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Willa Bennett
The following podcast is a Dear Media production.
Addison Rae
This is my first time ever doing something like this at all.
Willa Bennett
He knew I loved you guys, and he immediately was like, it's them. And I was like, done. There was, like, literally no other discussion.
Addison Rae
I actually don't know how I'm gonna ever do anything like this again, because I don't think anything can top it. You're the youngest editor in chief in Cosmo history.
Willa Bennett
It's been really amazing. I read Cosmo for so long growing up that feel very close, close to the audience, and I feel like I'm making the magazine I want to read, which is really cool. I've been in therapy since I was 7, so I'm like, oh, wow. I'm, like, very therapized. I think young people today, like, I really do hear about how anxious they are and everything. I read about the loneliness epidemic, and I really feel for them. And I think the best thing you can do is, like, find a therapist. And it doesn't have to be a perfect one, but just, like, someone to talk to. And I love, like, how you guys. It just feels very you and very sacred. And how do we take this, like, sacred thing you guys have built and let the readers in without also giving them too much?
Addison Rae
Like, no, that's literally so true. Taylor and I had the most fun day playing dress up. I don't often feel like I am second because Taylor literally will be like, babe, you're a celebrity. I'm like, honey, you are the celebrity. I am not. But thank you. I love you. But that's how he makes me feel with this. I really just felt so loved and.
Podcast Host
Heard and seen throughout the whole shoot.
Addison Rae
Throughout the whole interview. Taylor and I were reading it. We were like, oh, my gosh. Like, this is amazing.
Podcast Host
In love with it all.
Addison Rae
And how you were like, no, they're going to be equal parts Tay and Taylor in this. It's just, like, super important.
Podcast Host
Hello, you cutie little lemon drops. Welcome back to a very special bonus.
Addison Rae
Episode of the Squeeze.
Podcast Host
I am so excited about this one because this convo goes hand in hand with Taylor and Eyes Cosmo interview that we did. In case you guys missed it, we have been posting it all over social media, and we'll continue to post it.
Addison Rae
Because I am just literally obsessed with.
Podcast Host
Everything about this shoot. But this is our first ever cover story. It's my first time ever in print, which is so exciting. This edition is now on stands and available. I'm so excited to go to my.
Addison Rae
Nearest newsstand and grab one Because I'm going to buy by all of them.
Podcast Host
It's truly so exciting. But this episode we have Willa Bennett on and she's the editor in chief of Cosmopolitan and Seventeen. Willa is a media executive, editor and cultural commentator, best known for redefining legacy magazines for a new generation. She actually began her career at 17, where she helped launch its first ever queer vertical before moving into digital audience and social strategy roles at Bustle and GQ, becoming the first woman to lead GQ's social media strategy. She later served as editor in chief at High Snobiety, earning industry recognition for blending culture, fashion, and digital Commerce, and in 2024 was appointed editor in chief of Cosmopolitan and Seventeen. What is so cool about Willa's story is that she is actually the youngest editor in chief in Cosmopolitan history. She's known for her sharp editorial point of view, emphasis on curation over click chasing and social first yet authority driven approach to media. Willa has such a heart for her job and there is truly no one like her. I adore her and getting to sit down and talk with her and hear her story and to hear what it's like to actually be an editor in chief of such a huge publication was really fascinating. So I'm excited for you guys to hear this episode and be sure to check out our Cosmo feature.
Addison Rae
Willa, welcome to the Squeeze.
Willa Bennett
Thank you. Thank you for having me.
Addison Rae
This is so fun because we're like switching roles basically. You're in the hot seat today, truly.
Willa Bennett
I'm. I'm excited to be here. I. I loved having you guys on the COVID of Cosmo. So I'm very excited to be here and talk to your audience about it too.
Addison Rae
The honor was truly ours. It was literally the most fun thing.
Podcast Host
But we'll get into that. We start each episode off with this jar. It's a little game called Citrus Got Real. If you want to pull a little.
Addison Rae
Question, a little piece of paper out of there and made it to us. And let's see.
Willa Bennett
Oh. As I knock over everything. Okay. I love. What's your go to karaoke song?
Podcast Host
Oh.
Willa Bennett
Driver's License by Olivia Rigo. Every single time. But what's funny is it's actually so hard to sing.
Addison Rae
Yeah.
Willa Bennett
So I just commit to it.
Podcast Host
I.
Addison Rae
That's great. Ooh, that's good. I feel like mine would be something like some like Hannah Montana or like and Ali and ate like just some like 2000s good. Like throwback Disney.
Willa Bennett
Totally. Song seven things I hate about you is also.
Addison Rae
Oh yep. That's good. I love that you literally had that. It was just, like, it was prepared and it was ready.
Willa Bennett
Yeah, I'm like a big pop music at karaoke. I just feel like you need to, like, be in it. So. Yeah. 7 Things I Hate about you really? Slaps.
Addison Rae
Yeah, that's good.
Podcast Host
I'm excited to, like, learn more about.
Addison Rae
You and your just background and how you became editor in chief of Cosmo in 17 because you're the youngest editor in chief in, like, Cosmo history.
Willa Bennett
Yeah, definitely.
Addison Rae
I'm.
Willa Bennett
Yeah, I'm 31. I always get that question. People are like, wait, how old are you? And, yeah, I'm 31. I actually started my career at 17. I was an intern, and, you know, I kind of jumped around a bit. I went to Bustle Digital Group, and then I went to gq, and then I was running this brand called High Snob for a while, and now I've been at Cosmo a year and a half, and it's been really amazing. I read Cosmo for so long growing up that I feel very close to the audience, and I feel like I'm making the magazine I want to read, which is really cool.
