Extra Dirty with Hallie Batchelder - Willa Bennett: Dating in your 20s vs 30s

Episode Date: November 20, 2025

This week Hallie is joined by Editor in Chief of Cosmopolitan Magazine and Seventeen Magazine, the insanely impressive Willa Bennett! They get into it ALL: how Hallie and Willa met, Willa's blind date series, & how she personally navigates dating with her high profile career. Then Hallie gets all of Willa's hot takes on sex and dating topics: should a first date be coffee or drinks, when is it time to end a talking stage, the most wild pitch she's ever approved for Cosmopolitan, and if she's ever been cheated on! We love you Willa!!! Besos! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

How much stalking is acceptable before our first date? Um, like, are you zilloing? No. Because I zillow. I don't even zillow. I didn't even zillow people I date, like. Really? No. I love to zillow. What I'm a little freak? Okay, guys, I'm doing something really stupid right now.

We have an emergency debrief situation. Hi, this is hally from the streets of New York. every intention of staying in last night. Okay, guys, welcome back to Extra Dirty. I'm joined by Willa Bennett here, the editor in Chief of Cosmo, and 17 Mag. True. And honestly, one of the coolest girls, you literally know everyone in New York City, and you were just, like, such an amazing person.

I want to hear about everything. I want to know how you, like, started your career because you're, like, so young. Yeah, I'm 31. to be in this position this young is just so incredible like kudos to you i want to hear like the whole backstory like where you're from where did you start i'll tell you everything tell me everything give me the tea should we start with our origin story yes let's start with our origin story we can start okay let's start there okay so our origin story is i started following on instagram and i was like this girl is so fucking funny and i was single and i was like looking and i was just like she like really

gets casual dating in like a very specific way. So I followed you and you followed me back right away. Start DMing and then she came to a Cosmo dinner and you were like the star of the show. No, we had so much fun. I had 19 Cosmos. Yeah. And everyone, the group that you curated at that event, by the way, it was like no one kind of really like knew each other, but like everyone had something really to bring to the table, which I feel like was the kind of the point of how you sat each other around the table. And we had the best time. We were being so funny. We were being. fucking really funny. Like, who are we sitting next to?

It was like, me, you. Josie Tota. Sunni. Sunni Lee. Yeah. Yeah, it was amazing. It was just an amazing time. But you're really good at a dinner party.

So I just wanted to start there. No, yeah. So, yeah, we did that and we had a great time. And now we're just best season. Here we are. Yeah, I love it. Okay, where am I from? I grew up in L.A.

Yeah, I loved L.A., still friends with all my friends from high school. Honestly, more friends from high school than college, which we can unpacked. But I really truly have, like, all the same friends I met in kindergarten, which is pretty scary to think about. That's, like, unheard of usually. I know, especially L.A. That says a lot about you, actually, then it does about a lot of people. Because I feel like when people, like, grow, they just change their friend groups all the time. But if you keep the real ones and the OGs, then that's like a telltale sign about your character, I feel.

No, I always say the biggest red flag about someone is if they have different people at their birthday parties every year. That is like giving red flag. You cannot date them. Like, that's so scary to me. Yeah. Or they're having, yeah. or they're having like a ton of friendship breakups. I feel like I see a lot of that.

They're just always beiving with their friends. I will say I never really like fight with my friends. Like we'll have little things where it's like, hey, this are my feelings and I'm like totally by the way. Like there's like people who like challenge me in that way and there's obviously hard conversations. But I don't, I have never like trying to back check this. No, I've actually never cut out a best friend truly.

That's a flex, honestly. I don't know if that's a flex. It's just like I really am at the point where I'm like, I have my close friends. friends and like I feel really good about and solid about them. I think something interesting that you talk about a lot is like they're all married or engaged. It's a weird time I'm living the last one. I'm the last one too. But all love and respect. No like and I like appreciate other people's relationship statuses. Like for me I'm like I'm so happy when my best friends are like in love and in that step of life. But I feel like societally when you reach certain ages, you feel like you

kind of have to like meet the mark in some way like oh like i'm 28 right now i should have a serious boyfriend and i should be engaged is kind of like what society we want you to feel and then 30 you know people started getting married and then like 32 people start having kids but like you can like i just don't want to follow those norms yeah i am the fun one though at the wedding which is so funny because even last week there were like a series of events i had to go to for different friends and I was the last one there and I was like every single person was like Will is your best friend

like she's the most fun and I just thought that was so interesting because I obviously am fun and amazing but I don't really think of myself as that as the fun friend yeah we had so much fun what do you mean you're like obviously the fun friend I don't know I was just like wow

the stakes are really low the bar is on the ground being a good wedding guest though is like such an important thing because someone's got to keep party alive. I am really good at a wedding. Yeah. And one of my friends, all of her friends are in private equity. I know nothing about private equity, but like let me tell you I was talking about private equity. I just know I want to marry someone that is in private equity, hopefully, you know.

No, I was like literally keeping the event alive talking about private equity. And then somebody was like, what do you do? And I was like, I'm a writer. And they were like, what? Yeah. Well, you're also like a girl boss like through and through. Does that like affect like your dating life in any way, like having such like a high level position and just like crushing it does that intimidate anyone you're no i i don't think it does but i think i'm very protective over like dating in that way so i think that's maybe the biggest thing i like really like don't have my job listed on any dating profile and i don't think i ever would no raya kind of like connects your instagram but even then it's like i just am like i don't need people knowing that no yeah i don't either and yeah have you ever felt like

someone like used you or like oh yeah well for me it's like a little different you know i do have a podcast called like extra dirty so like i either first message like are you extra dirty no i either like kind of scare men away in a sense because i think they're kind of scared that i'm gonna one like talk about them publicly online and which i never like name drop or anything i protect most people's pieces unless they like cross me in some form of way but on the other end of it i like don't know people's intentions really at all like when you're in like the social media world and I'm sure you feel the same way like you don't really know what people are after like if they have good or pure intentions in that sense do people ever like be like don't talk about me in your podcast all the

