Trash Tuesday w/ Esther Povitsky & Khalyla Kuhn

Episode: Ivy Wolk Exposes Taylor Swift (Aired September 9, 2025)

Special Guest: Ivy Wolk

Overview: Main Theme & Purpose

In this lively episode, comedians Esther Povitsky ("Jules"), Khalyla Kuhn, and producer Jaime Garcia are joined by actress and comic Ivy Wolk, known for her roles in "English Teacher" and "Anora." The core focus is on dissecting contemporary pop icons—most notably, Taylor Swift, Brittany Spears, Madonna, and others—through raw, unfiltered conversation. The episode ranges widely, also touching dating stories, personal strategies for trapping men, celebrity crushes, sexual politics, and how pop culture reflects (and distorts) the female experience under fame and scrutiny. With Ivy’s sharp takes and unvarnished humor, the group explores the intersections of pop stardom, gender, fandom, and personal trauma—a true pop culture summit, “Trash Tuesday” style.

Key Discussion Points & Insights

1. Ivy Wolk’s Dating Life & “Trapping” Men

Timestamp: 01:27 – 06:21

• Ivy shares her experience dating a much older, promiscuous man (17 years her senior), describing her approach as “trapping” and her mixed feelings about the power dynamics.

  • “I'm working on trapping a promiscuous older man… we're five months in and you're already like, we should spice things up. It's ridiculous.” — Ivy (01:27)

• Ivy's attitude is simultaneously self-deprecating and masochistic about love:

  • “I like being really tested and having my ass whooped by life and love.” — Ivy (05:41)

• Discussion turns to ultimatums, boundary-setting, and women’s strategies in securing relationships, with Esther (Jules) admitting her own use of ultimatums in the past.

  • “Ultimatums are tricky… if we're not living together by this time, you don't call me until you're asking me to move in.” — Jules (04:52)

2. Ivy’s Perspective on Pop Stardom: “Exposing” Taylor Swift

Timestamp: 11:31 – 15:13

• Ivy launches into a viral, pointed take on Taylor Swift, characterizing her as a “corny theater camp alcoholic” whose stardom is more about narrative lore than musical distinction.
  • “Taylor Swift treated the situation … as so catastrophic because she’s, like, a corny theater camp alcoholic. … Like, if you listen to the music, this is a woman who's consistently sad… probably is like a varsity functioning anorexic.” — Ivy (11:31)
• Ivy claims most famous people are stunted at the age they became famous, and Taylor is “microdosing high school through her relationships in adulthood” (13:22).
• Taylor’s appeal to fans is seen as rooted in controlled lore-building and managing the relationship with fans:
  • “The lore is rich because she's been famous for so long and she's been so good at sort of keeping her fans at a distance, but also, like, letting them in on so much.” — Ivy (14:11)
• Critique of Taylor’s musicality and stage presence:
  • “You take your earbuds in and listen to the music… sonically the same, lyrically the same… She's just not interesting… not a good enough stage performer to get away with the fame.” — Ivy (14:33)

3. Contrasting Pop Icons: Madonna, Britney, & The Meta-Narrative

Timestamp: 15:13 – 20:39

• Ivy’s “North Stars” are Madonna and Britney Spears. Madonna is credited for being both artist and performance art icon:
  • “Madonna is really the apex for me because she was as much a pop star as she was a performance artist... she synthesized so many weird subcultural things and then made them big and popular.” — Ivy (15:26)
• Britney’s legacy is dissected as being one where the narrative was “not controlled by her,” unlike Taylor Swift.
• Insightful comparison: Taylor is the master of her narrative, Britney is the subject of others’ narratives—fans become “QAnon for white chicks” analyzing her every movement (17:20).