Podcast Host
That's so special.
Willa Bennett
Yeah, it really is.
Addison Rae
That's crazy. Was this, like, the goal of what you wanted? Like, growing up, you were like, I'm interested. Like, how did you. How do you feel? Like, editorial. And those things are so foreign to me. Like, this was honestly the first thing that I've really, like, done and learned about it.
Podcast Host
Wow.
Addison Rae
How did you, like, kind of pick this path? Like, what. What were you passionate about?
Willa Bennett
I love magazines, and I love storytelling, and I actually always wanted to write. Books was, like, a big. A big dream of mine. And I love writing. Like, it's just, like, the one thing that, no matter what, I'll do. Like, good day, bad day, hard day, good time. Like, it's just. I, like, can't not write. Like, anything happens to me, and it, like, flows out so intensely. So. I always loved books. I always loved magazines. I actually always used to write in my diary that I wanted to write the gay Twilight, which is funny that I'm here now. I, like, actually just put that together. I was talking. Yeah, I was, like, obsessed with Twilight. And I was like, I want to write, like, the gay Twilight. And then later on to all the boys I loved before really blew up. And I just watched these stories teach fandoms how to love and live. And I think at the same time, my love for magazines was part of that, too. It's like, you can give something to a fandom and make them see the world differently after. And I was just so inspired by it. I was mostly into men's fashion magazines, probably because I was coming to terms with my queerness and I was obsessed in men's fashion. But, you know, as time has gone on, I think the coolest thing about Cosmo that I really appreciate is how we do speak to fandoms directly.
Addison Rae
Yeah.
Willa Bennett
So that be Love island or, you know, real couples. Like, I really feel like we get to put. We got to put, at least in your case, like, your love on the COVID And that was so special. We did Brenda Song and Macaulay Culkin, too. Like, we do this thing where we, like, put couples on the COVID And it's one of my favorite things. Cause I feel like relationships take so much work and they can be so hard, but to really get inside someone's relationship, even from an editorial standpoint, is so cool.
Addison Rae
Yeah, I love it. I mean, I love, like, I love love. Clearly, I'm in love, but it's. I love, like, reading about it, and I think getting to hear, like, those stories about people and their relationships, especially, like, in the industry, because I feel like you just hear horror stories all the time, and it's like, no. Like, you can actually be in, like, a healthy, stable, functioning, like, in love relationship. Totally special that you do that. How. How have you have you, like, dealt.
Podcast Host
With imposter syndrome at all?
Addison Rae
Like, being. Or have you just. Are you just confident in yourself?
Willa Bennett
It's a good question. I. I really, like, am confident. Like, truly. I don't really struggle with that. I feel, like, very in tune with my instincts.
Addison Rae
I mean, you definitely, like, you have quite the resume to feel that, so.
Willa Bennett
But I definitely have moments where it feels hard and I'm like. Or I'll be like, I actually don't have the answer. And I think something really scary sometimes in general in life is when you're doing something or something happens, and you just are like, wait. No one around me has the answers. And I think that's something I've felt a couple times in media where it's like, things are pivoting, things are changing, and just there isn't an answer. There isn't anyone I can call to be like, what should I do about this? Because I think the times we're in, in the editorial space at least, are just very unprecedented. So that's definitely something I think about. But I think it's not imposter syndrome. It's more like Lonely. If anything, there's moments of loneliness, but there's not moments of, like, I don't know what to do or, like, I'm not good enough.
Addison Rae
Yeah.
Willa Bennett
Have you ever felt that?
Addison Rae
Yeah, I think so. But that's totally relatable because. Yeah, I feel like everything is, like, constantly changing in the world of entertainment editorial. Everything is just constantly moving and changing. Like, I feel like I learned something. And then, I mean, even, like, with Taylor and how, you know, he. Twilight was, what, like, 10, 15 years ago? Like, but it's crazy to see, like, how things have shifted even when he was, like, when he would be doing editorials then versus how it is now. And, like, he'll be like, it's so different now than it was then.
Willa Bennett
It really is unprecedented. I also think, like, the. The nature of the platforms are so much quicker now. Like, I don't know, I talk to editors who have been editors for, like, 10, 15 years, and they'll be like, yeah, like, there was no, like, Instagram posts. Like, you know, like, it was just so drastically different. Like, you would. Someone would be on the COVID or, you know, celebrities would also, like, give so much access, and, like, you know, storytelling and journalism were just so drastically different. And so I think it's interesting sometimes when people who have been editors for a long time will say to me, nothing like this has ever happened to me. Because then you just realize it's like, no one has the answers. We're all kind of figuring it out. And obviously, everyone makes mistakes, but it's less good or bad or hard or easy. It's more just unprecedented is the word. I really think about a lot, and I think any industry is lonely, like, inherently, like, work is so personal. But I think that's. That's the main big feeling I have sometimes.
Addison Rae
Yeah. What do you think over the years has, like, prepared you most for this role?
Willa Bennett
Hmm. It's a really good question. I think, just, like, honestly loving writing and, like, loving what you do. Like, I do genuinely feel so lucky to be doing this.
Addison Rae
Yeah.
Willa Bennett
And that's such a blessing. I can't tell you how many people, like, you know, I talk to them, and they, like, hate their jobs or they. It feels so impossible and unforgiving. And I think the end of the day, like, I really, really, really love my job, and I really believe in Cosmo.
Addison Rae
Yeah.
Willa Bennett
And I think it would be impossible to do this if you didn't.
Addison Rae
Yeah.
Podcast Host
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Addison Rae
Too many options, prices that made no.
Podcast Host
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Addison Rae
Few things really well every day.
