Are You A Charlotte? | S2 E10 – “Charlotte’s Wylie Coyote” with Brian Van Holt

Episode Theme:
Kristin Davis and guest Brian Van Holt revisit Sex and the City S2E10, “The Caste System,” exploring themes of class, dating, gender dynamics, and memorable behind-the-scenes moments—particularly Charlotte’s ill-fated romance with Van Holt’s Wiley Ford.

1. Setting the Scene: Revisiting “The Caste System”

• Opening reflections on what made Brian Van Holt’s Wiley Ford such a memorable foil for Charlotte York.
• Praise for director Alison Anders and writer Darren Starr—both celebrated for the authenticity and energy they brought to the episode.
• The central episode theme: relationships across class divides, and the social pressures that surface around money, status, and love in New York City.

“What worked so incredibly well with a part of Wiley is that you knew the character you were playing, but you weren’t that. So there’s a sweetness underneath where you totally understand why Charlotte is so excited and so into you. … But you, to me, that's a great combination of when you know, the milieu, but you're not actually that.”
— Kristin Davis (03:15)

2. Key Episode & Character Moments

A. Carrie & Big: The Complexity of Saying ‘I Love You’

• Carrie’s internal debate about telling Big “I love you,” and the vulnerability and withholding that characterizes Big.
  • Kristin admits that, looking back, Big’s behavior reads more toxic than she realized at the time.
  • Social media has reassessed his actions with a more critical eye.

“Sometimes I just hate him passionately. … It was such a thing we all went through — that withholding guy. … But at least there’s conversation around it and deeper understanding.”
— Kristin Davis (07:03)

• Memorable ‘Judith Leiber purse’ subplot: Gift as a symbol; the running joke of the odd-looking designer purse and its recurring appearances in the series and movies.

  • [08:22] – “This is when Big gets Carrie the supposedly semi-ugly Judith Leiber. … Judith Leiber was such a part of our whole lives that at one point HBO gave us Judith Leibers as a wrap gift … it ends up being a huge plot point in the movie…” (Kristin)

• Carrie’s night out:

  • Carrie meets a charming waiter/performance artist (with a mysterious ‘flower magician’ act), leading to a standout moment of drunken, joyful vulnerability from Sarah Jessica Parker’s character, including the impromptu singing of “Jeremiah Was a Bullfrog.”
  • [10:08] “Out of order here: it is one of my all-time favorite Sarah Jessica moments…” (Kristin)

B. Miranda & Steve: Money, Class, and Gender Dynamics

• The couple’s central tension: the awkwardness and pain of dating across a financial divide.
  • Steve balks at Miranda’s attempt to buy him an expensive suit for her law firm’s party.
  • The heartbreak of Miranda being “punished” for her success.

“Because it’s true … her line was, ‘I’m being punished for being successful.’ For a woman, that’s pretty profound. And there’s a lot of truth to that.”
— Brian Van Holt (16:55)

• Both hosts empathize from personal experience with the embarrassment and obstacles caused by status or income differences.
• Discussion broadens to social class in America and how Sex and the City was prescient in addressing these themes.

“You all are pretending that we live in a classless society … you can’t think about being with a guy whose income is based on tips, which is, like, so practical and weird. Like, I would never say that in life … but it is true, still today, that the class situation in America is complex and not worked out.”
— Kristin Davis (18:28)

C. Samantha: Class and Control

• Samantha becomes involved with a wealthy man whose servant mistreats her, highlighting dynamics of power and class even among the ultra-rich.
  • The servant’s cruel double standards become a surprising and memorable plot device.

