Erin Jackson and Josh Gondelman

Summary

Wrong Turns with Jameela Jamil

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

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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.

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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."

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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."

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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]

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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]

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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

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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.

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

Transcript

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[Josh Gondelman]

You look the same.

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[Erin Jackson]

You haven't changed your hair in 15 years. Selfies check, please.

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[Jameela Jamil]

Thank you for listening to Wrong Turns. Follow the show on Amazon Music for more future episodes or just ask Alexa. Play the podcast Wrong Turns on Amazon Music. Hello and welcome to Wrong Turns. This is a podcast that celebrates indignity. It's where dignity truly goes to die and then be buried. I get to bring on my favorite funny people and they tell me they're miserable tales that have no true redeeming qualities or life lessons learned. With me today, we have a writer and comedian with credits on Netflix, the Upshores Life, and Beth Late Night with Seth Meyers. Her comedy album Grudgery debuted at number one on the iTunes charts. It's Erin fucking Jackson. Hello. Hey.

[Erin Jackson]

Thank you so much for having me.

[Jameela Jamil]

Your love of grudges is why I first fell in love with you. We can get into that in a second. And we also welcome a comedian, producer and writer from shows like Desus Romero and Last Week Tonight with John Oliver, it's Josh Gundelman.

[Erin Jackson]

Hello.

[Hannah Berner]

Hello.

[Josh Gondelman]

Oh, my gosh. Thank you so much for having me.

[Jameela Jamil]

Thank you so much for being here. I think you're both so, so funny. How are you doing today?

[Josh Gondelman]

I had a nice morning. Yeah, I had, yeah. Drank a little coffee, hung out with my wife. She walked the dog. So very low impact morning for me.

[Jameela Jamil]

Oh, lovely. Is that like a morning tradition, walking the dog, walking the dog, or having coffee with your wife?

[Josh Gondelman]

Yeah, we both are. Well, you make it sound so sweet. It's both just that we're wildly unemployed, so like. Yeah. We spend a lot, like, drinking coffee together, walking the dog together, staring into the same void from slightly different axes. Yeah. So that's kind of. That's our life.

[Verizon Ad Voice]

Yeah.

[Jameela Jamil]

I still think it's romantic.

[Josh Gondelman]

Thank you.

[Jameela Jamil]

Yeah. My boyfriend and I have ceremony. Whether employed or unemployed, we refer to it as ceremony. We have to get that time. Cause that's when we gossip.

[Josh Gondelman]

Oh, yeah.

[Jameela Jamil]

So it's very important to have that time to unload all of the gossip we've retained in the day.

[Josh Gondelman]

Before she had come home, she had had one cocktail at a dinner with a friend and came home and was like, let's gossip. Like, last night at like, 9pm and we really got it. That terrible impression of her. She's a lovely lady.

[Erin Jackson]

I don't know why.

[Jameela Jamil]

I gave her, like, a Grouch, Like.

[Josh Gondelman]

A Gaston Cold, Steve Austin kind of vibe.

[Erin Jackson]

It was a ceremony, and it made me think of. Isn't that what they call it in the Handmaid's Tale?

[Josh Gondelman]

Oh, I don't know.

[Jameela Jamil]

Oh, yeah. No, I wear a bonnet and I. I give over control of my ovaries every morning in a ceremony. Yeah. Okay, cool.

[Josh Gondelman]

To Godspawn.

[Jameela Jamil]

Yeah.

[Josh Gondelman]

Yeah.

[Jameela Jamil]

It's really hot. Everyone should try it. What about you? How are you doing, Erin?

[Erin Jackson]

Well, it's another day in America in 2025, so, you know.

[Jameela Jamil]

No, pretty great.

[Green Chef Ad Voice]

Pretty great.

[Erin Jackson]

No, I just.

[Green Chef Ad Voice]

Really.

[Jameela Jamil]

Your time, I think. Yeah.

[Erin Jackson]

No, just bought traffic coming in from Jersey, so that's always fun. But I was happy to be coming here.

[Jameela Jamil]

So when it comes to disaster, what are your attitudes? I mean, are you open to it? Do you experience it often? Have you become kind of almost bored of it because it happens so often?

[Erin Jackson]

Yeah, honestly, I do. I mean, as much as I hate when people say it to me, you know what I mean? 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 as a community.

[Jameela Jamil]

That's pretty fucking rude, right?

[Josh Gondelman]

This will be great for material.

[Erin Jackson]

This will be great for material.

[Jameela Jamil]

You know?

[Josh Gondelman]

It's great for material.

[Jameela Jamil]

So when are we gonna retire? The bird shitting on your head being good luck? When are we gonna stop doing that? Please, God, yes. I was eating my first ever corn dog the first day I was in America. I was so excited. Something I dreamed of my entire life. I don't have big dreams. Okay, guys. But all I wanted was an American. And I was holding it up to the sky, being like, yes, I finally got to America and I'm gonna eat my corndog. And a seagull shat down my arm somehow into my coat sleeve so I couldn't see it. And it was only when I brought the corn, I felt something hit me, but I didn't know what it was. It was only when I brought the corn dog down, I started to feel the sludge.

[Josh Gondelman]

Oh, no.

[Jameela Jamil]

Of the seagulls. But it didn't get on your corn dog. It was a fucking shot. Yeah, it Was a hate crime. Didn't get on my corn dog. Didn't eat the corn dog just in case. Cause not an animal. Sure did consider it. Wow, the wrong turn sign is about to fall. That is so fucking perfect. Yeah, we'll keep going. This is St. Stuart, who's coming in and fixing it. I also broke it in half, as you can see, yesterday. There we go. Perfect. Erin, I first became aware of you because of a clip of yours that went viral about your love of grudges. Can you just briefly explain this?

[Erin Jackson]

I love hating.

[Jameela Jamil]

Yes.

[Erin Jackson]

I love it so much.

[Jameela Jamil]

Yeah.

[Erin Jackson]

So I'm still holding every grudge that I've ever held.

[Jameela Jamil]

So you.

[Josh Gondelman]

I think it's kind of beautiful.

[Jameela Jamil]

It's gone. It's gone.

