Sex and the City S1E4: "Valley of the Twenty-Something Guys" with Ryan O'Connell

Sex and the City S1E4: "Valley of the Twenty-Something Guys" with Ryan O'Connell

From Girls Rewatch: Sex and the City by Amelia Ritthaler & Evan Lazarus

February 24, 2026 · 1h 13m

About this episode

Ryan O'Connell joins the hosts to discuss the themes of dating younger men and friendship dynamics in the fourth episode of Sex and the City.

Ryan O’Connell, creator and star of the Netflix show SPECIAL whose third book (INSPIRATION PORN) releases this spring, joins us to discuss SATC Season 1, Episode 4 “Valley of the Twenty-Something Guys.” We discuss how Ryan could simply never relate to the notion of dating younger as Carrie and Samantha attempt in this episode, Charlotte’s true-to-form fear of becoming the “up the butt girl,” and the inevitability of a Mr. Big dating one of your friends. Our listeners get 15% off plus free shipping when they buy two or more pairs of prescription glasses at WarbyParker.com/GIRLSREWATCH — using our link helps support the show. #WarbyParker #ad Share a little extra love this February and wrap yourself—or someone you care about—in comfort that truly feels special. Head to cozyearth.com and use out code GIRLSREWATCH for up to 20% off. And if you get a Post-Purchase Survey, be sure to mention you heard about Cozy Earth right here! Learn more about your ad choices. Visit megaphone.fm/adchoices

People in this episode

Hosts: Amelia Ritthaler, Evan Lazarus

Guest: Ryan O'Connell

Topics covered

  • dating
  • relationships
  • comedy
  • friendship
  • cultural commentary

Keywords

  • Sex and the City
  • Valley of the Twenty-Something Guys
  • Ryan O'Connell
  • dating
  • relationships
  • comedy
  • friendship

Sponsors

Warby Parker, Cozy Earth

Mentioned in this episode

Organizations: Netflix

Books & works: SPECIAL, INSPIRATION PORN

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