Podcast Host
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Addison Rae
Is there a risk that you took that really, like, paid off? Maybe like, something you did differently that.
Willa Bennett
Proved yourself a risk? I don't know. Like, the. The thing that comes to mind is, like, the first time in college when I, like, let myself actually, like, have queer feelings towards someone, like, that felt, like, really scary and risky in the sense of, like, what it would mean later on. And obviously that was, like, the best thing that's ever happened to me. But I don't know. Professionally, I don't know. I, like, really am, like, sure of my instincts. Like, even when there's something that's, like, more controversial or more, like, questionable, like, I usually do know the answers. Or at least I find, like, I'm comfortable in my answers. So I think it would be probably more personally than professionally.
Addison Rae
Yeah. Given the nature of your job, obviously, you've been out here, and you've probably just been working and working and working. How.
Podcast Host
How do you. Do you struggle with burnout?
Addison Rae
Like, how do you. How do you set aside time to, like, you're like, I have no clue.
Willa Bennett
I'm like, oh, my. Okay. Burnout is really interesting. I think it's real. I think people really need to know their limits. And I think I often exist with a higher limit than I think a lot of my peers, which everyone needs to make the decisions that's best for themselves. I definitely can work to no end without feeling burnt out, but I've definitely felt it before, and I really just, like, sleep. Which is for better or for worse. I. I really like. You know, I've just been working for a couple weekends straight. Like, next weekend, like, when I'm finally off, like, I will probably sleep, which, like, great. You know, it's like, good and bad. I could think of worse things. But it is also just, like, funny. Cause it's like, my body is just, like, it's time to sleep. No more work. And I think I. You know, some people have asked me before, like. Cause I'll talk about this very openly. I'll be like, you know, I just sometimes, like, will sleep for, like, 14 hours and then wake up and feel completely fine. And what it is, I think I, like, process things in my sleep.
Addison Rae
Like, I think I'm the same.
Willa Bennett
Really? Yeah, Like, I really am. Like, I'll wake up and have, like, new conclusions about things. Okay.
Podcast Host
No, literally, that is.
Addison Rae
I'm like, that in with like, work like this podcast. I never, I, I still don't really, but I've. I never listened to podcasts. I was never like, wanting to do a podcast. And I just woke up one day and I was like, I think I.
Podcast Host
Need to start a podcast.
Addison Rae
And that's the same thing with my non profit. And that's like, I feel like I wake up and I'm like, oh, like, I should do this. Like, things just like, make sense to me. And even like, I grew up dancing my whole life and we would like.
Podcast Host
Learn a whole dance in one day.
Addison Rae
And I like, couldn't do it. Like at the end I'd be like, no, my brain's fried. But I would go home and sleep the next day. I know it 100. So I completely, completely relate to you.
Willa Bennett
Yeah. I said to my therapist before, I'm like, is this bad? And she was like, no, it's like, actually pretty normal. She's like, you just have to be careful that like, you're not sleeping to avoid things.
Podcast Host
Yeah.
Willa Bennett
But it's like, not like, I really don't sleep to avoid. I sleep to like, process in a, like, deeper way.
Addison Rae
Yeah, I, I relate to that. When you are like, this is like a side note, but I'm curious because I'm. Can't wait because we found one similarity between us. Are you sharing your emotions? Can you talk them or do you need to write them?
Willa Bennett
Ooh, that's a good question. Both. I, like, I've been in therapy since I was 7, so I'm like, oh, wow. I'm like very therapized not to brag. I know as I said that. No, we can talk about this more. But I have really been in therapy my whole life and very proud to be. And I love, love, love to talk, but there are times where writing, I'm closer to them and like sleep. It's a subconscious. I can actually handle them with more clarity. So I think I'm better at writing than talking, but I do love both. And I will find when I'm struggling with something, I will just talk, talk, talk, talk, talk, talk, talk, talk about it.
Addison Rae
Yeah.
Willa Bennett
With. With only like the closest people to me for sure. But yeah. What about you?
Addison Rae
I. It's.
Podcast Host
It's weird. It depends.
Addison Rae
And when I'm like, talking about something that I'm struggling with, like, if really anything like here or in therapy, I'm very articulate. Me and my therapist are actually just talking about this. But like, if, let's say Taylor and I are in an argument about Something or like, something bothered me and I want to bring it up. Like, I can't. Like, my brain, like, tells me I can't do it. And so, like, I'm not good at speaking when, like, my feelings are upset. But if it's like, something mental health that I've gone through, I'm fine talking about it.
Podcast Host
It's weird.
Addison Rae
I don't know what it is, but.
Willa Bennett
Yeah, everyone's on their own journey. I get it.
Addison Rae
Yeah.
Willa Bennett
No, but I'm like, how long have you been going to therapy?
Podcast Host
I started.
Addison Rae
Let's see, I started in, like, end of 2021. I started after I left the hospital because I was. I was, like, dissociating really bad. Well, I knew something was, like, going on before I quit. Like, probably like February of 21. Taylor actually was like, bro, are you okay? And I was like, I'm tired. I just worked, like, three night shifts. And he was like, no, like, you're not okay. Like, something's wrong. And I just kind of, like, clocked it and like, moved on. Because I had never personally really dealt with my mental health.
Podcast Host
To the depth.
Addison Rae
Of what I did, or at least I didn't realize it. I feel like I actually am learning now that I was struggling, but I didn't know.
Willa Bennett
Yeah, it's hard to know in the.
Addison Rae
Moment for sure, but I ended up leaving the hospital. And then a few months later, I just still, like, really felt like I was in a fog and I was.
Podcast Host
Dissociating, even from conversations.
