don't know anything. I know. Absolutely. And she knows it all. So I want, I want to ask her all these things.
Jessica Capshaw
Yeah, let's do it.
Kevin McHale
Let's bring her in.
Jenna Ashkowitz
Hi. Hi. Hello. How are you guys? What's going on?
Kevin McHale
Hi. Welcome to Call it what It Is.
Jenna Ashkowitz
Thank you so much. I'm so happy to be here. I'm so excited to have a chat.
Jessica Capshaw
We were just talking about you because I, I mean, I guess it was sort of like when, when, like, the TikTok, like, and then, like, if they. Everyone was talking about you, and I was like, I mean, like, how does this feel phone thing work? How does TikTok work? What's my name? What are we doing? And I got, I was like, this girl's like, I think everyone was talking about what you were talking about and you being in the zeitgeist of all the, the conversations. But I was actually going, damn, she's really smart.
Jenna Ashkowitz
So kind. Like, the way that you were putting.
Jessica Capshaw
It, the way you were positioning it, the way you were speaking about it had a lot of heart. And, you know, listen, there's a lot of noise. All of a sudden. You had, like, what you were saying had, has real teeth and, like, made people, I think, feel seen and then create a different dimension to how they were looking at their lives or, like, a perspective that maybe, like something that had been sitting in their blind spot. And I feel like whenever someone comes around that's smart and feels like I can trust her, you get a, you get a new take on it. So that's, that's how I remember coming to know who you are for you.
Kevin McHale
I'm. I'm curious because Jessica's talking about, like, the moment that you sort of, like, popped off. When did you realize, like, oh, people are really watching these tik toks? And, like, I have an audience.
Jenna Ashkowitz
I think the first time that I got a brand deal, I was so shocked that, like, you could get money for it because I had my job in Covid. Like, I had been consulting for a couple brands, kind of, like, doing this and that, and all the brands obviously didn't need any help in Covid. And so I was, you know, stressed about that. And I remember the first time that I got a brand deal, this brand was like, you know, we'll pay you 600 to wear our pants in your video. And I was like. I was like, shot. I. I was flabbergasted. I was like, can I keep the pants, too?
Kevin McHale
They're like, we need them back, though.
Jenna Ashkowitz
I just couldn't believe it. And I. I, like, didn't have a plan. I was like, you know, we were all out of our minds in the pandemic. We were, like, living day to day, like, doing whatever. Yes, I get through it. And I was, like, making these videos and.
Jessica Capshaw
With your teeny, tiny little microphone.
Jenna Ashkowitz
Like, I literally was the point where, like, I had so little going on because I was, like, living alone in my studio apartment in la. I was so new to la, so I didn't have a ton of friends, and obviously we weren't supposed to hang out anyway.
Jessica Capshaw
Yeah.
Jenna Ashkowitz
And, you know, I was just like, okay, well, I'll just do this to keep myself busy. And then my friends were like, I think you can, like, do this. Like, you should just keep going. And I was like, I feel too old to be on this platform. Blah, blah. And they were like, just keep making videos. And so I did it. And when I got my first brand deal, I was just so happy. I was like, I can't believe you can get paid to make content. And I was like, I'm gonna see.
Jessica Capshaw
How far I. Yeah. When look at you now.
Kevin McHale
I so feel jealous of that kind of knack for the social media, because I think it takes me a second to, like, sort of get myself into it. And I think just some people just take to it like a duck to water. And I feel like you. You are such a natural. I mean, I really was stalking you yesterday. How did you figure out what you.
Jessica Capshaw
Wanted to talk about first?
Kevin McHale
Like, especially in the pandemic, when you're not even going anywhere.
Jenna Ashkowitz
It was, like, trial and error. I was like, okay, let me make a video about this. Like, let me. I knew I couldn't do the dances. I was like, well these girls are 18 and they're so cute. So this is not my thing, but maybe I can make content for people my age. And I'm a millennial and I like, I love a listicle. I love like a jokey, you know, thing about. Sure. Like that's our, our shit, right? We grew up.
Kevin McHale
Yeah.
Jenna Ashkowitz
Feed lists. We love that stuff. I love like what Harry Potter character are you? Whatever, anything that coded. I like. So I was like, maybe I can do it for people my age. And I was just trial and error. I was like, okay, people love when I talk about this. They don't like when I talk about that. And it's, it's evolved.
Jessica Capshaw
What did they love and what did they not like? What did you see right away?
Jenna Ashkowitz
They love like self deprecating lists. Like I remember I did one like ranked how pretty I was in all the cities that I've lived in. I was like, okay, that's really funny, Francis. And I was like a four in New York and I'm a mine in la. Like they love that shit. They like. I used to also share way more of my personal life. Like I would share everything about dating and I think because I was a little bit older, it was a nice antidote to all of the like 18 year olds in the hype house who were. They were having dating drama. But there's something about like teenage drama that doesn't hit as hard. Whereas I would have my drama not as high stakes. Yeah, it's like I was in my, I was in my, I was like just turning 30. I was like in love with my best guy friend and I was sharing all of that. And people like that worked a lot too.
Kevin McHale
I. For people that don't know you and are listening right now, you have this theory that is slightly terrifying to me. What's the box dating theory?
Jenna Ashkowitz
Okay, box theory is my theory that when a guy meets a girl in a romantic setting, so a date, a, an app, a setup or something like this, he puts her into one of three boxes.
Kevin McHale
Now hang on, wait. Do you have to meet in person?
Jenna Ashkowitz
No, it could be dating app, but it has to be a romantic setting. Like it doesn't apply if say you've been friends with that person for a long time or you're. They're your colleague and you've seen them every day for ages and then like you one of them catches feelings or whatnot. I'm talking about, like a true. Like, it's a romantic setting.
Kevin McHale
Okay.
