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Randy Sklar
AI had the time of my life a I never felt this way before.
Jameela Jamil
From building timelines to assigning the right people, and even spotting risks across dozens of projects, Monday Sidekick knows your business, thinks ahead and takes action. One click on the star and consider it done.
Randy Sklar
And I owe it all to you.
Jameela Jamil
Try Monday Sidekick AI you'll love to.
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Jameela Jamil
Hello and welcome to Wrong Turns.
Randy Sklar
Hello. I feel like we made the we made the right turn coming here.
Jameela Jamil
Yes, you did. Well, we'll see. We're only at the very beginning. This is the podcast where shame loves company, misery loves friends, and I get to invite mine on to come and tell me their favorite miserable stories. Where there was no great silver lining, no great wisdom learned. We're here just to marinade in our shame. And I have two perfect people to do it with. Two incredibly funny comedians, writers and actors have appeared in It's Always Sunny in Philadelphia, Curb your enthusiasm and Better Call Saul. Together with Daniel Van Kirk, they host the hilarious podcast Dumb People Town. Randy and Jason Sklar, you are the best.
Randy Sklar
Hello.
Jameela Jamil
Welcome. How are you?
Randy Sklar
Wonderful intro. So nice to be here. Can I say that we once we're developing a TV show that took place in St. Louis, which is where we're from, called Missouri Loves Company.
Jameela Jamil
Yeah.
Randy Sklar
Why like we love.
Jameela Jamil
Why didn't that get made?
Randy Sklar
I don't know. I don't know title alone. It should have gotten a pilot. We always say in the world if we're going to have some experience with our family, with our lives, ourselves or whatever, it either better be really, really bad so that you get a great story out of it or really great if it's middle, then we're Miserable. What are we even doing? Miserable. Why?
Jameela Jamil
This is crazy. To experience you both together in person. Like the. The literal finishing of each other's sentences.
Randy Sklar
It's. Well, you say it's finishing each other's sentence. I say I haven't been able to finish a sentence in 49 years.
Sponsor/Advertisement Voice
Stop it.
Randy Sklar
God damn it. And it's 53. I don't know why I made us younger. I don't know why I made it that we started talking.
Jameela Jamil
No, I think you just made yourself younger and excluded yourself from the twin dynamic.
Randy Sklar
I think we started finishing other sentences at age 4.
Jameela Jamil
Which one of you would you say is more prone to bad decision making?
Randy Sklar
Ooh, I make a lot of bad decisions. I. I really. There are moments. Jay's a little more measured than I am, but I've definitely. No. I made some horrible decisions in my life. When you become a parent, that's like. You have to make a thousand decisions. Your receptors are down. You're tired.
Jameela Jamil
You haven't slept.
Randy Sklar
You've been worn down by the forces around you, beaten down by love. Like, in life, when you're out there and you don't have kids, like, you're number one on the call sheet. You come home and you're, like, the extra who has to wait till after the cast eats. There's no chicken left. Fine. Breadstick.
Jameela Jamil
And I love half a waffle fry.
Randy Sklar
One hot, like, burnt waffle fry. That's it. So, like, you're worn down, you make weird decisions, you make bad decisions, and that's. Oh, my God, I've screwed up so much.
Jameela Jamil
Do you recommend parenting to people when.
Randy Sklar
You'Re, like, meeting them 100 million percent? Yeah. Okay, wonderful.
Jameela Jamil
Because the way you sold it just.
Randy Sklar
Now made mine worst thing ever. That everyone.
Jameela Jamil
My vagina just went.
Randy Sklar
Yeah, I know. And it should. 2. I'm telling you, two things can be true at the same time. And that's something that I don't think we can hold anymore as, like, a people anymore.
Jameela Jamil
No, no, no, no.
Randy Sklar
There are two truths in your hands at the same time. It is the hardest. It is the most humiliating. It will destroy you. It will crush your confidence. It will bankrupt you. It will emotionally bankrupt you. It is also the greatest thing you can ever do in your life and will provide you with tons of comedy if you're a comedian, if it makes sense for you.
Jameela Jamil
I do it for the bit.
Randy Sklar
Oh, yeah. Everything for the bit. It'll provide you with joy like you've never known. And. And it's the thing you live for.
Jameela Jamil
Can you give me some examples of some micro humiliations? The type of things that might occur on a day to day basis?
Randy Sklar
I mean, so I, I will boil this down in the shortest way possible. I. My son's 16 and wanted a car. His kids didn't want to drive. And 17 and 19 and they don't. They don't have the license. My kid wanted a car immediately and he was. So I'm their father and their Uber. Thank you very. Where's my camera? Thank you. Talking about micro humiliations. All right, so I. My wife and I were like, yeah, you can get a car, but this is how much we're going to spend. He's like, I raised. I have more money from these parties he threw. I can't even get into it. And he had some more money.
Jameela Jamil
What parties was he throwing?
Randy Sklar
He and his friends figured out parties that freshman kids at all the high schools in the Valley had nothing to do. And so they would set up Instagram accounts that people could friend and they knew a bunch of kids from all these different schools. And then they would come to this party and they would charge 20 bucks ahead and they would have a DJ and they would have food and they would have security and all this stuff, and they just made a bunch of money. Overall.
Jameela Jamil
Little mogul Fire island boy going, so he.
Randy Sklar
It was probably better food than the Fire fest.
Jameela Jamil
Yeah.
Randy Sklar
No one. Who do I have to blow to get a bottle of water? No one said that. So. So my son. I'm actually asking that in here. Is that so we said, okay, if you want to use your money and, and upgrade to a nicer car, you can. So he got a way nicer car. And because I don't know anything about cars, we're leasing it. We're like, are you sure, like, you can handle this? You're new to the car. Yes, yes, yes. Here's how nice of a car it is. Every time he tells someone who knows about cars, who knows about cars, what the car is, they're like, whoa. Or I'll hear this. Oh. Anytime someone sucks in air and smiles at the same time, you're like, oh, we screwed up. That's a big. That's a big screw up.
Jameela Jamil
Big old screw up.