[Josh Gondelman]

It's over.

[Jameela Jamil]

So do you want to put it back up or do we just leave it? Okay, that was perfect. So you really enjoy when disaster happens to other people?

[Erin Jackson]

I mean, the people who've wronged you?

[Jameela Jamil]

Because I feel exactly the same. 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. I come from a tribe in the mountains, which is such an iconic thing to say, where the only stereotype known about us is that we live for revenge. And I was like, I think we're going to need to bring you into the tribe.

[Erin Jackson]

I think I'm already a long lost member. But here's the thing, though. I'm not really bent on revenge. I just enjoy the remembering that I hate you. It's not about the karma. I mean, it's always pleasant. I mean, I googled my high school arch nemesis and there was a mugshot. I mean, that I know that's how it all started.

[Josh Gondelman]

Yeah.

[Erin Jackson]

It brought me so much joy. I texted it to everybody that we knew together and I was like, look, but I'm not into getting revenge. I mean, 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.

[Jameela Jamil]

Agreed.

[Erin Jackson]

They motivate me.

[Josh Gondelman]

I think grudges are important. Cause it's like the interpersonal version of touching the stove where you're like, that grudge keeps me safe. It's keeping me from future pain and embarrassment.

[Jameela Jamil]

I find turning the other cheek hurts my neck and isn't safe. So I really prefer just to look you directly in the eye and watch your life fall apart. Give me some examples of some micro humiliations that you face.

[Josh Gondelman]

Oh, I live an undignified life. So the last one. And I feel like I plateaued on the embarrassment curve. I was really embarrassing when I was young and then I figured it out a little bit, but I just turned 40 and I feel like I'm about to be in a group of 25 year olds and be like, who's Benson Boone? And they're all gonna laugh at me and pull my pants down and send me out into the street in my boxers. And so this is the last.

[Jameela Jamil]

Do you think you're about to hit another incline?

[Josh Gondelman]

I think I'm about to. It's about to be a proceeding.

[Jameela Jamil]

Right, right, right.

[Josh Gondelman]

Okay, cool, cool, cool. I think I've come out the other side of like, I know how to manage in the world. And then someone's gonna be like, you don't know how to call a robot car to take you home, idiot. And then they just make me learn how to skateboard. They're like, take a skateboard, figure it. I'm like truly terrified that I'm about to hit that point. Cause even at my best, it was just kind of level. And so the last time I remember being like, oh, this is really humiliating was I had started dating my now wife and I had done Thanksgiving dinner at her parents house, we were living together and I had Thanksgiving dinner at her parents house. And then I came back to our apartment in Brooklyn because I was going to my parents house the next day for a late Thanksgiving celebration. And I was the only one that this happened to. I verified with everyone else who was at Thanksgiving. But I got home and I was like, I don't feel great, but it's probably just I got up early for Thanksgiving, got home late. I'll just sleep it off. I woke up the next morning, got dressed to go to the train, on my way out the door, violently, and there's no genteel way to say this, violently, shit my pants. And do you know how bad a situation it has to be to shit your pants while you're within your own house?

[Erin Jackson]

Right.

[Jameela Jamil]

No. It's because your bumhole has a sort of toilet radar, Right. It can sort of. I don't know if it could smell the toilet or something.

[Josh Gondelman]

That's right.

[Jameela Jamil]

But it has like, you know how like a dog knows when you're down the road? Your asshole knows when you're close to your toilet.

[Josh Gondelman]

Yep. And it was like, not close enough.

[Jameela Jamil]

It doesn't know how close, Right?

[Erin Jackson]

Yes. And if you rejoice too early, I find like if you walk in the door and think, I made It. You didn't make it.

[Josh Gondelman]

No, no, no.

[Erin Jackson]

Right.

[Jameela Jamil]

You made the mistake of breathing.

[Josh Gondelman]

That's. Poseidon's gonna get you from within. But so I. I'm like, well, I gotta take care. And now I'm running late for the train. So I'm like, pants off. I'm like, let's figure out whatever this is. As I'm figuring that out, I'm like, oh, I have to puke. And I not to brag. Very rarely puke. And so I slay. Thank you. That's Met Gala. Where was my invite? I very rarely puke. I run. I'm like, my stomach is sick. I don't know what comes over me. I puke in the. The bathtub.

[Jameela Jamil]

Yeah.

[Josh Gondelman]

Yeah.

[Jameela Jamil]

I did this two weeks ago. Wow.

[Josh Gondelman]

Okay. Puke twins.

[Jameela Jamil]

And I also am a rare puker. In fact, I tried to have bulimia for one year when I was 15, and I did all the binging, but then I could never one time make myself throw up.

[Josh Gondelman]

Oh, my gosh.

[Jameela Jamil]

So I gained three dress sizes that year.

[Erin Jackson]

And that just sounds like my regular life. Yeah, the binging without the purging.

[Jameela Jamil]

Had some great food. Didn't purge one time, gave it up. Sorry. As you were saying.

[Josh Gondelman]

No, that's.

[Erin Jackson]

Now we're twins.

[Jameela Jamil]

Yeah. Bonding, cute.

[Josh Gondelman]

Twins binge.

[Jameela Jamil]

Twins binge.

[Josh Gondelman]

We're kind of triplets by the transitive property now.

[Jameela Jamil]

100%.

[Josh Gondelman]

So throw up in the tub now. I'm like, I don't know how you clean puke out of a bathtub in 19 seconds before I had to run out the door. I did my best. Cleaned the pants, threw em in the washing machine. Not to brag in unit, washer, dryer. I know, I know, I know. So really, this is a story about my financial success? More than that.

[Jameela Jamil]

Your life as a billionaire in succession. Yeah.

[Josh Gondelman]

Yeah. Really making it rain. Yeah. I got in my helicopter, went up to Boston to see my folks, but I texted my girlfriend, now wife, and was like, it's a bad scene here. I hope I got everything clean. I'm really sorry if I didn't. I can't miss my train to visit my friend. She's like, don't worry about it. And then her parents dropped her off from New Jersey in the city, and they were like, we want to see your apartment. And so they all came up together. And I was like, how did I do getting the tub clean? And 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.

