Brooke and Jeffrey: Second Date Update - Awkward Tuesday: A.I Fail

Episode Date: April 1, 2025

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey',  that may have even more drama than a Second Date Update. Let us know what you think!  Is a gift on a first date too much? One of our listeners gifts may have crossed that line because he emailed us asking for an Awkward Tuesday Phone Call! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Hey all you women's hoops fans, and folks who just don't know yet that they're women's hoops fans. We've got a big week over at Good Game with Sarah Spayne as we near the end of one of the most exciting women's college basketball seasons ever. The most parody we've seen in years, with games coming down to the wire and everyone wondering which team will be crowned national champions this weekend in Tampa. Listen to Good Game with Sarah Spayne on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.

Imagine you're scrolling through TikTok. You come across a video of a teenage girl, and then a photo of the person suspected of killing her. It was shocking. It was very shocking. Like that could have been my daughter. Like you never know. I'm Jen Swan.

I'm the host of a new podcast called My Friend Daisy. It's the story of how and why a group of teenagers turned to social media to help track down their friend's killer. Listen to My Friend Daisy on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. In 2020, a group of young women found themselves in an AI-fuelled nightmare. Someone was posting photos. It was just me naked.

Well, not me, but me with someone else's body parts. This is Levittown, a new podcast from iHeart Podcasts, Bloomberg, and Kaleidoscope about the rise of deepfake pornography and the battle to stop it. Listen to Levittown on Bloomberg's Big Take podcast. Find it on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. What's up, I'm Laura, host of the podcast Courtside with Laura Corenti,

a masterclass case study of the business of women's sports. I'll be chatting with leaders like tennis icon, Alana Kloss. I don't do what I do only for women, I do it for everyone, And I want the whole market. And innovators like Jenny Nguyen. I would say 50% of the people that come visit the Sports Bra aren't sports fans. They come to be in community.

They come to be part of this culture. Quartzside with Laura Currenti is an iHeart women's sports production in partnership with Deep Blue Sports and Entertainment. Listen to Quartzside with Laura Currenti on the iHeart radio app, Apple Podcasts, or wherever you get your podcasts. Presented by Elf Beauty, founding partner of iHeart Women's Sports. From the producers who brought you Princess of South Beach comes a new podcast, The Setup. The Setup follows a lonely museum curator, but when the perfect man walks into his life,

well, I guess I'm saying I like you. You like me? He actually is too good to be true. This is a con, I'm conning you to get the Dilawba painting. We can do this together. Listen to The Setup on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Hey, it's the Second Date Update podcast, Brooke and Jeffree in the morning. And today, of course, it's Tuesday, which now means it is an awkward Tuesday phone call. Yeah! I just want some comments on this one. Worst gift you were ever given by a significant other. You guys have any?

Yeah, not the worst, but I definitely remember getting gift cards once and they were empty. Oh, no way! I went to spend them and they were empty. Oh my god. No way. I went to spend them and I was with a bunch of friends. I was like, yeah, yeah. And then they were like, there's no credit on this. I was like, did I just get scammed?

That is so embarrassing. Did you have to take the stuff back from the counter or did you buy it? No, I bought it. Yeah. I mean, you got it without me. You had to commit. Yeah, and then return it later. How is that not the worst gift you've ever been given?

Empty gift cards. Yeah, maybe it's up there Oh that was a gift because I didn't give it back do you still use it no no I preserved it into my closet Oh, I could actually use umbrella. That's kind of nice My memory of her. It's the X-Tri in Hosea's house. Alright, well leave your worst gift in the comments here. We'll read some comments from earlier this week. What do we got, Alexis? Yeah, I saw one from Soph King that said,

It's crazy how my sister used to make me listen to you guys in the car, and I thought you guys were annoying. And now I listen every day. Sadly, I've heard this before. Other people that forced us and they're like what is this garbage and then two days later They're like to do the second day nothing. Oh, are we like the broccoli of podcasts like you hate it as a kid? And then once you get older you're like this is delicious Okay with that thanks for your comments. Thanks for listening and sit back and enjoy today's awkward Tuesday phone call.

When it comes to giving gifts, they say it's the thought that counts. Aww, that's such a nice sentiment. Yeah, okay, sure. But then I buy everyone personalized coffee mugs for Christmas, and then suddenly you're all mad at me because they cause fires when you put them in the microwave. So I'm sorry, which one is it? Mine's a decorative ornament. And I think it's hand wash only too. It is. Oh, that's not good enough for you all of a sudden.