Randy Sklar
We're like, no, he can handle it. He's a mature, responsible kid. Six weeks after he had a total sakara. Now.
Jameela Jamil
Yeah, he's throwing illegal parties. Like, this is who I want to trust with my finances.
Randy Sklar
This level of car. Correct. The young Egan Schrager. So he. So he totals the car but because it's a nice car, we get the insurance back and it's, it's worth more than we leased it for. So now he made a few thousand more dollars.
Jameela Jamil
Do you give him that money or.
Randy Sklar
Do you keep that money all wrapped up in BMW financials so that they now force you to get another car? So, so then he comes back to go see, he's like, okay, I need to level up to a slightly better car. I'm like, what are we doing? He's like, you can't fuck up and then level up.
Jameela Jamil
He's the epitome of the American dream. He's going to be the President of the United States one day.
Randy Sklar
Thank you. Thank you.
Jameela Jamil
This is a mentality.
Randy Sklar
This is more important than I would say, calculus, right?
Jameela Jamil
Yeah.
Randy Sklar
100%.
Jameela Jamil
Who needs geography? Who needs igneous rock?
Randy Sklar
Thank you. Chemistry. Like, what elements? Here's the one element you need. The ability to level up.
Jameela Jamil
Shamelessness.
Randy Sklar
Yeah, shamelessness. So he writes a 12 page essay, Google Doc shares with my wife and I, and he's like, I think we need to do this. And if we do this, then we can sell the car before I graduate. We don't have to lease a car. So now he's in a nicer car and I'm like, am I the dumbest parent in the world? Am I just too tired to fight this fight all the way to the end? Am I or am I the greatest parent in the world? I don't know. But it is a borderline humiliation when people ask me every time they say, what car is your. Oh, your son's driving. What car is he driving? And I literally have to be like. I can't say the word out loud.
Jameela Jamil
It's a Bugatti, isn't it?
Randy Sklar
No, it's not a Bugatti. I would be amazing if it was a Bugatti.
Jameela Jamil
I mean, it feels like a Bugatti.
Randy Sklar
What it is. Say what it is.
Jameela Jamil
Say it.
Randy Sklar
You've owned up to own up. I already said the name of the company. It's a BMW M3. How old is he? He's 16.
Jameela Jamil
For sake.
Randy Sklar
Humiliation. Micro humiliations.
Jameela Jamil
100%.
Randy Sklar
Right? So I don't, I can't talk. My kids don't talk.
Jameela Jamil
You know, doormat's already lying down before people wipe their feet all over it.
Randy Sklar
Like, I get it. Micro humiliations. I brought it on to myself. Or am I creating a future mogul? Am I an oligarching? Yeah, right? And as we all know, oligarchs run this country. Right?
Jameela Jamil
100%.
Randy Sklar
You hear that, Beyonce? Sorry. No, we can do it. We're Jews. We're taking it back. We get to do this. All right. We're literally taking it back. Point is, maybe now that we ever had it in the first place, but whatever, we're taking it from that.
Jameela Jamil
Did you just pull it back?
Randy Sklar
Yes. I take it. And a lot of people think that Elon Musk was doing that. That was my favorite one. People were trying to say that he wasn't doing a Nazi. They're like, he's autistic. He was trying to dab. Stimming. He was trying to dab. He forgot half the dab. He was a dab on the spectrum.
Jameela Jamil
But my favorite thing was when everyone was like, no, it's clearly everyone knows the Roman salute, guys. We all know. As if it was the Dougie. You know what I mean?
Randy Sklar
Exactly.
Jameela Jamil
Come on.
Randy Sklar
I was thinking back to the time we were first moved to LA and. And we were living. We moved from New York City. We had like a very small apartment.
Jameela Jamil
You and your wife?
Randy Sklar
No, it was me and Jason and our best friend. So we threw this huge party. We'd just come to LA and we had all this space. It's like you moved to LA from a smaller. You move from any. Anywhere.
Jameela Jamil
Big party throwing runs in the bloodline, doesn't it?
Randy Sklar
We're like, well, let's throw this. Exactly. Let's throw this party to my son and we'll invite all of our friends who are comedians, who are out here and we're just gonna have a good fun time. So we went around to all of our neighbors and said, we would like to invite you to the party.
Jameela Jamil
Oh. Because that's how you stop them from complaining about.
Randy Sklar
If you have a problem with the noise, call us. Come by and tell us. Just turning.
Jameela Jamil
Come join.
Randy Sklar
Come drink on us. So we invited like the 90 year old couple who lived like ness. No way they were coming. There was the woman across the street who at the time we were 30. We were younger than that, maybe 29. She was like mid-40s, exercised all the time. So, like in great shape. She had a horrible sob. Like old sob car.
Jameela Jamil
Okay, I thought you meant she was going.
Randy Sklar
Whatever she was doing to her face, it was time.
Jameela Jamil
And you could hear it from your.
Randy Sklar
The car was like that. So she would constantly wash her car. And she was washing it so much every day, like even the people who love their cars, it almost seemed like she was trying to water it to become a better car, to hopefully grow it into that. It could grow into a better car. So we went out and we talked to her and we said, susan, we are having this party and we'd love for you to come by, knowing that she's probably.
Jameela Jamil
Did you fancy this woman?
Randy Sklar
I didn't fancy this woman, but she was like one of the most uptight people we've ever met in entire lives. But we're like, we gotta nip this in the budget. She would call. She would call the cops. That's who would we need to get her here. She's gonna call the cops.
Jameela Jamil
What have you lined up? Let her wash your car. Maybe. Maybe that's her thing.
Randy Sklar
So we were. So we were very excited. Her fetish. This is like, gosh, cars. Other people's cars. So we go back into. This is how long ago it was 1999. We're making a mixtape off of our CDs. That's the party tape. Mixtape. So she call. So the phone call comes in on the. To the landline. Okay. This is how long ago it is. Multiple phones. Jay picks up the phone. Hello, it's Susan.
Jameela Jamil
You know, I'm not that much younger than you guys. So you keep talking to me as if like you're explaining like a land before type. So I'm from the 80s, from the 70s.
