Every Outfit Podcast: Episode 266

Title: Three’s a Crowd
Hosts: Chelsea Fairless & Lauren Garrone
Date: March 27, 2026
Main Theme:
A sharp, playful rewatch and deep-dive into the Season 1 Sex and the City episode “Three’s a Crowd”—the so-called “threesome episode”. Chelsea and Lauren blend their signature “bitchy” fashion/pop-culture commentary with a broader cultural analysis, including a spirited discussion of recent high-profile polyamory discourse. They also dish about beauty conventions, mother-daughter dynamics, and, as always, fashion and friendship.

1. Episode Overview

Theme:
The nature of threesomes—on Sex and the City, in late 90s New York society, and in today’s era of polyamory. The episode explores the social, gender, and psychological politics around threesomes, critiques how they’re depicted (especially through a male-centered lens), and connects the show’s dated view to current headlines, especially involving writer Lindy West’s real-life throuple and public response to “poly under duress.”

2. Key Discussion Points & Insights

Opening Banter & Personal Updates

• Hosts catch up with each other:
  • Lauren shares motherhood struggles (“my life has been reduced to a teething infant.” — [02:09])
  • Chelsea details her spring cleaning, driven by attending Sephora’s beauty convention (“it was basically adult trick-or-treating for Fenty body butter” — [04:20]).
• Both jokingly reflect on how their sweet, gentle mothers produced two “bitches,” and dream of doing a future episode with them [02:49].

Why Rewatch “Three’s A Crowd”?

• Chosen because it’s a standout Season 1 episode and written/directed by “OG Sex and the City queens” Jenny Bix and Nicole Holofcener [01:47].

Sex and the City: “Three’s a Crowd” Breakdown

Charlotte’s Threesome Plot

• Charlotte dates Jack, a philanthropist architect, after several charity encounters (“a night of a thousand Tourette’s”—[11:01]).
• He asks Charlotte her fantasies—she naively replies, “running a gallery, maybe a cottage in Maine.” Jack wants a threesome, specifically with another woman [11:51, 12:07].
• The hosts dissect the gender politics: Is it always the man who wants the threesome? Why is “the devil’s three-way” (two men, one woman) never considered? (Chelsea: “In this episode...the devil's threesome doesn’t exist. A threesome is two women and one man.” — [13:01])
• Charlotte confesses her fantasy is “sex in her parents' bed,” which is met with skeptical amusement [13:12].
• The hosts note the early-series “down-market diner” scene where the friends debate the wisdom and mechanics of threesomes (lighting, bad ketchup bottle, etc.) [13:38–14:16].
• Samantha’s advice: Only be the “guest star” in someone else’s threesome—don’t get involved with your own couple [14:56].
• Discussion of jealousy, relationship fragility, risks, and the infamous “no friends, just a random” rule [15:09–15:50].

Miranda’s Therapy & Outcast Arc

• Miranda, feeling rejected that no one wants to include her in a hypothetical threesome (“It’s like picking teams for dodgeball all over again. No one wants to have a threesome with Miranda, even hypothetically...” — [16:25]), processes feelings in therapy.
• The therapist never questions Miranda’s sexuality despite her “full-blown dyke” Season 1 wardrobe (K.D. Lang jokes abound) [37:00–37:50].
• Miranda later answers a personal ad for a threesome to boost self-esteem, but ghosts the couple after being found attractive [55:44–56:19].

Samantha’s Married Man

• Samantha sleeps with a married man, delighting in the no-strings-attached dynamic. “Thank god. Who needs the trouble? No muss, no fuss.” — [44:51]
• The man’s wife later proposes including Samantha in a threesome to save the marriage: “I’m willing to join you in the bedroom.” (Samantha: “Samantha was a guest star. Series regular was not in her contract.” — [51:29])
• The hosts compare this to modern polyamory drama and poke fun at the deeply transactional, awkward nature of this 90s “solution” [51:16–51:29].

Carrie’s Jealousy and Big’s Revelation

• Carrie’s voiceovers and analogies (“Fat, low fat, non fat... Mo, Larry, Curly. Maybe we were never meant to do it with only one other person.” — [18:10]) are criticized for their forced metaphors.
• Carrie discovers Big was married—thanks to a confession about a past threesome with his ex-wife [42:58].
• Stalker subplot: Carrie engineers a fake publishing pitch meeting to meet Big’s ex-wife. She forms an odd, faux-friendship under false pretenses [48:38–53:19].
• This behavior is called out as “fully psychotic... diabolical...” [53:19].
• Carrie and Big ultimately confront the truth directly (“This is truly an outlier for Sex and the City dialogue. Because Carrie and Big have never been this honest with each other.” —[57:41]).

Man on the Street Sequence – Personal Ads

• Highly memorable “Village Voice” personal ads montage, with the hosts reading out the best ones:
  • “Wall street honcho seeks two horny gal pals for East Hampton fuckfest at my summer home. No fatties, please.” — [40:23]
  • “X Files fanatic twosome seeks Scully lookalike for abduction fantasy. Me gorgeous with big boobs. You a couple with class. Let’s experience everything the city has to offer. I’m into museums, blowjobs, theater and golden showers.” — [40:43]
• Chelsea: “This is truly the best of all the man-on-the-street sequences, hands down.” — [41:23]

Commentary on Threesomes, Polyamory, and Gender

• The hosts draw strong parallels between the episode’s male-centric take on threesomes and the real-world story of writer Lindy West and the “poly under duress” (PUD) phenomenon [22:51–24:20].
• They discuss West’s recent memoir revealing her throuple, the backlash, Dan Savage’s commentary, criticism mainly targeting West’s husband, and speculation regarding financial imbalance and emotional labor [21:06–29:51].
• Lauren: “It is a very male-centric idea of what a threesome is... brought up by the man, the woman feels pressured, under duress...” — [24:21]
• Dismantle the idea that polyamory always fails while pointing out the dysfunction in many monogamous relationships [31:34].

