Willa Bennett
Appearances
Therapuss with Jake Shane
Session 57: Willa Bennett
And you're putting something out there. I'm sure you feel this way where you're like, I think this is clear, but you just never know. You just never know.
Therapuss with Jake Shane
Session 57: Willa Bennett
That's interesting. I, it wasn't about that. It was more like, it was so clear to me what I was trying to say, but I was like, will that translate? You just never know. Right. Um, and I wanted them to feel good about it. They never do press together. Um, This is really intimate. I mean, you're really you're really this is the first time they've ever done something like this.
Therapuss with Jake Shane
Session 57: Willa Bennett
So I wanted them to feel comfortable. I wanted it to do well. I wanted subscriptions to do. I wanted to do online. It obviously has surpassed all expectations, but you just never know, especially with the Internet. Sometimes I'm like, you do never know. Yeah.
Therapuss with Jake Shane
Session 57: Willa Bennett
It's a really hard time to be a young person on the internet. I really cannot say this enough.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. It, I guess for me, it's more just like so much feedback. I mean, right. Yeah. When I was a dancer, like I would do, I would, I would present my art and then it would be done. And people would like maybe say one or two comments. This, like everything I put out, every piece I write, I obviously think about it so deeply. And,
Therapuss with Jake Shane
Session 57: Willa Bennett
so in my head and then it's out there and it's like i'm reading everything from like good bad ugly people who like don't even know what they're looking at and um i think there's also you probably actually know this more than me like there's a point when anything goes viral like this did where then it just hits a different audience yeah yeah but i was lucky that most like this i feel like people got that it was celebrating their love and that's why i'm like very proud of that i also will say well congratulations thank you
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, it's a really tough place, and I think it's – I have two teen sisters, and they, like, even talking to them, like, the things they have to navigate are just so drastically different than anything I did in high school. And I obviously was on Tumblr. I obviously was on LiveJournal. Yeah, I was – MySpace.
Therapuss with Jake Shane
Session 57: Willa Bennett
Tumblr's amazing. I want Tumblr to have a wild comeback. Can it? Let's do it.
Therapuss with Jake Shane
Session 57: Willa Bennett
It was something about Twilight. I was like the biggest Twilight fan. Like if you asked me what I wanted to be when I grew up, I would be like magazine editor, ballerina. I'm going to write the gay Twilight. Like obsessed with Twilight. So I think it was like, it was probably something about like team Bella, LOL, I'm gay. Like now it aged in a certain way.
Therapuss with Jake Shane
Session 57: Willa Bennett
But at the time I was like, I'm just really team Bella.
Therapuss with Jake Shane
Session 57: Willa Bennett
I love that. I was too. But like something about Twilight like had a chokehold on me. And it kind of still does. Like I see merch. I'm always like buying it on Instagram. I'm like, stop doing that.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I love it. I mean, that was always like my dream. I was like, I'm going to write the gay Twilight. Bella's going to love Bella.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, one day. I think this storytelling to me is like so much, is just really impactful right now. And I, again, like going back to what we were saying earlier, like I do think young people need this right now and that's what's exciting me. But I would definitely write books, especially like, but it would be like Twilight is the thing.
Therapuss with Jake Shane
Session 57: Willa Bennett
It would be like almost like fanfic, fanfic, I think. Did you write fanfic?
Therapuss with Jake Shane
Session 57: Willa Bennett
As someone who's edited your writing before, you'd be great at fanfic. Thank you so much. Wow, Jake Shane fanfic. I love writing. You and Tucker. Oh, my God. I love Tucker.
Therapuss with Jake Shane
Session 57: Willa Bennett
Oh, yes, of course. Actually, this is fun. I just remembered this fun fact. I actually profiled him at GQ.
Therapuss with Jake Shane
Session 57: Willa Bennett
is he's the same we went to carbone actually and we went on like i've never talked about this before what a great question uh we went on a date at carbone and um it was it was amazing he's so funny like his humor it's like we spoke for like two and a half hours and i remember looking through the transcript being like what did we even talk about no because it's nothing but everything yeah i'm like that was so deep do you have a favorite piece you've ever written
Therapuss with Jake Shane
Session 57: Willa Bennett
Oh, that's a good question. My Billie Eilish profile is pretty special to me. I profiled Noah Beck pretty early and that felt special because no one was like writing about TikTok in that way.
Therapuss with Jake Shane
Session 57: Willa Bennett
And I felt like I was taking it seriously. So that was exciting. And you just had him on. He's really sweet. He's the sweetest. Yeah.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. I wrote this one profile on Cole Sprouse that also is really special to me. He like hadn't done press in a while and I like went to his house and we, am I allowed to talk about cigarettes on here? Yes. Okay. We like chain smoke cigarettes all day and I don't really smoke cigarettes, but there was like something with the piece. I was like, I'm living my writerly dream. Like this is awesome.