Jenna Ashkowitz
The guy will put the girl into one of three boxes, wants to date her, wants to hook up with her, doesn't want anything to do with her. Okay. The third box is easy. You can usually tell when a guy is just like, yeah, I got.
Jessica Capshaw
Bye.
Jenna Ashkowitz
You can usually tell.
Jessica Capshaw
I mean, it still stings.
Jenna Ashkowitz
Like, it still stings, but, like, yeah, where people get confused is between the date box and the hookup box. And the point is, you can't move from box to box. This is what really trips people up because. Stings it. Thanks. And I stink because I was in the hookup box.
Jessica Capshaw
Actually stabs.
Jenna Ashkowitz
Like, for all of my 20s, I would be in the hookup box and I would be like, if I just act perfectly enough, I will. I will want to date me. And the truth is, that's not how it works. When a guy meets you, he's like, yeah, I want to date her. And there's very little you can do to make him not want to date you. Because we've all been on the end of that where you know, you're seeing a guy, you're not that into him, and he's just, yes, he will follow up. He's asking for drinks, he's booking the next date. He remembers that your sister is having foot surgery, and he's following up about it. And we've all also been on the other end where you're like, I'm acting so perfectly. Like, I'm.
Jessica Capshaw
Yeah, I haven't everything right.
Jenna Ashkowitz
I'm talking about, you know, Jesus and golden retrievers, like, he just won't date you. And it's because they put you in these boxes. And then people say to me, like, well, Tinks, you're putting all the power in the guy's hands. That's not really how I look at it. I look at it as like a self awareness thing so that you don't ever act in a way that's not in accordance with who you are. Because speaking from personal experience as well, I think a lot of girls think, oh, well, I should, like, write a text a certain way or I should do this a certain way or about a certain way. You need to be yourself because the right guy will like you instantaneously. And like I said, there's very little that you can do to make him not like you after that. Like, girls will always call my show and be like, oh, my God, like, things were going well, I thought. And then I put two exclamation marks instead of one text.
Kevin McHale
This was me dating, by the way.
Jenna Ashkowitz
I'm like, no, you're. You're boxing. It's fine. It's just, like, it's good to know where you stand so that you don't waste time on someone who is. Wouldn't mind losing you.
Jessica Capshaw
Does it work both ways? Do girls put guys in boxes or just the guys? The girls.
Kevin McHale
I don't think girls do.
Jenna Ashkowitz
Girls do something, which I call reverse box theory, which is where girls will elevate a guy to a crazy status without him really being worthy of it. And so by that, they'll see a guy on a dating app, and they'll. And he'll. They'll be like, oh, my God, he has a dog. I have a dog. Oh, my God, he has. He has a picture with his mom. He's a family man. He went to Michigan. I have been to Michigan. Like, we are.
Kevin McHale
Yeah, yeah. Twin flames in your head.
Jenna Ashkowitz
And again, I've done this 10 times. I. No judgment. You're like, we're having. We're having a May wedding. Like, we're gonna get married. My husband. Then you go to the date, nervous as hell because in your head, you up that this is the father of your children.
Jessica Capshaw
Yeah.
Jenna Ashkowitz
Need to get a ring in six months.
Jessica Capshaw
Yeah.
Jenna Ashkowitz
Act like a freak because you're so nervous. And the truth of the matter is, this guy hasn't done anything to prove that he's a good guy, that he your time, that he deserve your effort. It's not our fault. It's just that women. And I think especially with the. You know, the dating apps, they really do, like, future trip, and they make you imagine something before it's real and the only thing.
Jessica Capshaw
But I think that it's also. I mean, I'm sure you've already, like, scratched at this, but I think it's also science. I think it's neurobiological. Like, I think it hearkens back to the days, though, really old ones.
Jenna Ashkowitz
We're looking for the signs. Like, yeah, I'm gonna be a provider. It's totally normal. My point is just that, like, don't make him greater than he is in your mind, because the most important thing is how he treats you and how you feel. If you leave the date and you're like, I feel funny. I feel sexy. I feel beautiful. I feel seen. I feel like he listened. Then, sure, you can think that this dude is great, but not before he's actually shown you, yeah, he's a good person.
Kevin McHale
Okay, I'm raising My hand. I have a question.
Jenna Ashkowitz
Yes?
Kevin McHale
How quickly do you think guys are boxing us?
Jenna Ashkowitz
Very quickly.
Jessica Capshaw
It's like the Terminator helmet.
Jenna Ashkowitz
It's like they scale you, like, first hangout. First hangout.
Jessica Capshaw
I think it's like you might get boxed at the bar, just standing there.
Jenna Ashkowitz
Like, it's. It's. You're in the box, but it's not as scary as it seems. It's like, it's honestly really freeing because then once you know, you're just like, oh. Like, you want to be in someone's. Everybody deserves to be in someone's date box. And you will.
Jessica Capshaw
Yes.
Jenna Ashkowitz
Date box. So if you're not. Like, if you're hanging out, dating with someone who texts you sporadically doesn't make you feel. Seen all this. You're like, okay, I'm in their hookup box. And that's okay as long as I know. And then I can make a decision, like, do I want to see this person casually or am I looking for something real? And then I can move on.
Jessica Capshaw
Yeah. Knowledge is power.
Kevin McHale
What is, according to you? I want to know what has been the worst city to date in.
Jenna Ashkowitz
Oh, that's a good one. I. I would say la.
Kevin McHale
Oh, my God, I thought you were gonna say New York.
Jessica Capshaw
No, not. I'm, by the way, in case you didn't know. I'm in New York and she's in la. Yeah, we have LA New York, and.
Kevin McHale
We both lived in both places too. Okay, tell us why.