Addison Rae
But also, like, I was forgetting things, which was weird. Like, I would forget my friend's name.
Podcast Host
Like, it was like, things that I knew.
Addison Rae
Like, it was weird. Like, it was like a brain fart, but, like a scary one.
Podcast Host
So.
Addison Rae
So that was actually what got me into therapy in the first place. And it's literally been my favorite thing.
Willa Bennett
It's the best. It's so helpful. Yeah, I have therapy really, really early on Monday mornings. It's like at like, 6:00am, which is nuts. But it's really cool because it, like, starts the week.
Addison Rae
Yeah.
Willa Bennett
With, like, understandings. And then I feel like I process, like, what I'm working on all week. And then it also. Because then I go into work at like, 7 or 8. It's like 7:30. And by the time I get to work, like, I've already, like, feels like sometimes, like, had a full day and like, this, like, clarity of, like, who I am. And, like, my sense of self is really strong. So. Yeah, it's interesting, but I feel you sometimes, like, in retrospect I'm like, oh, that was really hard. And then in the moment, I was just like, kind of like disassociating a bit.
Addison Rae
Yeah. Why were you in therapy at 7?
Willa Bennett
My parents got divorced pretty brutally.
Podcast Host
And.
Willa Bennett
Honestly, like, my school was like, I think it was just noticing that I was anxious. But anyway, they called my parents and I started seeing a therapist then. And I like, I was like, obsessed with it. It was so healing for me. And I remember being at 7, like, kind of embarrassed to my friends that I was going to therapy, but also, like, they never did anything to make me feel that way. They were just like, oh, yeah, of course. And then when I was in college, I like, stopped going to therapy for a little bit just because, like, you know, I was busy and I was in college and I was actually a dancer too, so my schedule was crazy. And then I started feeling anxious again, so I went back and it was like, amazing and immediate. So I've had three different therapists my whole life. One when I was really little through high school, one when I went to college. And then I recently switched therapists. And she's kind of like, therapist career coach. Like, she helps. Like, her specialty is people who, like, have really high pressure jobs and they, they kind of need, like, emotional help on, like, how to handle certain things. And I tell her a lot, and it's amazing. Have you ever seen a career coach?
Podcast Host
I haven't. And it's so interesting that you're bringing.
Addison Rae
This up because I just had someone.
Podcast Host
On and she was telling me that.
Addison Rae
That is her therapist is basically also like career coaching. And I have never really, like, heard of that being a thing.
Willa Bennett
Yeah, I don't think she would call herself a career coach, but it's very much like she's like, she, like. I mean, I obviously don't know her other clients, Like, I could never know. But based on my research, which we should talk about later of like, how I do, like, I always Google my therapist, which is like, not what you're.
Addison Rae
Supposed to do, by the way.
Willa Bennett
No. So she, she sees like, a lot of creative directors and like, actors and people who like, have externally jobs with external pressure, as she would say.
Addison Rae
Yeah.
Willa Bennett
Someone recommended me to her at my last job when there was just like, a lot of different things I was fielding. And she was like, you should honestly try this person. And then coincidentally, that week I opened up New York Mag and it talked about her, which I was like, that's crazy. Like two for two in the span of a week. So I honestly cold Emailed her being like, I've been only with two therapists my whole life, and I'm not really. I wasn't looking to switch therapists, but I love talk to you. And I spoke to her once and I was like, oh, my God, you're amazing.
Addison Rae
Wow.
Willa Bennett
But our relationship is kind of funny. She's like. She's like, I've had different types of therapists. I think my other two are very psychoanalytic. So they're very like, why are you acting that way? Why, like this? Or why did you act, like, dissecting the past? She's very, like, funny and, like, kind of brutal.
Addison Rae
Yeah.
Willa Bennett
Have you ever had one of those?
Addison Rae
Yeah.
Podcast Host
No.
Addison Rae
My therapist is definitely, like, he puts me in my place. If I'm like, out of line, I'm like, got it. Okay, great.
Willa Bennett
Which I totally love.
Addison Rae
Like, I need that.
Willa Bennett
Yeah. It'll be like 7 o' clock in the morning. And she's like, so why do you think you did that? And I'm like, I don't know. That's why I'm here. And it's also in person. So she's like, literally, like, sometimes, like, like, like ripping me a new one at like six in the morning. But I love it. And it.
Addison Rae
That's good.
Willa Bennett
I think it's really good to, like, practice going to therapy. And like, I think it is hard to find a really good therapist. So I always feel really grateful that, like, I've had three incredible therapists in my life.
Addison Rae
Yeah.
Podcast Host
Is there any.
Addison Rae
Anything else about your mental health journey? Because I feel like being in therapy for that long. You definitely have been through some stuff, but anything you.
Willa Bennett
I think you have to work on it. I think, I think young people today, like, I really do hear about how anxious they are and everything. I read about the loneliness epidemic and like, how the way young people connect with each other, like, it is. It's pretty scary. And I. I really feel for them. And I think the best thing you can do is, like, find a therapist. And it doesn't have to be a perfect one, but just like, someone to talk to.
Addison Rae
Yeah.
Willa Bennett
I definitely notice my phone makes me really anxious sometimes. So I really try to work on that. But I will say I think we're all so hyper connected online while also being so alone, and that just can't be good for development. And so I have two younger sisters and I really do worry about that. And I think a lot about how Cosmo can bring people together and make them feel less anxious. But I think we're again, to use that word. We're in really unprecedented times and no wonder we're all anxious.
Addison Rae
Yeah. I can't imagine how you feel. Like, have you had to set boundaries with it? Because you're constantly like having to keep up with everything that's happening. And I'm like, don't have to do that at all.