Therapuss with Jake Shane
Session 57: Willa Bennett
And we hung out for like three hours and like talked about everything. And I like when I can really hang out with someone. In this issue, I wrote two things. I wrote, I gave advice to questions about romance, which we'll do later with prescribe. Yes. It was really awesome. And I wrote a Gracie Abrams profile. That's also very special. Big fan, obviously.
Therapuss with Jake Shane
Session 57: Willa Bennett
It's special. Um, Eli Russell is this photographer, uh, that has been like obsessed with Gracie for a while. And, uh, it was fun. It was like a day in LA shot in the studio. Um, and I think, yeah, she's just so special and like should go person.
Therapuss with Jake Shane
Session 57: Willa Bennett
yeah that's awesome yeah like that's like pretty cool to me but like you're like we're basically dated we're basically dated but she um did you watch her were you able to watch her work in the studio no but i i profiled her at gq in i think it was 2020 and i profiled her i didn't profile her but she was in high snobiety um we did digital cover with her and then this is kind of like full circle
Therapuss with Jake Shane
Session 57: Willa Bennett
She's just real as hell, honestly. She's like so real. She's just a real friend. Like you could call her right now about a breakup. She would be the best person to talk to. You were actually one of the first people to text me. You were like, oh my God, I love Cosmo and I love you. It's so cool.
Therapuss with Jake Shane
Session 57: Willa Bennett
I'm really excited. And this is only in the beginning. And like, I really feel like so optimistic about it and excited.
Therapuss with Jake Shane
Session 57: Willa Bennett
What are you... Yeah, okay. I am, like, the biggest Sex and City fan in the world. So I was actually thinking. I was like, what am I going to prescribe? Like, thinking on the way here. And I was like, every single thing that came to my mind was a Sex and City episode. Which is, like, probably not it. You need to have some variety.
Therapuss with Jake Shane
Session 57: Willa Bennett
No, I've seen it. I've seen it. I've just never had like a phase where I'm like, oh my God, girls.
Therapuss with Jake Shane
Session 57: Willa Bennett
A lot of people feel this way and I respect and love. I think Rachel Sennett's show will also have that effect.
Therapuss with Jake Shane
Session 57: Willa Bennett
It's going to be amazing. What am I watching right now? Suddenly I can't remember anything. I just watched Hacks for the first time actually.
Therapuss with Jake Shane
Session 57: Willa Bennett
I'm like 10 years late. I just watched it for the first time. Yeah. What else have I been watching?
Therapuss with Jake Shane
Session 57: Willa Bennett
It's, Basically amazing. Okay. Like it's basically nothing makes sense. The challenges like don't always work out. You're like, what am I watching? But then they're at the round table and they're like having the craziest negotiation of a lifetime and they think they caught the traitor and it's only been the traitor once.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, you could definitely catch up. It's really easy viewing.
Therapuss with Jake Shane
Session 57: Willa Bennett
But I love it. I'm like, Thursday nights, traitors, like, love.
Therapuss with Jake Shane
Session 57: Willa Bennett
I know. I have to get into Housewives more. I've been following the Giggly Squad drama at Cosmo.
Therapuss with Jake Shane
Session 57: Willa Bennett
Just, like, who they are. You know, they're both two women in media, which I think is cool.
Therapuss with Jake Shane
Session 57: Willa Bennett
No, no drama. Just like... Sorry, I used that word way too late. You're like, what drama?
Therapuss with Jake Shane
Session 57: Willa Bennett
What else am I watching? It has to be something. What's on right now? Anyone know? Severance.
Therapuss with Jake Shane
Session 57: Willa Bennett
I feel like it'll make me, like, anxious a bit, no?
Therapuss with Jake Shane
Session 57: Willa Bennett
Enora. Turn to page something in there. There's an amazing... Is it called a centerfold? Do you know what that is?
Therapuss with Jake Shane
Session 57: Willa Bennett
Okay. A centerfold is basically like... It's exactly halfway through if that helps you at all. Okay. Perfect.
Therapuss with Jake Shane
Session 57: Willa Bennett
Thank you. Thank you. Wow. This is like the first time I've seen... Yeah. That's from Enora.
Therapuss with Jake Shane
Session 57: Willa Bennett
He was amazing. He was amazing. We did get in trouble because he... he like lit a cigarette inside the studio and that was obviously not allowed.
Therapuss with Jake Shane
Session 57: Willa Bennett
Like Dochi at the Grammys was incredible. Oh, it was really amazing. Like the outfit, like I was like blown away. Chapel sounded also amazing. Huge belly Stan. Um, but Dochi's performance was seriously amazing.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. I'm going on a red eye tonight. So I'm trying not to think about it, but yes.
