Bad Dates with Jameela Jamil - Speed Dates: A Third Thing (w/ Zach Zimmerman)

Episode Date: May 8, 2025

On this Speed Dates episode, host Joel Kim Booster talks to the hilarious Zach Zimmerman about growing up in and escaping the church, and the reality show moment that’s making him believe in love, but really he is here to tell us not about a bad date, but about the viral fallout from a date that never even happened! And actually, the joke’s on you, because Zach’s mom DID buy him those shoes. If you’ve had a bad date you’d like to tell us about, our number is 984-265-3283, and our email is [e-mail], we can’t wait to hear all about it! Subscribe to our YouTube Channel for video clips. Subscribe to our YouTube Channel for video clips.Merch available at SiriusXMStore.com/BadDates. Joel Kim Booster: Psychosexual, Fire Island, Loot Season 2Zach Zimmerman: @zzdoublezz on Insta, new stand-up special Surprise Me on YouTube Subscribe to SiriusXM Podcasts+ to listen to new episodes of Bad Dates ad-free. Start a free trial now on Apple Podcasts or by visiting siriusxm.com/podcastsplus.

Hello and welcome to another episode of Speed Date, the bad dates mini episode, where we sit down one on one with one of our esteemed guests from the past or maybe somebody new to the podcast altogether. But either way, we slow things down, we get to know each other on a deeper, more meaningful level. And this guest today, I'm so down, we get to know each other on a deeper, more meaningful level. And this guest today, I'm so excited to have him back. He's been a guest on the main pod before. He's a comedian and a writer whose work has appeared in the New York Times and Washington Post.

His debut comedy special, Surprise Me, is available on YouTube, and he is the author of Is It Hot In Here or Am I Suffering For All Attorney For The Sins I Committed Here On Earth? It's Zach Zimmerman. Hey Zach, welcome back to the podcast. Thanks for having me, Joel. Hope you're well. Of course.

Thank you. You are looking well as well as always. And this is gonna be a little bit of a different format for the mini episodes. But before we dive into what is gonna make it a little bit different, I did wanna talk to you. We both share a similar background. Both of us escaped evangelical Christianity at some point in order to live big gay lives, which has undoubtedly scarred us and, you know,

traumatized us on some level. But I wanted to ask, do you think your upbringing in the church is affected, how has it affected your dating life and do you think it is still affecting your dating life now? Oh wow, fantastic question. I would say it fundamentally affects my dating life because I have an anxious attachment style that came

from praying to a God who didn't exist for validation. I'm sort of programmed and expecting to like, please love me and then to get nothing in return. Is that, is that your experience? That is so real. No, no, no. That is exactly, I didn't pinpoint, you know, I knew I had an anxious attachment style, but I did not pinpoint or was not able to pinpoint until right this very moment of where it all came from. You've just saved me years of therapy right there. You're welcome. I'll send you a bill.

Yeah, exactly. And it took me years to figure that out. And there's no way to like solve it other than to know like, oh, I'm being ridiculous right now because I used to lay in my bed and worry about hell all day. Yeah. Oh, that is so real. And like the I don't think I even began. It was like a year or two after I came out that I even stopped believing in hell.

Like it takes a while. Like there's so I lived like a full year of my gay life, like thinking like, well, I'm going to do this anyways, but I'm going to go to hell for it. Oh, so you really such a such a really dark place. I had space to be in. So, yeah, terrible. I still have, you know, in the darkest of moments, I still have a little doubt. You know, that's what's sinister about it I have a line in the

Special that Christianity carves a hole in you only it can fill Uh-huh. Oh man that is What? That's like a punch here. Yeah, it's like hey, here's a problem. It's you're gonna suffer forever and the only solution is us Yeah, it's like fuck that is I, and the only solution is us. Yeah. It's like, fuck you. That is. I got high on Easter and went to church

because it was 420. You did? Yeah, and I wasn't triggered, which I was very proud of. Like I just healed enough. That is great. What kind of church was it? It ended up being, there were four around the place I was staying. One had a sculpture that was like, for the innocent lives lost to abortion.

