Are You A Charlotte? – "The Writing's on the Wall with Cindy Chupack"

Season 2, Episode 11: “Evolution”
Release Date: August 25, 2025
Host: Kristin Davis | Guest: Cindy Chupack

Episode Overview

This episode features Kristin Davis (Charlotte York from "Sex and the City") in conversation with acclaimed writer and producer Cindy Chupack. The main theme centers on the creative evolution and behind-the-scenes stories from "Sex and the City," particularly focusing on the episode “Evolution” (S2E11). Cindy shares insights from her time joining the show, how real-life experiences shaped storylines, and the enduring impact of SATC on women’s storytelling in television.

A blend of nostalgia, industry candor, and humor, the conversation explores the intersection of writing, acting, and personal growth—from the early days of SATC to the modern day, including the legacy show “And Just Like That.”

Key Discussion Points & Insights

1. Cindy Chupack’s Path to SATC

• Transition from “Everybody Loves Raymond” to “Sex and the City” (03:19–06:03)
  • Cindy describes the “affair” she had with "Sex and the City" while working on "Everybody Loves Raymond," guided by her friend Jenny Bicks (writer on SATC).
  • "I was so excited to pitch because everything I had written... everything could work on that show. Because I was the same age as you guys at that time. It just felt like everything I talked to my friends about and everything I wondered about." — Cindy Chupack (06:13)
• First Impressions of SATC’s Impact
  • Watching the baby shower episode at work, Cindy found herself deeply moved:
    "I was sitting there, and I was, like, crying by the end of it. I couldn’t believe how much it spoke to what I thought about and how deep it was to me." — Cindy (06:42)

2. On Writing Iconic Episodes & Using Real Life as Inspiration

• “Chicken Dance” Episode Origins (07:39–13:26)
  • Cindy wrote this classic episode as a freelancer; the story was rooted in personal experience—hosting people at her house who got engaged, mirroring Charlotte’s arc.
  • “Everything… My boyfriend at the time… he had given me the pink toothbrush head, which was big to me… they met, got engaged, we’re getting married, and he’s just my date.” — Cindy (12:29)
• How Close Were Stories to Real Life?
  • Kristin explains that stories were from the writers’ lives, not the actors’, often “once removed.”

3. The Atmosphere and Legacy of SATC

• Lightning in a Bottle (10:02–10:41)
  • “I feel like this is everybody. Lightning in a bottle.” — Cindy
  • Kristin recalls not realizing the import until Season 3 but remembers the “joy of the actual experience.”
• The Rare Female Focus & Industry Changes
  • “It was never could just be about friendship and dating… in the way that [SATC] was.” — Cindy (16:51)
• Impact on Social Discourse
  • Both reflect on how SATC catalyzed open conversations about formerly taboo topics, changing the landscape for women both on- and off-screen.
    • “When we were out at flight, there was still things to be said that people hadn’t said aloud. And now I feel like… maybe even partly because of us.” — Cindy (11:40)

4. Behind the Scenes: Writers, Actors, & Collaboration

• The Unique Set Dynamic (33:36–40:36)
  • The show’s collaborative spirit: writers frequently on set, accessible to actors, unusual in the industry.
  • “We got to really, like, see the process. And also, it was great for us because… if we had a question, we could just go over to you and… check in with you guys, which was amazing.” — Kristin (34:20)
• Comedy Writing & Word Precision
  • The importance of exact dialogue for comedic rhythm and character specificity; Kristin notes the struggle when transitioning to “And Just Like That” for new actors.
  • “It’s very specific, you know, and each character is also very specific from each other. And like, my rhythm of talking… is not the same as Charlotte’s syntax.” — Kristin (39:22)