Therapuss with Jake Shane
Session 57: Willa Bennett
No, that's so, that's so scary. I'm going on a red eye tonight and I like really don't love red eyes. Like I think they're really like, Really uncomfortable. What do you think about red eyes?
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. The plane part is fine for me. But I like I guess tonight I'm going on a red eye back to back to school, back to work. And I land and go straight to work. And I think that's the part that like by 4 p.m. tomorrow, I will be like exhausted.
Therapuss with Jake Shane
Session 57: Willa Bennett
Coffee, chilling, listening to music. It definitely helps to like your job. But it's it's red eyes like it's like the 3 p.m. that always gets me.
Therapuss with Jake Shane
Session 57: Willa Bennett
Like traveling, touring, not like the actual act. I was like, are you good on tour?
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I definitely relate to that. Do you have that feeling where, like, after you put something out or after you do something, you're, like, so awake after? Yes. Like, always when I, like, put a story out or, like, I've been working on something and it's out there, like, when the issue came out, I was just, like, all day, like, very calm but, like, just, like, I'm not going to bed.
Therapuss with Jake Shane
Session 57: Willa Bennett
Totally. And you, like, actually care about it and you've thought really hard about it. And then you're just, like, okay, it's not mine anymore. It's yours. Cosmo for everyone. And it's really cool. When readers email me, like, it actually means the world to me.
Therapuss with Jake Shane
Session 57: Willa Bennett
All the time. And, like, someone stopped me on the street and was like, oh, like, I read this Cosmo article. And it, you know, made me think that, like, I should potentially break up with my boyfriend. And I didn't. And then I did. And I feel so much better now. Like, thank you. And I was like, well, I wasn't an editor yet. But, like, I love you for telling me that.
Therapuss with Jake Shane
Session 57: Willa Bennett
I just thought that was so, like, I really like that stuff is, like, why we do it.
Therapuss with Jake Shane
Session 57: Willa Bennett
That happens to you all the time. It's like – I like it when people tell me that I've made them feel better about their OCD.
Therapuss with Jake Shane
Session 57: Willa Bennett
What do you feel like most people don't get about OCD? School.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I think the way you talk about it in your show is amazing. Thanks. And I know so many young people I feel so close to because of it. So it's really special, truly.
Therapuss with Jake Shane
Session 57: Willa Bennett
And I am such a fan of her work that... I was just like, I'm so obsessed with her work. Truly, it was just so hard to write about something I was so close to. And then every Ed Letter, for some reason, it never gets easier for me. Every single issue has an Ed Letter, an Edder's Letter. And this one was so hard.
Therapuss with Jake Shane
Session 57: Willa Bennett
I was like, there is so much I want to say to this audience and to introduce this new era. Yeah, I don't know. Billy was like more writer's block. This was more like nothing I do will ever say what I mean.
Therapuss with Jake Shane
Session 57: Willa Bennett
you know what the best pieces are thinking of what you were just saying about like you had started a piece and then it came out later. Like the pieces that are like in your subconscious or in your brain, like for years before you actually write them are always the best.
Therapuss with Jake Shane
Session 57: Willa Bennett
A hundred percent. That's like the Billy one. Like by the time I sat down to write it, I was like, Oh, I've been writing this my whole freaking life.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. Oh my God. Like 2017 teen Vogue, my shit. Like I was upset. I was like the OG Billy fan. Um, And she was my first cover at High Snob. But I feel like this actual album is my favorite, which is kind of a controversial take.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, but like every album of hers is so amazing. But I think it's a lot of older Billy Stans wouldn't say that as quickly. And I'm like, I just think it's so cohesive. It's so clear.
Therapuss with Jake Shane
Session 57: Willa Bennett
it's shorter but it's like it's all meant to go together and that's kind of like a good magazine not to bring it back but it's like this is like all about love like it's it's like an album in that way that it's like clear intentional um we thought really hard about the writers the contributors the pictures we chose the size of the images like i do think there is some similarity between those creative processes in that way right yeah i'm sure you feel that way about tour
Therapuss with Jake Shane
Session 57: Willa Bennett
It's just like you're yeah, you're kind of like making on the spot a lot of it, which I love.
Therapuss with Jake Shane
Session 57: Willa Bennett
But isn't it such a cool feeling? Like whenever someone stops me and talk about Cosmo, I'm like, it's so freaking cool that like we make something that people like have their own relationship with and their own like feelings about. And, you know, especially with your podcast, I feel like you have such loyal listeners.
Therapuss with Jake Shane
Session 57: Willa Bennett
And then someone will stop you and be like this moment on this one interview with Charlie XCX.
Therapuss with Jake Shane
Session 57: Willa Bennett
It's a really, yeah. I was saying before we turned the cameras on that I really loved your Charlie episode. And it was just, I just thought I like learned a lot about her.
