Podcast Summary: Extra Dirty with Hallie Batchelder

Episode: Willa Bennett – Dating in your 20s vs 30s

Date: November 20, 2025
Host: Hallie Batchelder
Guest: Willa Bennett (Editor in Chief, Cosmo and Seventeen)

Episode Overview

This episode of Extra Dirty dives deep into the realities of dating across your 20s and 30s, with Hallie Batchelder and guest Willa Bennett offering a candid, unfiltered look at love, relationships, and the chaos of New York City life. Willa, a powerhouse young editor known for her fresh perspectives on sex and dating, joins Hallie to compare generational dating trends, share lessons from careers in media, and swap wild, hilarious stories about first dates, texting etiquette, and the pitfalls of modern romance.

Key Discussion Points & Insights

1. Their Origin Story & Backgrounds

• [02:44] Willa and Hallie recount how they connected through Instagram, quickly bonded over their humor and perspectives on casual dating, and became fast friends after a memorable Cosmo dinner.
• Willa grew up in LA, retains close friendships from childhood ("all the same friends I met in kindergarten, which is pretty scary" [04:00]), and describes never having cut off a best friend—a rarity she and Hallie unpack.
• Both women reflect on the significance of stable, long-term friendships and how red flags arise when someone’s friend group dramatically shifts year to year.

2. Being the “Fun Friend” and Navigating Social Norms

• Willa shares feeling like the perennial “fun one” at weddings and social events, not always seeing herself that way, but embracing her role in keeping things lively ([05:41]).
• Conversation pivots to the external pressures of hitting relationship milestones: "I should have a serious boyfriend and I should be engaged… but I just don’t want to follow those norms." – Hallie [05:10]
• The struggle and stigma of being the last single in a friend group is discussed with humor and honesty.

3. Career and Dating: Intimidation, Privacy, and Public Life

• Willa prefers not listing her impressive job title on dating apps, while Hallie talks about how hosting “Extra Dirty” complicates her dating life as potential matches worry about being discussed on the show ([07:12] – [08:47]).
• Both critique the challenge of determining authentic intentions in New York’s influencer scene.

4. The Biggest Relationship Lesson: Open, Honest Communication

• "There’s one common theme through everything, and it’s open, honest communication. And it’s like, don’t play games." – Willa ([09:29])
• Hallie candidly admits to still being entertained by “the games,” though she recognizes it’s immature and is self-aware about her patterns ([09:47]).
• Both note the shift from ambiguous texting in your 20s—agonizing over meaning and reading into everything—to more direct communication in your 30s: "You don’t want to waste any time being blind. Get to the point." – Hallie ([11:08])

5. The Role of Texting and Phones in Modern Romance

• Discussion of the new Cosmo cover story: "Is great texting better than good sex?" prompts debate over the importance of digital communication ([13:06]).
• They discuss generational differences: Gen Z’s expectation for frequent, meaningful texting, and the anxiety driven by ambiguous digital contact.
• Willa notes: "Part of the new commitment for young people really has come with like contact over the phone. Maybe it’s like an Instagram like, maybe it’s a DM." ([14:19])
• Anxiety over being surveilled at parties (videos/photos) and the effect on intimacy in the social media age ([15:05]).

6. Ghosting Debate—Context and Compassion

• [20:28] Willa offers her "professional opinion" that ghosting after only a few dates may be acceptable, though a direct conversation is ideal if intimacy has occurred.
• Hallie: "I’ve gotten a whole paragraph describing why they didn’t want to continue seeing me… It was easier to get over than a ghosting situation, you know?" ([21:42])
• Both agree that directness is ultimately more respectful, though gray areas remain in the early dating stages.

7. Directness and Generational Shifts

• Exploring whether Gen Z is more or less direct given their hyper-online lives. Willa argues doomscrolling may make going out and connecting in person harder, yet Gen Z is admirably uninterested in wasting time ([23:01]).
• The rise of speed dating and blind dates reflects a cultural yearning for authenticity and spontaneity in a digitized dating landscape ([23:52]).

8. Dating App Etiquette and Talking Phase Timelines

• Discussion of how long to keep “app to text” banter going before meeting up (Cosmo recommends three to five messages, then suggest a plan; if no follow through, it’s not ghosting, just a non-starter) ([33:38]).
• Both joke about “pen pal” scenarios where texting substitutes for actual dating, sometimes with people they’ve never met and don’t intend to!

9. First Date Logistics—Drinks, Coffee, and the Rules

• Both prefer drinks (ideally at a wine bar) but support coffee dates too ([29:19]).
• Wildest drink order discussed: "What if you were on a date and they ordered a pina colada?" – Hallie ([31:56])
• First date drink order as personality indicator; consensus is nobody is “worth the hangover” ([31:09]).