[Jameela Jamil]

Oh, that is absolutely horrifying.

[Josh Gondelman]

Yeah, it was really bad.

[Jameela Jamil]

What a lovely impression you must have made.

[Josh Gondelman]

Really bad. We're cool now.

[Jameela Jamil]

Yeah.

[Josh Gondelman]

They're so sweet, my in laws. They're really nice. But this was not a. You know, we'd met each other. Fortunately, their first impression of me wasn't puke, but that was their first impression of how I live.

[Jameela Jamil]

Yeah, lovely, lovely. What a nice animal for their daughter to live with.

[Josh Gondelman]

Yeah.

[Erin Jackson]

I just have a question, please, because. Okay, so in showing them the house, is there a shower curtain? I'm just wondering why she was showing them the tub.

[Jameela Jamil]

I felt the same way. I felt like she could have protected your dignity a little better. Yeah, she's going into our grudgery now.

[Josh Gondelman]

No, no, no, no, no, you can't.

[Jameela Jamil]

I'm joking. I'm joking, I'm joking.

[Josh Gondelman]

She's so good.

[Jameela Jamil]

No, she sounds wonderful.

[Erin Jackson]

That's a great question. I'm just kidding.

[Josh Gondelman]

Maris you've met.

[Erin Jackson]

I don't know if I've met her, but I've met her on social media.

[Josh Gondelman]

Yeah, she's the best. My guess is either I didn't curtain hand up, that's on me. Or they just had to use, you know, they were like, oh, well, let us use the bathroom before we head home. And then I feel like a bathtub with even a little puke in it is kind of a noticeable.

[Jameela Jamil]

It's a red flag. Yeah, it's a big red flag.

[Josh Gondelman]

There's more senses than just vision involved.

[Erin Jackson]

Got it.

[Jameela Jamil]

100%. Oh, thank you for telling me that, Erin. Tell me, do you have an example of a micro humiliation?

[Erin Jackson]

Micro in several ways, yes. So this actually kind of started from a date too, but went out with this guy that I met. This is years ago, still living in D.C. and I met out. I went out with a guy I met on a dating site before Abs, and right away I knew wasn't gonna be a great date. We didn't have anything in common. He drank a ton.

[Jameela Jamil]

Did he look like he did on the app?

[Erin Jackson]

He. He looked like. He was definitely him, but just. Yeah, just not interesting. And I was just like, let's get out of it. He had a ton to drink at dinner. Check came. He didn't, you know.

[Jameela Jamil]

Did you also drink at dinner?

[Erin Jackson]

I did not. Because I just knew I didn't enjoy him.

[Jameela Jamil]

That is, by the way, the fucking weirdest thing. If someone has one or two drinks, that's fine. But if someone drinks loads and you're not drinking they're leaving your plane of reality and going on to theirs and leaving you behind. I think it's the. It's Trudy, what he's saying.

[Erin Jackson]

Yeah, no, he was totally at a different party. And I like to drink, but I just knew. I'm not trying to prolong this evening.

[Josh Gondelman]

Sure.

[Jameela Jamil]

Yeah.

[Erin Jackson]

I don't wanna. You know, I was just like, I'm in, I'm out. Let's eat the food. And then I ended up paying for the meal. The whole meal, which. Okay, fine.

[Jameela Jamil]

He got you to pay for everything.

[Erin Jackson]

He didn't wanna break his last 20 because once you break it, it's gone. That happened in real life. But that's not even. I mean, I was embarrassed for myself for paying for it. But that's not the embarrassment. The embarrassment was leaving the restaurant. And for some reason, again, lots of embarrassing things along the way. For some reason, I let him drive me home. So as we're leaving the restaurant, he had to pee because he had to drink so much. And so he just pees on the street, on the sidewalk. He was that drunk. So he just. And that was a micro embarrassment.

[Josh Gondelman]

Oh, no.

[Erin Jackson]

For him.

[Jameela Jamil]

Am I right?

[Erin Jackson]

No. But he's peeing on the street, and I'm here standing there with this man, and I'm, like, mortified, like.

[Josh Gondelman]

So now you're peeing by association.

[Erin Jackson]

Exactly. By the transitive property. I am now peeing on the sidewalk. And that was. And I was like, do I. And I. I was young. I don't know why.

[Jameela Jamil]

There's no desire to impress you or no chivalry present.

[Erin Jackson]

I don't think he. No, there was chivalry.

[Josh Gondelman]

He did put his jacket over it and let her walk over.

[Jameela Jamil]

He's lovely.

[Erin Jackson]

He's said, that's so funny, because when I told that on stage, I used to say that.

[Josh Gondelman]

No, that's so funny.

[Erin Jackson]

But what he actually did was he was like. He got done peeing and he zipped up. And then he was like, I'm gonna.

[Jameela Jamil]

He was like, move.

[Erin Jackson]

Let me walk on the. On the street side. He was like, my mom raised me to be a gentleman. Let me walk on the outside. And I was like, I've never prayed for a car to hit a person before. Like, I don't know if God does, like, on demand, vehicular on the side. But I was like, I'm gonna just see what he says. People are, like, walking by, like, what is happening? And I'm just like, yeah, that's the one.

[Jameela Jamil]

I'm with my guy.

[Josh Gondelman]

And he's just like stumbling like I'm a gentleman.

[Erin Jackson]

It was the worst.

[Jameela Jamil]

Oh, man, that is. It's a visceral feeling of feeling trapped where you can't get away from someone who shows. And also, it just says, why is the universe persecuted me like this? What does the universe think of me? That this is who they sent. And also, I keep saying this everywhere I can. The dating apps only show you something, like less than 20% of the people that you're actually compatible with so that you stay on the dating apps for longer. So the right person who doesn't piss all over the road and who doesn't make you pay for their night of getting drunk alone is out there. You're just not gonna find out.

[Josh Gondelman]

He's never gonna meet him. Did he try to charge you for, like, an Uber ride on the way home to you?

[Erin Jackson]

No, he didn't. But I don't know why I didn't hop in a cab.

[Jameela Jamil]

I'm amazed.

[Erin Jackson]

I just felt like he spent too much.