Therapuss with Jake Shane
Session 57: Willa Bennett
So you interviewed her before hearing Brad at all?
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I agree. I thought that interview, I guess I did hear it before I heard the full album. I guess I'm just putting that together now. I do feel like it really articulated what she was going for, and it was so clear, and I love when that happens.
Therapuss with Jake Shane
Session 57: Willa Bennett
Ooh, all time. Yeah. I love driver's license. I know it's on an album. That's a song.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. Sour was, was huge for me. Truly huge. Like 10 out of 10. Um, I love most of Billy's pretty much all of them. I can't think of one I don't love. Um, I'm a big pop girly.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. Through and through, you know, something surprising like brat I appreciated, but I, I wasn't obsessed with. And I think that's crazy because I love all the pop girls. There was something about it that I did not relate to.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I, like, love Charlie, and I think what she's done is incredible, by the way. Like, I'm such a fan of what she's done. There just, like, weren't songs that I was relating to, and I think maybe that speaks to, like, the Billie Olivia, like, Gracie, like, taste that I have. It's just, like, I like sad girl music.
Therapuss with Jake Shane
Session 57: Willa Bennett
Like, I'm not trying to, like, go to the gym and listen to Billie, you know? You go to the gym and listen to Charlie, but then it's, like, I don't know. Maybe I just don't go to the gym enough. I'm just, like, there weren't times in my life where Charlie was, like, fitting in seamlessly.
Therapuss with Jake Shane
Session 57: Willa Bennett
I think you're right. I think the remix ones, like I really did love, like the Japanese house remix was amazing. And I love the Japanese house, but, I think that's more my taste, like, what I actually listen to. But culturally, like, I very much appreciate everything Charli's done. And I've been a fan for so, like, I've known her forever, you know?
Therapuss with Jake Shane
Session 57: Willa Bennett
Like, she's been doing this for so long. She's been at it. Yeah. And, like, especially, like, in the queer scene. Like, I feel like I've seen her DJ parties, like, since I, like, came out.
Therapuss with Jake Shane
Session 57: Willa Bennett
You're wearing Miu Miu. Look at these Dior sneakers.
Therapuss with Jake Shane
Session 57: Willa Bennett
Most gay straight person. Like, do you know what I mean?
Therapuss with Jake Shane
Session 57: Willa Bennett
That's gay math. You know, like, girl math, that's gay math. Wait, something that you put, like, put into my brain the other day. So you posted, you were like, Phoebe Bridgers, when's your new music coming out?
Therapuss with Jake Shane
Session 57: Willa Bennett
And I literally have not stopped thinking about it since. I think she... is one of the best artists of all time. I'm huge, huge, huge Phoebe. But when you put that into my brain, I was like, holy shit, I want that so badly.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. No, some of her lyrics are, like, truly amazing, and I think such an amazing, I mean, talk about writing, but you, like, I saw that on your Instagram story, and I was like, holy shit, I need this today. Today.
Therapuss with Jake Shane
Session 57: Willa Bennett
Do you remember the first time we met, actually?
Therapuss with Jake Shane
Session 57: Willa Bennett
yeah it's like how you like listen to phoebe songs and you're like wait am i heartbroken or in love but i'm crying like it applies to every single part of intimacy it's it's amazing special oh i love i could go on about her she no she's amazing we need more we need more music we need more music it's been five years since punisher it's been five years do you like doji
Therapuss with Jake Shane
Session 57: Willa Bennett
I mean, the Tom Brown. Like, I was, like, I was also just, like, how did they do, like, how did my friends at Tom Brown, like, much love? How the heck did you get that many outfits there?
Therapuss with Jake Shane
Session 57: Willa Bennett
There were so many. I was, like, trying to count. And I was, like, someone has been truly, like, working so hard at Tom Brown.
Therapuss with Jake Shane
Session 57: Willa Bennett
Okay, you're really, you're really good. That was really impressive.
Therapuss with Jake Shane
Session 57: Willa Bennett
And I was, like, sending love. Like, it was so beautiful. So cinematic. It was so intentional. Like, I was blown away. And then also Chapel. I...
Therapuss with Jake Shane
Session 57: Willa Bennett
seriously die for her yeah like I know when my mom is texting me about someone like it means something wow my mom was like texting me about chapel at the Grammys or just she was like what where have I been her voice was so beautiful in that room and I think it's really hard to perform at the Grammys oh my god could not yeah could not even guess what that feels like but like
Therapuss with Jake Shane
Session 57: Willa Bennett
Chapel, yeah, she was a really amazing performer.
Therapuss with Jake Shane
Session 57: Willa Bennett
Okay, interesting. That sounds like there's a lot going on. I would say don't ghost because that doesn't solve anything. Always have a conversation, but I would turn that down.