Randy Sklar
My God. Back up. So. So. Phone rings. And Jay picks it up. Hello, it's Susan. Okay, now we've invited all of our friends to this.
Jameela Jamil
Yeah.
Randy Sklar
Music blasting. I pick up the line in my room. Hello. Loud. And she's like, hello. I'm like, what's up? I think it's my friend Lisa Delarious. Okay. I immediately know by how he's responding to this woman that he has no idea. And if you didn't know if. If I knew who it was the second I said, you commented. Night. She's like, yeah. I'm like, do you know where. Do you have directions? Do you know how to get here? Do you know how to get here? Jay is like, you definitely don't know who you're talking to. Susan from across the street. This is where I should have stepped in. Stepped in? You should have stepped in. But then you were like, let's see what Randy, right? See how I'm going to step in on this plays out. So she says, can I bring a few friends tonight? Again, I think this is our friend Lisa Delarious. To which I say to. She would think this is funny. Lisa would think this is so funny. I said, sure. The more pussy, the better. To a very uptight 40 year old woman. There was a long pause. So long. Literally all of us are just listening to the mix that's being recorded. And she's like, okay. And I was like, all right, see you later. I hang up and Jay's like, and.
Jameela Jamil
You still at this point, don't know.
Randy Sklar
I run to the back.
Jameela Jamil
You think Lisa's just being very non fun.
Randy Sklar
Being non plus. She thought, like playing. He thought she was being like, fake offended, the thing. So I run back in the room like, dude, that was. That was our neighbor across the street. He's like, no, it wasn't. I'm like, yeah, it was our neighbor from across the street, you dummy. And the worst part is that, like, because every day she was out, like, watering her car, anytime I had to leave our house, she always there. I had to like, go in, park our car in the back. And then even if I wanted to go like half a block down, I just had to get in the car and drive it because I didn't want to interact with her because I knew I'd probably make it way worse. It's just the dumbest thing.
Jameela Jamil
Did you see it? Yes.
Randy Sklar
Yeah, I saw her and I made it worse by saying like, you're not that. I thought I was talking to my friend. You're not our friend. You're not. Clearly not now.
Jameela Jamil
She's like, so you don't want to fuck me and my friend?
Randy Sklar
No, I want you to water my car for. God.
Jameela Jamil
I love that. She didn't show up at the party, right?
Randy Sklar
She definitely did not, no.
Jameela Jamil
Did she call the police on you though?
Randy Sklar
She did not call the police. She did not call the police. So I think she was just stunned that I would say that.
Jameela Jamil
Oh, God. We're going to be right back after the break.
Randy Sklar
Monday Sidekick. The AI agent that knows you and your business thinks ahead and takes action. Ask it anything seriously. Monday Sidekick AI you'll love to use. Start a free trial today on Monday.com. did I talk too much? Can't I just let it go?
Jameela Jamil
Thank you so much. Take a breath.
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Jameela Jamil
Let's talk about what's going on.
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Jameela Jamil
And we are back. All right, Randy, what was your big wrong turn?
Randy Sklar
Oh my God. So I'm about to celebrate my 24th wedding anniversary with my wife, 25 next year. It's a biggie. They're all big. They're all big. If you make it this far, it's.
Jameela Jamil
All, oh my God. Yeah. In Hollywood as well. That's 75 years. It's a diamond jubilee.
Randy Sklar
I love that she put us in Hollywood. I love it. I'll take it. I'll take it.
Jameela Jamil
So especially when you're near Hollywood.
Randy Sklar
Yeah, yeah. Hollywood adjacent.
Jameela Jamil
It's a big deal.
Randy Sklar
So this is like the very first and last time I've ever planned anything remotely near a certainly an anniversary trip or anything.
Jameela Jamil
Who planned the other 23?
Randy Sklar
She did. From this point on. So on our first anniversary, like I basically. And maybe this was just me being smart about not wanting to plan anything ever again.
Jameela Jamil
You fucked it up. You gave the bad first blowjob, you know, the toothy blowjob that I'm just giving anything.
Randy Sklar
It was the toothy blowjob of anniversary trip planning. So it was toothy blowjob with braces. That's how bad this was. So like vampire tooth filings. Right?
Jameela Jamil
So just after eating some cholula.
Randy Sklar
Yeah, terrible. So I, so I planned this trip to Napa. We've never been in Africa and of course I don't do the necessary research to realize that you shouldn't really stay in Napa proper. You should go north of there. There's like nicer places. And I just was like, napa, let's go to Napa. Gotta go to Napa. This is what the 28 year old me said. We're going to go to Napa. Or 29 year old me. So we go to this place that is kind of in a neighborhood in like downtown Napa. There's Construction everywhere. It's not nice. We get up, there it is. Bed and breakfast, right? Bed and breakfast. This is pre Airbnb bed and Bed and Breakfast. It's very purple, like, and very, like Ms. Havisham, like, curtains and doilies and stuff like that. We get into our room, there's a book on the bed, and that the title of the book is the Nation's Best Christian Bed and Breakfasts. Now, I'm Jewish, and so is my wife. And I flip through to see that there's a bookmark in one of the pages that has the place that I booked as the number six Christian bed and breakfast in the country again, something I probably should have researched, did not research. And I pick up the book, and I'm like, son of a bitch. To which someone walks in, I say it out loud, and it's like, we don't curse in here. So I'm like, oh, my God, I'm so sorry. You were very cross at that moment. Terrible. So the next day, I said, I got this. We're gonna get out of here. We're not gonna hang out here. We're gonna wake up very early morning, and we're gonna take a hot air balloon ride, which I'd never done in my life. One mile up, one mile over, one mile down. That's what it's supposed to be.
Jameela Jamil
Fuck. In the room.
Randy Sklar
Oh, in that room. Yes. We got our Jewish seed all over the place.
Jameela Jamil
Yeah, yeah, yeah, yeah, yeah, yeah.
Randy Sklar
So we killed your Lord, and now we're doing this. Now.
Jameela Jamil
Came all over.
Randy Sklar
Yeah, all over it. Something's got to clean it up. So anyway, so we.