4. Gender, Dating, and Sexual Politics

Timestamp: 20:39 – 31:50

• Conversation on relationship “strategies” for hooking up with celebrities (e.g., Harry Styles), shadow networking, and staged serendipity.
  • “You have to employ some like, shadow strategy… being near [them], looking good, gaming the system…” — Ivy (21:57)
• Sharp takes on class, background, and their impacts on stardom—comparing Britney’s rough Louisiana upbringing to Taylor’s upper-middle-class roots (23:30).
• Discussion of female child stars (Britney, Amanda Bynes, Lindsay Lohan) and the psychological toll of early fame, with an emphasis on “cultural reappraisal” only happening after tragedy or “a good facelift.” (24:51)
  • “It's the fact that she looks young again, and that's when we remember her being clean and good to us.” — Ivy (25:26)

5. Celebrity Crushes & Power Dynamics

Timestamp: 27:28 – 31:50

• Ivy candidly shares that her longstanding “attainable” celebrity crush is Louis CK, humorously describing how she could manipulate him:
  • “I would just probably like make eye contact with him and be like, I know that you're like a sick motherfucker… you do nasty things so you can hurt your own feelings.” — Ivy (28:53)
• Commentary on pursuing the unattainable in personal vs. celebrity life, with Ivy preferring “achievable” targets due to struggles in real-life dating.

6. Subway Takes, “Hot Takes” on Modern Life & Gender

Timestamp: 36:05 – 48:34

• Fun rapid-fire round of "Subway Takes" highlighting Ivy's wit: public restrooms (“agree”), Happy Birthday songs in restaurants (“do it, grin and bear it”)— briskly sifting through cultural pet peeves.
• Spirited debate about tipping and the culture shift (“always tip, because I know what it's like to have tips be concealed”—Ivy, 42:31).
• Analysis of NYC dating culture, “internalized misogyny” discourse, and the kind of women men choose to date:
  • “Most male comics I know date girls who are quiet and in grad school… never much to show for themselves, want a very subservient woman… it’s all optics.” — Ivy (44:53)
• Group agrees that men do most things “for each other,” with mirror insight that women dress for the approval of other women, not men (46:56).

7. Lingerie, Sexual “Realness,” and Style Choices

Timestamp: 48:37 – 56:13

• Ivy, Jaime, and Jules riff on lingerie, “real” sex, and how men’s preferences often miss the mark:
  • “What sex with a woman is… my pubes have a clump of discharge… we’re volleying yeast. … That’s what it is, not Love Shack Fancy lint.” — Ivy (48:40)
• Debate about “trying” to be sexy, men not noticing effort, and the role of gesture versus outcome.
• Iconic moment: Ivy’s description of “sexing up an outfit”:
  • “My idea of sexy is so unbelievably skewed… I used to dress like Turtle from Entourage…” — Ivy (52:22)
  • “Can't you just appreciate the sheer gesture of it?” — Ivy (53:10)

8. Iconic Messiness: Morrissey, Courtney Love, & Female Cultural Villainy

Timestamp: 56:28 – 61:03

• Ivy’s deep love for flawed icons like Morrissey and Courtney Love, and the cultural mechanisms by which women are “villainized”—the apex being accused of killing a man (Courtney/Kurt; Asia Argento/Bourdain).
• Ivy on Courtney Love:
  • “She’s so important... just had beef with absolutely everyone. Still beefing with Madonna.” — Ivy (58:19)
  • “That’s kind of like the apex of allegations you can get as a woman when people hate you culturally—‘she killed a man.’” — Ivy (60:01)

9. Trauma, Fame, and Female Pop Stars (Ariana Grande, Lady Gaga)

Timestamp: 61:03 – 64:48

• Discussion of Ariana Grande’s unparalleled trauma (Manchester bombing), and the degree to which fame distorts identity timelines.
• Ivy draws the distinction: Gaga is an "adult" pop star; Taylor is still “microdosing high school,” and Ariana shapeshifts with her relationships.
  • “This pop shit is serious to her. … I think Gaga, especially now… just posted up in her mansion with her little bit fat, rich husband, doing pharma ads. That’s grown lady shit.” — Ivy (63:20)

10. Queerness, “Reactive Lesbians,” & Final Takes

Timestamp: 65:07 – End

• Ivy coins “reactive lesbian” (used for Chapel Roan): women who, having been so wronged by men, embrace lesbianism as partial identity or refuge (“It happens, I saw it in my own grandmother”—65:59).
• Endearing closing moment: Ivy reassures a Harry Styles mega-fan (Jules) that sometimes, “if you squint, you can pretend he’s Latino.”

