Wrong Turns with Jameela Jamil

Episode: Shapel Lacey and Aaron Branch
Date: December 11, 2025

Episode Overview

This riotous episode of Wrong Turns features comedians Chappelle Lacey and Aaron Branch joining Jameela Jamil for a cathartic, hysterical exploration of life's most mortifying disasters — from micro humiliations to epic bodily mishaps. With no morals or lessons promised, the trio gleefully swap their worst sexual, social, and physical "wrong turns," punctuated by relentless teasing, oversharing, and laughter. This is a celebration of human embarrassment, complete with vivid stories, painfully honest confessions, and plenty of irreverence.

Key Discussion Points & Stories

Introductions & Ice-Breakers

• [00:57] Jameela Jamil welcomes the guests, giving an irreverent intro: "This is the show where dignity goes to die."
• Banter about Chappelle's cheerleading background and Aaron's acting/comedy credentials.

Are You Drawn to Disaster or is Disaster Drawn to You?

• [02:05] Jameela: “So you’re here because of disaster. Are you drawn to disaster or is disaster drawn to you? Whose fault is it, man?”
• Chappelle jokes about anger management, Aaron muses whether they’re doing a podcast or therapy (“Wait, I thought this was a podcast or a therapy session.” [02:18]).

Micro Humiliations

Chappelle’s Worst Stand-Up Experience

• [03:01] Chappelle recounts his “worst show ever” (his 4th ever stand-up gig):
  • Mistimed gig at a nightclub after music acts and a DJ, where no one wanted comedy.
  • Aggressively heckled; retorted "man shut your dumb ass up."
  • Escalated to shouting “yo, suck my dick, bro,” and was brilliantly heckled back: “your dick’s the joke” ([05:36]).
  • Many friends (including his adopted Christian dad) in the crowd — utter humiliation.
  • “I had a crash out. I just started telling the crowd, yo, suck my dick, bro. And then there was one guy. One guy that got me. He goes, 'man, your dick’s the joke.'” — Chappelle Lacy ([04:49])
• Jameela and Aaron express their horror and sympathy, with Jameela noting she's grateful many of her humiliations took place "pre-social media" ([07:13]).

Aaron’s Accidental Grandpa Kiss

• [09:10] Aaron shares an awkward family story:
  • Accidentally kissed his grandfather on the lips at a nursing home in front of his whole family.
  • “Both of our heads turn at the same time and we kiss each other on the lips.” ([09:32])
  • “Was it your first kiss?” jokes Jameela ([10:49]).
  • He never discussed it with family; it felt like a weird secret. Grandfather also had schizophrenia, which complicated things.

“Pretty Girl” Mix-Up

• [11:39] Aaron’s great-grandmother, due to dementia, never realized he was a boy, always telling him, “You sure are a pretty girl.”
• His diplomatic response: “Thank you.” Jameela compliments his resilience: “You’re quite a pretty man. I completely understand.” ([12:20])

Big Wrong Turns: Sexual Misadventures

Chappelle's Bleeding "Wrong Turn"

• [14:10] Chappelle delivers the episode’s most cringe-inducing story:
  • Lost his virginity at 21 to a girl from Applebee’s — “I just wanted to fall in love.”
  • Second time having sex, at cheer camp, his lack of sexual experience led to not preparing his partner, resulting in severe "carpet burn" to his uncircumcised penis.
  • Discovered bleeding everywhere in the bathroom, panic ensued. Teammates had to help clean up, “bloody sheets” thrown onto the beach.
  • “So I pull out, and there was blood. … I was like, the blood’s not stopping. … It was me.” ([19:19–19:21])
  • Jameela: “So just to be clear, you tore your foreskin.” Chappelle: “Yeah.” ([22:28–22:31])
  • Story spread to the entire cheer squad and even the coach. Trauma led him to avoid sex for years, and permanent nerves about it.

Jameela Shares Her Own TMI Story

• [24:49] In the spirit of oversharing, Jameela shares a story of a sexual partner whose penis was "so big" it supposedly relocated her womb, necessitating a hospital visit. The group collapses into shocked laughter.

