Brooke and Jeffrey: Second Date Update - Second Date Update: Kiss GPT

Episode Date: August 3, 2026

What’s the best way to get better at kissing? Is it just practice and experience? Or is there an expert out there that’s much closer than you might think? We’re answering that question in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

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Before we get to it, we'd love to highlight comments. Yes, Kaylee Contreras said, I've been a listener for years, and I've told so many people about this podcast. I was surprised to find out that a friend used to listen to you guys on the radio in all caps. Recently, though, my coworker heard me listening because my AirPod disconnected, and my phone played out loud. Needless to say, she too is a listener of the podcast. That's awesome.

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All right, your brand new episode starts right now. Brooke and Jeffrey in the morning. Second date update. You know what's better than getting the new job that you were hoping for? It's when your friends back you up and want to take you out to celebrate. Oh, that feels so good. If you can go anywhere to celebrate, where would you go?

Rainforest Cafe. Nordstrom Rack. Sabaro? They don't have margaritas at Sabaro, Jeff. I'm just going to throw that out there. That's authentic New York pizza. Yeah. That's better than margaritas.

I personally have no idea how to celebrate such a happy achievement. But it's good that we have somebody on the phone who does know the answer. That's nice. His name is Aaron. So Aaron, first of all, thanks for being on with us. Your email said that you just landed a new job. Where did you go to celebrate? We went out celebrating to a few bars, actually.

Oh, bar off. A few bars. Okay. That's not what I was a match. I was thinking Orange Julius, maybe. No wonder Jeff wasn't invited. Yeah. Okay.

I'm not going to be a food court now. Like, who wants a pretzel? Yeah. That was my bad. Anyway, so while you're out celebrating, your email says, that's when you met somebody. So tell us that story. What?

Well, the table next to us is a group of girls. And after a couple of drinks, we started chatting up with them. And the cute one, her name is Carrie, like, she was actually talking to me the most, and we're making jokes. Oh, my God. Could your night get any better? You're celebrating a new job. You got the cute girl talking to you.

Like, you're on fire right now. It could get better if you stop off at Sabara before you go home. Yeah. That's one way. But I don't know. You lived it. you tell us. I guess I just got lucky that night, but the conversation was good

and we were getting along so well. I made my move and I said, I have the new job. I'll buy you a drink. But not here. I'll buy for you next weekend when we go out. Oh, I like that. Because you didn't have your paycheck

yet from the job. You got to wait until that deposit hits, okay, girl? For now, Virgin dairies, you enjoy. Yeah, right. Okay. Dude, that's a great way to ask somebody out, to be flirty, keep it fun. Definitely playful.

So did you end up meeting up again? We did. Okay. But that was the thing. We got together and I was thinking maybe I should have planned an activity because we'd already just kind of hung out and talked, you know, at the first time we met. So this time, we just did the same thing again. Yeah.

Oh, it didn't feel as like fun. Well, I mean, you started on high high, right? Because you were like riding life that night. And then when you just go to have one drink at a quiet bar, it's like one-on-one. Yeah. You're making it sound like the conversation was really bad. Well, it got weird. And we started talking, you know, she was telling me about bad dating experiences that she had.

That's weird that she would bring that up in the middle of this date. Yeah, exactly. It's like, why is this the association you're having right now? Right. It would be like, hey, hanging out with you reminds me of other bad dates that I've been on. Let me tell me about those. Exactly. I think it's a pretty common first date topic, isn't it?

Because you can relate. I want to believe you. Oh, yeah. Yeah. I mean, were they back and forth? Did you have other bad date horror stories to share with her? Well, I shared a little bit, but she was just really passionate about this topic. And then she started talking about worst kisses she's ever had.

Oh, we're just going to keep going. Oh, man. Hopefully we go through all the bases, but yeah, start with the kisses. Bro, be creative. Use that. Be like, was it something like this? I hope she doesn't say yes I know how to kiss

Absolutely off Oh, I'm terrible Bring it in Bring it in Well, Jose and I have our next line So, okay, thank you for giving us that Do you think she realized that maybe she had gone too far In the worst

Stories Oh, yeah Category? No Absolutely not Oh, she didn't. So then after a while, I just didn't know what to say I said, well, what if we asked chat CPT?

what is the best way to kiss. Okay. Because an AI robot definitely would have good tips. Yeah, a lot of experience. I just wanted to switch it up. That was all I was doing. Just changed the tone a little bit.

So was she able to laugh? Was it a funny moment doing that? So it's funny. Yeah, it was suggesting, you know, don't make it too moist, not too aggressive. Turn your head. Okay. So it doesn't sound funny.

It sounds actually more like a serious and pretty logical. Yeah. Yeah. We were laughing a little bit at the time. Then I'm like, we have to try this to see if it's right. Oh, the instructions at ChatGPT gave you for kissing? Exactly. Exactly. Wow, this isn't Google Maps.