Notable Quotes & Memorable Moments

• On Taylor Swift:
  "Taylor didn’t have a normal high school experience. She’s microdosing high school through her relationships in adulthood." — Ivy (13:22)
• On pop music appeal:
  "With her, I think the appeal is, like, the lore is rich... It’s a weird balance that she walks with that." — Ivy (14:11)
• On Britney vs. Taylor:
  "The thing about Taylor is like, she’s been in control of her meta-narrative… with Britney, that’s so compelling is, it’s [not] controlled by her." — Ivy (18:51)
• On male comics’ dating preferences:
  "Most male comics I know date girls who are quiet and in grad school… never much to show for themselves, want a very subservient woman… it’s all optics." — Ivy (44:53)
• On lingerie and sex “realism”:
  "What sex with a woman is… my pubes have a clump of discharge… we’re volleying yeast. … That’s what it is, not Love Shack Fancy lint." — Ivy (48:40)
• On being a sister:
  "If I had siblings, my siblings would be on TikTok, like: nobody talks about how actually hard it is to have Ivy Wolk as your sister!" — Ivy (40:15)

Timestamps for Important Segments

• 01:27 — Ivy on “trapping” an older, promiscuous man
• 04:52 — Esther on issuing ultimatums in relationships
• 05:41 — Ivy’s masochistic love philosophy
• 11:31 — Ivy’s Taylor Swift takedown (“the white devil”)
• 13:22 — Taylor Swift as “microdosing high school”
• 14:33 — Ivy on Taylor’s limited musical prowess
• 15:26 — Madonna as Ivy’s pop music apex
• 17:20 — “QAnon for white chicks”; fandom lore
• 21:57 — Ivy on shadow strategies for celebrity crushes
• 23:30 — Pop stardom & class backgrounds (Britney vs. Taylor)
• 27:28 — Ivy on Louis CK as her fantasy “attainable” celeb
• 36:05 — “Subway Takes” segment, quirky urban opinions
• 44:53 — Men’s optics-based dating & “the curated girlfriend”
• 48:40 — Ivy’s “real talk” about sex vs. sexy signifiers
• 53:10 — Appreciation for the gesture of trying to be sexy
• 58:19 — Ivy’s devotion to Courtney Love & messy icons
• 63:20 — Lady Gaga as “grown lady” pop star
• 65:07 — “Reactive lesbian” theory introduced

Tone & Style

• Unapologetic, irreverent, deeply honest
• Frequent use of humor, dark wit, and shock value
• Candid take-downs of pop icons balanced by genuine admiration

Closing & Plugs

• Ivy Wolk: Promotes her Brooklyn show “Struggle Bus” (a competition to see which comedian had the most traumatizing life) and her Instagram: @wolkmindvirus2
• Jules/Esther: Touring with Pretty Little Baby Tour (info here)
• Jaime Garcia: Evolution Club hair care (evoceanclub.com)

Summary

This episode is a hilarious, transgressive, and surprisingly insightful pop culture roundtable. Ivy Wolk’s sharp tongue and vivid storytelling spark honest talk about sex, fame, trauma, and what it means to be a female pop culture icon in the age of internet lore. Whether dissecting Taylor Swift’s fanbase or exploring why men love sundresses and lingerie, the episode remains hilariously honest, sometimes biting, and always a love letter to hot messes—the perfect "Trash Tuesday."