Bad Dates with Jameela Jamil - BACKGROUND CHECK: Daniel Webb

Episode Date: September 24, 2026

We're kicking off a new series of bonus episodes where we revisit classic tales from our guests' past appearances, it's Background Check! Daniel Webb was on Intimacy Coordinator this week, so we wanted to replay his Bad Dates segment from 2024, alongside Joel, Zoë Chao, and Olivia DeLaurentis. In this clip, Daniel tells two stories, one about what it looks like when you randomly hook up with a guy who might have just won No Nut November, and another about an encounter ruined by showtunes and a parakeet.Daniel Webb: @thedanielwebb on socials, tickets at TheDanielWebb.com Subscribe to SiriusXM Podcasts+ to listen to new episodes of Intimacy Coordinator ad-free. Start a free trial now on Apple Podcasts or by visiting siriusxm.com/podcastsplus. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Heart less. Me. Hey, it's Joel here. One of my favorite guests, Daniel Webb, was on the show this week and referenced his bigger in Texas bad date story from one of our previous episodes. Sharing it again here. Enjoy. This gentleman, he has both a quick amuse-bush story at the top, a hookup story, I'm told. And then we will be going into a dating story because hookups count here. Otherwise, I would not be qualified to be speaking on this mic because I'm not a dater.

I've never been a dater. So I got on the elevator in the hotel, I was saying, and this guy was already in the elevator. So we just stood there and he did the bro, the bro nod, right? He did the, like, the that. And so I, and I'm also from, this is not a visual medium, but everyone at home listening knows exactly what you just did.

Yeah. And unfortunately, I'm from Texas, so I revert back to my, like, don't let him know. You know what I mean? I brocode back. As humiliating and non-convincing as that might be. So I nod yak, right? And then as the elevator doors open for him to leave, he literally says, he goes, room 805, 10 minutes.

And then the doors closed, and I'm still on the elevator. I'm going up to my room. And then my horny inebriated ass is like, yeah, let's do it. So I grab my poppers and I go, I wait to, I'm standing at my door for nine minutes. That's the time. And then I go down to his room. He answers the door. He's hot.

He's shirtless. He's just in like shorts and stuff like that dark room, which I'm into, but also is very suspicious. And so we just, I'm a busy man, so I just get straight to business. So I'm like down on my knees. And all of a sudden I hear this like, and like he is taking his shorts off and I look up and he has this like medical, not diaper, but like medical like underwear on. And when he velcroes it in the front, he presents the hugest set of balls, like inflamed, elephantitis, like watermelon, watermelon testicles that the velcroed underwear were damming up, essentially. Yes. You got a warner person about this. Thank you. That is exactly what I said. That's the headline. Oh, my God.

I'm not a size queen. I'm not anything like that. But you got to give some people heads up if there's a curve ball or in this case, two of them. But like there. And then he had like a normal dick, right? Like a lovely, lovely penis. But on top of these two mammoth melons, it looked weird and minuscule and strange. And so I didn't know what to do, mainly because he didn't give me a heads up, right?

It was like, oh, what am I going to do I unwrap these? Do I pot? What do I do? Do I juggle them? Do I, like, I would be concerned that it would hurt to even. like mess with them. He was totally acted like nothing was unusual about this. Nothing, not the Velcro, not the swollen tight skin of the testicles.

Oh, my God. Yes. In the middle of a medical emergency and he was acting like it was just Saturday night, right? Oh, no. I blew him, but it was like blowing. Oh, my God. You don't know what I? You felt the balls way before you were like, you were like titty fucking him.

Like you were like motor. voting him at the same time as you were blowing him. Well, I could hear the kickback. You know when you're performing in a large space and you can hear the kickback of your voice? It was like that. You hear a kaka, ka, ka, ka. So I fucked with it for a little bit. And then I literally, I kind of like sat back and he got on grinders.

Like, we need to get some more guys in here. And that's why rule number one is never let them come to your room. Always go to their room so you can leave. So I was like. I was taking notes. I totally said. I was like, that's not really my scene, even though it is. and left because I was like,

I don't want to get into a group situation, which it would have been. But I, like, I just had to bow out because I didn't know. Did you ever find out, Daniel, what happened, like, what was happening to his balls? Was this temporary or permanent or what? Yeah. I think it was a very, like, Willy Wonka situation,

like, Violet, like, he, like, chewed the gum and his balls kept swelling. And then, you know, like, I think I left and they just kept getting bigger. That's what I assume. Oh, my goodness. And he needed to be exported out. He was like, this is my last night on earth. I'm going to be. What if it was just like, what if he just had the, I would have stuck around just to see the load attached to those balls, you know?