Therapuss with Jake Shane
Session 57: Willa Bennett
Oh my God, that's so savage. Yeah, no judgment on age gap relationships, but yeah, I would.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, totally. But I just think like a conversation, turn it down, keep it moving.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I kind of agree. I have three sisters and like none of that would fly. However, I think you can have that. Like you could. You could be like, hey, I like this is happening. I'm feeling this and like let's be honest about it. So I don't know.
Therapuss with Jake Shane
Session 57: Willa Bennett
I'm like, hey, Jake Shane recommended you to be on the cover of Cosmo. Wait, who would you put on the cover of Cosmo?
Therapuss with Jake Shane
Session 57: Willa Bennett
So nice. No, we were like across from each other and we were like, wink, wink. Hey, hey, hey.
Therapuss with Jake Shane
Session 57: Willa Bennett
I know you did text me at 4 a.m. and I was like, you good. But then I was also up responding. So I was like, I'm not good.
Therapuss with Jake Shane
Session 57: Willa Bennett
It's not the biggest ick of 2025, I'll tell you that much. It's not the biggest ick.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I mean, in 2025, that's not the biggest ick, to answer the question.
Therapuss with Jake Shane
Session 57: Willa Bennett
And I was like, you like pop music. And you were like, I love pop music. And then we walk out and literally everyone's screaming like, Jake Shane, Jake Shane.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. And I think like, I don't know. Everyone has their stuff. It's okay. Yeah. Maybe that's very Cosmo of me, but I'm like, we accept all types of things that you need to do.
Therapuss with Jake Shane
Session 57: Willa Bennett
That's interesting. So enjoy the drink. It's more like intuitive eating or drinking.
Therapuss with Jake Shane
Session 57: Willa Bennett
That's smart it is. I really, I agree with that.
Therapuss with Jake Shane
Session 57: Willa Bennett
I'm so sorry. He's pressing the rewind button. Okay.
Therapuss with Jake Shane
Session 57: Willa Bennett
Is that movie? It's like an English. Long distance. No.
Therapuss with Jake Shane
Session 57: Willa Bennett
I've got to see normal people. Okay, wait. The twin brother. Remind me of the story.
Therapuss with Jake Shane
Session 57: Willa Bennett
I don't know. I'm thinking like siblings. I'm only thinking of Little Women for some reason, which is not what this person should watch.
Therapuss with Jake Shane
Session 57: Willa Bennett
It's incredible. So that's why I'm like, huh, it's not the right answer for this person. I don't know. Sex and the City is the answer to everything.
Therapuss with Jake Shane
Session 57: Willa Bennett
Can I prescribe Earth Cafe or is that not allowed?
Therapuss with Jake Shane
Session 57: Willa Bennett
And I know because yesterday I went to be like, I want to go to Earth Cafe. The first thing that pops up is your, and I was like, I'm going to confront him about this.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, of course. But why? What is your what is it? Is that an ick for you? Speaking of icks. So like I. It's perfectly good, by the way.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, that's a big deal. I definitely think it's different in real life than what you see on Instagram. And there's very few things that are like that. But a fashion show, it is very surreal.
Therapuss with Jake Shane
Session 57: Willa Bennett
Lots of places don't have french fries. Okay, but if you were on a date and somebody was like, let's go to Earth Cafe, would that be an immediate ick for you?
Therapuss with Jake Shane
Session 57: Willa Bennett
No, friends are everything. I'm very like, I love how much you love your friends. Yeah, I do. Yeah, I'm like still best friends with like all my friends from elementary school. Isn't that crazy? Yeah, we have a group chat. That's a green flag. Called Tappan. Tappan. Actually, one time I said the biggest red flag about someone is if they have different people at their birthday party every year.
Therapuss with Jake Shane
Session 57: Willa Bennett
And no one talks about it, but if you have different people at your birthday party every single year, scary.
Therapuss with Jake Shane
Session 57: Willa Bennett
do you how do you what is your experience like with them you're the you're the real expert I like trying to like like what Jake no no you were great I feel like you were like a fixture at the Tommy Hilfiger show you like people were loving you people were like you look great and you were like what's how do you like my outfit it was denim right
Therapuss with Jake Shane
Session 57: Willa Bennett
I would prescribe a Cosmo drink and also a subscription to Cosmopolitan.
Therapuss with Jake Shane
Session 57: Willa Bennett
Okay, I would prescribe Now and Then, the movie. Have you seen it?
Therapuss with Jake Shane
Session 57: Willa Bennett
It's like about a friend's group and they start off as elementary school and it's like how their lives change. Really special.
Therapuss with Jake Shane
Session 57: Willa Bennett
Troubled Pants, that's what I was going to say. I'm not kidding. That's what I was going to say. Oh, that was cute, girls.
