Wrong Turns with Jameela Jamil

Episode: Erin Jackson and Josh Gondelman
Date: October 9, 2025

Episode Overview

This episode of "Wrong Turns" is an uproarious celebration of embarrassing, mortifying, and downright disastrous life moments with comedic legends Erin Jackson and Josh Gondelman. Host Jameela Jamil invites her guests to share their most cringe-worthy stories, digging deep into the humor and communal catharsis found in indignity, without attempting to spin a lesson or silver lining. The conversation swirls around everything from holding lifelong grudges to dating disasters, onstage humiliations, and failed romantic gestures—making it a full buffet of secondhand embarrassment and laughter.

Key Discussion Points & Insights

1. The Ceremonial Importance of Daily Routines

• Morning rituals and "ceremony" with loved ones are touched upon as soothing routines, correlating to unemployment jokes and gossiping sessions.
  • [01:54] Josh Gondelman: "It's both just that we're wildly unemployed...staring into the same void from slightly different axes."
  • [02:13] Jameela Jamil: "...ceremony...we have to get that time, cause that's when we gossip."

2. Embracing Disaster and Indignity

• The guests and Jameela quickly establish a shared philosophy: life’s disasters are best relished for their storytelling potential, not learned from.
  • [03:27] Erin Jackson: "Sometimes I look at things and I go, eh, at least there's a story to tell. I don't like when other people say that to me..."
  • [03:43] Jameela Jamil: "So when are we gonna retire the bird shitting on your head being good luck?"

3. The Art of Holding Grudges

• Erin’s viral love for holding grudges sparks a deep, eyebrow-raising conversation about the utility and joy in grudgery, free of revenge.
  • [04:51] Erin Jackson: "I love hating. I love it so much. So I'm still holding every grudge that I've ever held."
  • [05:22] Jameela Jamil: "...you said in your clip that you wouldn't even need to eat if you owned your own grudgery because the hate would fill you up on the inside."
  • [06:02] Erin Jackson (on karma for enemies): "It brought me so much joy...[but] I'm not into getting revenge. If karma hits you, then fine. But I think the rap that grudges are harmful and, like, weigh you down, I don't believe in it."
  • [06:21] Josh Gondelman: "Grudges are important. It's like the interpersonal version of touching the stove. That grudge keeps me safe."

4. Micro-Humiliations: Stories of Everyday Shame

• The panel takes turns sharing (mis)adventures ranging from bodily mishaps to dating woes.

  • Josh’s Thanksgiving Incident

    • [07:12] Josh recounts violently soiling himself on returning home after Thanksgiving, leading to a disastrous clean-up and a not-quite-sterilized bathtub—discovered by his future in-laws.
    • [11:04] "I texted my girlfriend, now wife...it's a bad scene here, I hope I got everything clean...She said, you got most of the way there. Which is, I think, very kind, loving life partner code for, you did not clean all your puke out of the bathtub."
    • [11:26] Jameela (laughing): "What a lovely impression you must have made."

  • Erin’s Disastrous Date

    • [12:33] Erin describes an abysmally bad date where she paid for dinner, her date drunkenly urinated on the street, and she had to endure mortification by association.
    • [14:26] Erin Jackson: "...by the transitive property, I am now peeing on the sidewalk."
    • [15:21] Josh Gondelman: "And he's just like stumbling like I'm a gentleman."

5. Major Wrong Turns: Stand-up & Public Humiliation

• Erin’s Jumbotron Debacle

  • [20:49] Erin recalls bombing spectacularly at the Black Family Reunion on the National Mall, leading to being booed by thousands—with her parents witness her public shaming for the first time.
  • [23:16] Erin Jackson: "Maybe three words into my five-minute set and it's boo. But it's like, it's boo just for the cause...I was like, I haven't even said anything not funny yet."
  • [24:53] Erin Jackson: "I do the time, I come off, and I'm like, wow."
  • [26:03] Erin: "It's called the Black family reunion. But they didn't make me feel very welcome."

• Falling Off the Stage After COVID

  • [27:48] Erin recounts her return to her home club, DC Improv, and taking a triumphant fall off the new stage—immediately after a great set.
  • [28:55] "Oh yeah, like it was like, oh God...they didn't laugh in my face...but I went into the green room and just didn't want to come out and greet anyone."

