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Therapuss with Jake Shane

Session 57: Willa Bennett

Sat, 15 Feb 2025

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I think you’re the coolest person in the entire world… Learn more about & Donate to the Support of California Here: Direct Relief ► https://www.directrelief.org Los Angeles Regional Food Bank ► http://www.lafoodbank.org/fire Los Angeles Fire Department Foundation ► http://supportlafd.org California Fire Foundation ► http://www.cafirefoundation.org Altadena Children's Book Drive ► https://vromansbookstore.com/childrens-books-altadena-book-drive Altadena Girls & Boys ► https://www.pledge.to/altadena-girls https://www.instagram.com/altadenaboys/?hl=en Tell Me What's Wrong at ⁠ passthatpuss.com Follow Me! Instagram | @passthatpuss TikTok | @octopusslover8 Follow Willa & Subscribe to Cosmopolitan! @willahbennett https://www.cosmopolitan.com/ Listen to "THERAPUSS" Spotify: ⁠⁠⁠⁠https://open.spotify.com/show/1BHDdC0OVuHqZ706FobfOF ⁠⁠Apple Podcasts: ⁠⁠⁠⁠https://podcasts.apple.com/us/podcast/therapuss-with-jake-shane/id1723626781⁠⁠ Amazon Podcasts: ⁠⁠⁠⁠https://music.amazon.com/podcasts/93117357-1f23-46e1-8f26-88f5182a68b8/therapuss-with-jake-shane⁠⁠ YouTube: ⁠https://www.youtube.com/@octopusslover8 Learn more about your ad choices. Visit megaphone.fm/adchoices

Audio
Transcription

Chapter 1: What is the main topic of this episode?

10.563 - 36.198 Jake Shane

Hi, pussies. Welcome back to Therapist. Happy Valentine's Day. Sorry, I am so cold. It is very cold and rainy in Los Angeles, but, you know, we need the rain. It's a good thing, so thank God. I am once again single this Valentine's Day. I've never experienced a Valentine's Day taken, but Peyton and I are going to go out to dinner with the kids, so we're really excited.

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36.878 - 51.01 Jake Shane

February is always a tough month. February is always like where's March is how I feel about February. I've also never once again experienced Valentine's Day enjoyably. So I would know that's a lie. I'm sorry. I always have my Galentine's Day, but I've never had like an actual Valentine's Day.

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51.03 - 51.91 Unknown Speaker

I know.

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51.99 - 53.792 Willa Bennett

Is that a video I sent you, Tucker?

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Chapter 2: How does AI impact content creation?

54.352 - 74.598 Jake Shane

Real? No. Oh, my God. I have seen so many people fall victim to AI recently. It's like actually alarming. I'm like, I feel like I can, I'm pretty good at like calling out AI, but like Louise sent me a video yesterday that like, I'll play it right here. And she was like, is this real? Were you high?

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74.618 - 76.98 Willa Bennett

No, like it just seems so realistic.

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77.14 - 92.128 Jake Shane

No, it's not. You guys, that's the scary part about AI. It's like, God, AI is not right. But I feel like I can call out AI pretty quickly. But no. I've been seeing a lot of people be like, look how cute this is. I'm like, that's AI.

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92.908 - 93.648 Matt

What was the video?

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94.269 - 95.649 Jake Shane

Tucker kissing me on the cheek.

96.01 - 97.75 Matt

Oh, really? I swear that happened.

98.991 - 110.317 Jake Shane

No. Tucker would never show me affection like that. We go on tour very soon. We've actually spent the past few weeks planning the show. Matt flew in. Should we call him?

122.267 - 125.849 Matt

I was on the phone, Jake. Jesus. What's wrong?

126.309 - 128.41 Jake Shane

Nothing. I just wanted to say hi. You're on Therapus.

Chapter 3: Who is Willa Bennett and why is she featured?

145.46 - 145.9 Matt

Yeah.

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147.241 - 148.481 Jake Shane

What are you doing for Valentine's Day?

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150.242 - 150.923 Matt

Buying a house.

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154.79 - 156.551 Jake Shane

That laugh was harder than it should have been. Legit.

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156.571 - 158.331 Matt

That's what I'm doing.

161.692 - 162.613 Jake Shane

Um, what's up with you?

164.833 - 169.475 Matt

Nothing, man. Nothing. Just the same old, you know. Is that all?

170.455 - 170.955 Jake Shane

Yeah, that's all.

172.576 - 173.636 Matt

You sure? There's nothing else?

Chapter 4: How did Willa Bennett become Editor-in-Chief at Cosmopolitan?

623.149 - 646.145 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?