Jenna Ashkowitz
I think that it's the flakiness combined with all the normal dating hell. Like, I think at least York you have, you can go on a date. Like, if you're jonesing to go on a date, you can 100% make the plan on Hinge. People will follow through. People date there. It's like going to the gym, you know, you can feel like, well, what you do. Last night I went to the gym, I went on a date. Then when I'm in shape, you know, it's just a thing that people do. In L. A, People are like recluses sometimes. And I'm not here to bash L. A, but I just. There's not a place where people congregate enough ever go. Like, if you were in a flirty mood, you and your girlfriend were single and you wanted to go, like, catch a vibe. It's pretty hard to find that in la, like maybe Venice, but even then, it's so touch and go on whether there's actually going to be people out, people just in their homes more. And that makes it harder to just meet people out and about. And also with the dating thing, it's just like, I find people are more flaky because of the driving. You know, if you match with someone on an app, if you live in West Hollywood and they live in Venice.
Kevin McHale
No, it's not happening.
Jessica Capshaw
That's a problem.
Kevin McHale
It's done.
Jessica Capshaw
Didn't start. Never started.
Jenna Ashkowitz
I know. My friend, my, one of my best friends, she was just telling me that on her first date with her boyfriend, he drove an hour and a half. Wow. Like, I didn't do like, I was like, that's insane. And he was like, yeah. I looked at my GPS and I was like, oh, am I going to cancel this date? And then he was like, got to go. It's a setup. I got to go. And now they've been dating like seriously for a couple years, but like an.
Jessica Capshaw
Hour and a half.
Kevin McHale
No, that. And they moved in together probably after a week because they're like, the freeways are. It's such a block.
Jessica Capshaw
Coming back to New York, I'm shook by how quickly people move in together.
Jenna Ashkowitz
Because like, oh, it's like six months. And they're like, okay, well, I guess we're on Zillow. And I'm like, oh, okay.
Kevin McHale
Do you find, do you find that one city is. The men in one city are more commitment phobes than another?
Jenna Ashkowitz
I think that everywhere right now people are just having an aversion to commitment. I think people are.
Kevin McHale
You do. What do you chalk it up to?
Jenna Ashkowitz
I think just like the paradox of choice. Like that it feels like there's infinity hot people. It feels like there's. You can, you know, see a million hotties on your phone every day and you know, women are certainly staying single longer. The stats are all showing us that a record number of women over 30 are single and unmarried. And so I think on the women's side they're just being a little bit more choosy about, you know, ling down with. And I think also people are a little bit like, you know, why, why rush into it?
Jessica Capshaw
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Oh wow, a real person.
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Well, I've got a complicated project.
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Kevin McHale
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Jenna Ashkowitz
Wow.
Kevin McHale
I mean, I always thought I needed a designer to come to my home, but scheduling's always a Nightmare.
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Jessica Capshaw
Hmm.
Jenna Ashkowitz
I just might have to do more.
Camille Ludington
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Kevin McHale
Okay, then. So the first room we're looking at is for guests coming over. And I'm thinking of something.
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Kevin McHale
Things. I have to talk to you because it's very rare that I see anyone whose upbringing, like life, beginningness, looks like mine and yours does, because I'm from England, born and raised. And I went to my, you know, I went to all girls Catholic school and for a little bit, Nascot, and I moved here when I was 19. And. You were born here but lived there and moved back.
Jenna Ashkowitz
Yeah.
Kevin McHale
Okay. Yeah. When you were 19. And do you miss home? Or what do you consider home?
Jenna Ashkowitz
You know, I think it's like, I don't really think of home home. I think of, like, where I grew up. You know, it's just like my young chapter of my life, all my childhood, and I do miss it sometimes. There is a certain. There's a certain vibe to London and to British people and British culture that I really, really relate to, and that makes me feel very comfortable. The humor, the sarcasm.
Jessica Capshaw
I love the humor and the sarcasm.
Jenna Ashkowitz
It's amazing. It's like. It feels like a breath of fresh air. And it feels like. Oh, like every time I've been in LA for too long, I'm like, I need to go home and just, like, be with my friends from high school and. Oh. Like, they just don't. I don't know. There's like, I'm generalizing hugely here, obviously.
Jessica Capshaw
But that's what we're here for.
Jenna Ashkowitz
A little bit less, like, vanity. And I'm like, the most vain person, so I can say that. But, like, they. It feels like they don't think about themselves as much as I think about myself or something. And maybe that's the industry I'm in. I get that. I'm an influencer. That's the most vain.
Kevin McHale
Yeah.
Jenna Ashkowitz
You can have, but it's just a little bit more chill and you know, even like the drinking culture, you can go to the pub and it's not such a, like, it's not like blackout or, Or. No, no.
Kevin McHale
Yeah.
Jessica Capshaw
It's just kind of like, oh, let's.
Jenna Ashkowitz
Meet and have a drink and like, we'll chat. It just feels a little bit.
Jessica Capshaw
Okay. Speaking of high stakes socializing, hotter in the Hamptons. How did you know you were going to write a book about the Hamptons? Because you went.
Kevin McHale
So this weekend sort of inspired it.
Jenna Ashkowitz
Well, it's so funny because that weekend that I went, I hated it. And I was like, I hate the people here. Like, they're so snobby. And the honest to God truth is then, then I like became an influencer and I made my own money. And then a couple years ago, I was able to rent my own house and invite my friends for the month. And we did what you did. We just hole up, we barbecue, we came yard, we drink wine till three in the morning and like, we just have so much fun. And then that's the right way to do it. If you go as like a guest knowing nothing and not having any, you know, it's just one of those places, which I hate to say, but it is. It's like a little bit. I mean, obviously the locals would probably be. Be like fu. You know, it's a beautiful place all year round for everybody, but I'm talking about the vacation Hamptons. Or the right way to do it is to just hang with your people.
Kevin McHale
Friends.
Jessica Capshaw
Yeah.
Jenna Ashkowitz
Really fun. And then you kind of get to know what you like and what you don't like. So.