Jameela Jamil
But wait. Were you having to have, like, sort of quiet mime sex, or did you have, like, crazy loud sex?
Randy Sklar
Weren't you by the kitchen? Yeah, we were kind of near the dining room. It was near the kitchen. I could hear.
Jameela Jamil
Communal dining room.
Randy Sklar
I could hear. Oh, yeah. I could hear silverware clinking.
Jameela Jamil
So were you doing it quietly?
Randy Sklar
Were you doing it quietly?
Jameela Jamil
Or were you trying to piss each other off? Being like, oh, God. Oh, God.
Randy Sklar
Dear Lord, our Lord Savior high hath risen again. All right, anyway, so it's an Easter, so we go to this place, we go to the balloon ride. And what I really didn't check as well is that my wife is very afraid of heights. I should have thought of that up to 23 years. So we'd only been together for, like, four years, and, like, we didn't really go to a lot of high places. And so I was like, I'm kind of A little bit afraid of heights, too, but. But I was like, we should do this. It's going to be fun. It's going to be really pretty. And it was a beautiful day. It's not like just you two. You're in a basket. We're in a basket with other people. So there's like, the German.
Jameela Jamil
Why would you book her a private.
Randy Sklar
No, no. This is a big basket with like, 12 people in, including a German couple that were very menacing. I would just say describe them as. And I just was, like, uncomfortable by everybody. The pilot. The guy who pilots the thing, which I found out that's his name is he's the pilot of the balloon.
Jameela Jamil
Okay. I'm using that term quite easily.
Randy Sklar
He's up in the balloon, and there's a van driving down below that's gonna then drive us to lunch or brunch or whatever it is after we come down. So he's radioing back and forth with the van, and I find out that his nickname or his name, I don't know, is Maverick. Not a great name for a guy who's piloting a balloon. Oh, he's gonna go rogue. Yeah. And I said, no, no. I look down at his hand, and he's missing two and a half fingers on one hand, which means he's either really unlucky or really bad at what he does. Okay, so both options are terrible. I don't want to be like. That's like a. Yeah, I don't want an unlucky. Yeah.
Jameela Jamil
You don't know if it's on purpose or mistake. I don't know which one.
Randy Sklar
Either way, it's.
Jameela Jamil
Yeah.
Randy Sklar
So he radios down to the van again. My wife does not. Like, she's like, please let this be tolerating. She's like, please let this be over soon. And I'm looking at the Germans like, you know what I mean? We go up, and he's in the air, and he radios down to the van. I've got a wind and I'm going with it. What does that mean, Maverick? What does that mean? You got a wind and you're going with it? Here's what it means. We go 15 miles, like, supposed to go one mile over and one mile down. We're 15 miles. We're 14 miles away from the landing spot, and now we don't have a place to land. So he's. And the van. We see it, like, scurrying down below. The van is trying. And he's like, knock on.
Jameela Jamil
The van's gonna run out of Petrol.
Randy Sklar
At some point, he's like, knock on doors and find if we can land. I'm like, we're now at the knock on doors and find out if we can land in their lawn sort of a place. And then he's like, Maverick's like it. I see his little spot between the hill and this in this farm over here. I'm going to land it down here. Yeah. You shouldn't be wedging a hot air balloon into a tight spot. It's not like a compact carpet parking space and you're in an suv. All I know is he's like, I see a spot between this hillside and the thing is. And the last thing I heard from the fan was, don't.
Jameela Jamil
Oh, my God.
Randy Sklar
I'm like, he's going to do it. So as we start to go down and last words he heard when he was like, should I put my hand next to this fan? Don't, don't. So we go to the spot and it's like right before it's about to land, he's like, when the basket hits the ground, everybody jump up. I'm like, that can't be protocol in this instance right here.
Jameela Jamil
Now, everyone's going to lose their thumb.
Randy Sklar
Everybody jumps when the basket hits the ground, Right when the bodies hit the floor. So baskets the ground. Everybody jumps up, the basket tips over, and I'm now laying on the Germans. Okay. I get up, we come out, we realize that we're just in a farm area, like a farmland. And there are cows, which I've always thought cows were nice. They've always been nice to me. Have they ever been mean to you? No. And I watch. They'll talk shit. They won't. Like, they won't act. You met many cows.
Jameela Jamil
Are you talking about the fact that you just like brisket? Like, what's happening?
Randy Sklar
I know I didn't reveal that I like brisket, but the cow. I saw a cow chase a woman around a tree several times around the tree.
Jameela Jamil
One of the women from the balloon.
Randy Sklar
Yes, yes. Like, she basically treat her ass. Finally, the van pulls up on the road and we have to exit this farmland and climb through a barbed wire fence. Again, I jokingly said, as people were climbing through the barbed wire. This was not on the brochure. Okay. He's holding open the barbed wire, and I go to climb through and I rip my favorite jeans. Now, now, now, you're. Now, this is personal. So I'm sitting at the lunch that we're sitting at after they drive us 15 miles. And I'm like this son of a. I'm so mad. I'm like, I can't believe my. And I'm getting mad. And. And I was. I got so mad that I asked my wife to go up and complain. And she did. And she comes back. Exactly. I'm like, they're gonna listen to you more than me. And so she comes back with this, like, in a plastic sort of like, package.
Jameela Jamil
Two thumbs.
Randy Sklar
No.
Jameela Jamil
I can't believe he had those thumbs.
Randy Sklar
What a wonderful thing to know. Who's got one thumb that doesn't know how to fly air balloon? This guy. Anyway, so he. And it's like this little. It's this golf shirt. It's an orange golf shirt. That's a little rainbow balloon. Rainbow balloon on it. And I was like, okay, I'm gonna try. I'll try it on when we get back to the bed and breakfast.
Jameela Jamil
What is that? That's their consolation price.
