Every Outfit Podcast – Episode 253: On Sex and the City: The Perfect Present

Release Date: December 26, 2025
Hosts: Chelsea Fairless & Lauren Garroni

Episode Overview

In this episode, Chelsea and Lauren embark on their monthly Sex and the City rewatch—this time tackling “The Perfect Present” (Season 6, Episode 5). Although the episode is set in summer, the hosts confess they’re scraping the barrel for winter or Christmas-adjacent Sex and the City episodes for their end-of-year theme. Anchored by Jennifer Coolidge’s iconic guest spot and Mr. Big’s “green screen” appearances, the hosts dissect the episode’s “baggage” metaphors, fawn over fashion, and deliver their signature snark about characters, writing, and 2000s pop culture.

Key Discussion Points & Insights

1. Why "The Perfect Present"?

• The hosts admit they’ve run out of winter/holiday SATC episodes and chose this for Charlotte’s summer Christmas tree and Jennifer Coolidge’s perfect cameo.
  • “We are truly grasping at straws at this point to find a winter and or Christmas themed episode related to Sex and the City.” (Lauren, 02:41)
• Rewatch reveals Jennifer Coolidge as the sole true highlight.

2. Carrie & Berger: Relationship and Apartment Tour

• Dissecting the opening narration — Carrie’s “three important firsts” (sex, good sex, seeing a new guy's apartment).
  • “Okay, is she talking about these are the first in a single relationship, or… over the scope of a single gal’s life?” (Chelsea, 03:50)
• Carrie analyzing Berger’s very yuppie apartment (pristine exposed brick, custom tile) and deducing he must own it.
• Ex-girlfriends turned “decorators” — Berger’s apartment was done by Lauren. “Decorator” becomes code for “ex.”
• The infamous Sharper Image sound machine (“Amazonian Rainforest”) and ex’s therapist…
  • “I found this to be strange because wasn’t it Berger that was initially triggered and traumatized when Carrie opened the X File and dumped on him about her ex?” (Chelsea, 08:35)

3. Jennifer Coolidge’s Purse Party & The ‘Baggage’ Metaphor

• Jennifer Coolidge nails the role as a glam “post-breakdown” divorcee: “The good news is I’m off the Zoloft, I lost 10 pounds, and after that asshole dumped me, I realized I have this amazing gift for designing bags.” (Coolidge as guest, 11:14)
• Bags as literal and figurative baggage.
  • “The idea of her having a vanity bag line is to introduce the other theme of this episode, which is baggage in all of its forms.” (Chelsea, 12:27)
• Miranda’s meta callout: in 2003, failed “it” girls launched handbag lines; in 2025, the fallback is a podcast.
  • “The fallback career is having a podcast—that is the vanity project of 2025.” (Lauren, 12:59)
• Samantha/Sex and the City “butterfly effect”: Her stairwell hook-up with Smith Jarrett only happens because of this party.
• Comparison to Monica Lewinsky’s real-life 2000s handbag line.
  • “I do kind of have to shame her for these handbags though.” (Chelsea, 17:46)

4. The Past—Present—Future Relationship Loop (“I Couldn’t Help But Wonder”)

• Carrie’s inner monologue gets extra wordy (“can you get to a future if your past is present?”).
  • “She uses the word past and future like 50 times.” (Chelsea, 29:38)
• Host analysis: Is Carrie’s “Big” baggage always sabotaging her relationships?
  • “Wouldn’t Carrie know all about this, seeing that the fact that she could not get over Big and still had Big in her life derailed a good part of her relationship with Aiden?” (Lauren, 27:50)
• The ambiguous role of exes—Berger’s trauma with “Lauren” unearthed; Carrie never owns up to her own cheater history with Aiden.

5. Side Stories: Charlotte’s Christmas Tree & Conversion to Judaism

• Charlotte negotiating with Rabbi Minch to keep Christmas traditions while converting:
  • “Can I keep the Christmas tree? … but what about caroling?”
• Charlotte’s “wooing” of the rabbi, and the “minch who stole Christmas.”
• The waspiness of Charlotte’s background clashing with attempts at religious sincerity; hosts question Harry’s supposed religiosity and authenticity.
  • “Harry isn’t religious enough to necessitate Charlotte converting… and he eats pork.” (Chelsea, 56:43)

6. Miranda, Steve & the 'Condoms in the Diaper Bag' Plot

• Miranda unravels after finding Steve’s condoms in Brady’s diaper bag, learning he has a new girlfriend (Debbie).
• “Miranda basically described the plot of Antichrist when she’s like, you could be fucking in one room while our baby is suffocating.” (Chelsea, 41:05)
• Hosts joke about how SATC plot points echo Lars von Trier and the logic gaps (like why Steve would store condoms in the diaper bag).

7. Samantha, Smith (Jerry), and the Value of “Boy Toys”

• Samantha tries to compensate Smith for losing his cater waiter gig by handing him $300 cash (from an MCM wallet, naturally), which, to her surprise, offends him.
  • “Not the same at all.” (Carrie to Samantha, 39:53)
• Reveal of Smith’s real name (“Jerry”) and his actor aspirations (“there goes my hard on”—Samantha, 48:16).
• The hosts debate: Is paying someone you had sex with for lost wages sex work-adjacent? Would you buy new bedding for a hookup?
• A confusing roleplay scene (“waitress” vs. French maid vs. customer—logic holes abound).