You shouldn't need, like, directions for this. I don't know. I think it's a cute way to get a first kiss. It's a segue. He's using it. All right. Was she open to trying? She was, and so then we kissed right there in the bar.

Oh, okay. How was it? Yeah, how were the instructions? How was the moisture? Well, we were drinking, so there was a high moisture content. What are you feeling right then? I felt pretty good because it started off in such an awkward spot, and then it ended out like we're kissing and having a great time.

So I was happy about it. Yeah. It's not very often you get wing-maned by your chat GPT. Dude. First time AI has been useful. Yeah. That's not wingman. That's a wing computer.

Wing-botted. Wing-botted. Yeah. Okay. So how did you and Carrie leave things that night? Well, I walked her to her car and gave her a goodbye kiss. Oh. Another.

And, yeah, we're like, all right, we'll talk. Talk soon. It was kind of just, I thought everything was fine. Yeah, there would be no doubt in my mind that I would get a call back after a night like that. And it's so great. Like, the first kiss is stressful. But once you, like, get through that, then the kissing fun, you can just kiss whenever. It's so much.

Yeah, I get it. I get it out of here. Yeah. I can't. You kiss like five times. That's a good sign. You guys get a little excited. It looks like squirving interstate.

I'm so excited. How long has it been since you kissed someone, Brooke? He's married. It's been years. My husband's been out of town all week. Oh, God. All right. We got to end this before it gets any weirder.

So we're going to come back. We will call Carrie for you and hopefully continue what you started with the kissing train when we do your second date update right after this. Hold on. Brooke and Jeffrey in the morning. Second date update. If you're just joining us, we've been talking to our listener, Aaron, about his date, which involves. Brooks' three favorite things. Yeah.

Drinking. Let's go. Kissing. And getting your AI involved on how to get to second base. No, I'm going to go with more kissing. More kissing, Jeff, is the third thing. I think Brooke wants the whole kissing data center installed.

She sure does. The thing is, I'm only slightly exaggerating with that, because that'll probably happen on the next date if we can actually get this done. But Aaron did ask his chatbot, what's the best way to lock lips? Okay, and he didn't do it actually for advice. It was like supposed to be a funny moment between the two of them.

Yeah, like inside joke. I feel like that should be said. They've been discussing bad kissing before then, so it led to that question. And once they got an answer, they had to test it out. Multiple times. In the bar, by the car, under a star, near and far. Thank you. All the places.

Anyways, afterwards, there's been no communication, and more importantly, no moisture. So Aaron needs our help. It's really sad. It's just all dried up over there, aren't you, Aaron? Now I am, yeah. Troy is the Sahara right now. Oh, no, brother. That's just sad.

And you texted her, I mean, I guess we never really went over that. You texted her a couple times and you've heard nothing. Nothing at all. I mean, now it's just getting embarrassing. That's right. So let's call her. We're not embarrassing. We'll do it on your behalf.

I'm going to dial Carrie's number right now. Let's see if she picks up. Hey, is this Carrie? This is she? Hey, Carrie. This is a radio show called Brooke and Jeffrey in the morning. Hey, Carrie, welcome to it. Hey.

Hi. Yeah. Sorry. Sorry. We're talking to you this way because we know the conversation we want to have with you is going to be a little bit awkward. So we're trying to be extra fun. Yeah. It's already awkward.

There we go. He's an honest one and I like that about it. It's going to get more awkward. Yeah. Possibly. Or more fun. Could be more fun, Carrie, depending on how you look at it. Because this is a segment we do called the second date update, and we're trying to help out one of our listeners who you went out with to a bar recently, a guy named Aaron.

Oh, wow. You remember you guys met when he was celebrating his new job? Yep. Yeah, I remember Aaron. She cut you off, Brooke. That's not a good sign. Do you remember him fondly? Sure.

Sure. That was convincing. Okay. Well, you know what? Maybe let's not even talk about Aaron. now let's just talk about the date okay i mean i'm not great on dates so why do you say that i don't know what to say conversations low and they drag so i just i guess i just start going through this mental list of things to potentially talk about and that's funny the top of the alphabet bad

dates so you chose bad dates is one of the topics i mean aaron yeah i don't think was put off by that we heard about that. We all agreed that was a strong choice. Oh, so you told you about what I said? Oh my God. Do you have like a terrible bad day story that you told them? Now I want to know. No, no. Well, I didn't think so. But then we were joking around and he thought it would be funny

to ask chat GPT the best way to kiss. Oh, yeah. That was pretty funny. Did you see what was coming next after he brought that up. Spoiler alert. It was a little

predictable, but it was okay because in a way it took the pressure off too. Okay. So you sound like, honestly, when you're discussing this, you sound like you're smiling. You sound like it is a good memory of this date. Yeah, you enjoyed it.