Randy Sklar
Yes. Here's your golf shirt. And I was like, it's kind of a cute shirt. I'll put it on. But I'm like, let's see if this is. Let's see if it fits. Let's see if it's good. Of course, I open up the package. It is two sizes smaller than what I would normally wear, so it is as skin tight as possible. It's got a rainbow balloon on it. It was as if. And I put it on, and it was so tight, it was as if I was suddenly full gay cruise. Right? I was like the master of ceremonies of the gay pride parade. I put it on, and I just looked in the air, and I was like, son of a bitch. And then someone came and was like, you can't say that. And you also can't be gay. I don't think I could be gay in there either. So, like, that was. It was just bad decisions all around. And since that point, I have never, ever planned and ever planned anything. And my wife has never let me forget about it. It's kind of wonderful. It's, like, really hilarious. Part of the lore of our lives.
Jameela Jamil
I think you did all of that on purpose. I think. I think you're a deviant. Thank you for that wrong turn. We'll be right back after the break.
Randy Sklar
AI had the time of my life.
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Randy Sklar
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Jameela Jamil
Take a breath.
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Jameela Jamil
And we are back. Okay, that's quite the ride. No pun intended. Even though I know you love a pun. Jason, what's your wrong turn?
Randy Sklar
I mean, so many wrong turns. I was trying to think what would be the best for this show and I think it had to come when I was coaching my son's little league baseball team and they were terrible. And look, I don't expect them to be great, but.
Jameela Jamil
Are you good? We were.
Randy Sklar
I was. We were good. Yeah, we were good baseball players when we were younger and we always played on like travel teams and then played in high school.
Jameela Jamil
But how does one apply? Do you have to compete with the other dads to become the coach?
Randy Sklar
No one wants to be the coach. No one wants to be the coach. And, and I also, because we're comedians and sometimes tour and go on the road, I can't be the head coach, right? Because I there will be like three games out of a season that I out of a 12 week season that I will miss. So I'm like, all right, I'm going to miss some games. So I can't do that. So I'll be the assistant coach. I'll be the bench guy, which is like a notch below being The Vice President of the United States. Like, no power. Nothing you can do. No one respects you. Whatever.
Jameela Jamil
Great eyeliner, though.
Randy Sklar
Great eyeliner. Banged a few couches. So I'm on the bench, sitting on the bench with the kids, and I'm like. And my son's young enough that I get a phone call from my friend in New York, our friend Leslie. And I hadn't talked to her in a while, and I'm like, I'm taking this call. Our team's. There's no way we're winning. Take the call. I'm taking this call, and we're playing the best team. You didn't put the call on speaker? No, it's okay.
Jameela Jamil
He's not an animal.
Randy Sklar
What? No. I'm not a turtle. So I take the call, and I start talking to her. And as I'm talking to my friend interrupting me, I can hear from the field, we're batting. So our team's up to the plate. The other team's in the field. There's a kid. There's twins on the other team. All right? Two twins. She already predisposed to hate him. I'm like, these assholes. These guys. And they're. The dad of the twins is the coach of the other team. And he's really loud. It's like, Jack, dude yelling at his son on the mound about his pitching. And I'm like, you're beating us by, like, 11 runs. Like, ease off this kid. Like, he throws one bad pitch or two Badge. And the guy's yelling at him. And then, like, our guy takes another pitch, and then he comes out to the mound to have, like, a discussion with this kid. I'm, like, talking to my friend, and I'm like, okay, this is really bothering me. Like, I'm gonna go talk to this guy.
Jameela Jamil
Yeah.
Randy Sklar
And she's like, yeah, you should talk to him. And I'm like, yeah, I should talk to this guy, right?
Jameela Jamil
Fucking hero.
Randy Sklar
That's right.
Jameela Jamil
Yeah. Yeah.
Randy Sklar
She's like, why are you still in front of people?
Jameela Jamil
Are you gonna do it in front of people who talk to this guy?
Randy Sklar
She's like, why are you still talking? He's like, literally, you're only talking to me, and you're not talking to that guy. Get the fuck out there and talk to him. I'm like, I will talk to this guy. Hang up the phone with her. It's in between innings, all right? And now, like, you have to understand, I've never been in a fight in my life. I've never even, like, confrontations I kind of, like, try to cool stuff down. I don't pipe up. Right. I walk across the diamond while the kids are warming up. I go straight to this dude. I'm like, hey, man, I gotta talk to you about something. And he spins around and he's like, oh, yeah, I gotta talk to you about something first. And I'm like, oh, I'm getting my ass.
Jameela Jamil
Yeah.
Sponsor/Advertisement Voice
Yeah.
Jameela Jamil
This is something that, like, a kid immediately backfired. Had it even, like, it said to you, this is gonna happen.
Randy Sklar
I don't know what I was expecting him to say. At first, you started to blame our friend Leslie. Like, why did you make me do this? I'm like, my friend in New York said I should talk to you. Like, I was like, how can I back out of it? I was like, how do I get out of this? I don't even know what I expected him, like, what did I think he was just gonna be like, oh, yeah, what? And I. He's like, I gotta tell you something first. And I am now terrified that we're gonna get into a fight. So I'm now being so loud, even over my shoulder to the other parents so they know that something might happen in case someone needs to run in and separate a fight. I'm like, oh, yeah? What. What do you have to say to me that's so important? Just, like, over here, I'm throwing everything off there. And he. And he's like, I'm gonna tell you right now. I'm like, well, say it to my face. He goes, I love it when you and your brother fill in for Jim Rome on the radio. I'm a huge sports fan. And I was like, hey, man, keep up the good work coaching. You're doing a great job. And I walked straight back. I think I even said, like, yell at some of our kids. They're kind of like, maybe I need to yell at somebody. You can hit my kid. I literally say, you can hit my kid.
Jameela Jamil
Is that just because you were relieved he didn't hit you, or is it because the flattery?
Randy Sklar
No. And it's also, like, on all principles, if you get, like, one compliment. Yeah. I'm like, this guy loves our. He loves my work. Yeah. Really? What big.
Jameela Jamil
Are you both like this?
Randy Sklar
No. Easy to melt like this. I'm like, yo, compliment me and I'll be your friend forever. Come on. And then how about his kids? So then. So then later. Later, we're playing basketball in the league of that little rec league, and this guy's got a basketball team, which by the way. So the way it works is if you coach your kid, you get your kids automatically. And his two kids are great. So we're playing against this team, and they're full court pressing, which is like, don't do that.