[Josh Gondelman]

Yeah.

[Erin Jackson]

You know.

[Jameela Jamil]

Fucking nightmare.

[Josh Gondelman]

Also, you paid for his drinks. Might as well let him drive you home.

[Jameela Jamil]

Did he just leave the night there at the front door and kiss you goodnight? Was there anything like that?

[Erin Jackson]

He was having a great date. He wanted to come up. He was like, can I? I was like, of course you can't come up. Oh, my God. I can't believe I let you know where I live.

[Jameela Jamil]

He drove you home? Joking.

[Erin Jackson]

The way you looked at me, I wish he hadn't.

[Josh Gondelman]

Yeah.

[Jameela Jamil]

Did he try and kiss you?

[Erin Jackson]

Oh, God, no.

[Jameela Jamil]

Okay.

[Erin Jackson]

No. The whole ride home, I was, like, in the door, like, I just wouldn't. I just kept thinking I smelled pee. Like, I just was making things up. I was just like, oh, this is all this guy's.

[Jameela Jamil]

I can't believe you let him drive you home. I'm very. I'm impressed with you and disappointed all at the same time.

[Erin Jackson]

I'm glad I did because it would be great for material.

[Jameela Jamil]

Yeah, exactly.

[Josh Gondelman]

Which you can say no.

[Jameela Jamil]

Also, you weren't about to spend one more damn cent on this evening.

[Erin Jackson]

Thank.

[Jameela Jamil]

Thank God he drove you home. All right, we're going to a break.

[Green Chef Ad Voice]

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[Erin Jackson]

Dude, did you order.

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[Josh Gondelman]

You look the same.

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But with this camera everything looks better. Especially me.

[Erin Jackson]

You haven't changed your hair in 15 years. Selling please check Please New and existing.

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[Josh Gondelman]

AI had the time of my life. AI never failed this way before.

[Paige Desorbo]

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[Josh Gondelman]

And I owe it all to you.

[Paige Desorbo]

Try Monday Sidekick AI you'll love to use on Monday.com hey, I'm Paige Desorbo and I'm always thinking about underwear.

[Hannah Berner]

I'm Hannah Burner and I'm also thinking about underwear, but I prefer full coverage. I like to call Them? My granny panties.

[Paige Desorbo]

Actually, I never think about underwear. That's the magic of Tommy John.

[Hannah Berner]

Same. They're so light and so comfy. And if it's not comfortable, I'm not wearing it.

[Paige Desorbo]

And the bras. Soft, supportive, and actually breathable.

[Hannah Berner]

Yes. Lord knows the girls need to breathe. Also, I need my PJs to breathe and be buttery, soft, and stretchy enough for my dramatic tossing and turning at night. That's why I live in my Tommy John pajamas.

[Paige Desorbo]

Plus, they're so cute because they fit perfectly.

[Hannah Berner]

Put yourself on to Tommy John.

[Paige Desorbo]

Upgrade your drawer with Tommy John. Save 25% for a limited time at tommyjohn.comfort. see site for details.

[Jameela Jamil]

And we're back. Okay, Erin, give me some wrong turns. Big ones.

[Erin Jackson]

So, Josh, you will. You will know this.

[Jameela Jamil]

He's so excited.

[Erin Jackson]

Whenever. When you're young in comedy, you absolutely think you're funnier than you are.

[Jameela Jamil]

Okay.

[Erin Jackson]

Right. And you absolutely think that you are ready for. I mean, people have laughed at you. So. Yes. Accept opportunities to make people laugh. And so this is when I was still living in D.C. and there was this event called the Black Family Reunion. And it's like a big celebration on the National Mall. You know, there's food vendors, all kinds of stuff, performances. And they were. They were looking for comedians. I saw this, and I told one of my other comedy friends, they're looking for comedians to do this. You had to go and you had to audition with, like, one minute of material.

[Josh Gondelman]

Oh, yeah.

[Erin Jackson]

And then you got the opportunity. You got the opportunity to perform on the Jumbotron, on the stage or whatever. And I was like, oh, my gosh. They picked me. Absolutely. Now, what I didn't know is no comedian wants to do this. Like, nobody. So outside in the daytime on a giant stage. And it was like, it was not a comedy stage. It was like, we have a dance troupe. We have a judo. Like a karate exhibition. We have, you know, and now Joe. And so, of course, me not knowing.

[Jameela Jamil]

It again, you also are, like, just sort of dwarfed by this massive stage. And you're just there, and it's not built for interactions. Yeah.

[Erin Jackson]

I mean, I'm not gonna pretend I was good at that point. I mean, I probably had, you know, maybe five, ten minutes, maybe five, six minutes of jokes, but I'm gonna do five.

[Josh Gondelman]

Yep.

[Erin Jackson]

So I think that also when you're.

[Jameela Jamil]

Young, you're the funniest person, you know, at that point. You know, that's the thing that pushes you towards comedy. You're the funniest Person in your friend group, everyone dies over you.

[Erin Jackson]

So I was excited about it. And so I invite tons.

[Josh Gondelman]

That's the twist.

[Erin Jackson]

I invite, so you don't invite. My parents did not live in Washington D.C. they drove to see me almost three hours from where they live in Virginia. It was the first time they were seeing me do comedy.

[Josh Gondelman]

No.

[Erin Jackson]

Since their daughter pursuing this crazy dream.

[Jameela Jamil]

Be like, I'll show them, I'll show them.

[Erin Jackson]

I mean, I hadn't quit my job yet, but. So they drove up and they were like, wow, you're gonna perform at this? Like, wow, maybe you're way funnier than we ever knew in the years we've known you.

[Jameela Jamil]

It's like that scene in Sister Act 2, you know, where the mum finally gets that Lauryn Hill can sing and she's like, he's so wrong.

[Erin Jackson]

Except the total opposite.

[Josh Gondelman]

It's just like that classic reverse Lauryn Hill situation.

[Erin Jackson]

Reverse Lauryn Hill. So yeah, I get on stage and.

[Jameela Jamil]

I'm.