Therapuss with Jake Shane
Session 57: Willa Bennett
Breakups are hard. Listen to Gracie Abrams, eat ice cream, watch a shit ton of movies, honestly. Start a new TV show. I would start The Traitors, honestly.
Therapuss with Jake Shane
Session 57: Willa Bennett
Red. August. Incredible. I mean, she is really an amazing songwriter.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yes, it was Maroon. You're right. August was the night after and I was like.
Therapuss with Jake Shane
Session 57: Willa Bennett
It was truly amazing what she accomplished. And like, I don't know, we are never getting back together. Like that song at the heiress tour was like healing. Like I was just like, I feel like I'm like 12 again.
Therapuss with Jake Shane
Session 57: Willa Bennett
You know what? Another song that was really good live was Wildest Dreams.
Therapuss with Jake Shane
Session 57: Willa Bennett
There have been two shows that I've genuinely cried at. One, Bodhi in Paris. It was the first time she did a co-ed show. Emily Bodhi, she rented out this theater and it was about someone in her life that had passed away and I was so moved. I literally started tearing up and I was like, I think of fashion so differently. And then the second one was Dries Van Donen's final show.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yes. This is crazy. No, but isn't it? It's like a historical piece of...
Therapuss with Jake Shane
Session 57: Willa Bennett
No. Print is, it's part of the whole ecosystem of Cosmo. It's not the only thing we do, but it's part of it. And I do think, I mean, especially like this. Oh, my God.
Therapuss with Jake Shane
Session 57: Willa Bennett
But it's so cool. And I brought back the Cosmo Quiz and the new issue. So I was very inspired by like, you know, like we have Rihanna's, we have Taylor's, we have, it's great. We have Zendaya. Like it's so freaking cool.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. I mean, that's so, I'm dying to know. Oh my God.
Therapuss with Jake Shane
Session 57: Willa Bennett
Try it. Try it. Oh, my God. Do you have this fragrance?
Therapuss with Jake Shane
Session 57: Willa Bennett
Basically, the Cosmo Quiz is like this iconic franchise. It's like you come, you do the Cosmo Quiz. And it was like my first day. I said to the staff, I was like, we're bringing this back.
Therapuss with Jake Shane
Session 57: Willa Bennett
No, this one, you can see Sholo from Cobra Kai did it. Uh-huh. Not out yet, so leaking it here on Jake Shade's podcast, but it's cool.
Therapuss with Jake Shane
Session 57: Willa Bennett
And sometimes I'm there and I'm like really not feeling it or I'm not feeling the emotional connection. But every once in a while, those two shows I think about like they actually do make me emotional.
Therapuss with Jake Shane
Session 57: Willa Bennett
If you could have anyone on your podcast ever in the entire world, who is it?
Therapuss with Jake Shane
Session 57: Willa Bennett
I want Bella Swan making out with Edward Cullen. Again?
Therapuss with Jake Shane
Session 57: Willa Bennett
I like still think that they're going to end up together. End game? Like I'm just like it's end game.
Therapuss with Jake Shane
Session 57: Willa Bennett
Brenda's talking about Clay Culkin like our end game. You know what I mean?
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, it's all in there, baby. You got to read it, you know, check it out online. Follow Cosmo on Instagram. No, take your sweet, sweet time.
Therapuss with Jake Shane
Session 57: Willa Bennett
Uh, honestly, my journal, I like really will be like 20 minutes. This 20 minutes. This is what I'm doing. You know, I really like plan out my days to a T honestly, like you need to be journaling and you need to be like putting boundaries on things.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. And like, try not to go to sleep on your phone. Honestly, it's really not great for your brain.
Therapuss with Jake Shane
Session 57: Willa Bennett
But like, yeah, it's just it's not good for you creatively. I'm going to try. I mean, it was my New Year's resolution that I haven't done, but I really want to try to like sleep in my phone in the other room or something.
Therapuss with Jake Shane
Session 57: Willa Bennett
Wow, yeah. So I need help. I also need help with my phone. I really like, I really think I, I just have a strong pull.
Therapuss with Jake Shane
Session 57: Willa Bennett
Art, totally. Yeah, it's, like, it's not, I mean, we can get into this. I honestly wear the same thing every day. Like, truly have a uniform.
Therapuss with Jake Shane
Session 57: Willa Bennett
What's the longest you've been not on your phone? Your flight the other day.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I relate to that. I feel like something that I hear from a lot of Cosmo readers are like, I am more connected than we've ever been online. But like, The loneliness is like something I hear constantly from readers. Like I answer questions on TikTok and I put them in the magazine and always loneliness. Loneliness, loneliness.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yes. I have a uniform. But I really, like, appreciate the art of clothes. And I was a really serious dancer growing up. And there's something, like, theatrical about it.