Jameela Jamil
What does that mean?
Randy Sklar
That means it's like, as soon as the ball gets in, they're. They're crowding up. Basically, you can. You can either start defense as soon as they pass the ball in, or you can wait for them to get across half court. They're starting their defense so aggressively and so early that they're stealing the ball every time. Because we only have one kid who can control the ball, and they're just steel. Steel. Bucket. Bucket. And the twins are just crazy. Twins are dominating. Twins are dominating the ball. And it's not something that I can watch anymore. And of course, I'm coaching this team. I'm the assistant coach. And I'm like, I'm calling timeouts. I'm like, f. These kids. I hate these. I hate these. I hate these twins. They're the worst. They're the worst. I'm so angry at these kids. I'm, like, getting vocal, like, loudly being like, I hate these kids. Like, other people are hearing me say, horrible, horrible, horrible behavior as a dad. And I've, like, yelled at other people's kids while coaching basketball. And their dads came down almost to fight. But this after the game, we lose, like, 60. I'm walking off the court with my son. But these kids. These kids, I'm literally, to my son, these twins. I hate him. I hate him. And I hear from behind me, excuse me. And I turn around, and it's the twins. You're like, what? What? What? What do you want? I'm, like, gonna get in there. I'm gonna fight your dad. But I could take both of you. I know I could. So, like, what? And they're like, we love you and your brother on the Disney show. Mighty. You're like, God damn it, can you stop liking my work as a family, compromising all of my principles? I damn you. And you literally walked to the court and you said to your son, could be more like them. Yeah, they respect that.
Jameela Jamil
I respect you left your child there and you took them home, and they are now your sons. I'm a really big fan of yours. Money.
Randy Sklar
Yeah, sure.
Jameela Jamil
Thank you.
Randy Sklar
Oh, my God. Right? That intro. Let me.
Jameela Jamil
Brilliant. Yeah.
Randy Sklar
Do you take a combination. Take a combination of Venmo and Zell. Do you take Vel. It just showed. I've got Zenmo. Is what. What a wrong turn for me to cave on every single person.
Jameela Jamil
Also, what you're modeling to your children.
Randy Sklar
Is also terrible on any principle of someone's nice finless. After just telling my son how much we hated these kids. I mean, it was. Did my son flatter me to get the good car? He might know anybody.
Jameela Jamil
Oh, my God. That's what happened.
Randy Sklar
Were you on tv? And I'm like, all right, was there.
Jameela Jamil
Some flattery in the 12 page document?
Randy Sklar
There was some flatter.
Jameela Jamil
What did he say?
Randy Sklar
He said, I know that I screwed up. I know. And I respect you and mom so much. And I know you guys have to make hard decision. And you guys have done such a good job raising. I'm like, we have done a good job of raising you. Give him a car.
Jameela Jamil
God, he played you like a car.
Randy Sklar
He's so easily played.
Jameela Jamil
I'm gonna vote for him.
Randy Sklar
Is it worth. Is it?
Jameela Jamil
I know he's not even on the bill, but I'm gonna vote.
Randy Sklar
Who are you, Bill? I don't cry in movies when someone dies. Never. I never cry.
Jameela Jamil
You cry when someone flatters you?
Randy Sklar
When someone does something nice for somebody else. Yeah, I lose my. I cry. I lose it in an Applebee's commercial where, like, they give the coach a plaque. It's 30 seconds long. I'm like, I can't. This is they love. They know he comes in here every time and they know he's gonna walk by that hallway. I lose it.
Jameela Jamil
You have just armed this entire audience.
Randy Sklar
I know.
Jameela Jamil
Your DMs are gonna be crazy.
Randy Sklar
Flatter us. Does your wife use this on you? Straight to the heart.
Jameela Jamil
Does your wife use this on you as well?
Randy Sklar
No, she doesn't. She, like. I'm like, the opposite.
Jameela Jamil
You'll fool her. We need to send this episode.
Randy Sklar
That's right. Flatter me up the razzie. She's not gonna listen to this. No, she won't listen to this at all. She doesn't know I'm on this. She thinks I'm at Trader Joe's right now. That'. Babe, it's really bad. Parking lot. Parking lot's insane. I'll be there in an hour and 20.
Jameela Jamil
So ridiculous. I was thinking just then about a bad date that I planned because this guy, who's a very successful comedian, took me on a first date and he opened the vna, the Victoria and Albert, as in like Queen Victoria and Albert Museum for me at night because there was this exhibition I really wanted to see.
Randy Sklar
It was like Russell Brand knew that Hollywood. Oh, My God, that's so weird.
Jameela Jamil
Nope.
Randy Sklar
Then he made you do a cold plunge, and then, wow. Had you listen to how, like, vaccines don't work.
Jameela Jamil
Yeah, that's great. Yeah.
Randy Sklar
Sounds like a fun first date. What a fucking terrible day.
Jameela Jamil
So he takes me, so he knows that I really want to see the Hollywood exhibition, you know, of, like, all the old iconic, like, the original Batman suit and all the, you know, Liz Taylor's stuff. And I was like, oh, I've missed it. And he was like, oh, you know what? I know John Landau, whose wife, I think, or something, had curated this exhibition.
Randy Sklar
Amazing.
Jameela Jamil
He's like, I'll get you in. And he gets me in at night, just the two of us alone, to walk through the vna, which is, look at this exhibition.
Randy Sklar
Don't ever do that night.
Jameela Jamil
Yeah, I know, but it was the most amazing, like, just intoxicatingly cool first date. So I was like. I'm like, I'm never gonna be able to carry this. On the second date, he takes me to, like, the top of the Shard, this brand new building that's open.
Randy Sklar
He took you there?
Jameela Jamil
Took me to the top of the Shard for the second.
Randy Sklar
Where's date three?
Jameela Jamil
Exactly. Exactly.
Randy Sklar
So it ain't gonna be wagamamas.