3. Behind the Scenes: Chemistry, Awkwardness & Iconic Lines

A. Charlotte & Wiley Ford: From Cute to Unsettling

• Art gallery date & Limousine makeout:

  • Both actors recall feeling a real (but professional!) crush—an undercurrent fueling the on-screen energy.
  • [28:17] “There was, to be honest, a crush. … I’m a Charlotte, for sure.” (Brian)

• That jaw-dropping bar scene:

  • Wiley’s crude proposition to Charlotte is called “the hall of fame line and moment of my entire career. I still get recognized for it.”
  • [41:40] “Charlene, I want you to go to the bathroom, stick your finger in your hoo-ha, come back, and let me smell it.”
  • Both laugh about Brian’s nerves performing the shocking line, and how audiences (including construction workers shouting at Brian in public) have kept the memory alive for decades.

“That was the hall of fame line and moment of my entire career. And I still hear from it. I still get recognized from it — no way — to this day.”
— Brian Van Holt (41:02)

• Kristin describes precisely how Charlotte navigates the moment: “There is a moment there where I’m like, please, God, and I didn’t remember … I think I’m contemplating how to politely get out; Charlotte always wants to be polite. But also, you have pushed me too far …” (44:52)

4. Reflections on the Show’s Social Impact

• Ongoing cultural conversation about SATC’s effect on gender politics, women’s voices, and relationship expectations.
  • Brian notes that some men criticized the show for “ruining” dating; Kristin pushes back on the double standard.
  • [13:19] “Some dudes would say, ‘You ruined my dating life, man.’ I was like, ‘No, you ruined your dating life, dude!’” (Brian)
• Appreciation for the bold, boundary-pushing writing, and how themes around class, gender, and power remain deeply relevant.

5. Standout Quotes and Moments by Timestamp

• [03:15] Kristin on Brian’s character: “...there’s a sweetness underneath… great combination…”
• [07:03] Kristin on Big: “Sometimes I just hate him passionately.”
• [08:33] Judith Leiber purse discussion.
• [10:08] Kristin’s favorite SJP moment: “Out of order here: it is one of my all-time favorite Sarah Jessica moments…”
• [14:25] Miranda’s heartbreak: “Her line was, ‘I’m being punished for being successful.’”
• [16:55] Social class relevance: “It is still, it’s interesting that it’s a real thing … almost 30 years [later].” (Brian)
• [28:17] Brian admits being a “Charlotte.”
• [41:02] Hall of fame cringe line revelation.
• [49:17] “Did you smell it?” — The line’s lasting legacy.
• [46:11] On Big finally saying ‘I love you.’
• [47:02] Carrie’s therapy arc and Bon Jovi cameo (upcoming).

6. Closing Thoughts: Why “The Caste System” Still Resonates

• Both hosts reflect on how much ground the episode covers in just 22 minutes.
• Pride in being part of a show unafraid to mix “heart, humor, and some optimism” with social critique.
• Brian and Kristin’s mutual admiration: for the writing, each other’s performances, and the way SATC continues to spur conversations.

Summary Table of Main Segments

| Timestamp | Section/Highlight | |---------------|--------------------------------------------------------------------| | 03:15–05:34 | Working with Alison Anders & Show’s Emotional Tone | | 07:01–09:13 | Carrie & Big dynamic; Judith Leiber purse subplot | | 10:08–12:03 | Carrie’s performance artist date; SJP singing scene | | 13:09–17:11 | Miranda/Steve storyline; money, class, and “punishment” for success| | 18:28–19:52 | Charlotte’s comments on class; intersection with money and love | | 26:04–28:17 | Charlotte & Wiley: Art gallery, limo make-out, romance dynamic | | 40:01–41:55 | Wiley’s crass line; its ongoing impact; behind-the-scenes | | 46:06–47:11 | Carrie & Big’s ‘I love you’ resolution | | 49:14–49:54 | Brian on being recognized for the notorious line |

Final Word

This episode is a rich, funny, and bittersweet deep dive into the legacy of Sex and the City’s social commentary, highlighting why the show endures as both a pop cultural touchstone and a protest against the boundaries of its time. The chemistry between Kristin Davis and Brian Van Holt is palpable, refreshing, and filled with delightful honesty—making for a must-listen for fans and first-timers alike.