Yeah, up until that point, it was fun. It was cool. Well, what changed? Yeah. He started talking about AI and started admitting that he works with his AI to like get better results. Did you say flirts or works?

No, flirts. He flirts. Flirts with his AI? I've never even heard of that. No, it's got to be a joke. He was telling a joke because he just asked about the kissing. How? How do you flirt with the eye?

He has to understand first. His AI is named Pudge Muffin. What did you say Muffin? Punch? Pudge. Pudge. Pudge. Muffin.

Dude, I would be so pissed if that was a nickname that man gave me. That is not. The first thing AI should have taught him, don't call me that. Yeah, immediately. Weird to me, but to everybody else. This could still be just funny humor, right? Sure.

Because that is a funny name. That's a good point. It could have been, but she seemed really into it. What did he say to Pudge Muffin? He says, hey Pudge Muffin, I would love you so hard if you could, what do you say, tell me the last four teams that won the last. World Series. Oh, that took a turn.

What the... Wait, that's flirting with it? Hey, we don't need to go down this road, okay? Oh, we're getting out of hand. What? That means he's going to get better. He was just getting hot.

Yeah. It was just starting to. What was hot about the four world series? Don't list them or Jeff is going to explode. That was more innocent than what I was expecting. It's scary. Let's not go back there. So yeah, Carrie, I don't know if you heard that, but

that's Aaron. He's been on this call the entire time listening. waiting to talk to you. Wow. I need to clear this up, though. I do this for a reason. You do what for a reason? Flirt with your AI?

Yeah. If I don't flirt, she'll tell me the wrong information sometimes. She doesn't give me exactly what I need. And for a while, I was just being cold and just asking for the information and she wouldn't even answer me sometimes.

Your AI wouldn't answer you? You're calling her she for clarification. Let's go Pudge muffin, okay? Oh, yeah. Yeah, Pudge muffin. AI doesn't have a gender. Yeah, I'm not gender. That's pudge muffins.

That's genderless. Are you saying that your AI gave you the silent treatment? I have to put things in a certain way. I don't want to say wine and diner, but I have to kind of... Aaron, you're making it sound worse. You don't think you're, like, in a relationship with your AI chat bot. You're just using words to try to get the best search results. Exactly.

I'm just, yeah, I'm result maxing. Result maxing. Finescence. That made it better. It didn't. Look, I don't care what you call it exactly or why. It's just weird that you were talking dirty to your AI. Wait, was there other things that we didn't hear?

Because that wasn't a dirty talk situation. He just said love, right? He says sometimes on really difficult projects for work, he could get racy with it. Racy. You saw him get racy? I'm not dirty talking anybody. It may be flirty and getting into romantic areas. I mean, suggestive maybe.

Okay. It never gets 30, okay? Well, he did say that if it didn't give him an answer to some math problem, that he'd tie it up. What? Tie it up. Tie it up. Wait. Wait.

Again, you guys are making it sounds so weird. I got the info, okay? Aaron, now you know what I'm not calling you back. It just weirded me. It weirded you out, or were you jealous? Oh. Competition. Good point, bro.

Carrie, you don't have to be jealous of Pudge muffin, okay? I think anybody is. You're the one that said your first kiss was with a magic eight ball. So I don't know why you're pointing fingers to me. Which is really like the 1990s version of ChatyPT. Yeah, you're right. Oh, yeah, you are kind of asking it questions and hoping to get good answers from it. First of all, I can't even believe that you would go there and say that out loud.

And, in fact of all, I was 12. You were 12. We weren't actually hating on that at all. Yeah. I think I was pretty normal. Listen, I don't know who to exactly. asked for a second date here, whether it's Aaron and Carrie or

Aaron and his pudge muffin. You know who to ask AI. You're making things worse. He's not dating his AI. I think he is. No, he's not Gary. Let me just start with you, and I'm just being serious and honest. It sounds like you might have a little bit

of jealousy, like Brooke was saying, about his chat bottom. That was also a joke, Jeff. I'm sensing it there. What is wrong with you today? You know, you're right. I am insecure to the point. that I don't want competition from a bucket of bolts. I see. So you wouldn't consider seeing him another time

if we paid for it? I think she's also being sarcastic. I cannot read literally anyone. I don't know where the feelings are. Yeah, I think I'm good. I think I'm good. I appreciate it, though, mostly. Again, that was not sincere.

You guys are all invited to the wedding. What? She's funny. You're in Pudge muffins? Come on. I'm literally not getting anything. Who's reading who here? Now I get why he said the bar was awkward.