Jessica Capshaw
But there must have been something about it where you're like, this is the backdrop because then you decided to write a book.
Jenna Ashkowitz
Yeah, well, it's, you know, I used to do these rich mom starter packs and there's. Yes, I know the content of.
Jessica Capshaw
Oh, yes, I know.
Jenna Ashkowitz
You know, wherever. I love Rich moms and all the, you know, all the places. And it just made sense for the first one to be in the Hamptons. I have this whole idea for a whole series where each book is going to be in a new rich mom location. We're going to have a new badass heroine. We're going to explore a new fantasy. And so it's kind of going to be like slutty White lotus without the death.
Kevin McHale
Mm, I love a slutty White Lotus sold. If I was a studio head, I'm like, that's all I need to hear. Slutty White Lotus.
Jenna Ashkowitz
So I thought Hampton's made sense, because I have been spending more time there the past couple years just with my friends. And did you.
Jessica Capshaw
And have you hung out with Aaron and Sarah when they've been in there? Is that how you guys met? Did you meet socially or did you meet through work?
Jenna Ashkowitz
You know, I think we met because I was on their podcast a couple years ago, and then we've done a few things together, like I did.
Jessica Capshaw
It makes perfect sense to me, by the way, because I've known them both for a very long time. I, I. We're talking about Sarah and Aaron Foster. I say this to Camilla all the time. Truly two of the most whip smart.
Jenna Ashkowitz
Smart.
Jessica Capshaw
Yeah, like, crazy with. And you don't. I mean, I don't know about you, maybe I'm slower, but, like, I don't see it coming. And then all of a sudden, the punchline's there, and I.
Kevin McHale
They're funny.
Jessica Capshaw
They're so funny.
Jenna Ashkowitz
They're so smart. They're so on it, and they just kind of get what people want. You see it in everything they do. You see it in their clothing line. You see it in their podcast last year. Like, they just get it. They really intuitively get it. And, I mean, it's a dream come true. I couldn't be happier.
Kevin McHale
Such a perfect pair. When does it start filming?
Jenna Ashkowitz
We're still in the beginning stages. We're, like, interviewing writers now, which is such a fun experience. Obviously, it's all new for me, but I'm loving every second, and they're being so teaching me, and so I hope we could move fast, but I'm, I'm so excited.
Jessica Capshaw
Oh, it's so exciting. I cannot wait to watch.
Kevin McHale
This is like my cup of tea, by the way. This is like I'm seated, I have my glass of wine. My kids, they gotta zip. Mommy's watching.
Jessica Capshaw
I know.
Kevin McHale
Like, tell me when it's on.
Jenna Ashkowitz
Honestly, I'm inspired by any movie or TV show that's set in the Hamptons because it's just fun to look at. Like, I know.
Jessica Capshaw
Do you remember when Sex in the City went to the Hamptons? And then who was it that got crabs?
Jenna Ashkowitz
Yeah, the most. Like, remember, she's so flattered that they think she's young. Yeah.
Kevin McHale
Who is for your show? Who would your dream casting be? And you can say Jessica and I. That's fine. And then we can just move on.
Jessica Capshaw
If we're too. Talking about too old. We're too old.
Jenna Ashkowitz
I have. You're not. I have a dreamcast in my phone. I don't jinx it, but like, I'm manifesting really hard.
Jessica Capshaw
Oh, you should. Oh, you know, by the way, with manifesting something I just learned, you're probably gonna be like, hello. Just because I already know this, you're actually not meant to think about it over and over and perseverate about it. You're actually meant to think that it's already happened.
Jenna Ashkowitz
No, I have it. It's happening.
Kevin McHale
It's done. You just haven't sent out the contract right now.
Jenna Ashkowitz
I'm just. So that we can send the contracts out. Like, I just have to.
Jessica Capshaw
Yeah.
Jenna Ashkowitz
Okay.
Jessica Capshaw
Great, great, great. Well, we will. We'll be in season two since there will be one. And. And. Or if you just need any support, we're there.
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Jenna Ashkowitz
Oh, wow. A real person.
Jessica Capshaw
Yep.
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Well, I've got a complicated project.
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Kevin McHale
I didn't realize you did that.
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Jenna Ashkowitz
Wow.
Kevin McHale
I mean, I always thought I needed a designer to come to my home, but scheduling's always a Nightmare.
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Jessica Capshaw
Hmm.
Jenna Ashkowitz
I just might have to do more.
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Kevin McHale
Okay, then. So the first room we're looking at is for guests coming over, and I'm thinking of something.
Jenna Ashkowitz
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Jessica Capshaw
Diana asked, how do you know when to give up on a relationship?
Kevin McHale
It's a great question.
Jenna Ashkowitz
That's tough.
Jessica Capshaw
I know. There's not a box for that.
Jenna Ashkowitz
I know.
Jessica Capshaw
Oh, there's too many boxes.
Jenna Ashkowitz
I think that when you feel like there's no path forward, like, if you can't see a path, like if you can't even imagine what it would take to move forward, then you have to. You have to leave, and you have to advocate for your future happiness. I think, like, another trick that I have is if you can't imagine doing the next thing with them. So, like, if you're dating casually, you see being exclusive with them. If you can't, then it's not your thing. If you're dating and you can't see moving in with them or living with them. At some point, not your person, you have to be like would I do the next step with them? And that's like a good barometer for if there's a future.
Kevin McHale
Do you have like a little rule for if, for if you've been with someone for like a really long time and they haven't proposed yet. Is there like a. You've hit eight years, like get the fuck out.
Jenna Ashkowitz
I don't really believe in ultimatums. I don't know though. That is really hard. What do you guys think that?
Kevin McHale
I think that if you're at like eight years, I like, I think you should and that's what you want. I think there is like a little bit of a get the fuck out. But I don't like ultimatums. I just think that it's because I don't think it should be like proposer, I'm heading out. You know, I think it's ideally, it's.