time so imagine all the people I don't talk about if someone asks drop a story drop a story no literally if people ask me not to speak about them I respect that I'm not about like disrespecting people's boundaries of course um but like my show is about like sharing my life and my experiences it's not really like commenting on other people so if it's like my experience with someone like I'll share that experience but I don't need to be like dropping their address yeah yeah I'll make sure I like do enough to not do that but it is interesting I feel like dating since I've gotten the space has become a little bit more difficult I thought it become easier like you know I don't know I thought it would be easier for some reason, but I feel like now I can't date someone that's also

you know, camera facing at all. Yeah, I have no interest in being a public relationship. Like, I think that would be so stressful. I also think like, I learned so much about dating from working at Cosmo. It's crazy. I feel like every day I'm learning more about like love and relationships and even just like being self-assured and getting reassurance for yourself. So it's like I just think, I think like I love that part and I love learning about it. It's like why, yeah, I don't know. It's definitely interesting. What do you think the biggest, like, as you probably hear so much like relationship dating advice, what is like the most like important little bit of information or advice you would share if you could think about everything you've heard like recently. I don't know if you're going to like this.

I want to hear it though. I think I need to hear. Okay. So honestly, there's like one common theme through everything and it's open honest communication. Open honest. And it's like don't play games. Like, yeah. And I think, yeah, I want to hear your take on this, but I actually think it's so hot if you're just like, this is what I want. Yeah, you're just blunt about it. Like, first date, you're like, hey, I actually, like, think this is going somewhere. Like, is that crazy? I don't think that's crazy. I just think I would like to think I'm a very self-aware person.

So I know I'm toxic and I know I probably shouldn't be in a relationship right now for the benefit of that person. Because I like like to play games. I still find that entertaining, which I think is very immature of me. and until I get sick of playing those games with someone, I feel like that's when I should be ready to enter a relationship. I still think my frontal lobes developing when it comes to that. That's really mature and special. And I think that is something, yeah, I mean, that's real.

I just think it's so interesting. Like, even being single in your 20s versus your 30s, like the biggest thing that I think I noticed was, like, people like on a first date are like, this is what I'm looking for. And I think from what I've learned through Cosmo is, like, really, like, it's the only way our relationship will work is like if you are truly open and honest. And I think, you know, I'm actually a millennial, so I'm not Gen Z, but something that I hear a lot from Gen Z readers are that like they're not sure what people think. And they spend all

this time, like, exhausted about like what this text could mean. And, you know, I've heard you talk about like putting your text through ChatGBT or like asking your relationship advice. Like it's so interesting. At the end of the day, like you could just ask. You can be like, hey, like, so are you into me? What's up? Like, I would do that. No, yeah. And I also feel like there's this element when you're like in your 30s versus your 20s where like you don't want to waste any time. Like being blunt, get to the point. Like don't waste my time. I don't want to waste yours. I feel like that's important. Do you feel like if you said that to a guy that you like actually had a crush on? You were like so are you into me. Would that like turn him off? I am just it's not it wouldn't roll off the tongue. Like I'm scared. I like I'm one of those like anxious people that like overthinks and will send a screenshot of a text. into chat CBT and be like, what does this mean? I'll send it to every group chat of all my different friends, be like, what do you think this

means and try to analyze it? And what do you think it means? And usually it just means they're probably not that interested or that's like usually like if you're really having to think about it and analyze it, then it's probably not right. It would be my guess. Okay, so our issue went live today. It's an online issue. And there is a cover line on it that says, is great.

texting better than good sex. And basically it's like thinking deeply about like what is the role of texting this? Because like I do think there are people who are genuinely not on their phone. And this is coming from someone who basically like is the quickest texter of all time. Like yeah. No matter what like I will text anyone back like. Yeah. I'm on my phone. But I know that you've also talked about not being on your phone as much. And like that's hard for you. It takes me like two business days. But like I usually get back to people. Well, I just want to say you did text me back this weekend. I did, I did.

It took me like 36 hours of producer, though. Really? Yeah, like, I'm so bad. Like, I have ADHD, so, like, I'll read a text, and then I'll be like, oh, crap, I thought I you sent it, and then I'll have to go back. My toxic theory is, like, I either respond right away or never. That's how it should be, honestly. That's why it's, like, even if a crush texts me, I'm responding right away because

they're, like, completely forget and never speak to them again. Yeah. But, so what do you think? Is good, is great texting better than good sex? Great texting better than good sex. See, this is why it's a good cover line. I feel like these are like their difference between like two different love languages though. Because if you're a great texter, you're obviously the lines of communication are really open

and that could mean like validation or affirmations over text rather than like good, not great sex. That's physical touch. And I feel like that's a, if it's just average. Is good average though? You mean good versus great? I'm asking too many questions. No, no, these are all the things. I'm overthinking it.

No, we all gathered in a room and really talked about this. We played with it being, like, good texting, good sex. But it's like, great texting is like, it's right for you. Like, some people don't care. I think, like, some people can be in a relationship for two years and, you know, rarely text their partner. And then there's other people in my life that, like, if they're not getting texts consistently, they're like, we're not together. Yeah, I guess it depends. I feel like it could depend on a lot of things, what phase of the relationship you're in.

True, true, true. Or if constant texting is important to you. Because like you said, not everyone's on their phones 24-7. I don't know. What did you decide on that one? Which one do you think is better? I think it's really interesting. I think we looked at it from a lot of different angles.