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646.185 - 654.792 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.

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655.112 - 655.732 Jake Shane

Interesting.

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655.772 - 671.564 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.

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671.684 - 677.208 Willa Bennett

And coming at it from a writer's perspective, even though I was working on social, it really was storytelling.

677.328 - 678.268 Jake Shane

Right. Of course.

678.668 - 695.452 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.

696.192 - 697.652 Jake Shane

I love that essay.

697.993 - 700.833 Willa Bennett

It did. Like, I remember all the comments being so sweet.

Chapter 5: Why are Macaulay Culkin and Brenda Song on the cover of Cosmo?

1506.052 - 1529.584 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

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1530.034 - 1541.142 Jake Shane

What is, quickly, what did you, since you said you profiled Gracie early on in GQ, is there something you noticed different from GQ to now in her?

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1541.653 - 1556.498 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.

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1556.558 - 1576.637 Jake Shane

It's just so, there's no one better. Like anyone else, you bring such a distinct voice to everything you touch. Thank you. It's true. It really is true. And there's no one better than, To take on Cosmo and change it and shape it for how the world we're in now. Thank you. That's so sweet. It's true.

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1576.657 - 1583.562 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.

1583.882 - 1585.864 Jake Shane

It's amazing. And you're like excited to go to work every day.

1586.084 - 1586.324 Willa Bennett

Yeah.

1586.604 - 1586.864 Jake Shane

Yeah.

1588.045 - 1589.106 Willa Bennett

Are you excited to go to work every day?

Chapter 6: How does Willa Bennett view fashion as art?

1855.68 - 1856.861 Jake Shane

I love him. I know.

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1856.901 - 1860.003 Willa Bennett

Isn't he so... He's so nice. How old is he?

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1860.023 - 1860.283 Jake Shane

I don't know.

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1861.336 - 1863.177 Willa Bennett

22. Cosmo knows it all.

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1863.478 - 1865.039 Jake Shane

Is he super Russian in real life?

1865.439 - 1873.567 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.

1873.667 - 1874.567 Jake Shane

What are you listening to?

1874.727 - 1889.173 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.

1889.393 - 1911.485 Jake Shane

I saw her Colbert performance, which was just mind blowing. I couldn't catch any of the Grammys because I was in the air. Like I was on a plane for, I, Oh, this is the second time I've said I was in the air, which is so weird. I said it this morning too. I was on a plane and then I landed. Jake Shane was flying. Yeah, I was fine. I landed and I turned on the Grammys cause I finally got service.

Chapter 7: What are Willa Bennett's favorite projects?

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3151.66 - 3154.002 Jake Shane

I would say like a cap is like maybe 50 something. Yeah.

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3155.458 - 3157.24 Willa Bennett

What's the oldest person you've ever dated?

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3157.881 - 3163.948 Jake Shane

I've never had a boyfriend, but the oldest person I've ever hooked up with, probably mid-40s.

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3164.729 - 3165.109 Willa Bennett

How is that?

3165.129 - 3169.314 Jake Shane

Well, I was like 20 or 19. Oh my God, I was 19. How is that? Horrible.

3171.217 - 3171.978 Willa Bennett

All right, next question.

3172.038 - 3189.468 Jake Shane

I don't know why I'm like, you should date a 50-year-old. You shouldn't. Hi, Jake. So I just got out of a three-year-long relationship with my boyfriend. Now all of these guys are hitting me up, including one of my twin brother's best friends. He keeps complimenting me and asking me out. Is that something I should bring up to my brother? What is going on?

3191.249 - 3199.975 Jake Shane

I would bring it up to my brother, but I wouldn't let what my brother says sway how I behave with this person. If you feel chemistry and it's there, then...

Chapter 8: How do personal experiences influence content creation?

4544.222 - 4544.903 Willa Bennett

Love the boat one.

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4545.243 - 4547.264 Jake Shane

So cool.

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4548.586 - 4550.027 Willa Bennett

What's your dream fashion show to go to?

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4550.401 - 4550.741 Jake Shane

Prada.

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4551.162 - 4551.782 Willa Bennett

Yeah, Prada's amazing.

4551.802 - 4552.903 Jake Shane

You know we've talked about Prada.

4552.943 - 4554.444 Willa Bennett

Yeah, yeah, yeah.

4554.464 - 4567.874 Jake Shane

By the way, you were like, Prada's so it. And I went, remember Louise? I went to you and I was like, Willis says Prada's it. Do you remember that? I love. I do love Prada. Prada and I love their new campaign with Harris Dickinson.

4568.246 - 4569.727 Willa Bennett

So good. Wow, you're plugged in.

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