Jenna Ashkowitz
Like you, ideally you don't get to that point. Ideally you're on the same page and you know, and by you know, you're like, we're working towards this. If you're eight years in and you haven't had a conversation about it, that's on you as well. You know you've got to talk about it too before then.
Kevin McHale
Yeah, sometimes I think you do have the conversation and guys are like just, you know, when it's right when it's when we're ready and then it feels like a little bit of.
Jenna Ashkowitz
It's like yeah, it's.
Jessica Capshaw
Yeah, yeah.
Jenna Ashkowitz
And he's just not that into you.
Jessica Capshaw
Yes, that's exactly right. When I graduated college and I came to Los Angeles I got a duplex in as one does right near Fairfax High. Yeah, yeah. And on the other side I like a single dude that was dating a lot the first year or two and then the second year this really cute couple moved in. They've just come from. She'd come from New York and he was in LA and he's a comedian, super funny and she was super funny and he would go and do consulting for Sex in the City because they would do the writers room in Los Angeles and we became really good friends and. And he would just always have great one liners and he is the guy who came up with oh well he's just not that idiot.
Jenna Ashkowitz
He's the one who. Oh my God. That in the writer really good claim the fame of his. That's a really good line. I mean, think about how people say that all the freaking.
Jessica Capshaw
I mean, all the time. And then they, and then, and then talk about how to, you know, figuring out how to scale it out before they were talking about scaling things out. And all of a sudden it, you know, obviously it struck such a nerve in the show and then they made it into a movie because it's so, you know, why. But I think it struck a nerve and I think it goes back to you and, and why. I remember in my, in the first times that I saw your, your videos. And it strikes a nerve when it's true, right?
Jenna Ashkowitz
No, it does.
Jessica Capshaw
And I think that's a beautiful part of influencing.
Jenna Ashkowitz
Yeah, No, I agree. I think, like, most of the time you, you just feel so crazy when you're dating and it's like if someone's just validating, like, you're not crazy. That's feels really good.
Jessica Capshaw
Yeah. Camilla says things all the time that I'm like, oh, yeah, that's true.
Jenna Ashkowitz
Yeah.
Kevin McHale
Because I know everything. I'm like the oracle for you.
Jessica Capshaw
Jazz, I agree with this.
Kevin McHale
Carrie wants to know tanks. What would you tell your 18 year old self?
Jenna Ashkowitz
I would tell her not to worry and to enjoy it and just take so many pictures and cherish your youth and have fun and just don't worry. It all works out like it really does. You just don't need to feel the weight of the world on your shoulders. As a young, as a young teen, you could just kind of try to enjoy the ride a little bit more.
Kevin McHale
I think that's true now for me. Like, I just gotta, like, like enjoy the ride.
Jenna Ashkowitz
I'm trying, but it's hard every day I do. I'm the same way. I'm like trying to remind myself all the time, but it's hard. You get bogged down. Hard work and stress and stuff and errands, and then you're just like. I'm like, why am I taking myself so seriously today? Like, oh my God. Like, it's not that deep tanks, but it's, it's hard to click out of it.
Kevin McHale
It is. Yeah.
Jessica Capshaw
Yeah. So Rory wrote in, she said, I'm 15 and I really like a girl, but I'm scared to ask her out. What should I do?
Jenna Ashkowitz
Oh, my gosh. I think you should ask her out. I think go for it. I think you should try it. There is. It's the sooner you learn that being rejected or someone saying, oh, I don't want to go out with you, it's not a failure. It doesn't matter. It's just. It's amazing to put out good energy in the universe. And it's also so nice to tell someone that you like them or you have a crush on them. And the sooner you can learn that, the better you, the happier you'll be because it's so nice. And it's low pressure, it's low stakes. Either she says yes, and that's great, or she says no, and that's also great, and you move it on and you'll. It's. It's all good either way. So I say ask her.
Kevin McHale
I love that.
Jessica Capshaw
Yep.
Kevin McHale
Okay. So Nikki says, my ex wants to go get sushi with me. He said it's friendly, but I don't know what to do because I don't like him. What do you think about the exes? First off, let's all be honest. This excellence to get back. There's no, like, let's just be buds.
Jessica Capshaw
Like, have some sushi on.
Jenna Ashkowitz
He's done a tour. He's realized that ain't that much. Oh, there. Oh, you have to think about it that way.
Kevin McHale
You have to think, yeah, no, no, this is great.
Jenna Ashkowitz
Be real with yourself, because sometimes you're like, oh, like, I'm so special. He's been thinking about me this whole time. No, he got rejected on his last three Tinder dates, and now he's looking for something nice and easy. And he wants to get sushi with you.
Jessica Capshaw
We talk about this all the time. I didn't used to think I had anxiety, and now I know I do. So Ashley has written in and said one of the best ways to help anxiety question mark.
Jenna Ashkowitz
I think that therapy is amazing. I think everybody want to talk to and just help process. I think journaling is really helpful. Reading really helps. Me showering, it really does help. Like, if you're having, like, you're feel really anxious and you're like, whoa, I'm, like, not feeling good. Take a shower. Like, it really does. They've proven it resets your nervous system. And you kind of feel a little bit more calm after you take a shower. Making sure you have good sleep, which is hard because usually if you have anxiety, you can't sleep that well. But if you anything to make sure you're getting good sleep, that will definitely help anxiety reduce. And honestly, like, it's all the. The kind of boring stuff that we don't like to do, but it actually does help. Like, going on walks really helps as well. If you do all of those basic things, it can really help.
Kevin McHale
I found putting my phone Away actually really, really helps me too. Sometimes I'm like, dude, put your phone away. So just two hours, like a shower and then a two hour away from your phone, you might start to feel a little.