[Erin Jackson]

Maybe three words in to my, to my five minute set and it's boo. But it's like, it's boo just for the cause. I'm sure I didn't even look like I belonged up there. I think I'm just telegraphing that I'm not. Cause I was like, I haven't even said anything not funny yet. I haven't said anything.

[Jameela Jamil]

Right.

[Josh Gondelman]

Nobody could have been funny.

[Erin Jackson]

Right? Nobody could have been funny.

[Jameela Jamil]

What happened? Why?

[Erin Jackson]

What happened was I think I just, just got overwhelmed and probably wasn't confident. So I was gonna say a thing that I knew was probably funny, but the energy. And you can't be not confident around black folks. When you hop on a stage, like if you've ever seen Showtime of the Apollo, you know you've gotta get em. And they were booing me like it was Apollo. It was like this, it was like. Cause it was like a sport now.

[Josh Gondelman]

Right?

[Jameela Jamil]

Right.

[Erin Jackson]

And the one thing we know about.

[Jameela Jamil]

Comedy, such a crazy contagion in society. It's so crazy sometimes you don't even. Sometime I don't even know what people are booing.

[Erin Jackson]

No, they did. And I'll just join in.

[Josh Gondelman]

Feels good to me.

[Jameela Jamil]

I'll just join in.

[Erin Jackson]

No, the booing way back, I'm like, you have no idea.

[Josh Gondelman]

You haven't even heard the light from me. Hasn't reached your eyeballs yet and you've already started saying boo.

[Erin Jackson]

And they always tell you in comedy, gotta do your time.

[Josh Gondelman]

Yep.

[Erin Jackson]

You can't get off early, you gotta do your time.

[Jameela Jamil]

How long is it on set. Okay.

[Erin Jackson]

But the five felt like 50. I mean, and I was just up there, and I could. Could see my parents.

[Jameela Jamil]

No, because it's daylight.

[Erin Jackson]

You can see everyone. And I just was like. And so to drive me back to my apartment, I get booed. I do the time I come off, and I'm like, wow.

[Jameela Jamil]

Do you get booed for the entire five minutes?

[Erin Jackson]

Yeah.

[Jameela Jamil]

So no one. Then there was, like, they were dancing into the booth.

[Erin Jackson]

There was because. And there was, like, somebody they knew was coming up next.

[Jameela Jamil]

So they were like, boot that.

[Erin Jackson]

Pretty much. I was like, are they trying to scare me?

[Josh Gondelman]

What kind of boo is this? We learned the choreo. How did they coordinate this?

[Jameela Jamil]

It's like a flash mob of boos. Yes. Oh, man.

[Erin Jackson]

So, yeah, it was a very silent car ride back to my apartment.

[Jameela Jamil]

So humbling. Yeah.

[Erin Jackson]

But I was really. I figured this. I'm like. I was on a Jumbotron. But like, in real life, like, once I got off that stage at the event, I was like. I was so little compared to how big I was on two Jumbotrons, one on either side of the stage. I was like, people probably didn't know that was me. You know what I mean? So I just kind of scurried, worried. Yeah.

[Jameela Jamil]

Delulud your way out.

[Erin Jackson]

Yeah.

[Jameela Jamil]

Yeah. That's what I had to tell myself. That's so insane. I can't believe you were on a jumbotron. You did not mention that at the start. I did not understand.

[Erin Jackson]

That's the only way at a national mall. Two giant Jumbotrons. And I've seen it.

[Green Chef Ad Voice]

How many people are in this crowd?

[Erin Jackson]

I mean, think about the memorial to the. I mean, it's a huge event.

[Josh Gondelman]

Several thousand.

[Erin Jackson]

The summer event. Yeah, yeah, yeah.

[Jameela Jamil]

Holy fucking shit.

[Erin Jackson]

And it's called the Black family reunion. But they didn't make me feel very welcome. I didn't feel like they loved me. Like family.

[Jameela Jamil]

I need you to go back there and get your fucking justice.

[Erin Jackson]

I will never.

[Jameela Jamil]

Okay. That's right. No, that's a better call. That's a better call. Give me another wrong turn that you have.

[Erin Jackson]

Oh, man. Another.

[Jameela Jamil]

Wait, did. She was there too.

[Erin Jackson]

No, I have another one. Yeah, I was being coy.

[Jameela Jamil]

Okay.

[Josh Gondelman]

Me.

[Jameela Jamil]

Oh.

[Josh Gondelman]

That was my one embarrassment.

[Erin Jackson]

I mean, it's the only time I've ever been embarrassed. Except for the time. Okay. Because I'm gonna give you two stories, but they're, like, both comedy related. Is that okay?

[Green Chef Ad Voice]

I love it.

[Erin Jackson]

Okay, so it's. Covid is not. Covid is winding down Cause Covid is still here. But, like, you know, the solo time was winding down and so started comedy in dc. DC Improv was my home club. Love that club. And when Covid was, you know, people could start gathering again for real. Like, the grand reopening of the Improv. They invite me to do it. I'm, like, so honored.

[Josh Gondelman]

That's really lovely.

[Erin Jackson]

It's my home club. I'm excited. I get to be around people again and perform for a room. And I was so excited. So, like, everybody that I knew, you know, from school and everything, everybody came out and I had a great set. And I was like, oh, man, these are my people, my club family, my Howard family, my friends. And I was like, you know, walking off at the end of the set. And they had changed some things from on this. You know, they changed. Redesigned the club a little bit. Stage was smaller. Like, things were. And so when I got ready to leave the stage, I literally stepped off the stage. Like, I stepped and there was not a step and I just fell and, like, fell in front of. And I didn't fall on a table or into people. Just.

[Jameela Jamil]

Which part of your body hits the ground first?

[Erin Jackson]

I caught myself.

[Jameela Jamil]

Okay, Okay.

[Erin Jackson]

I caught myself like a.

[Jameela Jamil]

How high is the stage?

[Josh Gondelman]

Start doing push ups.

[Erin Jackson]

I meant to do that.

[Josh Gondelman]

Just getting my workout in.

[Erin Jackson]

Would you say? How high was it?

[Jameela Jamil]

How high was the stage?

[Erin Jackson]

I mean, the stage is very close. It's not. I would say people are probably foot level. Okay, yeah, people, like, heads are a little above my feet.

