The Squeeze Podcast

Episode: Willa Bennett – Behind the Scenes at Cosmopolitan

Host: Taylor Lautner (Tay Lautner)
Guest: Willa Bennett, Editor-in-Chief of Cosmopolitan & Seventeen
Date: February 13, 2026

Episode Overview

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.

Key Discussion Points & Insights

1. Willa’s Path to Editor-in-Chief and Editorial Philosophy

• Early Career and Passions:
  • Willa started as an intern at Seventeen and worked her way through Bustle, GQ, and High Snobiety, before landing at Cosmopolitan.
    • “I started my career at 17. I was an intern…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…I feel like I’m making the magazine I want to read, which is really cool.” — Willa (05:26)
  • Her passion for storytelling, especially in queer spaces, drove her path:
    • “I always used to write in my diary that I wanted to write the gay Twilight, which is funny that I’m here now...I was obsessed with Twilight. And I was like, I want to write, like, the gay Twilight.” — Willa (06:24)
• Editorial Approach:
  • Focus on curation over clickbait, serving readership authentically, and connecting with fandoms.
  • Enjoys featuring real couples and authentic relationships, highlighting their significance in pop culture.
    • “The coolest thing about Cosmo that I really appreciate is how we do speak to fandoms directly…We do this thing where we, like, put couples on the cover, and it’s one of my favorite things.” — Willa (07:38)

2. Navigating Imposter Syndrome and Loneliness

• Instincts Over Insecurity:
  • Impressively, Willa rarely struggles with imposter syndrome, attributing her confidence to trusting her instincts.
    • “I really, like, am confident. Like, truly. I don't really struggle with that. I feel, like, very in tune with my instincts.” — Willa (08:40)
  • Instead, what she sometimes faces is loneliness at the top and the unprecedented nature of today's media landscape.
    • “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.” — Willa (09:39)
• Changing Industry:
  • Noted that fast-evolving platforms and the constant shift in journalism make things unique and sometimes isolating.
    • “There isn't anyone I can call to be like, what should I do about this? Because…the times we're in, in the editorial space at least, are just very unprecedented.” — Willa (08:53)

3. Mental Health, Therapy, and Burnout

• Therapy from a Young Age:
  • Willa has been in therapy since age 7, credits a brutal parental divorce and early anxiety as initial reasons. Therapy was a “healing” and even “obsessive” presence in her life.
    • "I've been in therapy since I was 7, so I'm like, oh, wow. I'm very therapized. Not to brag.” — Willa (20:28), (23:49)
    • “I was obsessed with it. It was so healing for me.” — Willa (23:54)
• Advice for Young People Facing Anxiety and Loneliness:
  • Willa emphasized the importance of finding any therapist to talk to, not necessarily the perfect one.
    • “I read about the loneliness epidemic…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.” — Willa (27:13)
• Coping with Burnout:
  • Willa operates at a high threshold but admits to sleeping as her main recovery tool and as a way to process.
    • “Burnout is really interesting. I think it’s real…I've definitely felt it before, and I really just, like, sleep…I process things in my sleep.” — Willa (18:13)
• Phone and Social Media Boundaries:
  • Struggles with being overly connected via her phone, both for work and personally –
    • “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.” — Willa (27:37), (28:20)
• Career-Therapist Hybrids:
  • Discussed having a therapist with a career coaching angle, specializing in people under external pressure.
    • “My therapist…her specialty is people who like, have really high pressure jobs and they kind of need, like, emotional help on how to handle certain things.” — Willa (24:27)
  • Noted that some therapists take a more analytical, others a more direct approach, and both have value.

4. Behind the Scenes of the Cosmo Cover

• The Idea and Process:
  • Willa explains the selection process, use of private finstas to follow prospective cover subjects, and the almost instinctual choice of Taylor and Tay for Valentine’s cover.
    • “I have a ton of finstas…sometimes I’ll follow someone on Instagram…so I’m very careful now. So you guys were followed by on my fence does…Maxwell…immediately was like, it’s them. And I was like, done. There was literally no other discussion.” — Willa (40:08)
• Equal Representation and Collaboration:
  • Both Tay and Taylor were represented equally, steering away from “wife of celebrity” narratives.
    • “I really just, like, felt so, like, loved and, like, heard and seen throughout the whole shoot, throughout the whole interview...there's one Taylor question or there's one Taylor Swift question, and then that's just the one question that's there...and with this, I really just, like, felt so, like, loved and, like, heard.” — Addison Rae (42:59)
    • “It just feels very you and very sacred, and that shouldn’t have been lost. That was the big ethos behind the creative...how do we take this sacred thing you guys have built and let the readers in without also giving them too much?” — Willa (43:43)

5. Love, Fandom, and Personal Goals

• Passion for Fandom:
  • Willa is personally invested in fandom culture; she insists on experiencing cultural events both as a media person and as a fan.
    • “I watch it twice. I watch it with the screeners, I make my decisions, and then I have to experience it with the fandoms.” — Willa (37:12)
• Vision for Cosmo’s Future:
  • Wants Cosmo to have meaningful impact, particularly serving readers and providing space for authentic, particularly queer, stories.
    • “I really want to be a publication that serves its readership and really cares about its readers. 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 cool and so gratifying.” — Willa (35:05)
• Personal Revelations & Relationship Equality:
  • Tay details her own journey from aspiring only to wife/mom to discovering her own identity and ambition.
  • The experience as a Cosmo cover couple made both feel seen and valued, setting a new standard for media representation.

Notable Quotes & Memorable Moments

On Representation and Editorial Choices

• “It’s important to me that everyone’s featured equally and everyone’s story is, like, heard, and it isn’t clickbait. That’s all very important.”
  — Willa Bennett (45:09)

On Mental Health & Therapy

• “I’ve been in therapy since I was 7…It was so healing for me.”
  — Willa Bennett (23:49)
• “I think you have to work on it [mental health]…find a therapist. And it doesn’t have to be a perfect one, but just, like, someone to talk to.”
  — Willa Bennett (27:13)
• “We’re all so hyper connected online while also being so alone, and that just can’t be good for development.”
  — Willa Bennett (27:37)

On Confidence and Instinct

• “I really, like, am confident. Like, truly. I don’t really struggle with that. I feel, like, very in tune with my instincts.”
  — Willa Bennett (08:40)
• “It’s not imposter syndrome. It’s more like lonely, if anything.”
  — Willa Bennett (09:39)

On Personal and Professional Growth

• “I always loved books...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.”
  — Willa Bennett (06:24)
• “I really love my job, and I really believe in Cosmo. I think it would be impossible to do this if you didn’t.”
  — Willa Bennett (11:45)
• “I’m like, who is going to send me to The Summer I Turn Pretty movie in Paris?”
  — Willa Bennett (36:56)
• “The response to everything has been, like, so sweet...my whole family is like, can you please, like, print it out and frame it for me?”
  — Addison Rae (45:59)

Timestamps for Key Segments

• Willa’s intro, career journey, and Cosmo’s audience: 00:22 – 07:38
• Imposter syndrome, confidence, and changing industry: 08:35 – 11:15
• Therapy origins and mental wellness journey: 20:28 – 27:13
• Phone, boundaries, and digital anxiety: 28:10 – 29:39
• Cosmo cover process and collaborative ethos: 39:32 – 44:30
• Reflections on relationship representation & media equality: 42:59 – 45:09
• Fandom culture, the future of Cosmo, and personal fulfillment: 35:03 – 38:34

Tone & Takeaways

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.

For Listeners Who Missed the Episode

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.