Willa Bennett
I'm really bad at it. Like my older sister this week, I was, I had dinner with her and she was like, you gotta get off your phone. So like, I. It's something I really deeply struggle with. Both because it's like work.
Addison Rae
Yeah.
Willa Bennett
And it is personal. Sometimes, like, I do find myself like, like wanting to talk to readers, like, genuinely. So, like a reader will be like, hey, I didn't like this. Or hey, I loved this. And I want to be like, tell me. Like, I really like talking to them. And I think that's something that I've also had to work on is like, I'm always like, cold. Email me like you have an idea. And it's like sometimes my therapist will be like, well, that's why you're exhausted all the time.
Podcast Host
Yeah.
Willa Bennett
Because you're. I'm just like so open to that. And I want people, I want readers especially to like, know that they can talk to me about their situationships and feel comfortable with that. But there are times, like usually on Sundays, I like really try not to be on my phone and not work and I go for a long walk and obviously I sleep a lot and I don't know, I just have little shows that I'll watch. Like, I love this summer I turn pretty. Like, it really is comforting. I love Twilight. Genuinely. I, like, I'm not a Harry Potter person, but I don't know, am I gonna get canceled for that?
Addison Rae
No, it's okay.
Willa Bennett
But yeah, no, I have my shows that like, I love SNL every Saturday. Like, I just have my things that I'm like, that are like my escape moments and I really don't touch my phone during them.
Podcast Host
Lately I've been thinking about how much of our lives are truly just constant little transactions. Splitting dinners, paying the dog walkers, paying rent, sending money to a family member. It adds up. And it's so much easier when everything is in one place and you can keep it moving without overthinking it.
Addison Rae
That's why Cash app is such a go to.
Podcast Host
It's simple, it's fast, it fits how people actually spend day to day. And now they just rolled out something new that's pretty interesting because it's built around your real spending habits and rewards you for things you're already doing. Cash App just released a new status program for the way people actually spend called Cash App Green and unlocks new ways for you to pay, get rewarded and easily grow or manage your money on your terms. Now, when you spend at least $500 a month with a Cash App card or Cash App Pay, you earn green status, which unlocks benefits like up to $200 off free overdraft coverage, higher borrow limits and custom personalized Cash Back offers every Friday at places you love to shop. Turn every day into status with Cash App Green. Download Cash App today or visit cash app.com new to learn more about this and other great content features. Launching now for a limited time, new Cash App Customers can earn $10 if they use the code CASH APP10 in their profile at signup and send $5 to a friend within 14 days. Terms apply. Cash App is a financial services platform, not a bank. Baking services provided by Cash App's bank partners Prepaid debit cards issued by Sutton bank member FDIC Cash App Green overdraft coverage Borrow Cash Back offers and promotions provided by Cash App a Block Inc.
Addison Rae
Brand.
Podcast Host
Visit cash app.com legal podcast for full disclosures well, we are into the new year and this is usually the point where I start thinking about how my space is actually working for my day to day life. I've been really focused on making my home feel more functional, more organized and honestly just nicer to be in and Wayfair has made that refresh feel really easy. What I love about Mayfair is that it really is a one stop shop. Whether you're looking for bedding, a mattress, towels, storage solutions, everything is in one place. And I've been especially into smaller updates lately.
Addison Rae
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Podcast Host
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Addison Rae
Paper is the best we can do?
Podcast Host
Because once you try a better option, you cannot unknow it. And for me, that upgrade has been Good Wipes Flushable wipes.
Addison Rae
Like would you wash your hands without water? Shower without water? No.
Podcast Host
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Addison Rae
Friend, I'd say this is the smallest.
Podcast Host
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Addison Rae
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Addison Rae
When you think about like future and goals for yourself personally and professionally.
Podcast Host
What are those?
Willa Bennett
It's really good. It's a really good question. I really just like want to feel like. I want to feel like I'm really serving these readers genuinely. I think, in terms of when I ask a lot of people this question who are in my industry, they'll rattle off a celebrity to get on the COVID or a certain photographer or a certain advertiser. And to me, I really want to be a publication that serves its readership and really cares about its readers. And I think the most gratifying part of my job is when readers tell me that they like something or even if they didn't, engaging in that with them, I think is so, so cool and so gratifying. So I think that's one thing. I also, like, have always wanted to just, like, put queer stories out there that are actually queer and are actually meaningful for this audience. I love what heated rivalry's done, but I think there's so many more to come, and I don't think that has to be the only queer show ever. And I think the way that it skyrocketed has only opened up doors for future stories like that. So that's exciting to me.
Addison Rae
Yeah, I feel like people who are in the entertainment industry and in your space that have grown up loving fandoms, I actually feel like it makes your work, like, so much more impactful and you, like, love it so much more. Because I feel that with my publicist, too. Really, Like, I feel like they, like, they're like. One of them goes to, like, literally, like, every concert of, like, every, like, they. They just, like, love, like, like, growing up. And one of them was obsessed with, like, stranger Things and she, like, just being a part of fandoms like that, I feel like it makes your job, like, you so much better at your job because you, like, appreciate it more. And I think there's a lot of people that could be, like, too cool for school.
Willa Bennett
Like, yeah, I'm not like that at all. I'm like.
Addison Rae
You're like, no.
Willa Bennett
I'm like, who is going to send me to the summer I turn pretty movie in Paris?
Addison Rae
We're going to go.
Willa Bennett
We're.
Addison Rae
We're going to go.
Willa Bennett
I'll cry. Like, I. Experiencing that, like, experiencing it in real time with the fandoms was so important. And I've talked about this a lot with Jake Shane. Do you know him?