3. Notable Quotes & Memorable Moments (with Timestamps)

• On Male Fantasy:
  Chelsea: “If any man asks you [about your fantasies], just be like, spit it out already. What do you want from me? What sick, nasty shit do you want me to do?” — [12:31]
• On Samantha’s Threesome Advice:
  Samantha (via Lauren): “The only role to play in a threesome is being the guest star.” — [14:56]
• Miranda’s Therapy Self-Deprecation:
  Lauren: “She says...I guess a dream of her own...in a sandbox with Charlotte, Sam and Carrie and they won’t play with me.” — [37:11]
• Best “Man on the Street” Ad:
  “You a couple with class. Let’s experience everything the city has to offer. I’m into museums, blowjobs, theater and golden showers.” — [40:43]
• On Polyamory & Lindy West:
  Lauren: “People are calling her a PUD, which is Dan Savage’s very clever term—an acronym for Poly Under Duress.” — [23:00]
  Chelsea: “People always get mad at poly people...but a lot of people are in deeply dysfunctional monogamous relationships.” — [31:34]
• Carrie’s Behavioral Red Flag:
  Chelsea: “This behavior from Carrie is fully psychotic. One of the craziest things she ever does...” — [53:19]
• On the Absence of Actual Threesomes:
  Chelsea: “Someone should have had a threesome in this episode.” — [64:24]
• On 90s Fashion Relics:
  Chelsea: “That is the fashion highlight for sure. But it’s better as a group look than as individual outfits.” — [62:16]
• On Liza Minnelli’s SATC2 Cameo:
  “She opens Sex and the City 2 and then the movie only gets crazier from there.” – Lauren [06:28]
• Dirty Diner Details:
  Chelsea: “The ketchup bottle on the table has seen better days.” — [14:06]

4. Timestamps for Important Segments

• Sex and the City Ep Recap Begins: — [10:09]
• Charlotte’s Plotline/Threesome Discussion: — [11:00–16:01]
• Miranda’s Therapy Sessions: — [37:00, 37:57]
• Carrie’s Fake Publisher Meeting / Barbara subplot: — [48:38–53:19]
• Man on the Street Personal Ads: — [40:01–41:41]
• Lindy West/Polyamory Discussion: — [21:06–31:13]
• Samantha’s Married Man Threesome Call/TikTok sound: — [50:02–51:16]
• Episode Reviews: Manolos & MVPs: — [60:52–63:16]

5. Fashion, Sex, and Character Polls

• Fashion:
  “Not a lot of fashion happening in this episode...but the Charlotte and Carrie walk and talk is the highlight. It did remind me of us on tour trying to coordinate our outfits.” — Lauren [61:21, 61:41]
• MVP:
  Lauren: “Barbara. Comes off the best in this episode.” — [62:24] Chelsea: “Maybe the girl from New Jersey [from the personal ads montage]. I love her.” — [62:16]
• Best Line:
  Lauren: “That was Charlotte. Just when you think she’s a Park Avenue Pollyanna, she’d say something so right on you’d think she was the Dalai Lama.” — [63:13]
• Biggest Trigger:
  Chelsea: “The nasty ketchup bottle at the diner.” — [64:11] Lauren: “The guy that’s trying to get Charlotte to have a threesome. I don’t think he’s hot enough...” — [63:50]

6. Closing Reflections & Tone

• Language & Tone:
  Sarcastic, affectionate, confessional, and loaded with contemporary culture references. The hosts are quick-witted and intersperse inside jokes, self-deprecating humor, and genuine cultural critique.
• Final Evaluation:
  “No one even has a threesome in this ‘threesome episode’.”
  “I wonder how chill her husband would be if she was like, ‘Great, I have a boyfriend. Let’s have a threesome with my boyfriend.’” — [29:51]
  “It would have been kind of transgressive if Carrie engineered a threesome with Big and his ex-wife.” — [64:43] Manolo tally: Lauren gives it 8, Chelsea 7, citing confusing dream logic and weak fashion [60:54–61:15].

7. Summary

A vintage “Sex and the City” rewatch becomes a springboard for the hosts’ classic banter, exploring the shifting boundaries of love, friendship, and sexual experimentation—on-screen and off. The hosts criticize the male-centric lens of 90s “threesome” fantasy, contextualize modern conversations about polyamory, and (of course) reference fashion and friendship along the way. All delivered in the sharp, funny, sometimes bitchy, always honest voice that “Every Outfit” fans love.

Perfect For: Longtime SATC fans, pop-culture obsessives, and anyone fascinated by the messy, hilarious intersections of sex, power, and female friendship.

Listen for:

• The “Mo, Larry, and Curly” rant [18:10]
• Chelsea’s take on Carrie’s “psychotic” stunt [53:19]
• “Village Voice” personals montage [40:01–41:41]
• Polyamory, “PUD,” and Lindy West deep-dive [21:06–31:13]
• That ketchup bottle! [14:06, 64:11]