I mean, you did kind of mail it in. Oh, they were not there on so nice? Personal coffee mugs. It's the opposite. They can't be washed because they're so nice. They said my full name. There's gold in them. But it said a B. I mean, any, like, obviously.

It was an ornate B, but fine. I just know one of our listeners brought a gift to his date with a special lady. And her response? Historic. So was it a mug that he gave her too? And the reaction, I don't even think was as bad

as the reaction I got from my gift. You're gonna find out what it was and why he turned to us for an awkward Tuesday phone call, this is much much bigger Than a regular second date. We're gonna make that call coming up right after this I've never personally matched with somebody on Instagram, but I've heard that people do do that. Yeah. It's Brooke and Jeffrey in the morning. And one of our listeners named Davis matched with a lady on IG two years ago.

Wow. I mean, to be fair, Jeff, you probably don't remember what your password is. So you probably have it lost. Yeah. You have it for me, right? No. Oh. No, I don't keep that. Okay. I would go to IT, but that department doesn't exist here anymore.

Yeah. So I'll figure it out some day back to Davis two years ago He took a chance asked a girl out on IG whoa and Nothing happened, okay That puts him in the 99.9 9 9 9 9 percent of guys who DM ladies with no answer Well, they don't even open it right unless y y'all left on red. It goes in the request folder. So you just have to see it. Or the hidden requests or just the blocked area. Oh yeah. That's true. So many options to avoid men. It's amazing.

But our producer insists that this story is different. Really? And he implored me to have Davis on the show to tell us what happened and explain why he deserves an awkward Tuesday phone call today. So I obliged, Davis, welcome to the show. Hey, thanks for having me, guys. Dude, we're so invested already in your story. What a setup. Yeah, I guess I'll dive right in. For sure.

Like you guys said, I met her about two years ago or on Instagram We started talking and we matched. Oh you were talking. Oh, okay. Yeah. Yeah, we talked a little bit I got her to agree to go out on a date with me, but we couldn't figure out schedules or time And eventually one day she just left me on red Okay, you're saying you match like you just follow each other without ever No, it's soul meeting You're saying you match, like you just follow each other without ever, like she's just a random person on Insta? You don't match on Insta. No, it's soul mating.

You guys soul mated on there. Follow, yes. You guys click. If you say match, I keep thinking Tinder. He commented on a bunch of her pics and she finally followed him. Got it. That's good. So two years later, I still follow her and I'm seeing her pictures a lot. Like she's still so cute.

And I decide, you know what? I'm going to try and reach out again. Well, I mean, she left you on red, but you could still see your photos. So that's a positive sign. Right. So she says, why not? I'm single. Let's try it. Oh, OK. Sure. God, I love a why not answer. Yeah. Take it.

I've got literally nothing else going on in my life sure. I finally hit rock bottom. Why not? And what's this beautiful Instagram girl's name? Samantha. Samantha's are always hot. Oh yeah. Just in the name. Makes sense. Yeah. Okay so did you guys finally go out? We went out on three dates. Oh. Our first two dates were really good. She's a lot of fun. She seemed to like my company and on our third date, you know, I was feeling really good and maybe too good about it. And this is where I screwed up. Okay. Set the scene. Where were you? What were you doing? Okay. First, I just want to say, like I work in tech. I work with AI programs a lot and things like that, okay?

Okay. We're hanging out at my place. She goes to the bathroom and when she comes back, I had a book out on the coffee table waiting for her, kind of like a scrapbook type thing, nothing too fancy. What? What do you mean a scrapbook type thing? So I basically made an AI scrapbook

of our life together over the next 40 years. Your future life? Oh wow. That is sad. Okay, creative, but you get it bro. I was thinking the other C word, creepy. Yeah, that's what I'm saying. So wait, can you describe some of these photos for us? Because maybe it's not as bad as we're thinking.