8. Fashion & Iconic Looks

• Samantha’s “subversive” color mixes: hot pink pea coat, yellow camisole, red hip huggers; later, chartreuse lingerie, “slutty French maid” garb.
  • “Chartreuse—a very difficult color to pull off. Looks great on Kim Cattrall.” (Lauren, 31:42)
• Carrie’s questionable pants-and-dress combo for the Coolidge party, with added critique of the outfit’s challenging length.
  • “It’s a lot.” (Chelsea, 55:44)

9. Big’s Green Screen Napa Scene & The Lore of Carrie/Big

• Notorious “fake hot tub” scene with Big, and sexual-memory phone call (“Remember when I found you in your closet…?”).
  • “10 out of 10. Great phone sex. Also, Chris Noth has a great voice for phone sex.” (Lauren, 24:06)
• Debate over whether reliving hot sex memories via phone counts as “cheating.”
• Outlandish speculation: “Would this fictional character (Big) have been friends with Jeffrey Epstein?” (satirical, 52:17)

10. Episode Wrap-Up: MVPs, Best Lines, Hottest Takes

• Both hosts agree Jennifer Coolidge is episode MVP.
  • “She is one of the great comedic actresses of our time and how much she does with such little time.” (Lauren, 12:01)
• Hottest take: Charlotte shouldn’t have to convert for a non-religious Harry; justice for Lauren (Berger’s ex).
• Best line (unanimous favorite; Coolidge’s storyline): “She tried to kill herself. She took 6 Advil on an empty stomach.” (Lauren, paraphrased, 11:08)
• Who are the hosts? Lauren: Jennifer Coolidge. Chelsea: Miranda.
• Who gets voted off the island? Both: Burger.
• Manolo rankings: 6.5 out of 10, one extra “for Jennifer Coolidge.”

Memorable Quotes & Timestamps

• On Jennifer Coolidge’s character:
  • “The good news is I’m off the Zoloft, I lost 10 pounds, and after that asshole dumped me, I realized I have this amazing gift for designing bags.” (Coolidge as Guest, 11:14)
• On fallback careers:
  • “Unfortunately, the fallback career is having a podcast—that is the vanity project of 2025.” (Lauren, 12:59)
• On Miranda’s meltdown:
  • “Like, when your penis is in some girl’s vagina and you’re having an orgasm while our baby is quietly suffocating in the other room.” (Miranda, 40:32)
• Phone sex or not?:
  • “10 out of 10. Great phone sex. Also, Chris Noth has a great voice for phone sex.” (Lauren, 24:06)
  • “Did you come on the phone with Mr. Big or not, bitch?” (Chelsea, 24:42)
• Best line recap:
  • “She tried to kill herself. She took 6 Advil on an empty stomach.” (Referenced at 09:20 and repeated in wrap-up, 55:46)
• On giving money post-hookup:
  • “I once accidentally destroyed a guy’s set of bedding because I brought the wrong lube…and so I bought him a new set of bedding.” (Lauren, 34:05)
• On Charlotte’s conversion:
  • “Harry isn’t religious enough to necessitate Charlotte converting… and he eats pork.” (Chelsea, 56:43)

Important Segment Timestamps

• [03:16] Big and Jennifer Coolidge set up as the episode’s main highlights.
• [11:08] Iconic Jennifer Coolidge purse-party entrance and “Advils on an empty stomach” line.
• [13:07] Podcasting as the ultimate vanity project for rich women.
• [18:00] Monica Lewinsky’s real-life handbag line brought in for meta comparison.
• [23:27] Mr. Big’s phone sex flashback (with audio playback).
• [26:38] Discovery of condoms in the diaper bag, leading to Miranda’s freakout.
• [29:31] Dissection of Carrie’s “I couldn’t help but wonder”—can we escape our past?
• [31:26] Samantha’s chartreuse lingerie/Smith Jarrett subplot.
• [35:43] Berger’s “fuck you” double middle finger at ex Lauren’s voicemail.
• [41:05] Miranda’s fight with Steve likened to Antichrist.
• [52:02] Jokes about “The Big-Epstein Connection” in fictional SATC universe.
• [54:00] Berger’s sarcastic “Pulitzer Prize” mystery.
• [55:46] Hosts pick “She took 6 Advil on an empty stomach” as best line.
• [56:43] Summary of the hottest takes, including Charlotte’s unnecessary conversion.

Final Judgments

MVP: Jennifer Coolidge and, in a surprise, Smith Jerrett for emotional intelligence.
Best Dressed: Samantha for pushing color boundaries and memorable looks.
Best Line: “She tried to kill herself. She took 6 Advil on an empty stomach.”
Episode Rating: 6.5 out of 10 Manolos (mostly for Coolidge).
Biggest Triggers: Lauren: Samantha’s MCM wallet. Chelsea: Berger’s weird apartment arrangement.
Who They Are: Lauren identifies with Jennifer Coolidge (unhinged but funny with a glue gun); Chelsea with Miranda (“unhinged reactions”).
Who Gets Voted Off: Burger.
Hottest Take: Charlotte shouldn’t have had to convert; justice for Lauren (Berger’s ex)—sometimes cheating is justified.

Summary for New Listeners

If you missed the episode, you’d know that this Every Outfit installment is a classic: Chelsea and Lauren mix hilarious fashion dissection with sharp cultural critique, taking a so-so SATC rewatch and mining it for gold—mostly through Jennifer Coolidge’s brief but brilliant turn, debate on podcasting as the millennial “handbag line,” incisive takes on relationships and emotional baggage, and a parade of sharp one-liners (both from the show and the hosts). The only thing more biting than their burger commentary is their nostalgia-drenched fashion roll call.