5. Episode “Evolution” (S2E11) Deep Dive

• Notable Themes and Storylines Explored (47:47–57:27)
  • Egg Freezing & Fertility (Miranda’s Arc):
    • Early mainstream discussion of egg freezing—then a new and often misunderstood concept.
    • “That’s how new egg freezing was… everyone was like, wait, what do you mean?” — Kristin (19:39)
  • Samantha’s Heartbreak:
    • Samantha’s storyline flips expectations with her being the one hurt by an old flame.
    • “There’s a moment where Charlotte is like, Samantha getting her heart broken was more confusing to Charlotte than a kiss from a gay man.” — Cindy (48:08)
  • Charlotte’s “Gay/Straight Chef” Storyline (with Dan Futterman):
    • The humor and confusion of sexuality labels at the time—“metrosexual,” gay/straight binaries—and how the storyline would be written differently today.
    • “At the time it seemed hilarious and forward thinking and now… I’m embarrassed that that was how we talked about it.” — Cindy (52:21)
    • Playful deconstruction, “I’m a pastry chef who lives in Chelsea. If I were gay, I would be gay.” — Dan Futterman’s character, as recalled by Cindy (57:12)
  • Reflection on Cultural Change
    • The writers note that certain elements haven’t aged perfectly, but defend the truth and specificity of the stories for their time.

6. The Emotional Depth of SATC

• Depicting Loss and Fertility Struggles
  • Cindy and Kristin discuss writing and performing the miscarriage and adoption arcs, recognizing only later how well the show captured those emotions, despite not having lived through them personally at the time (20:16–22:29).
  • “Sometimes when you’re writing and, you know, like, something’s going to be a real gut punch, you can feel it in your gut.” — Cindy (22:52)
  • Kristin: “Our show has the ability to have the incredibly serious storylines, but still be able to get out, you know, to come to a place.”

7. The Ongoing Relevance — and “And Just Like That”

• SATC’s Longevity & Cultural Evolution
  • Kristin observes that streaming has brought a new generation to the show: “All these new people discovered it… being on Netflix, right?”
  • “The joy of podcasting… all these people who’ve been our fans forever or new people can hear about what it was like to create it.” — Kristin (24:06)
• Reflecting on “And Just Like That”
  • Candidly naming the gap between fan expectations and the actual messy realities of aging:
    • “Maybe we were a little bit overly ambitious, thinking that our fans… wouldn’t want to see us, like, aging and talking about death and cancer… and then everybody was like, what are they doing?” — Kristin (25:21)

8. Memorable Quotes & Moments

• “I was already in love with this whole process of these people.” — Cindy (14:45)
• “The beauty of Charlotte: I think she was, like, very optimistic… and she was also like, she was going to work hard, she was not going to give up, you know. Gotta love that.” — Kristin (41:54)
• “You can tell any individual story that’s true, and that’s true to you…” — Cindy (54:29)
• “As someone who’s been confused myself and married someone who realized he was gay after being married, I feel uniquely qualified to say that. It’s confusing sometimes.” — Cindy (56:39)

Timestamps for Key Segments

• [03:19] – Cindy joins SATC, origins
• [06:40] – Emotional power of early episodes, “Baby Shower” moment
• [07:39] – “Chicken Dance” and real-life inspiration
• [11:34] – SATC as cultural trailblazer, HBO’s freedom, writing taboos
• [12:07] – Freelance process and spec writing for SATC
• [19:01] – Breaking down “Evolution”: egg freezing, social commentary
• [20:45] – Authenticity and emotional range in fertility storylines
• [33:36] – Unique, collaborative on-set writing culture
• [39:22] – The challenge of maintaining comedy’s rhythm
• [47:47] – Episode “Evolution” analysis: storylines, guest stars, themes
• [52:21] – “Gay or straight men” storyline, what’s aged and what hasn’t
• [56:39] – Personal note on sexuality and confusion, Cindy’s experience

Tone & Style Notes

• Lighthearted, honest, conversational—Kristin and Cindy both balance reverence for their work with candid acknowledgment of past norms and their evolution.
• Nuanced and self-reflective—willing to critique their own work while expressing lasting pride and affection for the entire creative journey.

For Listeners: Why This Episode Stands Out

• Offers a rare, inside look at how the personal and collective lives of writers directly shaped the SATC universe.
• Illuminates how much has changed in both television and cultural conversations around relationships, sexuality, and women’s lives.
• Brims with gratitude, self-effacing anecdotes, and genuine affection among creators—the “lightning in a bottle” that made SATC era-defining.
• Navigates the timeless vs. time-bound aspects of storytelling, and the ongoing ripple effect of pioneering female-driven television.

Recommended for:

Fans of SATC and "And Just Like That," aspiring writers, media/TV history buffs, and anyone interested in how truthful, funny storytelling finds its way into pop culture and hearts worldwide.