Jameela Jamil
Date three is gonna. Date three's gonna have to be on me. Yeah. And I'm like, I need to go weird, right? Because I don't have money. So I was like, I need to. He's got access money. He's friends with, like, fucking people who made fucking Indiana Jones, and I don't know shit. So I am like, you know what? I'm gonna take him to this restaurant where we eat dinner in the dark.
Randy Sklar
Oh.
Jameela Jamil
And it's called Dans Lenoir, right?
Randy Sklar
Yes. The dark restaurant.
Jameela Jamil
Fuck me. So it's completely in the dark. The waiters are all blind. Cause they're fine in the dark.
Randy Sklar
They're fine.
Jameela Jamil
And so. So I take him there that day. I've been filming outside in a chicken suit for charity, and someone steals my bag that's got my clothes for the date in it. And so I have to go to the date in the chicken suit. And I'm like, it's gonna be fine. It's five minutes and then we're in the dark, right? And then I can just charm him with my sexy ways, you know, my voice.
Randy Sklar
Can you feel sexy in the chicken suit?
Jameela Jamil
Not really. It turns out, no.
Randy Sklar
You are a bird, though.
Jameela Jamil
I am dressed like a full. And it's not like a sexy chicken, like Chicky chick. It's like a. I have red wings. I have, like a weird. Like a big tail.
Randy Sklar
Huge feet. Yeah, okay.
Jameela Jamil
Orange giant belly. Like, it's all. It's. It's. I really look like a full chicken. I have the. I've taken the cockatoo headdress off because I think that's too far.
Randy Sklar
Let me find out if he's a furry.
Jameela Jamil
Yeah, yeah, yeah, he's in.
Randy Sklar
It turns out. I know.
Jameela Jamil
Not a. I mean, let me just.
Randy Sklar
Say, you probably look delicious.
Jameela Jamil
Yeah. Thank you. So we go into the restaurant and we are, you know, queuing up for our table, and as we get to the front, the guy goes, oh, I'm so sorry. One of our waiters has actually turned up. And because, you know, we feed all of our waiters, he's turned up off his shift, and there's nowhere else for him to sit. But you two have the corner table, so there would be a third seat. Can he sit with you?
Randy Sklar
They know. At least could be the corner or not.
Jameela Jamil
They know. They're not blind, right? They're the people who are checking us in. So they were like, is there a chance that he could, you know, sit at your table? Now, we're both quite well known in England, and so we can't be like, no. To this blind man who is hungry. So we're like, of course. Oh, yeah, we'd love that. That sounds brilliant. That's gonna make the date even better.
Randy Sklar
Third wheel.
Jameela Jamil
Yeah. Fantastic. We don't fucking know that'. We go in, we're shown to our table, he sits down with us. He's a prick. I don't care. He just.
Randy Sklar
No, you do. Just because you're blind doesn't mean we have to be nice.
Jameela Jamil
Doesn't mean you're nice.
Randy Sklar
In fact, you're probably.
Jameela Jamil
I was in a wheelchair for two years. I was a fucking asshole, all right? That's just how it is sometimes.
Randy Sklar
Me calling him. You calling him a prick is actually showing him respect. That's right, because I'm not treating you as treating you discrimination. I treat your visibility. I see you as the asshole that you are.
Jameela Jamil
He was. Is such a bastard. And, like, we have, like, made space to make sure that he's got somewhere to, like, hang and chill comfortably and eat with us. And we're, like, welcoming in. And I'm trying to ask him loads of questions and involve him in the conversation.
Randy Sklar
He doesn't want to say anything.
Jameela Jamil
It's just monosyllabic and, like, nasty little snarky terms. So clearly Not a fan. Not a fan. And that's fine. But it's. But then we're trying to. So then we're like, let's try and talk to each other.
Randy Sklar
Just the two of us.
Jameela Jamil
Just the two of us. And then he keeps interjecting with snarky, mean comments or putting down our jokes or putting, like, us down. And it's getting really, really intense, but we don't know what to do. So then the food arrives, the food's disgusting, and we've gone for the chefs.
Randy Sklar
Are they cooking in the dark?
Jameela Jamil
Which is like. I think so. So we go for the chef surprise, which is always something that terrifies me because in my head, I'm like, the chef surprise means, like, you suddenly get, like, the chef's dick in your mouth or something in the dark. I've seen too many Judd Apatow movies or something. But I'm just like, turns out it.
Randy Sklar
Was the blind guy.
Jameela Jamil
Yeah. So we get the chef surprise. It's like zebra cheek and shark ass. And it might be the other way around, I think maybe more likely. But anyway, zebra's a shark cheek.
Sponsor/Advertisement Voice
Yeah.
Jameela Jamil
And it's completely unseasoned. And the whole point of this whole place is that you lose a sense, so your other senses are heightened. My sense of irritation is certainly higher. Yeah, exactly. So all I can taste is. Is seasonless shark cheek. You know, it's not making it. I don't want this to be more intense. So I become. When I get angry, I never show my anger outwards, which is why I'm always sick. I. I keep it in. I turn it in. I turn the knife on myself. Right, right, right. I turn it into a kidney stone and I stab myself.
Randy Sklar
Yeah.
Jameela Jamil
Oh, my God. And so I. So I just go completely silent because the food's disgusting. This guy's being an asshole. We've.
Randy Sklar
Now.
Jameela Jamil
This is my big date after all of his big dates. You know, it's really killed the vibe. It's already, like. Also, it's dark. We can't really talk to each other about our lives because he's got a very recognizable voice. It's not Russell fucking Brand. And so we're like.
Randy Sklar
Like Peter Sarah films. Yeah.
Jameela Jamil
Yeah. And so we can't even really engage. Like, this whole night is just ruining. We're trapped there in the dark.
Randy Sklar
Trapped in the dark, eating shark cheek with a guy who doesn't want to be there.
Jameela Jamil
So I'm quiet. He goes quiet. But now he thinks I've left because I'm so quiet. You can't even hear me breathe. So he reaches across the table to see if I'm still there, but I can't see him do this. And he's got massive fucking hands. Two big fingers just go up my nose.