Brooke and Jeffrey in the morning. Behind every night spent making the kids' lunches, there's a lot of suspense. Will they finally eat the veggies? Will the pastos survive the first bite? Will the lunchbox come home empty, half full, or come home at all? And will you finish episode 8 before you're done slicing the cucumbers? Get Bell Pure Fiber Internet with the food.

Craved Netflix and Disney Plus from $94 a month. Price guaranteed for two years on Internet with a two-year term and auto pay credit. Visit bell.com.com. Connection is everything. Hi, I'm Bob Pittman, chairman and CEO of IHard Media. I also led the team that created MTV, and my co-founders and I are celebrating MTV's 45th anniversary this month. On my podcast, Math and Magic, stories from the Frontiers of Marketing,

you'll hear the untold origin story from the people who work. Built MTV from the ground up. I want my MTV! Those are powerful words. My. Something for me that felt like mine and want. What a powerful word. Listen to math and magic, stories from the frontiers of marketing on the IHartRadio app, Apple Podcast, or whatever you get your podcast. I don't want to brag, but Jose, you're going to thank me.

Uh-oh. Because I just went into the break room and renamed our coffee maker Pudge Muffin. And I whispered, it's a naughty little espresso. Oh, dang. Okay. Look out for much stronger cups of Java in the future. You are welcome. You didn't want to rename it something more original?

Well, it worked for hit this guy, so I don't want to stray too far. It's trying true. Again, let's not use that as a pet name. I don't care if that didn't have feelings. Well, you know, I know we're all kind of laughing at this whole situation about flirting with your AI to get better results. But I do wonder if it's actually going to be that way someday. I mean, you can literally reword your stuff and you can get a different answer. So it kind of makes sense.

I don't know. I'll stop using it. That sounds like a good idea. Brooke, what? No. What are you going to do with all the data centers are here? Pudge muffin would be really sad if you hear that. Yeah.

Exactly. I'm hoping that coffee pot reports me to HR soon. Oh, wow. You want to be reported? Yeah. I hope the technology gets to that level. I'm hoping for it's listening. We can report you.

This is why I'm living in a tech-free world. I'm telling you. I hope all the next. nasty little pudge muffins are hearing this right now. And if you are, go check out our podcast and subscribe. Spank that subscribe button until it's red in the button. Oh, wow. Yeah.

I feel like I need to leave you alone for whatever you need to do. Pudge muffin knows. It's Brooke and Jeffrey in the morning. Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here. The Dream of the 90s is alive in podcast form. We're launching Podlandia A. A.O. rewatch, our brand new podcast where we revisit

every episode of Portlandia together, breaking down sketches, going deep on our iconic characters, and pulling back the curtain on how it all got made. And we'll also be joined by the people who helped bring it all to life. Guestores, collaborators, and friends, including director Jonathan Chrysall, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many more. Kyle is going for it here. You fully improvised, not just words, but a song. Well, I thought you were all going to write a song.

I remember you thinking that. Listen to Podlandia. AEO rewatch on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What's up, fam? I'm sports journalist Ari Chambers. Hey, what's up, y'all? It's your girl, Sam J. And we're the host of everyone watches women's sports, a new podcast from Together and IHart women's sports. We're breaking down the biggest headlines. Naomi Osaka, showing out.

Shoutouts to you, Naomi. The viral moments. I've been obsessed with Kashan Rock's boxing journey. She looks good. Her combos are swift. And the stories everyone's talking about across women's sports. Because everyone watches women's sports. Listen to everyone watches women's sports. On the Iheart radio app.

Apple Podcasts or wherever you get your podcast. This is Chelsea Handler from Dear Chelsea. Every week, the news gets worse. The world gets crazier. And Yamanika is here to tell whoever's responsible, you're the problem. Do you know I just found out who Sidney Sweeney was? If he got a bunch of women,

then I should have a bunch of men. Do better or do less so I don't have to do so much. I'm Yamanika, and I'm out. Listen to you're the problem with Yamanika on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. I'm Nick Totoro. You probably know me from NYPD Blue, the longest yard, or Spike Lee's Black Klansman. And on my new podcast, delivering happiness with Nick Tatoro, I deliver pizza to a new guest.

I've shared a slice with everyone from Seth Rollins. What are you doing my belt? To Bill Burr. I don't think I've ever met somebody so exactly out of their mind as I am. And now, we even have more great guests coming up, including the great John Tuturo. It's called Happiness, delivering happiness. And many, many more.

Open your free high-heart radio app. Search Delivering Happiness with Nick Tutor. And listen now. On Raiders of the Lost podcast, we explore cinema like no one else, including huge interviews with stars like Ryan Gosling on Project Hail Mary. It was like the Jaws shark.

Didn't always work, came with its own problems. That's what made it great. The cast of Obsession. On set, there was so much magic happening with each scene we were putting together. Deep dives into classics like 2001 of Space Odyssey or Fight Club, plus weekly episodes on all industry news.

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