Gen Z, like, obviously this is a generalization, but for the most part, most of Gen Z do want consistent texting, even in a situation. And when they don't get that, they do think it is less committal, which is interesting. like part of the new commitment for young people really has come with like contact over the phone. Maybe it's like an Instagram, like maybe it's a DM, but that was really interesting. And then in the cover story, we had RNA Greenblatt interviewed by Jake Shane, who I'm sure you and Jake know each other. Jake, who is amazing and did a fantastic job. But they both talk about like how important even just like going out and partying. Like they're so worried about like people taking videos of them and how that's kind of like influenced their relationship with

intimacy and that's something I truly did not experience growing up growing up in LA like yeah me and my friends like we would go out we just weren't we didn't feel like we were being watched we were growing up and like you know kissing boys and there was that wasn't a big deal so it's interesting yeah I mean I recently ran into that situation not too long ago like I go out and sometimes you get like a little tipsy and you're with the guy and you like do the dance floor make out but like you can't really like it's interesting like because people are constantly always watching you so like you can't really have like a intimate moment with someone like out in public anymore without people like clocking you immediately do you worry about people like photoshopping

because that's what they talked about in the cover story and i was like photoshopping yeah like photoshopping alcohol closer to them and like our inner grandma basically is like i don't like to indulge but i do get nervous at house parties because um like people photoshop stuff i will say the one thing i've been a little bit i mean everything i talk about on here here is basically I try to be super like that's exactly we're going to find out in public but I will say like I am trying to monitor how much I drink because when I do drink I get a little cross-eyed and then I get and then what's been happening to me is people like want to take a selfie and I'm cross-eyed and like that's on the internet and then like that's on Reddit and then I'm just like looking like

kind of like a mess you're always beautiful don't worry thank you well I need to hear that today Literally, of course. But it is funny, but that's just, I guess, the world we live in. Do you think that I actually saw that Alex Cooper just put out an episode about like doom scrolling and I thought it was really interesting, especially the night before our online issue where she kind of talks about how like our brains now are rewired because of like we're getting attention all the time. Do you think that has affected your relationship with intimacy?

Doom scrolling. Just like getting validation all the time. So it's like if someone's not texting, you're like, they hate me. But it's like, no, they don't. They just. Yeah. No. In private equity.

No, yeah. I like to think that too because my, you know, our jobs are like a lot of it is on our phone and we have to be consuming a lot of content, you know, like what to be talking about and stuff like that, which is so different from like a normal corporate like private equity, whatever job like where you probably can't be in your phone as much. Totally. Some people don't even have TikTok. I like forget that too.

There's people who don't have TikTok. No, which I would prefer to date someone that wouldn't even know what TikTok is. I'm not even kidding. Me too. I'm like, talk to me about private equity. No, literally, that's what I love to talk about. Not us targeting private equity. Wait, I wanted your opinion on this, ghosting.

Okay, so my professional opinion is like, it's not great. Have a convo. But sometimes I've gotten into these conversations at work where like, do you think it's like, and there's no right answer to this. But, like, this is a debate that's come up a lot on staff. Like, do you think, like, ghosting someone after, like, one or two dates, like, is maybe okay? Because, because, like, it's kind of self-important to text them being like, hey, I'm not

interested anymore. It's, like, assuming that they're thinking of you. I don't know. There's something that can come off as disrespectful, too. So I don't know. I'm, like, behind every ghosting story, there's two sides to every story. Yeah. I mean, I feel like if you've been intimate with someone, ghosting is kind of wrong.

But then I also, it also, like, there leaves too much gray area where you think maybe, like, excuse, excuse, excuse, excuse, maybe they're going to text you eventually, whereas if you just send like a hard, like a black and white text being like high, not feeling it, that might hurt more in the moment, but at least you don't have to, like, think about the what ifs and the maybes. If you were on the other side, what would you rather have? Like, would I rather receive that? Or just like a ghost? Just like you hit them up, like what's up? and then they just never respond again. I mean, both have happened to me. I've gotten a whole paragraph describing the reasons why they didn't want to continue

seeing me after spending like a whole week with them. And I don't know. I didn't like that. But then it was easier to get over than a ghosting situation. You know? Yeah. Look, I think like with every romantic dynamic, there's like so many things that go into it. But sometimes I'm like, I think ghosting is okay if it's very early.

I do think if you've been romantically involved for a while, like, it is important. Like, more than a month, it's like, come on. Yeah, more than a call. Like, do it in person. Do it in person. We publish this piece about, like, Texas Center situation ship based on, like, different ways that you're feeling. And again, the common theme is, like, just ask for what you want.

Like, if someone's, like, only hanging out with you at night, be like, hey, can we meet here instead this time? Like, you don't have to make it a big, big to do. You don't have to make it, like, that you're in love with them. You just literally ask for what you need. And I think directness is so hot. Yeah. And I think that's kind of what's missing.

It's like a lot of times we are conditioned to think that asking for what you want or showing, like not playing it cool isn't cool, but I don't know. Do you think this generation, old gen Z, is a less or more direct generation than, you know? Both because like they're so online. So in some ways, like I just think they're like. less, I think doom scrolling has like really made it harder to go out. So like in the same way that like me and my friends were going out in high school, you know, going on dates or like figuring out we wanted or experimenting with different things like that that doesn't seem to be the same.

But I think they're direct. I think they just like are like not trying to waste time. And that's admirable I think. Yeah. Do you think dating apps in social media in general has like affected how people date now do you think that's made people a lot more accessible or you know men are looking at women having too high standards because of how people like are you know what you know what I'm trying to ask yeah I think well we see it go up and down but I think speed dating and blind dates being back like kind of says it all it's like people actually do want to meet cute like people want to be like at a coffee shop and be like hey you're high here's my number I think like I see that even getting We talk about blind dates a lot at Cosmo, and I think what's so cool about blind dates

is like, if it's a friend of a friend set up, like, you know they're not going to be crazy. You know, like, at least they're in your wheelhouse. They know, like, you have mutuals. I don't know. I think it's cool. We know that we're speaking about blind dates. I saw your blind date series. Yeah.

Who is like your most fun person to chat with on that? Ooh, that's a good question. I love the concept. It's so cute. Renee Rap was honestly pretty, pretty wild. She seems super cool. She was like, line, after line, after line. Like, I kept being like, what?

She just, I think it's so cool how she just like truly is herself. Yeah. Like being. And she seems so comfortable too. She's always just like laid back and she never seems to like, everything just rolls off her tongue. Like every response. She's very like mysterious and cool.