Therapuss with Jake Shane
Session 57: Willa Bennett
I completely agree. And I also think that is another thing that excites me about Cosmo. It's like, if we can actually like bring people together and make people feel less alone, like we've done our jobs and your podcast, that too, right?
Therapuss with Jake Shane
Session 57: Willa Bennett
It's a really hard emotion. I agree. It really is. It's like, but you're on your phone. So you're like, I'm with 8 million people and I'm not alone.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yes, John Baptiste performed. But also, the Oyster Bar was so freaking cool.
Therapuss with Jake Shane
Session 57: Willa Bennett
Tell me if I'm wrong. You look amazing in Miu Miu.
Therapuss with Jake Shane
Session 57: Willa Bennett
He bought this last night because I was coming here.
Therapuss with Jake Shane
Session 57: Willa Bennett
I'm like, I think I would be like, Hey, I want to like have a conversation about how I feel about your boyfriend. These are the things he does of why I don't like him. I don't like if it's anything to do with like how they treat your best friend. Oh my God. Immediate red flag. But I think it's a conversation. I think going in being like, I hate you is like that person is going to isolate you.
Therapuss with Jake Shane
Session 57: Willa Bennett
And then you lose your best friend too. No, it's like they're dating. This is a dynamic. You have to,
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. You're a good performer. Like you can tell. And I feel like, yeah, I was a really serious dancer. And then eventually I got too injured and stopped and,
Therapuss with Jake Shane
Session 57: Willa Bennett
I agree. And you want to just make sure like you're still in your friend's ear and like helping them navigate it and see it for themselves rather than just being like no. Then it's like then you're just out of the equation.
Therapuss with Jake Shane
Session 57: Willa Bennett
I'm trying to think of like a, like a romance novel or something, but there surely is a episode that relates to this. No, definitely. Um, I feel like there's so many also rom-coms that are like the friend, but the friends are always right.
Therapuss with Jake Shane
Session 57: Willa Bennett
I had so much fun. I've literally just been hanging out with this guy.
Therapuss with Jake Shane
Session 57: Willa Bennett
I learned that you're so funny and nice and amazing. And yeah, I'm just so honored to be here. And you love fashion shows.
Therapuss with Jake Shane
Session 57: Willa Bennett
Oh, I love you. Thank you for having me, truly. Of course. Always, yeah. Write for us anytime.
Therapuss with Jake Shane
Session 57: Willa Bennett
went into writing but um you know I feel like sometimes when I'm watching a fashion show I really feel like I'm thinking about dance there's something so theatrical there's something so about like space and like the human body wearing clothes it's like messaging anyway we're getting very deep very quickly classic wait I love that I've never I've seriously never heard anyone speak about fashion that way oh that's so nice tell me about your day-to-day uniform
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I truly wear this like every single day. I have like a couple different iterations of it, but I love a tie, as you know.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I love a tie. I love a suit. I was at the Grammys and I wore a bow tie. I felt very, very proper and nice. I think the biggest thing I've learned from working in fashion is like black tie. Actually, you can't wear a tie. Did you know that?
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. You can't wear a tie. It's actually inappropriate.
Therapuss with Jake Shane
Session 57: Willa Bennett
You know, I have no idea. I've never thought to Google it actually.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah. There was this joke at GQ that was, I am the last employee to wear ties.
Therapuss with Jake Shane
Session 57: Willa Bennett
really because no one else wore ties at GQ it was like me and it was yeah there was a big thing where I was like oh black tie event and I think that's how I learned the hard I think I wore something to a black tie event somebody was like girl don't do that and I was like sorry lesson learned but yeah I'll never make that mistake again it's like Grammy's like no I'm wearing a big bow tie and I'm like talking about my bow tie obsessively where where was your bow tie from
Therapuss with Jake Shane
Session 57: Willa Bennett
It was a YSL bow tie and a blazer. I was going back and forth if I should wear heels or not. And one of my friends that was also going, I was like, what do you think? And she was like, do not fucking wear heels. You're going to be miserable. And I got there.
Therapuss with Jake Shane
Session 57: Willa Bennett
kind of how you ended up at cosmo like what because for those that don't know willa was editor-in-chief of high snob you worked at gq now you're editor-in-chief of cosmo okay so i was at high snobiety well i think let's start at the beginning please i was actually an intern it was technically called a fellow at 17 magazine i was like obsessed with it i cold emailed someone in college um and i basically was like what can i do to work at 17 it's my dream job like please please give me a job
Therapuss with Jake Shane
Session 57: Willa Bennett
And someone responded to my wild email that probably today wouldn't age well. I should probably find it. And was basically like, I'll get coffee with you, but we don't have a job. And so I remember leaving school, I went to Sarah Lawrence, taking a train down to the city, getting coffee with her. And she was like, you know, we're not hiring, but if there's, do you know anything about Snapchat?