So I was like, we're not going there. The other two started at 10 and it was like 1030. So I ended up going to a Baptist one where they had an egg hunt and it was cute. My, the high thought I had, I thought I might have some like spiritual insight, but the whole time the pastor's like this young guy and like a short button up shirt, He was hot. He had like a gay haircut from 10 years ago. And so all I could think about was like, can pastors get blow jobs? Like I couldn't get it out of my head. Is he allowed to get blown by his wife? I'm sure by his wife. Within Christianity?

Right. Oh, you know what? That's a toss up. It really is, especially with Baptists. Like being a former Baptist myself, there was, there were a few people who were like sexes only for procreation. Right, right. Sort of purposes. But that was such an old school way of thinking about it that I don't even think anybody that I knew was practicing that.

Because all the guys in my church were getting blowjobs. Oh, wow. Yeah. Well, not all of them, but the many of them were. In the like teen program? Yeah. Oh my God. And talking about it? Uh huh. Yeah. I mean, it was straight. So like it was like, it was still like we, you know, there were people who were judgy about it, but less judgy than they were, would be about like, uh, gay people.

Because like, I think it was like those guys getting a blowjob and, you know, at a retreat was like a moment of weakness that they could atone for and ask God for forgiveness for. But like choosing to live as a gay person, that is like an everyday you're waking up and choosing to sin is, to sin was seen as different. And so like, and honestly it's fucked up, but like I'm like, well, at least that's a consistent line of thought. Um.

You do have to celebrate like with my mom this year, she voted for Trump again. I was like, at least she's voting. At least she's, you know, engaged in the political process. I was trying to reframe the horrible as somehow positive. At least you're consistent, I guess. It really, that's the one big takeaway from that trauma is like really being able to twist your brain into a thousand different knots in order to justify and sort of like make excuses for.

Beautiful, beautiful way to open the pod with just a shared shared conversation about our travel alienate most people, but it'll delight a subset because I think a lot of people went through this shit. Exactly. Speed Dates. Normally on speed dates, we don't necessarily talk about one specific dating story. We sort of say that for the main pod, but this is so pressing that we had to get you on to a speed date to talk about this. This something that happened to you that probably re traumatized you in its own way. Take it away. What of course. Where are we? When are we? Why are we?

And I'm so glad to have your perspective because it touches on a number of very queer specific things, very fashion, fitness, how much you share on a day. Like maybe I'm not totally in the right, but I'm gonna pretend like I'm in the right. We'll see. But I'm in Florida at the time, where all mistakes begin, and I matched with a guy on Hinge, and a week goes by and then I message him like,

hey, let's chat. We start chatting a little, and we make plans to get a drink a week later. And it's Saturday. Why are you in Florida for so long? I've been at this writing residency. Oh, very cool. I guess Jack Kerouac lived here with his mom for a year.

And so they turned his house into a residency. So I've just been living by myself in the middle of Orlando, trying to work on a book, but also getting my heart broken, I guess. That is, I mean, that sentence was such a roller coaster. You know, it's like living in it by myself in Orlando. You know, like writing a book, though, and getting my heart broken, you know,

like so many ups and downs. Yeah, hard to keep track. That is useful for like the head space I was in because I was like craving a little community, queer connection, I to keep track. That is useful for like the headspace I was in, because I was like craving a little community queer connection. I don't know. So this date had some stakes to it. It wasn't just like a hookup. It was like, oh, maybe I'll make a friend. But it's Saturday and we're like, hey, should we just get a drink tonight?

Are you free? And he's like, yeah. So we start chatting and he's like, what are you going to wear? Like, I don't want to show up looking like a goober. And I am like, I hadn't really thought of it. I guess shorts, like it's hot outside. He's like, oh, yeah, I was thinking shorts, too. And he goes, send the fit. I was like, send the fit.