Yeah, I love that one. Conan Gray was really. funny just because like he I feel like the way he talks about dating is so him I don't know I just think with dating you have to be yourself and so I think the guests that come on and are like this is what works for me is so good I don't know so fun that series is so fun the hardest part though genuinely and you know this as like an interviewer especially doing it on camera it's like I don't know who the guest is so my biggest fear always is that it's going to be someone that like I can't ask them like the right questions. It's just really hard to go in blind. I mean, I can't imagine like doing this

blind and what's like a voice change or too, right? Yeah. So you have literally no idea who you're talking to. I have no idea until I take off the blindfold. And then once I take off the blindfold, I'm like usually like praying as I take it off slowly. I'm like, please, please, please be someone I like kind of know. Yeah. But it's pretty scary. That part. I think someone like Renee Rapp, like I genuinely know her music so well. Like that was fun. And we've like met. Conan Gray saying like There are people I vibe with Serena from Love Island. Like, I love Love Island. So that was easy.

Like, I love when there's something like that. But every once in a while, there's one that's, like, scary. And you just go with it. So that's fun. It's hard to roll with the punches. Yeah, you get it. Especially, like, when you don't know someone that well, you're like, okay, how much can I ask them about sex life and dating and stuff like that?

And you just kind of like have to, like, banter off their personality and kind of roll with it. But it's kind of like the fun in it, too. Logan Lerman though was another favorite I was like we're flirting He was like we're not And I was like no we're flirting After I was like was this not your favorite date you've ever been on And he was like no I'm married

Okay I'm gonna ask you a couple Your opinion on a couple Dating and relationship topics And you just like give me your immediate Whatever you think about them Can car sex actually be good like in like a like probably not like real romantic way but maybe like fun one night thing yeah like a swear the moment kind of situation depends on what you're calling good though okay

can you actually find a happy ending massage in new york city i don't think so no and like i kind of judge people that do that i'm not gonna lie i've never heard of anyone actually doing that have you yeah all my college friends all my college guy friends used to do that and i actually know a couple girls have done it I've literally never heard anyone yeah it's kind of sauce but I can say I've never done that I have never done that do you prefer coffee or drinks on a first date drinks drinks but we're very pro coffee at Cosmo because there was all that TikTok discourse that's like no coffee and like I disagree I think like there's no right or wrong first date and like if someone asked me a coffee date like no problem but my preference

wine bar wine bar because it's like quite enough to talk like I do want to actually talk on a first date yeah so it's like quiet enough to talk while also I love glass of wine I went to a whiskey bar on a first date that's fun and that was really unhinged because I don't know what I drink whiskey and I got like kind of fucked up and I was like oh shit like um but like how did I go about he was like meet me at this bar and you were like fuck it's a whiskey bar and I what am I going to suggest something else like I don't know um I also been seeing a lot of people like thinking that first dates like should like only be drinks and you it's okay to leave after two drinks have you yeah definitely I think it's okay to leave after one drink really I've done that

like 30 minutes yeah so you're just like but like does that mean you don't like them no you're just like I gotta go I'm obsessed with you I like can't not be myself I'm gonna in any situation it's like I'm still like okay you're just like you're just like I'm just like uh gotta go thank you for the margarita okay period on your margarita at a first date that's like you're to me that's a commitment what else that's another good question what would be like your go-to first drink order on a first date tequila soda i thought you're going to say a cosmopolitan let me try that again i only drink cause of faultless no they're my favorite no but i will say a margarita is like you're like committing to the night because you do get like a headache after that no like you're

committing to like being hung over tomorrow and like you want to like decide if like this person's worth the hangover tomorrow. No one's worth that. No one's worth the hangover. Even if you have a fat crush. Tequila soda. Or like a beer. A beer? I always do a dirty martini but people tell me not to do that because like olives and the blue cheese can like make your breast smell. Wait, I saw this somewhere. Yeah. That's your favorite drink. I've literally never thought to order that. Really? You've never tried a dirty martini? Oh. I know. I know. I know. I know. Everyone's face in this room just gasped. No, I'm like a tequila soda down.

I love a tequila soda. I don't know how people ordered tequila sodas at bars. They taste like, just like, tequila soda. I don't know what to explain it. That's the freaking problem. Like, I kind of want, like, what if you were a date and they ordered a peanut clotta?

I would be like, are you 21 years old? Because suddenly I'm confused. Like, it does say a lot about you. Like, that drink gives, like, like not drinking age yeah yeah they're like can i'm a strawberry dackery and you're like um okay strawberry decry's hilarious okay but estella has a hot drink again on a first day or like a corona light and you're like in miami yeah i'm down for i think like i'm just like confused but no worries i support what is it okay when is it time to end a talking stage okay talking stage on text

you just like no kiss i think talking stage is are anything before you declare that you're in a relationship, right? Oh. We, I think of it more as like talking stage is like you haven't kissed or gone on a date. You're just like texting or like entertaining the. How often do you think people should be texting during that weird phase? Actually, now that we're on the topic asking for a friend. To text.

Yeah. App to text. Oh. Like longer than a week is kind of two weeks. It. Yeah. But I don't know. Like I'm gone all the first.

freaking time so you probably are too like you're gone like it's like different um but i think yeah if you are on an app and you're trying to tradition to text i would do that as quickly as possible and then see if the banter's there if the banter's there go for a drink i don't know it's different for every dynamic but i would not give it more than a week we published in cosmo in this issue three to five messages on app and then if you suggest a place and there's no follow-up just to like let it go and I don't think that's ghosting like that to me isn't that's like because yeah there's no contact but I think sometimes people do just want to text I mean it's like it's like a pen pal some people just want like attention and sometimes it's over

text do you have people that like you texted for like a bit and then nothing ever happened and you just left it there like those are like scary to me I still have guys that like I talk to you regularly and like we like pretend to make plans or like link up or like late night link up and it just like never happens I just like needed someone to text in that moment but um usually the problem but do you think that like they think that like you guys had a thing probably you never met no we've met oh I have this guy like I yeah please tell you're like I have a couple of guys that aren't even living in this country that like we are we make plans staying out and we just go through like these little talking phases and then I'm like wait you live in like

Sweden it's never going to like highly specific no yeah it's so random but like sometimes I just need a pen pal have you ever had a fling at fashion week a fling at fashion week yeah like in Paris or Milan I wasn't invited to Paris or Milan this year I think we're bringing that off okay sorry to need to but people for this fashion week I actually did have a small he came in he came in from wherever the fuck he lives like gotta go the Mimu show beer Yeah, those are always fun. What do you think of Fashion Week? I love Fashion Week.

