Podcast Summary: Wrong Turns with Jameela Jamil – Episode: Ian Fidance and Nathan Macintosh
Date: November 6, 2025
Host: Jameela Jamil
Guests: Ian Fidance, Nathan Macintosh
Episode Overview
This episode of Wrong Turns brings together comedians Ian Fidance (“Being Ian With Jordan,” “The Last OG”) and Nathan Macintosh (“Positive Anger,” “Down With Tech”) for an uproarious, no-holds-barred exchange of their most embarrassing, disastrous, and outrageous life moments. In classic Wrong Turns fashion, the trio gleefully forgoes any inspirational takeaways, instead reveling in personal mishaps including childhood shame, sex capades gone awry, substance-fueled failures, and getting fired for remarkable reasons.
Key Discussion Points and Memorable Stories
Laughter, Sex, and Soaking: Kicking off with Taboo Topics
[01:54–06:59]
- The episode opens with playful banter about personal appearances and self-descriptions (“Excitable Boy” for Ian; “Happy Man” for Nathan) before derailing into an in-depth, hilarious discussion of the Mormon practice of “soaking.”
- Notable Exchange:
- Jamila: “Tell people what soaking is.”
- Nathan: “You just jam your dick into a woman and leave it there.” [05:11]
- Ian: “You have to be Mormon.” [05:36]
- The conversation escalates with the trio riffing on awkward, lazy sex and absurd religious loopholes.
- Ian (re: soaking): “It’s like the Catholic thing of having anal sex and being like, I’m still a virgin. It’s such a crazy religious thing.” [06:52]
Micro-Humiliations: Tales of Teenage Shame
[07:27–12:14]
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Nathan’s First Brush with Shame:
- Age 13, scouring a friend’s computer late at night with every possible porn-related search term. The friend’s ultra-religious mother finds the search history, bans Nathan from the house, and the friendship strains for years.
- Nathan: “I was up… I searched all of the—All of porn that I could think of. ...I don’t know anything about search histories. This is the internet now for—it just started.” [08:02]
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Jamila’s Social Media Mishap:
- Accidentally directs her young Twitter followers to a gross porn site, thinking “shitter.com” was a funny joke, not porn.
- Jamila: “I thought I was so funny and said... We should call it shitter.com... had no idea that it is a porn website.” [10:53]
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Ian’s Spice Channel Story:
- Discovers “the bad channel” at his grandparents’ house (scrambled softcore porn) and feigns a love of doing homework in the living room just to sneak peeks.
- “All of a sudden I could only do my homework in my grandparents' living room...” [12:29]
Phone Sex and Outlandish Phone Bills
[13:36–16:57]
- Nathan’s Confession:
- Racks up a $600 bill on pay-per-minute phone sex lines, blames others to avoid trouble with his girlfriend’s mom.
- Jamila’s Darkest Bill
- While addicted to prescription drugs, unknowingly spends £17,000 calling sex workers and psychics on late-night benders.
- Jamila: “There are thousands of calls of me saying God knows what to sex workers and psychics that exist from the year 2012.” [16:27]
- Nathan: “Seventeen thousand is crazy. I don't even feel bad.” [16:46]
First Times Gone Wrong
[17:01–22:02]
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Ian’s Missed Virginity Moment:
- Nearly loses virginity on 9/11, but his mother’s paranoia keeps him home; the girl ends up with another boy. Redemption arrives years later, but a mortifying, inept sexual encounter follows.
- Ian: “She was like, 'It'd be really hot if you came on my face.' And I’m 18...” [20:23]
- Ian: “If someone asks you to cum on their face, you say yes. You don't overthink it... No, you just rip it and run it.” [21:31]
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Nathan’s Teenage Virginity Story:
- Loses virginity at 14, inexpertly puts on a condom backwards, finishes in seconds, and has to hang out awkwardly with his crying girlfriend and her mother.
- Nathan: “I put it on backwards... I didn’t know what I was doing. She didn’t know what she was doing. ...And I came in four seconds.” [26:28–28:03]
School-Day Disaster: The Ultimate Childhood Humiliation
[29:23–33:46]
- Nathan’s Piss Story:
- Eight years old, too polite to interrupt during class, desperately holds pee until he uncontrollably soaks himself and his desk in front of crushes, forcing the teacher to call his mom.