Jenna Ashkowitz
Works wonders.
Kevin McHale
Crazy.
Jenna Ashkowitz
We have the entire world and every problem at our fingertips and we wonder why we're all freaking anxious the whole time.
Jessica Capshaw
It's.
Jenna Ashkowitz
It's a lot. It's bombarding us at all times and you have to know when to set boundaries and just be like, I need to put my phone away.
Jessica Capshaw
Yeah. Also self talk. I talk about this a little bit, but like, yeah, really figuring out like you're always your own little party of one. I used to think it was like so crazy to have a meal alone. And now I'm like, especially in New York City.
Kevin McHale
Love a meal.
Jessica Capshaw
Happy, happy, happy, happy.
Kevin McHale
Love a meal alone.
Jessica Capshaw
Yeah. I mean I'm just having like those. That relationship with yourself 100.
Jenna Ashkowitz
It's so important. It's the most important relationship of all.
Jessica Capshaw
Yeah. Yeah.
Kevin McHale
Isla asks, how do you know when your standards are too high? Is that even possible? I think it's possible.
Jessica Capshaw
Yes.
Kevin McHale
I think it's possible.
Jessica Capshaw
It's a good question, though.
Jenna Ashkowitz
I think mine might be too high.
Kevin McHale
Really?
Jessica Capshaw
What is it?
Jenna Ashkowitz
No, I think like, you know, I think gut check is if your friends are constantly being like, you're that's a crazy reason to dump someone. Or yes. Be more open. You know that your friends know you really well and they have your best interest at heart. So if they're constantly saying like, did you really dump that guy because he wore a blue T shirt and not a green T shirt? So then you're like, okay, I need to like check myself a little. But it's good to know yourself. It's good to have standards and it's good to know what are your non negotiables. I think that's another thing that can help you is like pick your non negotiables. Say this person has to be kind, they have to be smart, and they have to like, love their family. Okay. Those are the things that really matter to you. And everything else be a little bit more flexible on.
Kevin McHale
I remember dating, my big problem was like, I could get icked so easily.
Jenna Ashkowitz
Oh my God.
Kevin McHale
Beyond like to the point where it was like it was borderline offensive that I got icked by something. Like just the way they walked maybe in. Like, even if they like did like a. This is so mean. I feel like if they walked in and like maybe tripped a little bit, like, it's over for Me.
Jenna Ashkowitz
I agree. I'm with you.
Kevin McHale
Right? Okay. Liv's ass. I want to be with someone, but I also like being alone.
Jessica Capshaw
Oh, man.
Kevin McHale
Am I broken or is there hope?
Jenna Ashkowitz
You're definitely not broken. Definitely not really healthy and normal to want to spend time alone. I think it's really. I think it honestly makes you a better partner in the long term because you are independent and you know your likes and you're not someone who's gonna cling to someone or have an anxious attachment style like you like. To me, that means you like yourself. When you want to spend time alone. It means you have a good relationship with yourself. Doesn't mean you're broken. Doesn't mean you're not going to find someone who loves you. It means simply that you like yourself, which I would argue means you're going to call in someone who is even higher vibrational level. Like, really?
Jessica Capshaw
Yeah.
Kevin McHale
I love that. I think that's so true. Okay, Susie said, I am starting over at 57. I'm scared of dating and being alone. What should I do? Would you recommend getting on a dating app?
Jenna Ashkowitz
Yeah, I honestly would for.
Jessica Capshaw
For.
Jenna Ashkowitz
Especially for that age group. I think it's a really effective way to meet people.
Kevin McHale
Do you have an app that you prefer? Are you, like, not tender, but this.
Jenna Ashkowitz
Oh, I don't know. I think maybe Hinger Bumble could be good, but I think it's. I think you should view it as, like, an exciting new chapter. Like, it really is a new time where there. There are no limits and you shouldn't be afraid just because you feel like, oh, you have to start over again. It's. It's a new chapter. Like, it's a new era. It's so exciting. Life is short, but it's also long. And there's so many different eras that we all have and think that you should go into it with a mentality of like, I can't wait to find out what happens. Like, I get to write this next chapter and it's exciting and maybe I'll find someone and maybe I'll date around and maybe I'll have experiences. And it's a true period of unknown, which is so exciting.
Kevin McHale
Have you been on Raya? Is it Raya? Raya. Raya.
Jenna Ashkowitz
I've been on it.
Kevin McHale
What is it?
Jessica Capshaw
Like, I've been on it.
Jenna Ashkowitz
It's been on everything.
Kevin McHale
Is it? I know. I'm so curious because I feel like I miss the app thing. It was just happening like a game.
Jenna Ashkowitz
No, it's. It's. It's. It's a, it's. It's a normal matching dating app. I think that the problem with all dating apps right now is that we just have like, there's so many and there's so many matches to be had and I feel like there's almost too many matches where it's like, yeah, oh, you're not really dating with intention anymore. You're just like on a million apps and you're just like, people don't even meet up. They just match to match and then they're like, you know. But I have heard that with like the age limits like in an. Because it's a different generation. In the like older generation, they have more success rate because it's like they don't. The ghosting behavior. Like someone in a different generation wouldn't be so rude as to just like drop off the face of the planet and like not respond.
Kevin McHale
Yeah.
Jenna Ashkowitz
So I think that our 57 year old friend has a really great shot and I think it's, it's exciting.
Kevin McHale
I love it.
Jessica Capshaw
I love that.
Kevin McHale
Sean asks, what would be the best way to get over trust issues. I'm assuming this is probably in a relationship therapy.
Jenna Ashkowitz
Honestly, I think, yeah. So important and it can really help you work through like why it was so hurtful and like what being betrayed meant to you and like how it hurt you. So I'm a big therapy advocate. I think that, you know.
Kevin McHale
Yeah.
Jenna Ashkowitz
Getting the best.