I was like, fine. So I'm about to. Is this person Gen Z, by the way? He was 25. So is that Gen Z? I think that's like Gen Z. For sure. So I'm trying. I think he said bet at one point. I think that's like Gen Z for sure. So I'm trying. I think he said bet at one point.

Yeah, that's Gen Z. Gen Z coded. So I go to take a picture and I'm like, oh, I'll make a little video like a get ready with me. So I hit play or hit record. I'm like, get ready with me to go on a date. And I kind of like look at the outfit and for the listeners it wasn't great. It was a pair of khaki shorts. I had a t-shirt that I put flannel over because I didn't wanna show too much of my body.

And then I had like high white socks cause someone told me last year high socks were in and then the only pair of black tennis shoes that I brought to Florida. So I make the video, I go like, it's giving, it's kind of giving. And then I end with like, it's giving goober and I hit send. After I hit call back, it's like fun light call back. Yeah. We're having fun. And I was weirdly like proud of myself. I didn't do 17 different takes. I was just like, this is me in a nutshell.

And then I was like, it'd be so funny if he canceled. I was like, it'd be literally hilarious if I just. And this is the disease of being a comedian. Is that like, oh man. That's the, it's the blessing and the curse. Cause then like seven minutes later, he's like, hey, I'm not opposed to getting a drink. And I think you're attractive, but unfortunately I don't think we're going to be compatible.

And I was like, wow. And so I said, God bless. I was like, better now than before your drive to the place and God bless. And then I. I sat with the rejection for I was in I was in shock. Yeah, I was in shock. I was in a period of shock. It's a shocking thing to happen. It's a shocking thing to happen to you.

It's like, oh, I fumbled the bag, I guess. And so I called a friend and she was like, that's dumb of him. And then I was like, but cause I'm also salivating, I was like, this is gold. This is like hilarious. I'm experiencing it both as myself, like ouch, but also like jackpot. This is exactly like, and so I even gave and tweeted like, I, I just

experienced an L that's going to break the internet. And then the next day, the next day I put it on Twitter thinking like, Oh, this will be funny. People get a laugh out of it. Like that I got canceled on because of my outfit. But someone retweeted it and was like, it's so sad to see someone get rejected for showing who they are, but also what the fuck is this outfit? And then and then the whole Internet is is just roasting the fit.

They were like, why are you dressed like a lesbian? But also a school picture day like did your mom dress you I'm just getting like destroyed Oh, no, I did not know that part. I've been off Twitter. So I had no idea. I only saw the video On on probably Instagram or something like that. But I not realize. I was kind of unfazed. I talked to my therapist about this. He was like, since fashion isn't a part of your core identity, being fashionable, you were able to weather this.

So I was having fun. I was like, yeah, actually my mom did buy me these shoes and they're called On Clouds and they're very comfortable and help me not have lower back pain. And so I leaned into the madness of it all and took another awful picture in the same setting and like posted that and people seemed to have a good time. Yeah, I mean, it is, you're right.

And I suppose your therapist is right that like it is a low stakes sort of drag for you in particular because you just don't, that's not your lane. Right, I'm not trying, like if you had told me I was unfunny I'd be pissed off. Or if I was getting dragged for old tweets or something like, or being called a misogynist or racist, et cetera, et cetera, that would be less fun.

But I was kind of like, this is fun. And it's like, people can be mean about like the way you look when it's your clothes, I think. Like, because like if they were roasting you and saying like something you couldn't change. Cause the thing is, is like, you're just not gonna wear that outfit, you know? Problem solved.

And that, but like if they were like, your face looks like, you know, problem solved. But if they were like, your face looks like, you know, Sebastian Stan in Another Man. What are you supposed to do with that? That wouldn't roll off of you. That was getting dangerous. You were about to come up with a good read. No, no.

This was about to turn into a roast battle. No. No. I would never, I would never. Did you know, do you know if this guy has seen the viral video or seen the video at all? He didn't reach out, but what did happen is like, Twinks I hooked up with five years ago texted me and I was like, I don't remember.