It was so fun. What was their favorite show you had? I think what I loved about this season is like the energy was really there in Paris. Like there were so many debuts. So I felt like every single night there was like so much to do and so much to see. And favorite show. I mean, Chanel was truly like gorgeous. How much stalking is acceptable before our first date?

Like are you idyllowing? No. Because I Zillow. I didn't even Zillow people I date. Really? No. I love to Zillow. I'm like not a stalker.

Like I actually am not. Like I fully like I don't want to know things that I don't need to know. Ignorance is bliss. Yeah. And like especially when the early stage of dating, it's like I want people to tell me about themselves on their time. Turn, their turn. Their turn.

And so yeah, I think that would have. actually freak me out, but lots of my friends don't agree with this. And sometimes, like, they'll stock people and be like, did you know that? And I'm like, stop, stop, stop, stop, stop. So yeah, but I know that, like, people have admitted to stalking me. And I'm always like, that's so freaking weird. Why would you tell me that? You freak? This is why I prefer people with no social because it'll stop me from stalking them. But, like, I need to know everything. I need to know all our mutuals. Why are they mutuals? Where are you from? Where you live? Zillow. I'm a psychopath, I think, though. Okay. Would you ever date someone on a different city?

Or what do you think about people doing long-distance relationships? Yeah, whatever. I mean, we're bouncing around anyways. Like, I'm never here anyway. Yeah. Has the ick ever been damaging for relationships? No. Do you have any X, big X?

I think you said, do you have any X's? Then I was like, yeah. Unfortunately. Okay, do I have any X? No, I think, like, not being able to talk. And just, like, being mean. like I don't like people who are like mean as a way to flirt like I just don't like I'm just like come on I'm 31 like no yeah also people that mean mean to wait staff that too but they're usually

the same yeah usually the same people it's like people who like are like belittling of like my job as like a way it means of flirting is like immediate now why the why the fuck would they do that I don't know people just be flirting like I think that is something like people are mean by flirting and I always said that to my friends. Like, that is, like, actually, like, I'm, like, never good. That's such, like, a kindergarten, like, perspective. I feel like that's exactly how people flirt when they're, when they're six. You know, like, you push the girl, you, like, into the sandlot.

Hey, some things continue. Some things never changed. No one's ever been mean to you as a way to flirt. Oh, they were always mean to me. You should have seen my haircut when I was nine. No, I'm talking about now. I mean, people are mean to me all the time, but men? I mean, yeah, like teasing, but like...

Teasing's different than like... Nothing like Achilles heel where like I would want to like slap him right across the face, but close. Or just like commenting on like food and stuff I think is like inappropriate. Like this one girl was telling me she went on a date with this guy and she was like he kept commenting that I was eating and like girls that usually eat on a date and I was like he's out. Oh my God, that would throw me through a fucking wall. Like that is so inappropriate. Yeah. I mean, especially in light of this up, I'm talking.

about online with my eating stuff if a guy was commenting on anything about food or how how much I eat how much I don't eat I would kind of probably have a panic attack and that's just not funny or cute no that's like leave the restaurant that's leave the restaurant that's I'm going to the bathroom I'll be right back have you ever kicked someone out of the restaurant have you have ever kicked on a date like been like you have to leave this is going badly uh no I don't think so in case anyone is curious what was your worst first date experience though that I need to know I don't know were you just like this isn't working left at any times no I think I always politely I'm like I gotta go sorry I got things to do people to see yeah I don't

I'm not I don't really like drama well what's your love language um I think verbal affirmation like I really love like letters and like talking and la la la like romance romance in that way yeah I feel like I could be more romantic like I am I am I am I am named after Willa Cather oh my Antonia like I love romance like I work at Cosmo come on yeah I guess romance is everything romance needs to make a comeback because romance is making a comeback I love when guys are romantic to me and I feel like if they were a little bit more romantic than out it would open up the softer side to more woman but I think you'll find someone one day that like we'll bring that out of you. I think something so interesting about relationships is like,

you know, you even watch like, you know, like one of my friends will go through a breakup and like around this one person she was very anxious or she was very needy. And then like the next person she dates, she's like completely different. She's like, oh, I don't care. Like we can be an open relationship. And it's like, what? You're the same person. And I think different people bring out different things. And so I think you'll find someone where you're like, okay, I'm going to be soft now. Yeah. I just feel like when the time's right and I meet the right person, things will just like fall into place. But I'm not going to like force myself into dating

because I'm like a true believer in that too like to not settle. I'm like really getting settling. And I see a lot of my friends settling. Really? Not like my best friends. They're all in like pretty good relationships. But like people I went to college in high school with

they're like, oh, we're at a certain age. Like I feel like I have a boyfriend. Might as well marry them because I'm 28, 29, you know? Yeah. Do you see any of that? Yeah. I think all of my friends are with who. they're supposed to be but I think yeah I mean every single day on Instagram there's like a

new person from high school either with a baby or or a husband yeah and I'm just like on my own journey that's what I always say you and you both girl I'm on my own path um me and you both girl we're on the same major yeah um what's the wildest pitch or story you've ever approved for cosmo whoa um um wildest pitch or story Earlier in the year, there was this writer, Vera, who basically spent six months on right-wing dating apps. Oh. And that was pretty wild. It was before we knew Trump was going to be president.

So it ended up happening during. And it was just a really interesting, like, she was trying to be done. There's right-wing dating apps? Oh, yeah, yeah, yeah. There's a bunch. Oh, I didn't know that. And she went on a bunch of them and she went on dates and she tried to see if she could fall in love. as someone who she identified as like basically the complete opposite of that, to say the least.