Kevin McHale
Okay. Gabby asks, when do you think is an appropriate time to ask if we want to move in together? I feel like a lot of people are probably had that question.
Jenna Ashkowitz
I think that when you feel like you are getting ready, you're almost at the point where you want to move in. I think you should have a check in and be like, hey, like, I could see us, you know, when the lease is up, I could see us moving in. I think I'm a big fan of just being honest. Like, I don't believe in game. I don't believe in like timing it out or whatever. Like if you feel like you want to move in with someone, your lease is coming up. I think bring it up. Like, I don't think it can hurt again if you're with the right person. Even if they're not ready to move in with you yet, it won't matter. They'll just be like, oh, like I love my apartment. I want to live with my roommate for another year. But like, I'm so into you and like, let's keep doing this. Like, like with the right person, it won't Matter. So I think time to do it is when you, when you feel it.
Kevin McHale
This is hard for me because I'm thinking about me when I was in my dating years and if I asked a guy if I was kind of ready and I asked a guy and he was like, you know what? I'm not ready yet. Like, I kind of want to be, you know, but like, I like what we're. What's happening. I know that I would spot they'd.
Jessica Capshaw
Be in a different box.
Kevin McHale
Yeah. They would can move boxes. I don't know what it is, but it would sour it for me.
Jenna Ashkowitz
And I, and I totally get that. Yeah. And it's like. But that's also important to know.
Kevin McHale
It is. But I wonder, I wonder for someone like me, I could sour it and if I get sour on it. But then in a year if I just been more chill.
Jenna Ashkowitz
More way and chill. Yeah.
Kevin McHale
More weight chill.
Jenna Ashkowitz
You are who you are and you have to like honor who you are. You know what I mean?
Jessica Capshaw
And by the way, that might, that might bring out something in him. I mean, if you were like, oh, then it. I, I mean, my gosh, it's just we are living in this comfort. I mean, some people call it a comfort crisis. I, I sort of enjoy all the comforts and I'm very grateful for our evolution. I don't mind that I can get food at my house in 45 love.
Jenna Ashkowitz
It is my favorite app. Like, it's insane.
Jessica Capshaw
Comfort crisis. We're not evolving. I was like, I think we're good. I think we are. But I think that, that then you're reminded. Okay, great. I can get the, I can get the UberEats fast, but I can't get the relationship fast. And if I, if I up and I gotta go back and, and have a do over and repair and be like, can I. You know what? I said that. And I can feel your sour and I actually love you. And, and here's why I don't want to move in right now. That might not make you so sour. Like, I don't think that it's a sliding doors moment where like, if you just waited and chilled, he would have been the one or she would have been the one.
Kevin McHale
Right. I think it is true. I agree with this. I agree with this.
Jessica Capshaw
I think it's like, great, why don't you earn it? I mean, that's where I sit in. And maybe it's a fairy tale. I have no idea. But I just think that, I don't know, it's kind of like the old school. Like, nothing. Nothing that you really want comes to you without having to work for it.
Jenna Ashkowitz
Yeah.
Kevin McHale
Tinks, thank you so much for being here.
Jenna Ashkowitz
So lovely and fun. Both so wonderful and so easy to talk to.
Jessica Capshaw
So.
Jenna Ashkowitz
I appreciate you, too.
Kevin McHale
I'm such a fan.
Jessica Capshaw
I know we are. We were so excited to have you. And I also think that, you know, as you. As you start this next part of your life, you're taking this next step from creating content on one platform to another. We are so rooting for you, and we'll be along for the ride. And anytime you want to come back and talk about.
Camille Ludington
Yeah.
Kevin McHale
Next thing, promote the show.
Jessica Capshaw
Do.
Kevin McHale
And your dreamcast.
Jessica Capshaw
I can't wait until. Oh, my gosh. Your dream cast is so lucky. They got the fart.
Jenna Ashkowitz
Thanks, girls.
Kevin McHale
Love it.
Jenna Ashkowitz
Appreciate it. Appreciate it. Thanks so much. I'll see you guys.
Jessica Capshaw
So much fun.
Kevin McHale
Okay. Dude. Those kind of shows, like the Perfect Couple, by the way, that was, like, sort of set in that same, like, Nantuckety, like Hampton.
Jessica Capshaw
I know. The summer. The summer. The summer vibes.
Kevin McHale
Yeah. It's like, to me, it's like. It's like one of those summer books that you like, you know, take to the beach, but it's on YouTube.
Jenna Ashkowitz
Yeah.
Jessica Capshaw
My aunts used to always read them by the pool while they were tanning.
Kevin McHale
Yes. I feel like that's my TV version of that. But I would always.
Jessica Capshaw
I. They gotta be a little naughty.
Kevin McHale
Oh, yeah. Yeah.
Jessica Capshaw
Well, she was saying slutty White Lotus, but I was actually gonna insert. I was gonna go one step further and be like, I need a little slutty and maybe a little porny.
Kevin McHale
Well, it sounds like it's gonna be a little horny. Slutty and all the things.
Jessica Capshaw
Yeah.
Kevin McHale
And the Foster sisters, man, they're gonna kill it. What a great collab. And buy the book, guys. Buy. Go buy Hotter in the Hamptons. It's a book already. Obviously, that's what she's basing it on and read it first.
Jenna Ashkowitz
Yep.
Kevin McHale
All right, let's call it the end of the episode.
Call It What It Is: Episode Summary with Jenna Ashkowitz, Kevin McHale, Jessica Capshaw, and Camille Ludington
Release Date: May 5, 2025
In this engaging episode of "Call It What It Is", hosted by Jenna Ashkowitz and Kevin McHale, alongside special guests Jessica Capshaw and Camille Ludington, the crew delves deep into the complexities of modern friendships and romantic relationships. The episode is rich with insightful discussions, personal anecdotes, and practical advice, making it a must-listen for anyone navigating the tumultuous waters of dating and maintaining meaningful connections.