Therapuss with Jake Shane
Session 57: Willa Bennett
And I was like, I love Snapchat. Yeah. And it turns out Seventeen was launching on Snapchat. And so that I was basically like an assistant figuring out like how to package content on social.
Therapuss with Jake Shane
Session 57: Willa Bennett
So that was like the beginning. And then I kind of just worked my way up. I think GQ is really important for me because I really found my voice there. I was really close. I still am really close with Will, the editor. And like, I don't know, he really saw something in me. And really, he really helped me refine my voice.
Therapuss with Jake Shane
Session 57: Willa Bennett
And coming at it from a writer's perspective, even though I was working on social, it really was storytelling.
Therapuss with Jake Shane
Session 57: Willa Bennett
So I loved it. And I, you know, was there at a really interesting time where I think they were pushing and they still are. But it was this moment of like, what is GQ to these younger audiences? And it was amazing. And then from there, I went to High Snob where we met. You wrote an amazing essay for me.
Therapuss with Jake Shane
Session 57: Willa Bennett
It did. Like, I remember all the comments being so sweet.
Therapuss with Jake Shane
Session 57: Willa Bennett
Yeah, I think something I we're doing a package for Mental Health Awareness Month. And I remember texting you because I think the way you talk about mental health in your podcast is so relatable for young people. And I hear it all the time. They're like, I don't know the way you talk about. Just everything. It's like this transparency that doesn't always exist.
Therapuss with Jake Shane
Session 57: Willa Bennett
I mean, more so, I would say, with social media, but you do in a very specific way. So I remember texting you, and you responded within minutes. And by the way, you're early on your deadline.
Therapuss with Jake Shane
Session 57: Willa Bennett
That never happens. She? Are you sure? Yes, I'm sure. I was like, literally, I remember my executive editor, Genevieve, at the time was like, Jake Sheen turned in his piece early. And I was like, that never happens, by the way.
Therapuss with Jake Shane
Session 57: Willa Bennett
Okay, so that's honestly such a compliment today. So, yeah, high snobiety. I was there for a while. I think what was cool is creatively it felt like this –
Therapuss with Jake Shane
Session 57: Willa Bennett
niche audience that I was kind of making more broad and more mainstream and now at Cosmo I feel like it is this like you know it's been around for 60 years such an iconic legacy and now I'm trying to put like the voice back in and really refine and refocus what it means so it's almost the opposite creatively but I'm excited I wake up every day like so excited oh and I think it's such it's so the time for it right now it is so the time for it and I feel like
Therapuss with Jake Shane
Session 57: Willa Bennett
I brought you one. Actually, it's not even, you're like one of the only people in the world to have it. But it comes out on Valentine's Day.
Therapuss with Jake Shane
Session 57: Willa Bennett
They are truly, like I will not say this lightly. they are truly so in love. Like, the type of couple that, like, I just, like, on set watching them, I was like, holy shit, they are so deeply infatuated with each other and, like, bring out different sides of each other. It's so special.
Therapuss with Jake Shane
Session 57: Willa Bennett
She really, like, Hunter Harris wrote the story and I feel like there's this part in it where she's talking about how, like, Brenda does all the talking and Mac, like, does all the listening. And it's so funny because, like, Mac, like, brings her down to earth and then he, like,
Therapuss with Jake Shane
Session 57: Willa Bennett
needs her it's like they both need each other in a specific way and they're like the perfect balance and the way they talk i i was felt like so special to be hanging out with them oh my god that's incredible and don't you think it's hard to be like two a-listers in love like this like they're also child stars yeah and he's like infamously had it tough now yeah i think he's you know home alone is so iconic sweet life is so iconic and they found each other
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later in life. And, uh, it really, it's so meaningful. And I keep saying this, I'm like, we put their love on the cover. And I think for my first cover for Cosmo, like having someone's relationship on the cover is part of the story. And it coming out of Valentine's day, I feel like we're, we're really, I'm putting such a clear message of like what this new era is going to be about.
Therapuss with Jake Shane
Session 57: Willa Bennett
And it's, it's about love. It's about celebrating love. It's kind of going back to the original Cosmo, um, celebrating love relationships, growing up messiness.
Therapuss with Jake Shane
Session 57: Willa Bennett
I think it's because they're in bed and they're looking at you. And Richard Kern is a photographer. And I feel like he was really able to get this like intimate moment with them on camera. And Brendan Tan, who did the styling, I think someone actually on staff said this to me and it gave me chills. She was like, she was like,
Therapuss with Jake Shane
Session 57: Willa Bennett
I feel like when I'm looking at that photo, you feel like, oh, they've really been dating and they started like sharing clothes. And that feeling is captured in that cover somehow where you're like, oh, like they're really sharing closet. They're really like together and connected. And I think it's really hard to do that in a photograph. I knew it was special. I felt it, but you never know.