So it hit like some core in the game world. It hit the game world. Yeah. But he didn't strike me as super online. What was awful is since we were texting, iOS showed me his full name, which it shouldn't. So then I did a little like internet stalking and that was probably unhealthy, but I like, yeah, learned he was a ballerina, so he may have his own relationship with him. Oh, yeah. What I think actually was happening

was a little potential femphobia, because I did affect this voice in the video where I was just like, get ready with me, and maybe that gave him the ick, and he's allowed to get the ick. Sure, sure. It is a big thing though. Like I always I worry about that with my own voice a lot.

Like whenever a guy on Grindr is like send a voice memo, he's like, oh, like as you see, is this going to be disqualified? Let me smoke a couple of cigarettes for exactly. Yeah, I use my I definitely use a lower register, probably like my podcast voice Instead of the real one, but that is That's brutal top to bottom Zach. I'm sorry that happened to you, but I'm so glad that you got I'm sure some material out of it and

Certainly a few laughs of your own so and you're spreading joy just by being on this podcast, right? Oh stop and I think Maybe a slight lesson. Oh, what is that lesson? A moral, what's that? Well, it came, the Drew Barrymore show of all places, reached out and was gonna be like, hey, will you come ask a relationship expert this clip about this? And I was out of town so I couldn't do it. But they wanted me to ask

the question about like, over sharing before the first date, which I hadn't thought about it in that way. But in a way I did over, I showed too much of myself, I think some could say that that's fine. You got to the know faster. Yeah, that's kind of where I'm at. But I think I could have modulated more in person to kind of meet the other person where they were. Totally. Like in person, I'm not gonna come at you like,

get ready with me. Right, no, no, no, it is true. It is like you were, it's not even that you were showing more of you, it was the side of yourself that was maybe a little too intense for them in that moment. Yeah.

Yeah. But you know, love is still out there and that is connected to, I'm gonna ask you the same question I asked to end every mini episode and that is, what is having you believe in love this week? And that can be anything from a clip you saw, a movie you watched, a clip you saw, a movie you watched, a song you heard,

somebody doing in your life, doing something for you. Pretty much anything that is keeping you sort of pushing through tough moments like this in order to still find love. What made me feel love? That's a great question. I watched the special live and did not feel... Everyone was... Digital love is not real love. Like, I can't wait to be in physical space with someone

and experience love. The thing that's coming to mind is there's a clip from Love on the Spectrum where I believe her name's Abby is drinking a cocktail with her, I think now husband, or it's a glass of wine and she makes this face and the sommelier is looking at her and she's like, it's very interesting, but I'm not interested. I was like, that's such a great line.

Yeah, that is a really great line. It feels connected to love in that like, you have a, this has a lot going on, but it's not for me. And maybe sometimes rejection is an act of love. So I'm not gonna waste your time. Yeah, exactly. That is sort of what this gentleman did to you is he said, this is interesting, but I'm not interested.

And maybe you say that to the church as well. Exactly. You got a lot going on, but it's not for us. Not for us at all, not even a little bit. Thank you so much, Zach, everyone that was beautiful and poignant as always. Where can the people find you if they're looking for you these days?

Oh, I'm on the Instagram, the TikTok at ZZ double ZZ. That's at ZZ the word double and then ZZ and then surprise me is on YouTube. So if you go to YouTube and search sex and run surprise me, you can get an hour of laughs, a little poignancy and a lot of, I don't know, a third thing, a third thing. Trauma. Most trauma. Yeah. Got to check that out. Thank you so much, Zach, for joining us. This has been another Bad Dates mini episode. Speed Dates, new episodes of Bad Dates are out on Mondays. Speed Dates are out on Thursdays. Until next time, I've been

Joel Kabooster. Bye bye. Bad Dates is a production of Smartless Media created by Robert Cohen, executive producers R. Richard Corson and Bernie Kaminsky. We will be back for more Bad Dates. Smart. Less. Media. Plus, me and...