10. Modern Red Flags and the “Ick”

• Biggest “icks”: meanness as flirting, belittling someone’s job, being rude to wait staff ([36:41]).
• "I don't like people who are mean as a way to flirt. Like, I just don't. Like, I'm just like, come on, I'm 31." – Willa ([37:05])
• Offensive comments about food or eating habits are an automatic dealbreaker, especially given eating disorder awareness ([38:06]).

11. Love Languages, Romance, and Settling

• Willa: "I think verbal affirmation. Like, I really love letters and like, talking and la la. Like romance." ([40:59])
• Discussion on romance making a comeback, and how different partners bring out different sides of you.
• Both agree not to settle and not to force milestones just because of age or societal pressure ([42:01]).

12. Wildest Cosmo Stories and Generational Dating Trends

• Willa’s wildest editorial: commissioning a writer to try right-wing dating apps for six months ([43:00]).
• Cosmo’s “new casual” feature: "Hot sex. No sleepovers." Both agree sleepovers make things less casual, and clear communication about boundaries is essential ([54:55]).

13. Breakups, Glow-Ups, and the Value of Experience

• Both share experiences of college breakups, learning, and the importance (and benefits) of moving on: "I'm very pro-breakups. It's so good for you." ([53:19])
• Willa underscores that you always take something meaningful from past relationships: "Even if a relationship ended, it's not like you're starting from zero." ([60:06])

14. Cheating: Physical vs. Emotional

• Both discuss past experiences being cheated on and attitudes toward infidelity.
• Willa: "I think it's all not kosher. It's all bad. But I think open, honest communication… you can definitely talk through it, but it would be really hard." ([48:13])

15. Platforms & Gen Z’s Interests

• Willa plugs her newsletter “Love Willa” ([60:23])—a weekly roundup of dating trends, news, and TikTok-fueled discourse.
• Gen Z’s most common question: "situationships"—she advises: "Situationships can teach you about what you don't want." ([62:22])
• Cosmo’s current focus is the entanglement of romance and phone use, ChatGPT’s limits as a therapist, and the changing nature of dating communication.

Notable Quotes & Memorable Moments

• On the stakes of being the “fun” wedding guest:
  • "I obviously am fun and amazing, but I don’t really think of myself as that." – Willa ([06:08])
• On dating with a public persona:
  • "I either kind of scare men away because I think they’re scared I’m going to talk about them publicly… or I don’t know people’s intentions at all." – Hallie ([07:24])
• On communication:
  • "It’s actually so hot if you’re just like, this is what I want." – Willa ([09:39])
  • "If you’re really having to think about it and analyze it [a text], then it’s probably not right." – Hallie ([11:46])
• On ghosting:
  • "I’ve gotten a whole paragraph… It was easier to get over than a ghosting situation, you know?" – Hallie ([21:42])
• On the “new casual” dating:
  • "Hot sex. No sleepovers." – Willa ([55:06])
• On modern love and the pressure to couple up:
  • "I’m on my own journey. That’s what I always say. I’m on my own path." – Willa ([42:44])
  • "No one’s worth the hangover." – Both ([31:09])
• On emotional lessons from breakups:
  • "Even if a relationship ended, it’s not like you’re starting from zero." – Willa ([60:06])
• On the cultural obsession with ‘the ick’ and red flags:
  • "People who are mean as a way to flirt is an immediate no." – Willa ([37:12])
  • "If a guy was commenting on anything about food or how much I eat, how much I don’t eat, I would probably have a panic attack." – Hallie ([38:23])

Timestamps for Key Segments

• [02:44] – Hallie and Willa’s origin story
• [04:00] – Willa’s LA roots and rare lifelong friendships
• [05:41] – Pressures of being the last single
• [07:12] – Careers’ impact on dating (public personas and privacy)
• [09:29] – Most important relationship advice: honesty
• [13:06] – Cosmo’s big question: texting vs. sex
• [20:28] – Ghosting: When is it okay?
• [23:52] – The return of blind dates and speed dating
• [29:19] – Drinks or coffee for first dates
• [33:38] – App-to-text-to-in-person—time limits
• [36:41] – The "ick," dating red flags
• [40:59] – Love languages
• [43:00] – Wildest Cosmo story: right-wing dating apps
• [54:55] – The "new casual" (no sleepovers)
• [60:06] – Lessons from breakups
• [62:22] – Gen Z’s obsession: situationships
• [64:45] – Cosmo & Seventeen’s upcoming features

Tone & Final Thoughts

The conversation is breezy, brutally honest, and downright hilarious—packed with self-deprecating humor, hard-won insights, and the kind of sleepover gossip you’d only share with your closest friends. Both Hallie and Willa underscore the importance of staying true to yourself, practicing open communication in all relationships, and embracing the messiness of modern dating with curiosity rather than shame.

Willa’s insider view from Cosmo, combined with Hallie’s "too honest for her own good" vibe, gives the episode an infectious energy and makes even the trickiest topics (ghosting, cheating, post-breakup reinvention) feel accessible and real.

For more from Willa, subscribe to her newsletter “Love Willa” and catch the latest digital issue of Cosmo for trending stories on love and technology.