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.
5. Major Wrong Turns: Stand-up & Public Humiliation
6. Romantic Blunders and Trying Too Hard
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!