So that was pretty wild. Just like hearing her talk. Was that like a case study she was doing, like just to see if, or was it for her? She was just like, I'm very single and nothing's worked. And like I am curious like what it would be like, like could I fall in love? And do you want to know what happened? She said no. She did not.

She hated all. She just was like, I can't be sexually attracted to these men who, like, don't believe women should have rights. Like, it was, like, very fundamental. But, you know, she really tried to lead with curiosity and, like, openness. And that was interesting. She probably had to have a lot of patience and keep a really open mind to do that for six months. Six months also is way too long. That's, yeah.

A couple weeks. Maybe it would be a cap. Okay. Is a sex playlist hot or awkward? Like, one in general? Like, come on, give me some. Like, if you're, like, putting on a sex playlist when you have sex every time. Same playlist?

Nah. On shuffle, though, maybe. Man. No, not a thing. I mean, I feel like it was a thing. I used to be really... Is it called sex playlist? Like, if...

Yeah, in SoundCloud. Someone put that on, I'd be like, you're insane for that. I used to have a sex playlist in college. Who's on it? Wait, can I guess, actually? Yeah, it was like... It was, like, the weekend. Okay, hot.

A little Drake. Drake like the slower Drake songs when he was like in his like lover boy era but like also kind of like there was a mix of like rap in there and that didn't make any sense but I guess would pick up rhythm I guess it was like your playlist it was my playlist there was interchangeable playlist days on playlist was a non-negotiable but I don't do that anymore that would be kind of weird um okay what is an immediate turn on you have or an immediate turn off or both those are two different questions Ms. Journalist. Yeah.

I don't know. Being able to talk, hang out. Like, be fun to hang out with. Be fun to hang out with. And having your own friends is important. What is the turnoff? I don't know. Not being able to talk, like, truly.

It's like, and like not fun. I don't know. So you don't like, you hate introverts. No, I would totally date introvert. And I probably have if I, think back um but i think life is hard you gotta find like someone to have fun with you got to find some comedic relief and just be able to be silly with someone and just like loving life like i do think i wake up every day and i'm like very grateful and like do i'm naturally happy and so i can't be

with someone that's like ugh the world sucks all the freaking time yeah it's like no let's go out um do you like to go out a lot or you like more well which is funny you don't like to go out a lot? Well, I go out a lot for work. So on the weekends, I'm like, I'm out. You're like, so you go out during the week for work, yeah. And then you stay in on the weekends. Oh, yeah. I'm like watching TV. What's your favorite TV show right now? Okay, I just watched All of I Love LA by Rachel Senate. Ooh. So freaking good. So I just watched the entire thing in one sitting. And it was that good? Where's it on? Hulu. It's going to be on HBO. HBO? Okay, I'll watch it. Yeah. Have you ever been cheated on?

Yes. My. first girlfriend ever was in college and she cheated on me with someone and they are now married oh really the person she cheated on you with yeah so i'm honestly no worries because i'm like y'all were meant to be they should be thinking you because like we were not meant to be and i and i knew that at the time and now but like it just i was like you know what that's all good i mean cheating is crazy but i feel like it happens a lot in college unfortunately Yeah. And I think I have never cheated on anyone. I'm pretty anti-cheating. But I do think, like, for them, it was supposed to happen. Yeah. So I have no, like, I literally have, like, no anger. No anger towards it. But I do think, like, emotional cheating is tricky. And I think something that Cosma's audience is really interested in. And I think with, you know, with the rise of people dating AI bots or, like, the rise of, like, ghosting and all this. Like, it is a sticky slope that I think we're going to continue to cover.

Do you think emotional cheating is worse than physical cheating? One nightstand, no connection with that person. I think it's all not kosher. It's all bad. Yeah. Yeah. It's like all not good. And I think open, honest communication, I think it's one thing to, like, go to your partner

and be like, hey, I kind of have a crush. Let's talk through it. What am I not getting from this relationship? But then to just, like, do it is bad. Do you think it's a forgivable offense? Like, if they were honest about it? I think you can definitely talk through it. I know couples that have.

I think it'll be really hard for me, though. Yeah. I don't think I'd be able to, like, I think I'd always have a mental block. Yeah. And I think, yeah, I just think it depends on, like, how safe you feel in the relationship. But I really, like, I don't think I could do it. No. But I don't know.

Maybe one day. Yeah. I mean, I feel like that would be setting the bar. I feel like we don't need to be going after any of these cheaters. I've been every single relationship I've been in. I've been cheated on. Really? I've been even cheated on in situationships.

We're like, it's technically not even a real thing to be cheated on. Okay. What? Yeah. Wow. And I've cheated once, but they started it. How did you feel about cheating? Like, when you were doing it?

I felt horrible and disgusted, but I was trying to, it was a rebuttal cheat. He cheated first, and then I thought I would get back at him. This is all in college. And then I just felt, I have too much anxiety and guilt to hold serious. secrets like that in, which I guess is a good thing for a relationship. Usually when I am in a relationship, I'm extremely like loyal, but I go after like not loyal people. Yeah. Look, like everyone's on their journey. I think college is like a time where you do make a lot of mistakes. And yeah, everyone's learning, like truly. But I just think it like comes down to the couple or the

Threple or whoever's in the dynamic. And like I think it would be pretty tough. I don't know. Where'd you go to college? Sarah Lawrence, baby. Sarah Lawrence? Yeah. Is that out in L.A.? No, it's in Bronxville, New York. Wait, what am I thinking of?

I don't know why I just snapped. It's in Bronxville. It's just a short train right away. Is it small? It's super small, super queer. It was amazing. I loved it, truly. I went to school, a small liberal arts school in upstate New York.

It's cool. What's cool? Union College. Nice. I think I actually went to some parties there. Probably. It's so fun. I mean, it's only like, two and a half hours away from here.