Aaron’s High School Sexting Scandal

• [25:48] – [34:09] Aaron recounts a wild "humiliating" story, though Chappelle and Jameela skeptically probe whether it's actually trauma:
  • High school era: Aaron sexts with a girl who asks about his anatomy; he gives an accurate size.
  • Girl tells her next boyfriend, who spreads the story around school.
  • Contract written in geometry class: Aaron must provide photographic "proof" (for $20).
  • Ends up taking a picture next to a ruler; the photo gets shown to half the school.
  • Felt “everyone was talking about it,” painful embarrassment, then called to the principal’s office — but only to be rewarded $10 for returning lost cash earlier. “They saw my dick ... and they said it was amazing ... and my principal gave me money!” Jameela: “Are you joking? This is not your platform to get laid. This is real entertainment.” ([32:14])
  • Chappelle: “Sounds like a W to me!” ([34:42])

Aaron’s “Terrible” Campus Walk of Shame

• [35:51] Relates being “cut off” by beloved security guard after she saw him drunk for the first time:
  • “She saw me and what she yelled at me, I’ll never forget: ‘I thought you was good, but you bad just like everybody else.’ And then cut me out of her life.”
  • Chappelle exclaims, “I hate your stories, bro. I literally, I opened up my heart ... I talked about my dick bleeding!” ([37:06])

Everyone’s Most Mortifying Moments

• [37:47] Jameela finally shares: “I’ve shit myself in the road. I had an orgasm in front of 6,000 farmers … was hung upside down on national TV, snot flying, reading a teleprompter.”
• “No wonder you’re a comedian.” — Jameela, to her guests.

Listener’s Story: "Misery Loves Company"

• Jessica’s Date Disaster ([41:31]):
  • After a promising date with the “hottest guy in college,” Jessica, inquiring about his deaf sister, asks, “So does she read Braille?” causing him to instantly end the date.
  • “That is the most extraordinary moment of foot in mouth disease. And I love it so much.” — Jameela ([42:09])

Notable Quotes & Memorable Moments

• Chappelle’s on-stage disaster: “I just started telling the crowd, yo, suck my dick, bro. And then there was one guy … he goes, ‘man, your dick’s the joke.’” ([04:49])
• Jameela’s TMI: “I had sex with someone whose penis was too big. … I had to go to the hospital. It relocated.” ([24:49])
• Aaron’s high school ‘trauma’: “So then he’s like, I’ll give you $20. And I’m like, bet, right? So that night, I go home and I take a picture of my dick next to a ruler … then I go to school the next day.” ([30:07])
• Jameela skewers Aaron’s humblebrag: “Are you joking? This is not your platform to get laid. This is real entertainment.” ([32:14])
• Chappelle, resigned: “Sounds like a W to me.” ([34:42])
• Aaron’s lost innocence, per the security guard: “‘I thought you was good but you bad just like everybody else.’ And then cut me out of her life.” ([37:05])
• Jameela’s life parade: “I’ve shit myself in the road. … I got hung upside down on a bungee on national television … snot came out of my nose in a long two-foot line!” ([37:47])

Timestamps for Key Segments

• Introductions and setup: [00:57]–[02:21]
• Micro humiliations (Chappelle’s story): [03:01]–[07:23]
• Aaron’s first kiss… with his grandpa: [09:10]–[10:52]
• “Pretty girl” misgendering: [11:39]–[12:24]
• Chappelle’s epic sexual mishap at cheer camp: [14:10]–[24:41]
• Jameela’s own TMI “womb incident”: [24:49]
• Aaron’s high school sexting “scandal”: [25:48]–[34:42]
• Campus security guard disappointment story: [35:51]–[37:19]
• Jameela’s “greatest hits” of humiliation: [37:47]–[38:39]
• Listener letter (Jessica): [41:31]–[42:34]
• Outro and plugs: [42:51]–[43:30]

Guest Plugs

• Chappelle Lacey: @chappellelacey on all platforms
• Aaron Branch: @branchboycomedy on TikTok, always touring

Tone & Takeaway

The episode is fast, filthy, self-deprecating, and always gleeful. No pity, no sermons — just the unvarnished, hilarious truth of being mortifyingly, bodily, embarrassingly human. Whether you revel in misfortune or need reassurance that “you’re not alone,” this episode is a masterclass of cathartic chaos and comedic storytelling.

For more, subscribe or send your own disasters to PersonalDisasterStories@gmail.com.