The episode kicks off with a warm welcome to Jenna Ashkowitz, setting the stage for an in-depth conversation. Jessica Capshaw expresses admiration for Jenna's ability to resonate with her audience, highlighting Jenna's authenticity and intelligence.
Jessica Capshaw [03:07]: "Whenever someone comes around that's smart and feels like I can trust her, you get a new take on it. That's how I remember coming to know who you are."
Jenna introduces her Box Dating Theory, a framework that categorizes how individuals perceive potential romantic partners during first encounters. According to Jenna, when a man meets a woman in a romantic setting—be it a date, app, or setup—he subconsciously sorts her into one of three categories:
Jenna Ashkowitz [08:37]: "Box theory is my theory that when a guy meets a girl in a romantic setting... he puts her into one of three boxes: wants to date her, wants to hook up with her, doesn't want anything to do with her."
Jenna emphasizes that these categories are rigid and often irreversible, creating confusion when expectations between the Date Box and Hookup Box clash.
Jenna Ashkowitz [09:20]: "You can't move from box to box. This is what really trips people up because... I've been in the hookup box."
The conversation shifts to the contrasting dating landscapes of Los Angeles and New York City. Jenna articulates the challenges unique to LA, such as geographic dispersion and a culture rife with flakiness, making spontaneous meetups difficult.
Jenna Ashkowitz [14:17]: "LA has a lot of flakiness... It's so touch and go on whether there's actually going to be people out, people just in their homes more."
Conversely, New York City offers a more conducive environment for dating, where commitments to meeting up are usually honored, akin to regular social activities like going to the gym.
Jenna Ashkowitz [14:35]: "In New York, you can go on a date... People will follow through."
Jenna discusses the current aversion to commitment prevalent among both men and women, attributing it to the Paradox of Choice—the overwhelming abundance of options facilitated by dating apps.
Jenna Ashkowitz [17:22]: "There's infinity hot people... Women are staying single longer... There's a record number of women over 30 who are single and unmarried."
This societal shift leads to higher standards and longer periods of being single, as individuals become more selective, often influenced by the endless swiping culture.
Jenna shares her excitement about writing a book titled "Hotter in the Hamptons", inspired by her transformative experiences during a weekend getaway. Initially dismissive of the Hamptons' reputation, she found joy in hosting her friends, leading to a fresh perspective on the area.
Jenna Ashkowitz [25:00]: "We're going to have a new badass heroine... Slutty White Lotus without the death."
The book aims to explore various "rich mom" locales, blending humor and sharp social commentary, drawing comparisons to popular shows like "White Lotus".
The heart of the episode features a Q&A session, where Jenna and the hosts address pressing relationship questions from their audience:
When to Give Up on a Relationship (31:11 – 32:52):
Jenna advises recognizing when there's no viable path forward in a relationship, emphasizing the importance of envisioning a future together.
Jenna Ashkowitz [31:20]: "Another trick is if you can't imagine doing the next thing with them... that's a good barometer for if there's a future."
Moving In Together (44:19 – 46:19):
The discussion centers on the right timing to propose cohabitation, advocating for honesty and mutual readiness without resorting to ultimatums.
Jenna Ashkowitz [44:50]: "I don't think it can hurt... Like if you're with the right person, it won't matter."
Overcoming Trust Issues (47:44 – 48:19):
Jenna emphasizes the therapeutic benefits of understanding and processing past betrayals to rebuild trust.
Jenna Ashkowitz [47:45]: "I'm a big therapy advocate... it can really help you work through why it was so hurtful."
Restarting Dating at 57 (41:57 – 43:12):
Offering encouragement, Jenna promotes viewing it as an exciting new chapter and recommends dating apps tailored for older demographics.
Jenna Ashkowitz [42:03]: "View it as an exciting new chapter... there's so many different eras that we all have."
Throughout the Q&A, the hosts and Jenna provide relatable and actionable advice, grounded in personal experiences and psychological insights.
Jessica Capshaw and Jenna highlight the significance of maintaining self-awareness and setting personal boundaries, especially in an era dominated by digital interactions.
Jenna Ashkowitz [39:45]: "Pick your non-negotiables... Those are the things that really matter to you."
As the episode wraps up, the hosts express their gratitude to Jenna, applauding her insights and looking forward to her upcoming projects. The camaraderie among the hosts and guests underscores the episode's central theme of support and authentic connection.
Jessica Capshaw [48:22]: "Appreciate it. Thanks so much. I'll see you guys."
Jenna Ashkowitz on Box Dating Theory:
"Box theory is my theory that when a guy meets a girl in a romantic setting... he puts her into one of three boxes."
[08:37]
Jenna on the Challenges of LA Dating:
"LA has a lot of flakiness... It's so touch and go on whether there's actually going to be people out."
[14:35]
Jenna Encouraging Therapy for Trust Issues:
"I'm a big therapy advocate... it can really help you work through why it was so hurtful."
[47:45]
Jenna on Restarting Dating:
"View it as an exciting new chapter... there's so many different eras that we all have."
[42:03]
This episode of "Call It What It Is" offers a blend of personal stories, theoretical frameworks, and practical advice, all aimed at demystifying the modern dating landscape. Jenna Ashkowitz's Box Dating Theory provides a fresh lens through which to view romantic interactions, while discussions about the varying dynamics of cities like LA and NYC add depth to the conversation. The Q&A segment serves as a valuable resource for listeners grappling with their own relationship challenges, reinforcing the podcast's commitment to fostering genuine connections and personal growth.
Whether you're navigating the complexities of dating, striving to maintain meaningful friendships, or seeking insights into your own relationship patterns, this episode delivers thoughtful and actionable guidance, all wrapped in the hosts' signature wit and warmth.