Like, because what if it was just like a fire, a fire hose situation? Like, just blowing you backwards. They deflate the normal size. Yeah. Yeah. Yeah. If I would. They just got it.

He just got excited. Was this during no nut November? Was this like at the end? Yeah. This is the very end. Yeah. We spent so much time on these big balls. We got to get to the dating story now, Daniel.

We have to hear about the date. Okay, so I'll be brief on this on this since I took so much. I thought the balls sucked up all the time. I did. I actually went on a date with a dude. This was old school too. This is what, and he was hot. He was smoking.

We went to the falderall of getting drinks and like dinner. And then I didn't eat, but we went back to his place. And when we pulled. We pulled up. He goes, oh, shit, my roommate's here. I was like, roommate. That sounds either really hot or really awful. And so we go in, and his female roommate, no dis, was there, and she was such a fagag

that she, I could say that way. She was such a fag hack. She was just elated to meet, like, another gay man, right? And this is like two in the morning, three in the morning. So we've all been drinking wherever she had been. And so she's just, like, thrilled. She's like, show tuning. And she's like, you look Toriamos?

I love Toriamos and like, you know, and I'm chatty, so I can't help but participate in the conversation, even though all I want to do is like fuck a roommate. And he's sitting there not really doing anything about it. And then more time goes on, more time goes on. She finds a bottle of wine. Let's keep drinking. And it's like, no, so I didn't drink anything because I was trying to insinuate that, you know, we're going to go to bed. So she drank like all of it. And it's like, me and the dude are just staring at each other.

Like, when is this going to end? That's the difference between a faggag and a real ally is a faggagg will do this. A fagg will cockblock you because she's in the presence of a new gay man. A real ally, a real girl that has like real like down with gay friends. She knows what's up. She knows what you all want to do. And she says, I will be experiencing Shonda land in my room alone on my laptop. You guys go to town on each other.

Okay. Right. So she was in, and the saddest part was she was having the time of her life. And there's nothing sadder than watching someone have a great time when everybody else wants them to leave. You know, that's the saddest place in the world. And she was just eating it up. So finally, I'm like, I'm going to go to bed and you can wake me up when she's done.

So I go in his room and just lay down and then pass out. And then the next day, I wake up and he's in there, right? And he's like, she finally went to bed. I'm like, yes, it's on. And so we're in his room. But now that we're in his room, and the lights are on now that he's there, I notice that he has a parakeet, right? Like the little bird.

person, not a bird person. So scary. He lets it out because now he's home. And it has some fucking dumb medieval name like D'Artagnan or like Camelot, some bullshit. And it's, it's on his finger and it's on me. And he's like making out with me while the bird is biting my ear. No.

He thinks it's adorable. And I think it's disgusting. And it's a bigger cock block than his roommate. Yeah. I got to say birds during foreplay, no, thank you. It's a big. It was too beastial. It was very bee-seal.

No, only during regular sex. Yeah. Yeah. It's like, I have a dog. And when I'm fucking, he waits in the car. Do you know what I mean? There are no animal pieces. Yeah.

But so, yeah, finally the bird, of course, shit on the bed. And which was my job, right? That's what I'm supposed to do. I once met a bird that I think could smell that I had my period. And was psychotic. Like, really. It wasn't a goose, right? No.

It was like a regular bird. I wouldn't put it past a goose, but this was like a smaller bird that had big energy. And it felt like it was really scary. Like it was so small and we were such big humans, but we couldn't keep the bird away from me. Was this a bird in the wild or was this a bird? No. A pet bird. This was a bird of an ex-boyfriend's aunt.

Okay. I'm going to say this. I feel like I'm so glad you said that this was a pet bird because if this was a bird in the wild and I found out just today that this is a common occurrence that women experience on their periods was just walking through a park

and having birds attack them. I would be like, why is this not being out of the park this week? Get on a fucking like IUD or something to get rid of your period. There has to be an answer to this. Women can't go outside because birds are attacking them. I mean, the birds, but Hitchcock. You know that movie's about it?

It's about a bunch of women on their periods. On the rag. Tippy on the rag. Tippy hedron was just menstruating like a motherfucker. Into the sea.