[Jameela Jamil]

Oh, shit. Okay.

[Erin Jackson]

Yeah, but you know what I mean. So I'm not as high as their heads, but high enough that there was.

[Jameela Jamil]

That's a significant. Yeah, so you land like a cat.

[Erin Jackson]

So I land. I mean, I didn't land like a cat, but I caught myself. I didn't, like, hit my head or anything.

[Jameela Jamil]

Okay, fine, fine, fine. I'm imagining like a Catwoman or like an Avengers lab.

[Erin Jackson]

It will be in my. In my mini series. But. Yeah, and so then there's, you know, you go to the green room. You go off to the green room. And then it's like after the show and all these people are there to see me, and I'm, like, supposed to go out and greet them because of course I want to. I want to see people.

[Jameela Jamil]

But I was like, did the audience clock it? And.

[Erin Jackson]

Oh, yeah.

[Jameela Jamil]

Oh, yeah.

[Erin Jackson]

Like, it was like, oh, God. Oh, I'm leaving out the. Okay, so. But it was like, people I knew. A lot of people I knew. So the people, like, right in the Front were people like, were friends.

[Jameela Jamil]

Oh, yeah.

[Erin Jackson]

And so they didn't laugh in my face. Like, they're like, are you okay? And I was like, I'm fine. But I went into the game and I just didn't want to come out and greet anyone. And I just was like, they're not going to leave. They're waiting for me. And I was like, no, I would like to quarantine again. Sit in here and not talk to anyone. And if I could stay for another 10 months, that would be great.

[Josh Gondelman]

Don't come. You probably shouldn't.

[Erin Jackson]

I think I got Covid when I fell, so I think you guys should probably just back home.

[Josh Gondelman]

Who's on the ground?

[Erin Jackson]

Just go home.

[Jameela Jamil]

I licked someone sick on the ground.

[Josh Gondelman]

There was some loose Covid lying there.

[Erin Jackson]

Yeah, it was like. And you have to just.

[Jameela Jamil]

You just. Yeah, you had to eat shit in front of that entire crowd. I was once on television and having a paint fight with a picture and we. We're chasing each other and then he runs after me and the. Because we're painting for this show, the floor is covered in plastic lining and someone hasn't taped the plastic lining down properly. So I trip over on it. I go flying in the air and I break my fall with my face. No, I don't do an Avengers Landing. I do whatever the opposite of that is. I break my nose. I break my front tooth in half. I've still got it. I'll show you later. I A crack across the top and I had to stick it back on with eyelash glue to keep filming. I had a concussion and I think I fractured my elbow. Cause it bent way the wrong way in the video. And this was before the Internet and like virality was really a thing. So instead they just showed it every two hours on the biggest channel on national television in the United Kingdom. Me going in the ambulance, being pulled out, the ambulance going in without a tooth coming out with a sort of snaggle tooth. I did not make any more than scale. It was a charity project. So obviously I also wasn't going to sue, but. Yeah, I feel you. I don't know why we still feel so embarrassed about falling over. It's such a natural human thing. But it just feels so undignified. Whenever I see people in New York tripping over in the street, they always have to look back angrily at the road to see what tripped them up and make sure that people know it wasn't my fault. It was the fucking street. It was out there.

[Josh Gondelman]

There's a log there who is that log?

[Jameela Jamil]

Humiliated and angry. I feel you. I feel you. Yeah, comedy is in and of itself just. It's a call for indignity. Oh, man. Well, I'm glad to see that you're on two feet today. You're still, well, still happy. And thank you for those fucking wonderful stories. We'll be right back after the break.

[Josh Gondelman]

Monday Sidekick. The AI agent that knows you and your business, thinks ahead and takes action. Ask at anything seriously. Monday Sidekick. AI you'll love to use. Start a free trial today on Monday.com.

[Paige Desorbo]

Hey, I'm Paige Desorbo and I'm always thinking about underwear.

[Hannah Berner]

I'm Hannah Berner and I'm also thinking about underwear, but I prefer full coverage. I like to call them my granny panties.

[Paige Desorbo]

Actually, I never think about underwear. That's the magic of Tommy John.

[Erin Jackson]

Same.

[Hannah Berner]

They're so light and so comfy. And if it's not comfortable, I'm not wearing it.

[Paige Desorbo]

And the bras? Soft, supportive and actually breathable.

[Hannah Berner]

Yes. Lord knows the girls need to breathe. Also, I need my PJs to breathe and be buttery, soft and stretchy enough for my dramatic tossing and turning at night. That's why I live in my Tommy John pajamas.

[Paige Desorbo]

Plus, they're so cute because they fit perfectly.

[Hannah Berner]

Put yourself on to Tommy John.

[Paige Desorbo]

Upgrade your drawer with Tommy John. Save 25% for a limited time at tommyjohn.comfort. see site for details.

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[Jameela Jamil]

And we are back. All right, Josh, it's time for your wrong turn.

[Josh Gondelman]

Yeah, I'm again a really embarrassing person. I'm trying to cure myself of It. I used to just be too soft for this world, like, mentally. In addition, I'm a pretty.

[Jameela Jamil]

Why?

[Josh Gondelman]

I don't know. I think my parents did too good a job where I was just like, this is fine. It's out on Sesame Street. The trash can's gonna talk to me. There's gonna be a big ass bird I don't have to be afraid of. Everything's fine. They're just very sweet people. So I came out soft under baked. Like, if you. I needed a few more minutes in the oven, which as a Jew, pains me to say, but I did.

[Jameela Jamil]

Oh, my God.

[Josh Gondelman]

We're not supposed to pine for ovens, but I needed a little more baking. And so I realized the fraughtness of this metaphor. You don't have to leave this in the podcast or you can, you can.

[Jameela Jamil]

I truly, I was holding back, saying, this is why Indians use the slipper, is to. That's how we cook our children. And we cook them with the slipper.

[Josh Gondelman]

Just a little heat, a little slippery.

[Jameela Jamil]

Yeah, yeah, yeah.

[Josh Gondelman]

So I. Between my. At the end of my sophomore year in college, I was dating someone who's now a very good friend. We were great friends, but we weren't dating compatible when we were like 18, 19.