• Jameela’s Face-plant on National TV

  • [29:43] Jameela tells a story of breaking her tooth, nose, and possibly her elbow during a televised paint fight—an instant, viral humiliation.

6. Romantic Blunders and Trying Too Hard

• Josh’s College “Bits” Long-Distance Relationship

  • [33:53] Josh details a doomed long-distance romance maintained by care packages filled with outlandish “bits”—like a Bon Jovi comic book and elaborate notes—none of which saved the dying relationship.
  • [37:44] Josh Gondelman: "I wrote, I typed up a letter that was like, welcome to the Bon Jovi fan club. Here's what you've gotta know from me, the president..."
  • [39:40] Josh: "[We] broke up, my memory is within instance of her returning to campus..."

• Jameela’s Over-the-Top First Dates

  • [39:51] Jameela confesses to arranging thousand-dollar Paris day trips with elaborate prop shopping lists for virtual strangers, all in hopes of manufacturing romance.
  • [43:12] Jameela: "I was always trying to create a movie...I would take them to Paris, and then we would get home...and then I wouldn't kiss them because it takes three months for me to know someone before I can kiss them. So all of that, and then it makes signals."

Notable Quotes & Memorable Moments

• Erin Jackson [04:51]: "I love hating. I love it so much. So I'm still holding every grudge that I've ever held."
• Josh Gondelman [06:21]: "Grudges are important. It's like the interpersonal version of touching the stove. That grudge keeps me safe."
• Jameela Jamil [11:26]: "What a nice animal for their daughter to live with."
• Erin Jackson [14:26]: "...by the transitive property, I am now peeing on the sidewalk."
• Jameela Jamil [24:42]: "Did you get booed for the entire five minutes?"
  Erin Jackson: "Yeah."
• Jameela Jamil [29:43]: "I break my nose. I break my front tooth in half. I've still got it. I’ll show you later."
• Josh Gondelman [34:29]: "I came out soft, underbaked. Like, if you—I needed a few more minutes in the oven, which as a Jew, pains me to say..."
• Jameela Jamil [43:41]: "So I really understand that instinct of, like, I'm gonna fucking make this shit happen. I'm gonna make a movie out of this."
• Josh Gondelman [44:07]: "You've let out, like, the New York summer fire hydrant, kids playing in the…that's what you did to, like, the endorphins in my brain."

Timestamps for Important Segments

• Opening Banter & Ceremony Chat: [00:32]–[02:57]
• Attitude Toward Disaster & Grudges: [03:16]–[06:32]
• Josh’s Thanksgiving Incident: [06:46]–[11:26]
• Erin’s Date from Hell: [12:33]–[16:57]
• Massive Stand-up Humiliation: [20:49]–[26:03]
• Comedy Falls & Public Accidents: [27:48]–[31:22]
• Josh’s Long-Distance “Bits” Fiasco: [33:53]–[39:40]
• Jameela’s Wild First Dates: [39:51]–[43:53]
• Closing Round-up & Plugs: [45:06]–[45:49]

Overall Tone and Takeaways

The conversation is playful, self-deprecating, and raucous—each guest eager to top the previous humiliation, with Jameela joyfully steering the show toward more indignity rather than away. The spirit of camaraderie in shame is palpable, leading to a sense of relief and joy in shared disaster, not redemption.

As Jameela sums up, "now that I have been established as the greatest of all the losers of all time...you've both made me feel less alone and more alone in just one hour." [44:36]

Guest Plugs

• Erin Jackson

  • @ejthecomic everywhere 🌟
  • Tour dates and videos on all platforms

• Josh Gondelman

  • @joshgondelman (“G-O-N-D-E-L man”)
  • Newsletter: That's Marvelous
  • New stand-up special coming soon

Listen if…

• You crave laughter over your own trainwreck moments.
• You want to feel better about survived humiliation.
• You enjoy comedians being raw, real, and absurdly relatable.
• You’re allergic to forced moral-of-the-story “inspiration” podcasts.

For more, follow Wrong Turns with Jameela Jamil on your favorite podcast platform!