So it was like quick. I loved college. It was amazing. I feel like I learned so much. Really? I feel like what I'm doing now, I don't know if I needed college. I know. You've said that before.

But it was an option not to do college. Yeah. Your dad was very adamant. My dad was like, you're getting a college education. And I was a classics major, art history minor. And now I'm just an influencer podcaster. So I don't know how that pipeline made sense. It all goes.

I think it all informs each other, really. And I don't think it necessarily matters what you study in college, but I think it does teach you how to think, and that's what I'm grateful for. And I don't know, even just like in terms of romantic relationships, I learn so much. Yeah. I also think it's about a lot of learning about relationships, whether that's platonic relationships or romantic relationships. You learn a lot in those four years.

and I feel like you have to be in that kind of social setting where it's like the first time you're living without your parents and you're kind of out of the nest and you're like being thrown into situations that you have to learn how to navigate. Yeah, and just like be accountable with your friends, like talk about things, feed yourself, like go on time to class. I have two sisters in college right now and like reliving it with them.

I'm like, wow, college is actually so hard. Like, I don't know. Especially freshman year. Oh my God, yeah. Like I hated freshman. year. My sister's like loving it and I'm like that's awesome for you but I also like don't relate because I think it was hard. Yeah, it was hard. And I also went into college with a boyfriend, which I actually did too. Really? What do you think about that? People that are going into college

that are wanting to do. I think we broke up two weeks before my freshman year. I think we did too. Okay, twins. Twini. But I just, it doesn't work. He had too much temptation at the college. He was at and I was just like you're juggling too many balls I think what was hard about our breakup is that he went to Columbia and I would Sarah Lauren so like we were actually close enough to make it work so it's kind of like this thing where we like broke up but it was like why um yeah and then I think it was like such a good thing though to like I saw this TikTok of Rachel Senate actually just talking about on Jake Shane where she's like I'm very pro breakup it's like so good for you like you learn so much and that's really how I felt at the beginning of college

where it's like you go in and you're like kind of sad and heartbroken and so you're actually like so energized and you're just like want to make the most and go out every single night and like talk to everyone and I met all my best friends at orientation like I don't know I think that time of my life was fueled by the breakup in like a magical way because it like kind of forced you to like push yourself outside of your comfort zone make new friends meet new people I think especially now it's so easy to like be on FaceTime with your boyfriend and your dorm room but it was like I had the exact opposite experience.

I was like literally like it was great. Yeah. How I handled breakups like was kind of similar. I would just be like I need to get off my phone and just like go out and distract myself because I feel like distraction is so important when you're going through a breakup. Yeah. But I really relate to what Rachel was saying where she's like, she was like, I am so pro breakup. Like it's always good.

Yeah. And the glow up after. I feel like everyone has a post relationship like breakup glow up too. Totally. and like you you become so close with your friends again yeah i don't know i agree friends person what's something about modern dating you wish more people were honest about ooh i think that people i think people just need to be honest about where they're at and that no one wants to be like i think like this whole like it's cool to play hard to get is so lame like yeah i'm learning um but like i also

i also like respect everyone's process and i think also like people can bring things out of you but I think like if you're just like hey I'm like actually just looking for casual sex like you should just say it yeah I mean I'm pretty pro that I'm not like pro that I'm not like pro I'm just like pro whatever works for you in this point in your life yeah but I don't think casual sex unless like unless you're being safe should be like looked down upon too heavily totally do you think there's such thing as casual dating yeah we published this uh Okay, the Margaret Qualey issue, so not this one, but the one before, which is our 60th anniversary. We coined this term called the New Casual, which is hot sex, no sleepovers.

That's what I say. What do you think? I think sleepovers kind of make it too serious. Yeah. And well, you're like, sleepovers are for gossip, which I actually like. And pillow talk. Yeah. But like, that's what, like, pillow talk is where you form those emotional bonds and inside jokes.

I don't think it's necessarily that, but I think, like, I think there's something there. Like, it definitely is the new casual. Yes. The sleepover makes it not casual. And that is something we wrote about explicitly. But I think as long as you're communicating with that. As long as you're both on the same page and, like, not one person wants to have the sleepover. But, like, I'm pretty upfront, like, not wanting to do the sleepover thing.

But also, do you think both people are, like, I don't want to have a sleepover, but both people always want to have a sleepover. Well, that's what your point is. People should be more honest. So, like, if you want the sleepover, just say you want the sleepover. but if you don't, then say you don't. Yeah. It's an interesting concept. I think people are still very scared about hurting the other person's feelings to still

in the day and age. And that's like what the issue with being super honest with people is. I feel like they're probably just worried they're going to hurt the other person's feelings if they're too blunt. Yeah. Or it's just like scary. No one wants to be like, yeah, I'm actually looking for something more even though I met you 25 minutes ago. Is that what you do though?

No, no, no. But I'm just saying, like, I do think there's a world in which, like, yeah, you just have to be okay with, like, learning each other on a slow pace and being honest, like, hey, I'm actually not down for sleepovers right now, but maybe in the future. Yeah. It just sounds so clinical. And it's like, I think what we see in pop culture, like, it's not hot to be like, actually, I'm looking to have a sleepover in six to eight weeks. Like, you know what I mean? Like, who wants to talk like that? No.

But I think there's a way you can do it. that's like flirty and fun yeah I don't know I mean it's all trial on error I just feel like dating in your 20s what do you think dating in your 20s is very what's like the biggest difference between dating in your 20s and dating in your 30s everyone's very direct dating okay I'm trying to think um in my 20s um I felt like well no one around me was getting married yet I don't know if that just has something to do with my like friends group I think there are lots of places where people are so it felt less serious but again like as the token like young fun friend yeah I actually have the pressure on my back to be like the fun one who's like

friends with everyone yeah at the wedding so I don't know like I think I have a very specific experience I also like truly did prioritize my career so that also is like another added layer where I just like I've never once in my life like gone out being like I need to be married by a certain age like I just don't feel that pressure so you've never felt that problem pressure at all. Maybe subconsciously, but not, no. Like, even my family, like, they're not like, oh, Willow, aren't you married? Everyone's like, yeah, duh.