[Jameela Jamil]

Is it cause of pheromones?

[Josh Gondelman]

It might have been a pheromones thing.

[Jameela Jamil]

Right, right, right.

[Josh Gondelman]

They might have been wrong.

[Jameela Jamil]

Okay.

[Josh Gondelman]

Yeah, yeah. So we'd started dating and then she went away for the summer. But I was living on campus and I could feel this was like flip phone era. And it was pre unlimited minutes. You never think about how many minutes you can talk on the phone for. But it was like rent. You were just obsessed with minutes, amounts of minutes, thinking about them all the time.

[Jameela Jamil]

Yes, I remember this time.

[Josh Gondelman]

And so this was the minutes era. And so we would talk. Like, I would buy a phone card and call her home. She was living with her parents. And I would call from my, like, dorm room phone. And I could feel that she was like, not feeling it. And instead of having.

[Jameela Jamil]

Yeah. What was giving it away, just like.

[Josh Gondelman]

Harder to schedule phone calls with. It was more. And then more time of like, oh, yeah, you caught me just running out the door, so we'll catch up later. And I would be like, I had like a 9 to 5 on campus. And I would be like, oh, this.

[Erin Jackson]

Would be so fun.

[Josh Gondelman]

We'll talk at the end of the day. And she'd be like, oh, I'm like, doing other things.

[Erin Jackson]

And I'm like, oh, okay.

[Josh Gondelman]

And it like, nightmares are free. Yeah, right, right, right. Well, that's part of it too, where it would be like, well, she's on.

[Jameela Jamil]

The west coast, but we're really showing our age that we remember three nights and weekends, right?

[Josh Gondelman]

Yeah, that's when you're free. It's like, no, that's when the minutes are free. It's all about the minutes. And so, you know, it just like she, we were on different wavelengths, which is totally fine. She wasn't doing anything, like, wrong or cruel. And so I, I, instead of having any kind of human dignity and going like, I feel like we're maybe not.

[Jameela Jamil]

On the same planet, I'm using my minutes on someone else.

[Josh Gondelman]

Yeah, that's right. I'm saving my minutes for someone who vet.

[Jameela Jamil]

I'm saving all my minutes for you.

[Josh Gondelman]

Perfect. I got into like, I was like, I'm gonna solve this with bits. Like, I'm gonna bit my way through. The only way out is bits. And so I started sending care packages. I was like, oh, this is fun. We're long distance. This is a fun, romantic thing. So I was doing these elaborate bits.

[Jameela Jamil]

Oh, bits, sweetheart. What was in them?

[Josh Gondelman]

Oh, boy. We'll get there. An example is I once was out at a bookstore and they had or used bookstore and they had a Bon Jovi themed comic book. It was like, here's the comic book tale of Jon Bon Jovi. And so I bought the, bought the Bon Jovi comic and I put it in an envelope and 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 of the Bon Jovi fan club.

[Jameela Jamil]

And is this a running joke between the two of you? Oh, my God.

[Josh Gondelman]

I was trying to get it running. You know, I was trying to couch to 5K this week.

[Jameela Jamil]

But also, if someone can't hear you, right, if someone hasn't got your turn, they're not imagining the fun movie voices of welcome to the Bon Jovi. They're just imagining welcome to the Bon Jovi.

[Josh Gondelman]

Hurtful impression of me, but sure, yeah, yeah, yeah.

[Jameela Jamil]

That's not my impression.

[Josh Gondelman]

We all heard it.

[Jameela Jamil]

That's my impression of someone who starts at actual Bon Jovi film.

[Josh Gondelman]

Oh, sure, sure, sure.

[Jameela Jamil]

You know what I mean? It's like, you know that guy who's like, welcome to Earth Day. This is my girlfriend, the guy on TikTok.

[Josh Gondelman]

So yeah, she. And it was like, you know, she was very gracious and I sent one that was like a spy thing. It was like.

[Jameela Jamil]

And did she Send you anything back? Any cash packages?

[Josh Gondelman]

Occasionally, yes. She sent me cookies. They're really good cookies.

[Jameela Jamil]

Cease and desist.

[Josh Gondelman]

I was like, why does this. Why is the return address a law office? No, she sent cookies one time, but I was like so committed and kept like escalating these bits. So I got like cassette tape for a boombox, an audio cassette. And I unspooled the thing and I wrote a message that I taped along it and then tried to spool it back in and sent that in an envelope and just chaos. And it was like we broke up. My memory is within instance of her returning to campus. I think it was probably within four days. And it was like. Yeah, it was just so. I just didn't know how to be, you know, and instead of being like an adult at all and just. And you know, I was 19. This wasn't like I did this in my mid-30s and was like, hey babe, wanna. How about bits? Which I still do, but in a less embarrassing way, I think. And we just like really did not help. Humiliating.

[Jameela Jamil]

Yeah. I mean, just for whatever it's worth. And I'm not hitting on you. You were exactly my cup of tea. And if we'd been 19 together, that's very cool. I would have written you back. Way too much back.

[Josh Gondelman]

That's really nice.

[Jameela Jamil]

Thank you. I went through a phase of taking people on the most expensive, elaborate first date you've ever heard of. And it's so humiliating when I now go back and look and also like these were both men who don't love to be chaste. I feel like as a gender where I'd be like, hey, I've got a really funny idea. I've got this date I want to take you on. It would always be like the early date, like second or third date. I was like, meet me at, at 7am on Tuesday morning. And I want you to take this shopping list and you have to go and you have to buy everything on this shopping list beforehand. It's like $100 worth of shit. Right. It's 12 toilet rolls, six eggs, a Brillo pad, which is what you use to scrub the really difficult parts off a dish. It's a tartan paint which doesn't exist. So I'm just sending them on a wild goose chase. Hiking socks, but not shoes. A tuxedo and a passport. So they think they're being sort of sex trafficked.

[Josh Gondelman]

Sure.

[Jameela Jamil]

And I'm telling them to meet me at 7:00 in the morning. By the way, not 19, not 19.