Addison Rae
Yeah.
Willa Bennett
Yeah. So, like, I've talked about this a lot with him because sometimes we'll get, like, screeners before just being in our industry. And I'm always like, I watch it twice. I watch it with the screeners, I make my decisions, and then I have to experience it with the fandoms.
Addison Rae
Yeah.
Willa Bennett
So, like, a big movie will come out and, like, I'll be like, okay, like, I'm gonna go Wuthering Heights. I'm go to the screening next week. I'm gonna see it. And then I'm also gonna see it when everyone else sees it, because I'm so curious, like, how people experience it in real time. And I went to the ERA Store twice. I really do love.
Addison Rae
I was just gonna ask if you're a Swiftie, because you brought up Jake.
Willa Bennett
I am a swiftie. I really am. Let it be known. But I didn't grow up a Swiftie.
Addison Rae
Yeah, that's what I'll say.
Willa Bennett
I am. I really have rediscovered Torture Poets department recently. And I think. I think the reason that's. That album specifically hasn't gotten as much love as the rest is, like, I think there's so many songs that, like, people don't. It's too much for them. But I think it's, like, one of her best. I love Life of Showgirl, even though people are being critical of it. I'm like, haters are everywhere.
Addison Rae
Yeah.
Willa Bennett
So I am a Swiftie, but when I was growing up, I really wasn't. I was way more into, like, Alanis Marset and Avril Lavigne, to be honest. But, you know, I'm coming around. And I will say, like, everyone at Cosmo is addicted to Taylor Swift, and they are legitimate fans. Like, we covered it like sport.
Addison Rae
Yeah.
Willa Bennett
Like, every single ERA short. Be like, Atlanta. Like, there'd be a writer on covering, like, the different songs. So I think because of that has rubbed off on me, and they've kind of made me a Swiftie.
Addison Rae
Yeah. Okay, let's talk about. Let's talk about our cause of thing. Obviously, Lemon Drops. Those are our listeners. You guys have probably seen all of the. The posting that we've been doing, and I probably am still posting about it when this episode is coming out, because it truly was, like. It was just the whole experience has exceeded. Like, I actually don't know how I'm gonna ever do anything like this again, because I don't think anything could top it just from, like, just every aspect of it. You guys have definitely been like. That's actually something that my team has said is how collaborative you guys have been with everything. Um, but us getting this was my first, like, in print feature thing. I just. That's the correct verbiage. I don't even know. Yes. The correct verbiage. But this is my first time ever doing something like this at all, which is crazy.
Willa Bennett
Because I was, like, obsessed with you guys for so long. I think I told you this on Friday when we were together, but I was like. I was telling. I was telling her that, like, I, like, love them and I think it's so cool that you guys have the same name. And I was just, like, obsessed with. Again, fangirling. I was, like, obsessed with that. And, you know, we were thinking about couples again. Like, we love putting love on the COVID And it was so perfect. And I was so surprised no one else had done it yet.
Addison Rae
Yeah. They missed an opportunity.
Willa Bennett
Well, now they can be the second.
Addison Rae
They missed an opportunity. What is the process look like on your side? How does it basically go from your brain to it happening?
Willa Bennett
Okay, so I have a ton of finstas. Because I was telling you, sometimes I'll follow someone on Instagram and I'll be like, willow follows Addison Rae. There must be a cover. So I'm very careful now. So you guys were followed by on my fence does and. Which is funny. No one will ever know what it is because I follow zero accounts on there. And yeah, I was, like, following you guys for a while and then I, like, sleuth around. And then Maxwell, who you met, right?
Addison Rae
Yeah.
Willa Bennett
He's amazing. He. I messaged him being like, we gotta do some couples for Valentine's Day because it's like our one year since Brenda and Macaulay on the COVID Yeah. And he knew I loved you guys. And he immediately was like, it's them. And I was like, done. There was like, literally no other discussion. It was like that click. Because, you know, it's tough and we like to have people, like, promoting certain things. So I think that when we reached out to your team, it was like, what are they promoting? What other press are they doing? And you ask a ton of questions. And we kind of went back and forth and it was like an. Every single person was like, no brainer. And it was like a Valentine's Day story.
Addison Rae
Yeah.
Willa Bennett
Which is cool.
Addison Rae
Yeah. No, it was so sweet. And I told you this, but it's so obviously, you know, being married to a celebrity, it's not that I'm like, I don't often feel like I am second because Taylor literally will be like, babe, you're a celebrity. I'm like, honey, you are the celebrity. I am not.
Podcast Host
But thank you. I love you.
Addison Rae
But that's, like how he makes me feel. It's like he. He doesn't make me feel less important than him. Honestly, he makes me feel more important than him. So, like, when you know Things like this come up when it is about Taylor, not me. I'm like, I also am, like, social. I really don't care, but sometimes, you know, I do.
Podcast Host
In which we talked about in the.
Addison Rae
Interview is like, I do, like, want to be known for more than just being a wife, and that is something that's important to me and something that I've grown up realizing, like, later in life. Like, I. I always, like, growing up, I always just wanted to be a mom and a wife.
Podcast Host
And it's been really cool since meeting Taylor. I was like, oh, I actually don't.
Addison Rae
Feel like I need to get married right away. And then, like, we get married, I'm.
Podcast Host
Like, oh, I actually don't feel like.
Addison Rae
I, like, need to have kids right away. Like, I actually want to, like, experience a career. And that was something that I never wanted for myself. And so it's been really cool to, like, find those things out about me. So I love being a wife, but also, like, I work so hard and feel like I have, like, other talents, too, so.
Willa Bennett
Totally.