I mean, I have a sister that's 15 months older than me, completely different than me, introverted, sober, Pilates instructor. Wow. I know, like, completely, literally 180, like, very shy and very sweet. Not that I'm not sweet, but she has a live-in boyfriend, like, they're about to get engaged we're like only 15 months apart and i to me i'm like part of me is like a little like oh crap like am i should i be in that phase of my life right now but then another part of me is like i'm doing so many things right now in my career and do you

think that people find it hard to balance the both yeah i think that's like a tale as as tall as time like it's always hard to do it all but i also think like when you meet the the right person it's like just makes sense and it's fine yeah um i don't know i just really like don't feel the same pressure i think a lot of my peers do about finding someone like i yeah i don't know it's just like i think a lot of it also is like being queer like queer people like we do find our people later because we only started like i only started really like being queer or like saying i was queer in college so i don't know i wonder if that has something to do with it i just think there's like one there's no one size fits all there's no like perfect path you find your

person we're supposed to it feels right people get divorced many times like everyone is just like on their own journey professionally and personally and if there's one thing I've learned from running cosmo it's like romantic relationships like they're something you always have to work on same with your friendships like and it's all like coming to the same place and another thing about breakups that I think really put a lot into perspective for me is like when you you when you end a relationship I think there's like this misconception that like it's over and like it was horrible but like really you learned so much and you bring that into your next relationship and so I always say like even if a relationship ended it's not like you're starting

from zero no yeah I always say this too like even if it's an end to something I you always have to look at the glass half ball and be like what did I what lesson did I learn that I can take into my next relationship whether that's a platonic relationship like you always feel like you gain something and not lost something. Totally agree. And I always say that. Let's talk about Love Willa, your newsletter. I want to take a little money.

Yes. I'm so excited. I loved our interview that we did together. So fun. How do you think you're able to connect differently with a newsletter versus on social media? Yeah, we have so many platforms and I love it. So we have blind date, which is like you want a blind date with me. And we basically like, we look at old relationship advice from Cosmo and like see how it age.

Sometimes they're hilarious. Sometimes they don't age well, but that's like what makes it interesting. Love Willa is my weekly newsletter where I basically go through like all the dating trends of the week or anything love related even and talk about it. So like, you know, last week was about like Trump's executive orders, how they're affecting IVF. The week before that, you know, we did, we've done a lot on like Cougar Talk actually because that's been interesting trend. the week before that I had Audrey Hobert on which was fun who writes like iconic summer songs about dating so different you know different types of angles but really it's like a roundup of the week in love and a lot of it comes from TikTok so yeah that's why you're going to be

such a star on it I know I'm excited for that you like set the trends I mean I just sometimes feel like I have pot takes about things and people are like I don't know what you're talking about for this one but I'm excited for that to come out yeah subscribe it's so fun and also if you're single like it's such a great place to like see what's happening like we did a whole debate about the coffee debate actually and I get so many responses the coffee versus drinks yeah just being like is it you know there's a side to the debate that's like it's like cheap to just get a coffee date yeah but I kind of was like some people don't drink so yeah and it's like okay like sorry we want to like speak in broad daylight so we were actually defending the coffee

date. What is Gen Z like asking you most? I feel like people Situationship, situationship, situation. Really? Yeah, they're just like abolished situationships. And what do you say? I say situationships can teach you about what you don't want. I like that short and cute. Yeah, or they can teach you great stuff. And then I'm like, send me the text and then I look through them. And a lot of times I'm like, yeah, this person sucks. You should just go through people's texts and be like analyzing them. People send them to me all the time and I'm like, hey, I'm going to say that this is a no go. Yeah. But like, usually it's like you just want someone else to tell you yeah and I think a lot of times when you show

someone text you're like wait but he likes me you're like looking for the benefit of the doubt exactly but like he was busy like but wait like I think he probably worked late he had a dinner which is why he's texting me at 1 a am to come over it's like no by the way like even in my busiest moments like if I have a crush I'm texting someone back like it's fine if you want to do you will yeah it's like whatever you don't have time like sorry I don't agree you yeah like everyone has time everyone has time to send like a short little text also like you're on your phone all the time everyone is everyone's on their phone all the time so I agree I also think like you don't have to text them back all the time um but again I think be a front with what you want and what

you're you know if someone's not texting you like be like hey you never freaking text me what's good you can do it in a fun way like it doesn't have to be so clinical no I agree with that do you have any um upcoming articles projects any fun things you wanted to use while we're sitting here oh my god so much so the online issue came out today it really investigates our relationship with their phone and how it is like become almost this like romantic relationship in some ways so we talked about it um Lauren Greenfield who is the brilliant documentarian behind the book girl culture I don't know if you've seen it um and she has like a a big series on who Louorraine out of social studies. She shot Ariana Greenblatt. Jake Shane wrote it. And we're really like

documenting this moment in time where we're all doom scrolling to no end and it's affecting how we're experiencing romantic relationships. Inside the issue, we have a piece on ChatGBT, Not Being Your Therapist. We recommend. I'm learning so many new things today. It really, really, really should not be your therapist. What else is in there? It's so special. There's a couple projects I can't quite disclose but somber is on the cover of 17 that will be out by the time this comes out how old is he and uh he's 19 let's fact check that but I'm pretty sure he's 19 he's so crushing it right now I love him he's crushing it and basically on the cover of 17 they're very it's historically very selective about men and so he's we're kind of putting him

on the Justin Bieber path and we're anointing him as this like male pop star so very exciting check it out next week and yeah no thank you for having me i'm so excited to have you on my newsletter no i'm so excited it's like i could have talked to you for hours i feel like i need you as my new therapist literally call me anytime i'm gonna be sending you screenshots later but i'm gonna be like he doesn't like you um but anyways thank you so much for coming on thank you and guys i'll see you next week like subscribe you can watch me on youtube listen to me on any other platform willa extra dirty my queen you're extra dirty that was amazing thank you Thank you.