Randy Sklar
Oh, my God.
Jameela Jamil
But I'm in the dark, so I have no idea. So I start screaming. I think it's the fucking blind guy, right?
Randy Sklar
Exactly.
Jameela Jamil
Someone's got their fingers up my nose. And at first I'm like, it's the chef. Surprise, dick. It's the chef. Surprise, dick.
Randy Sklar
This is the chef's surprise surprise.
Jameela Jamil
I start screaming, chef, surprise.
Randy Sklar
Chef, surprise.
Jameela Jamil
And I flip the table on the blind guy and on my date. And the wine goes all over him, the food all over everyone. But no one else can see what's happened either. So we're all in the dark. It's a big time. It's not long after a lot of the terror attacks in England. I'm Pakistani already. Not a good sign. Everyone thinks it's some sort of attack. Everyone starts screaming. Now everyone's crashing into each other. The blind people now no longer can find their way around the restaurant because everyone's screaming all over the place. Everyone's starting to flip the tables. We all get thrown out, and I'm banned there for life. You're banned from the dinner, B.
Randy Sklar
You're cool with being banned there for life?
Jameela Jamil
Yeah, I'm fine with that. We are the same.
Randy Sklar
We are so the same. And I appreciate that.
Jameela Jamil
Yeah, it makes me feel very good.
Randy Sklar
No, no, no. Never.
Jameela Jamil
Yeah, everything's gonna be planned by you.
Randy Sklar
No, I will plan everything. You guys need to take care of yourself.
Jameela Jamil
We'll just flatter you.
Randy Sklar
Flatter the.
Jameela Jamil
That's all that has to happen.
Randy Sklar
Everything we want.
Jameela Jamil
Tell everyone where we could find you and what you want us to watch and look at and read, et cetera.
Randy Sklar
Okay. We're sklarbrothers. Spelled fully out B R O T H E R S on all platforms, on Instagram, on TikTok, on X, on Facebook, whatever. So follow us there supersclars.com for all of our tour dates, which we're. And we do a great show at the Comedy Store every month called Tag it, where our friends are doing their sets of comedy. We're on stage listening and writing tags that we pitch them on stage afterwards. It's like. It's really fun. It happens in green rooms everywhere, and we bring it to the stage. It's so collaborative. It, like, shows that we as comedians aren't lone wolves. Is it wolves? Wolves. I think it's wolves. I think it's wolves. I think it's wolves. Like the wolves are coming over. Put on your nice blazer. Fine. All right, so we're not lone wolves. Wolves, whatever. And that. We are. It's actually a very good. It's a community, so it shows how much we love the comedy community and our friends. And it's great. And we have a podcast ourselves called Dumb People Town, which you were going to do. Which. Will you come and do that?
Jameela Jamil
Have I proven that I'm a dumb person?
Randy Sklar
No, you've proven that you can actually dissect dumb behavior even within yourself. And, and otherwise you're, you're perfectly engineered. Yeah, we break down three insane dumb stories, usually from the state of Florida, of people doing dumb things. And we try to understand why instead of pointing a finger and going, that's dumb. We're like, why? Why would this happen?
Jameela Jamil
I've been training for the this my entire life. Thanks for coming on Wrong Turns. I love you.
Randy Sklar
Thank you. Love you too.
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 full length videos of our episodes on YouTube. And don't forget to subscribe, like review wherever you get your podcasts and tell your friends about us. 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. Bye.
Randy Sklar
Hi, this is Knox from the podcast with Knox and Jamie. And maybe like us at the podcast you also know people who have been smokers or vapers and Zyn is the one product it seems like everyone is talking about. Because there are many good reasons to make a change to Zyn nicotine pouches. Reasons like Zyn Nicotine Pouches are still America's number one choice for smoke free, hands free nicotine satisfaction. And you can choose between 10 varieties. Each variety available in either 3 or 6 milligrams. Check out zen.com find to find Zyn at a store near you. Warning. This product contains nicotine. Nicotine is an addictive chemical. Acast powers the world's best podcasts. Here's the show that we recommend.
Jameela Jamil
Are you a fantasy reader looking to cure your book hangover? Then welcome, welcome, welcome to the Fantasy Fangirls podcast. I'm Lexi, older sister and fantasy lore nerd and I'm Nicole, younger sister and romantic at heart, and we love exploring these stories, worlds and characters well beyond the last page. Fantasy Fangirls is not your typical book. Deep Dive Podcast when we say deep dive, we mean Deep Dive, where every episode covers a stretch of chapters and is structured with five segments to easily follow along. We are currently deep diving Quicksilver by Callie Hart in the lead up to its highly anticipated sequel, Brimstone. We're so excited. We hope you join us as we travel through the Quicksilver to dive deep into literary and character analysis, theories, lore, themes, and so much more.
Randy Sklar
ACAST helps creators launch, grow, and monetize their content. Podcasts everywhere. Acast. Com.
Episode: Randy and Jason Sklar
Date: October 16, 2025
Guest(s): Randy Sklar & Jason Sklar
This episode of "Wrong Turns" with Jameela Jamil is a hilarious deep-dive into the mortifying, embarrassing, and downright disastrous moments that make up life. Jameela is joined by the comedic twin duo, Randy and Jason Sklar, to swap stories where there are no moral lessons—just reveling in shared humiliation and mistakes. If misery loves company, this episode is a full-on party.
[01:36-04:54]
[04:54-09:10]
[09:39-14:26]
[16:14-25:44]
[28:02-36:02]
[35:00-36:21]
[36:41-44:38]
Parenting Reality:
Shameless Resilience:
Party Invite Fiasco:
Anniversary Disaster:
Coaching Gone Wrong:
Flattery Vulnerability:
Jameela’s Date Nightmare:
The tone is open, self-deprecating, and riotously funny, with all parties embracing the cringe and chaos of their misadventures. There's a strong camaraderie, a lack of moralizing, and a willingness to dissect even their worst moments for entertainment.
The Sklar Brothers:
Jameela Jamil:
Wrong Turns:
Where dignity goes to die, but laughter is guaranteed.