Addison Rae
But it just was really sweet how I think also, because we've just dealt with this before when it has. We think it's going to be both of us, but then it just, like, ends up being only Taylor, or. I've done interviews where I talk about all this mental health stuff, and there's one Taylor question or there's one Taylor Swift question, and then that's just the one question that's there, and none of the other stuff makes it. And it's just like, okay, well, like, did you want to hear anything else I had to say? And with this, I really just, like, felt so, like, loved and, like, heard.
Podcast Host
And seen throughout the whole shoot, throughout.
Addison Rae
The whole interview, how everything, like, turned out. Like, Taylor and I were reading it, we were like, oh, my gosh, like, this is amazing. Like, we had no notes. We're so in love with it all. And how you were like, no, they're going to be equal parts like, Tay and Taylor in this. It's just like. And I think that is really. Even if, you know, the readers aren't married to a celebrity, I think that's something that is super important to carry throughout any form of relationship, like, any. Any partnership, any marriage. Like, you know, we. Being with someone that you feel. Being in a. In a way that you feel, like, equal or just, like, loved and heard equally as much as the other, I think is super important.
Willa Bennett
Totally. I agree. And I think. Look, like, I think it's so hard to navigate a relationship in public. And I love, like, how you guys. It just feels very you and very sacred, and that shouldn't have been lost. And that was, like, kind of the big ethos behind the creative was like, how do we take this sacred thing you guys have built and let the readers in without also, like, giving them too much, like, what you guys felt comfortable with? But I was so, like, honored because I felt like you guys really, like, committed to it. And, you know when you're, like, putting on fancy clothes, like, we were kind of, like, putting you more in, like, a fashion context, I thought. And I, at any moment, we would have, like, done less. But I thought Marcus, really. Marcus Allen is the stylist.
Addison Rae
Yes.
Willa Bennett
I thought he did, like, a fantastic job and, like, elevating you guys. But also, it didn't look not like you guys.
Addison Rae
Yeah. No. That's literally so true. Taylor and I had the most fun day playing dress up. Like, we were like, I literally left, and I told my publicist, I was like, I think I need a model more. Like, I literally just like, oh, my God. I had the most fun day. And Taylor, too, because I feel like he can, like. Like, he has a much less social battery. Battery than I do. But he was, like, literally, like, just. I checked in with him a couple of times the other day. I'm like, you good?
Willa Bennett
You good?
Addison Rae
He's like, yeah, like, I'm chilling. Like, he, like, it was equally having so much fun, and he's done this, like, however many freaking times. But it was, like, really just, like, such a fun day and team.
Willa Bennett
And I thought the story, like, what I loved about the text is, like, I could really hear both of your humors.
Podcast Host
Yes.
Willa Bennett
Which is really hard to do as a writer. And I think the writer did a fantastic job. Like, yeah, I really felt like I was talking to both of you in it, which is what a lot of the audience said. A lot of the comments on it were like, this is my favorite interview of them. They actually feel like themselves. This is why we love them. Thank you for getting in. And again, I love when the fandoms tell us we did it right. Cause that's just such an important part. And Serena and Cordell was the other couple. We did where Marcus, who styled you guys, actually styled that one too. All the comments were like, this is it. Like, you guys got their relationship. So it's important to me that everyone's featured equally and everyone's story is, like, heard, and it isn't clickbait. Like, that's all very important. But I Don't know. Sometimes couples, like, they kind of want a different hierarchy, so that's different. You guys were very like, we trust you, which I appreciate.
Addison Rae
Yeah, that was sweet. Yeah. The response to everything has been, like, so sweet. And my. The whole family is like, can you please, like, print it out and frame it for me? I'm literally, like, getting the photos framed.
Podcast Host
I.
Addison Rae
There's this one photo of me that's now my profile, like, photo on everything. I don't think I'm ever gonna look better than I do in that photo.
Willa Bennett
I literally makes me cry randomly.
Addison Rae
I'm like, I will never look this good again. It was. It was literally. It was.
Podcast Host
It was.
Willa Bennett
Wait, which photo was it?
Addison Rae
Crop top. It's the one of me, like, on. It's the solo shot. So there's two. There's like a long one of me on the beach with, like. Yeah, it's like. It's the T shirt that's, like, tied with the glasses, but it's the close up up one of it. I just, like.
Podcast Host
It's amazing.
Addison Rae
I love that. So cool. Like, I literally could. I could never do that again.
Willa Bennett
So good. And it's co's on stands February 14, so when they come, you should definitely frame it.
Addison Rae
Yes. Oh, no.
Willa Bennett
I'm.
Addison Rae
I'm going in.
Willa Bennett
Like, that is Macaulay Culkin always says about his Cosmo shoot. He said to me, he goes, this going on the mantle because, like, apparently, like, they have family photos there. And he was like, this is for the kids.
Addison Rae
Yeah, I know. I'm gonna. I'm gonna start to, like, make a little shelf because I don't really have, like, anywhere in the house where I like, display stuff like that. Like, we have, like, our wedding photo, like, when we walk in, but there's not really, like, anything else. So I need to, like, get a little, like, shelf going.
Willa Bennett
Yeah. Mantle things.
Addison Rae
Get Taylor's Kids Choice Awards. Little stuff on there.
Willa Bennett
No, it's Choice Awards, Cosmo.
Addison Rae
No, we literally have his. Yeah.
Podcast Host
Wait, which one's the surfboard?
Willa Bennett
That's good choice.
Addison Rae
We have the surfboard in the garage. Wrapped in.
Willa Bennett
Or is it Teen's Choice Award?
Podcast Host
Teen.
Addison Rae
Oh, wait.
Podcast Host
One of them.