[Josh Gondelman]

Love. Sex trafficking a man in a tuxedo. Like, how about this one?

[Jameela Jamil]

Didn't kiss anyone until I was 21. So I'm in my mid to late 20s when I'm doing this shit. Okay. Should know better at this point. So inept. So they meet me and I feel like you guys are gonna be with me on this, right? They meet me at 7am in the. Exhausted, terrified, holding two bags of really expensive bullshit. Annoyed to be up at 7, not sure what this is gonna be. Not really in the mood to have sex. And I'm like. I blindfold them, which escalates the trafficking fear for sure. I take them in a cab to an undisclosed location and I sell them. No, I don't. And so I, and I, I remove the blindfold and we're at King's Cross station in England, which goes directly to Paris on the Eurostar. And I've bought them a ticket to.

[Josh Gondelman]

Paris with me for like a third, Second. Third day.

[Jameela Jamil]

For a second or third day. Don't know these people at all. Such a long time to commit if you don't know you have any vibe with each other. So then we go on the two and a half hour train to Paris at 7am when we get there, I've arranged for lockers that we will put our tuxedo and my lock, like ball gown in. And we.

[Josh Gondelman]

This is incredible.

[Jameela Jamil]

So mad. And I would think I was just always trying to create a movie.

[Josh Gondelman]

Yeah.

[Jameela Jamil]

And so we're in. So ball gown and tuxedo in the lockers, we lock them up, we go to Disneyland Paris.

[Josh Gondelman]

The most romantic place.

[Jameela Jamil]

The most romantic place. And we go on enough roller coasters that we almost throw up. And then at 4pm we have to go back to the lockers in the station, change into tuxedo and gown, we make a run for it across Paris to the Eiffel Tower where there's a restaurant. It's costing me like a thousand dollars. It's a long time rent.

[Erin Jackson]

Did you do this?

[Jameela Jamil]

I did this several times with several different men, none of whom know until this moment now that that was a bit that I did. Like, they all thought that they were the only one who. I did this like, crazy thing because I was so in love, by the way. Didn't even feel anything for these people. I was trying to create momentum, right. I was like, oh, it's not there. It's because I'm not trying harder. I need to create. You were romance pe.

[Erin Jackson]

Yeah.

[Jameela Jamil]

You're like, I need to create. I need to cook the romance you know, but that's not a thing, and I know that now. So. Yeah, So I would take them to Paris, and then we would get home on the last trip 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.

[Josh Gondelman]

International Travel Day 2.

[Jameela Jamil]

Yeah. Yeah. So if that makes you feel any better, I was older than you.

[Josh Gondelman]

I had no idea how much better.

[Jameela Jamil]

This makes me feel. 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. I know exactly what you were imagining when you sent those packages.

[Josh Gondelman]

Extremely beautiful. This is like, you've, like, let out, like, you know, the New York summer fire hydrant, kids playing in the. That's what you did to, like, the endorphins in my brain. You just, like, fucking banged at that with a wrench until endorphins started flooding out.

[Jameela Jamil]

I'm so happy that I'm so pathetic that I made you feel better about yourself.

[Josh Gondelman]

You went over the top on both. Financial capacity, effort. Now I'm starting to feel bad that I wasn't as good at being a loser. I was just a regular loser.

[Jameela Jamil]

Oh, no. And I'm a super loser.

[Hannah Berner]

No, you're like a.

[Jameela Jamil]

No, it's true. It's true.

[Josh Gondelman]

Well, look, we've heard your impression of me, so we don't kind of lose.

[Jameela Jamil]

Well, mine is. Welcome to Paris.

[Josh Gondelman]

Thank you.

[Jameela Jamil]

So, yeah, on that note, everyone, now that I have been established as the greatest of all the losers of all.

[Josh Gondelman]

Time, that was so generous of you to share.

[Jameela Jamil]

Thank you.

[Josh Gondelman]

And it, like, really means the world to me, so thank you.

[Jameela Jamil]

You're welcome. Well, on that note, I feel like you've both made me feel less alone and more alone within just one hour. You're both such a fucking delight and I adore you so much, and I feel so thrilled to get to meet you in person to hear your tales. Can you kindly tell where they can find you and what you want them to watch and listen to?

[Erin Jackson]

Sure, you can find me at ej the comic on every platform. And yeah, watch videos and yeah, like, pictures and come see me. There's a tour. Ah, there's a tour link on my pages. So if I'm in your town, come see me. Be funny and I'll try not to.

[Jameela Jamil]

Fall off the stage 100%.

[Josh Gondelman]

I am Oshgondelman G O N D E L man across social media. Joshgondelman.com for clearinghouse of you can find my specials and a book and tour dates. New Stand up special coming soon and I write a newsletter called that's Marvelous. That's full of jokes and pep talks and that also has my tour [e-mail] Amazing.

[Jameela Jamil]

Subscribe yeah. Thanks for watching Amazing. I adore you both. They're both so fucking funny. Go watch everything they do. You are delights. You restore my faith in humanity. Thanks for coming to Wrong Turns. Sorry this line fell off at the fucking star.

[Josh Gondelman]

No, it was so perfect. The medium is the message.

[Jameela Jamil]

Wrong Turns was created and produced by me, Jameela Jamil and Stuart Bailey. And thank you to consulting producer Colin Anderson. You can email us a voice memo of your own Wrong Turns. All you have to do is email personal disaster storiesmail.com you can find fun length videos of our episodes on YouTube. And don't forget to subscribe like review wherever you get your podcasts and tell.

[Green Chef Ad Voice]

Your friends about us.

[Jameela Jamil]

And if you are also enjoying me as a person, I have a substack. It's called A Low Desire to Please. That's enough of me. I'm gonna fuck off now. By.

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[Josh Gondelman]

You look the same.

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[Erin Jackson]

You haven't changed your hair in 15 years. Selfies check please.

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[Jameela Jamil]

Boost Mobile Boost Mobile will give you a free year of service. Free year when you buy a new 5G phone.

[Josh Gondelman]

New 5G phone enough, but I'm your hype man. When you purchase an eligible device, you get $25 off every month for 12 months with credits totaling one year of free service. Taxes extra for the device and service plan online only.