- Nathan: “I absolutely erupt. Fully pissed myself. You know those wooden desks... piss is flying down these sides. …Dan’s looking, Christina’s looking, and I’m just sitting there.” [31:08]
- Nathan, on impact: “I will not ever wait to use the bathroom ever again though, in my entire life. I’ll tell you right now, I’ll get out of any situation…” [33:53]
Substance, Jail, and Job Fails
[37:03–41:04]
- Ian’s Wrong Turn:
- Arrested (for drinking on the street) the night before a job interview. After a harrowing jail experience involving confiscated shoes and aggressive cellmates, he goes straight from jail to a financial job interview, still in withdrawal. Keeps the job only due to a contract, constantly drunk/high, and is finally fired after the probation period.
- Ian: “Men were taking their shirts off and doing push ups and throwing orange peels at this guy who was going through alcohol withdrawal... I was the last kid picked at kickball.” [38:36]
Workplace Disasters: Epic Firings
[41:24–45:48]
-
Jamila’s Firing:
- Devours two full fridges of Haagen Dazs ice cream meant for customers, blaming a “broken” freezer. Caught by staff replaying CCTV footage of her repeat trips to the freezer.
- Jamila: “She makes me stand there and watch me on fast forward going back and forth across two weeks to the refrigerator again and again and again before she fires me.” [43:24]
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Nathan’s Failure at Future Shop:
- Friendly to customers but never sells anything, costing the store $25,000 in lost sales. Relegated to assembling TV stands out of customer sight.
- Nathan: “Last month, you were supposed to sell $25,000 worth of stuff… You did… zero. You sold nothing.” [44:44]
Listener Story: Fish Hook Catastrophe
[46:41–47:31]
- Sarah’s Fishing Horror:
- At 16, drags up a fish with such force that the hook ricochets into her eye. After multiple surgeries, she retains only 80% vision and different-colored eyes, but finds it makes for a killer dinner party anecdote.
- Jamila: “Oh my Jesus. Fuck me. Christ, Sarah.” [47:19]
- Nathan: “I wonder if one of them’s like a fish eye. Like just a black, dark death eye, like a pirate…” [47:31]
Notable Quotes
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“This is a show where dignity goes to die. Where we celebrate the fuck-ups that we endure without having to turn them into some sort of disgusting inspiration porn.” — Jamila Jamil [01:54]
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“I searched all of the—all of porn that I could think of. Every single piece of a human woman.” — Nathan Macintosh [08:02]
-
“So there are literally thousands of hours somewhere…of me saying God knows what fucking shit to sex workers and psychics that exist from the year 2012.” — Jamila Jamil [16:27]
-
“If someone asks you to cum on their face, you say yes. You don’t overthink it…You just rip it and run it.” — Ian Fydance [21:31]
-
“I absolutely erupt. Fully pissed myself…piss is flying down these sides. Rip. Just raining. People are looking. Dan’s looking, Christina’s looking. And I’m just sitting there.” — Nathan Macintosh [31:08]
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“My dream was to do that forever. Forever. But then, obviously, the internet murdered my industry.” — Jamila Jamil on her video store job [41:28]
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“I will not ever wait to use the bathroom ever again though, in my entire life. I’ll tell you right now, I’ll get out of any situation.” — Nathan Macintosh [33:53]
Closing & Where to Find the Guests
-
Nathan Macintosh
- Instagram: @NathanMacintosh
- Comedy specials on YouTube: “Money Never Wakes” and “Down With Tech”
- Host of “Positive Anger” podcast
-
Ian Fidance
- Instagram: @ianimal69
- Website: ianfinance.com
- Special: “Ian Fidance: Wild, Happy, and Free” on YouTube
- Podcast: “Being Ian with Jordan”
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Host: Jameela Jamil
- Instagram: @jameelajamil
- Writes on Substack: “A Low Desire to Please”
The Wrong Turns Formula
No morals, no silver linings, just genuine, raw, and frequently outrageous tales of humiliation and disaster—told with wit and camaraderie. This episode is a relentless festival of “dignity going to die,” bound to make you laugh, wince, and (maybe) feel a little better about your own wrong turns.