Addison Rae
Whatever the surfboard is.
Willa Bennett
Has he been slimed?
Addison Rae
He has been slimed.
Podcast Host
We actually.
Addison Rae
My dad actually randomly asked him that the other day. We were watching him. He has, like. So I just cleaned out his closet.
Podcast Host
I'm like, the clean freak of the.
Addison Rae
Two of us, so I have to do things for him. And he's very nice and lets me clean out everything. But I was freaking, like, cleaning out his T shirts, and I pull out this little, like, crop top that says Alan. And it's literally from when she had him on in the middle of Twilight and was, like, trying to get him to put a crop top on.
Willa Bennett
On.
Addison Rae
And they, like, got him. What? It was just like. It's so funny that he's lived a whole life before me. He'll be like, oh, yeah, I did.
Podcast Host
That with this person. Or this.
Addison Rae
This person was blah, blah, blah. I'm like, what? Like, I don't even know who that is. Like, what are you talking about?
Willa Bennett
That's so funny.
Addison Rae
It's really. It's really fun. But also, it's really cool for me, like, going into the space.
Willa Bennett
Yeah.
Addison Rae
Now, like, I have someone that's really been through it, so there's no, Like, I don't really feel, like, pressure with stuff or I'm not really, like, scared. Like, people always ask. Like, our first date, there was paparazzi, and we literally just, like, got in the car, and Taylor, like, put my little visor down and just, like, drove off and didn't say anything. And I was like, we're not gonna, like, address what just happened. Like, it's just. It's funny that, but. Because he doesn't put what she's had.
Podcast Host
To learn, he doesn't put value, like, into it anymore.
Addison Rae
It makes it, like, the stakes are so low. Like, we come home and we have each other and our dogs and our family, and that's.
Willa Bennett
How do you think he learned that time?
Addison Rae
I definitely think that's something that he learned. So basically, when we first started dating, he kind of, like, stepped away from everything he was filming.
Podcast Host
Right.
Addison Rae
When we started dating, he did one more, like, Sandler movie, which is very. Just, like, fun little lift. But he definitely, like, finally took some time to, like, be, like, not in the industry. And I think me being the first person, like, since he was a teenager that hasn't been in the industry that he's been with. And, you know, we hang out with a lot of my friends that aren't also, like.
Podcast Host
Are also just normal.
Addison Rae
Grew up in the suburb, like me. I think he kind of just processed everything over the past few years and really, like, had to learn that he. He learned that he was, like, putting value into, you know, paparazzi.
Podcast Host
Stopped following him, how that made him.
Addison Rae
Feel, or when, you know, people, he.
Podcast Host
Would be in the second row of this.
Addison Rae
Like, just, like, little things like that. You're, like, built so high and expected all of these things and when they don't happen because, like, I feel like it happens a lot. Like Taylor, Robin, Kristen, we're all put on these like impossible, like, pedestals. And when you can't achieve whatever that goal is because it's unachievable, then everyone's like, oh, well, they're failed. They like, don't. So he's definitely has like, had to have some time to learn that.
Willa Bennett
But I'm sure it's changed so much too. Like in the time of like, like how Twilight blew up versus even how like heated ravelry. So generational and so different. So I. I can't even imagine.
Addison Rae
Yeah, it's cool now. Like his mindset going into like this new project that they're he's developing with Amazon. Like, he's like, excited to like, go back to work and it's really, it's really sweet to like, see his mindset. Like, he knows if like, it flops, then like, okay, you still have dinner. Yeah, he's still got to make me dinner when he comes home. That's the thing. He is the cook. I love it. Well, thanks for coming and chatting.
Willa Bennett
Thank you for having me. I truly loved having you in Cosmon. I loved hanging out with you on Friday. And we have to text about the submarine. Pretty.
Addison Rae
Oh, yes, absolutely. We're going to. You know there's a movie, right?
Willa Bennett
Yes.
Addison Rae
Okay, great. We're going to. We're going to. We're going to.
Willa Bennett
We have to go and like, oh my God. I addicted.
Addison Rae
Yeah. Great.
Podcast Host
I love it.
Willa Bennett
Okay, thank you so much. Please note that this episode may contain.
Podcast Host
Paid endorsements and advertisements for products and services.
Willa Bennett
Individuals on the show may have a.
Podcast Host
Direct or indirect financial interest in products.
Willa Bennett
Or services referred to in this episode.
Host: Taylor Lautner (Tay Lautner)
Guest: Willa Bennett, Editor-in-Chief of Cosmopolitan & Seventeen
Date: February 13, 2026
This episode of The Squeeze features a candid conversation between host Taylor Lautner and Willa Bennett, the youngest editor-in-chief in Cosmopolitan’s history and a transformative figure in new-era magazine publishing. They discuss Willa's personal journey in media, her vision for Cosmo, the realities of modern editorial careers, coming to terms with mental health from a young age, and the unique pressures and fulfillment in her high-profile role. The conversation also spotlights their recent collaborative Cosmo cover shoot featuring Tay and Taylor, exploring representation, love, and equality in media.
The episode is candid, warm, and conversational, balancing professional insight and personal vulnerability. Willa’s approach is self-assured but deeply empathetic, and the mutual respect and admiration between the hosts and guest is palpable. The discussion offers actionable advice on mental wellness, behind-the-scenes magazine leadership, and setting equitable standards for love and partnership in media.
This conversation is essential for anyone curious about the inner workings of a major magazine, the pressures and joys of leading as a young queer woman, and the value of honest storytelling in mental health and media. If you’re looking for authentic dialogue about modern relationships—both in life and in print—this episode delivers, with laughter, warmth, and a sense of genuine care.