What was in the scrapbook? Well, that's the thing is that I did do like future vacations like us in Mexico with dolphins jumping over us Hey, I dolphins. I thought it was funny. It was obviously AI. Okay, so it was meant to be a joke Okay, that's good. It was going for funny not yeah Okay. Yeah at one point. There's an AI like of her in a delivery room with our first baby. Okay, that's what we were worried about The dolphins jumping over the That would be awesome, yeah, we got the awesome no, what were you thinking? Why would you put any woman in the delivery room? I thought she'd be laughing but she looked more shocked than anything

yeah yeah when you just told us what you did none of us even thought of that before that's a mind-blowing thing to actually see it would be crazy did she run from the apartment yeah what happened so she did say she was like wow you put a lot of effort into it but it wasn't like a happy tone. Yeah, yeah. I think polite. Yeah. So this obviously was a big mess up and I never got to explain that this was like all meant as a joke and she hasn't responded to my text and this is like over 10 days now.

Okay. So you think maybe she took it like a little bit too seriously than you wanted her to take it 100 percent. Why weren't you able to explain it like a little bit too seriously than you wanted her to take it 100% Why weren't you able to explain it's a joke? I think I was so mortified after like her response of like oh you put a lot of effort into this Yeah, okay, I just like to tell her like hey I didn't mean this to be creepy and maybe get some advice on how to say it Oh, okay, so this is what you want to do with the Awkward Tuesday.

We're reaching out to Samantha here, hoping to walk back a little bit of the damage that you've done. That's exactly what I'm hoping for. God, that is so hard. I feel like you miss your opportunity to tell her it was a joke. I feel like if you tell her now, she's going to just assume you're saying that because she was freaked out by it. This is good advice, Brooke. You know, I don't know. Sounds like Brooke because she was freaked out by it. This is good advice Brooke. You know what?

I don't know. Sounds like Brooke's advice is lean harder into it. I don't know. Like I was super, there's way more pictures if you want them. It's surprising. When she picks up just say, gotcha! Yeah. I just think it's gonna be harder than you think.

Well, we're gonna work on how to give you the best advice we could possibly come up with. Okay. And then call your, what is what is she's not even your girlfriend No, just a girl. He's talking to yeah, the girl you're talking to some future wife. We have pictures Your possible future wife and let her know the AI scrapbook wasn't meant to be serious phone call right after this. It's awkward. It's Tuesday.

It's awkward Tuesday phone call. We've got a tech whiz on the phone with us today named Davis, who recently used his super AI powers to scare a woman that he just started dating. That's not wrong. Oh man. He didn't mean to. No, he didn't. It was all meant as a joke when he made an AI scrapbook that showed their

future life together over the next 40 years. Again, a joke. The good news is it wasn't on the first date that he did this. He waited till the third date. Okay. Means that the pictures of her, the AI photos of her in the delivery room should have been so funny. Yeah. But now it has been 10 days since then, and she did seem a little bit freaked out by some of the photos that he showed her. So I mean, David, would you say that that's accurate? That's accurate. I mean, I think the one that got her the most was our wedding day and I photoshopped her parents into it.

Oh, God. Parents are there. Yeah. We hadn't heard about the wedding photo. You haven't even met her parents, have you? No. I mean, I found them on Instagram. wedding photo. You haven't even met her parents. Have you know, I mean I found him on Instagram Well, that's fair

So now you just need a couple pieces of advice before we call Samantha and try to explain to her It's not as serious as it seemed in yeah. So what do you think he should do? This is a little bit of a white lie But you just tell her that your other nerd Coworkers were like all making up for their girlfriends and their girlfriends thought it was so funny You got carried away You realize that your girlfriend you're not together yet, and it was too much too soon So sorry bully yourself by calling you a nerd and all I'm sure I'm sure you would consider yourself a nerd, right? Oh, yeah

No, I'm a big nerd. Okay, Jose. What's your advice? Well, you told us in the first part that you froze up when you were with her Yeah, you need to feel and sound confident here. So right now with all the confidence in the world Tell me what is the one thing you like most about yourself? Oh On the spot oh come on brother I can tickle myself and laughs and I don't think other people can do that okay laugh I will go with just funny maybe just do I'm funny just say you're a nerd again that gives him confidence let him be confident in the things that he likes about himself All right

We're running out of time, but remember you're a nerd, but you're a confident nerd So here we go with a good sense of humor the dollar number and let you make your awkward Tuesday phone call. Good luck Hello? Hey, Samantha, it's Davis. Hi. Oh. Hey, um, so I just, I was trying to reach out a few days ago and I just wanted a chance to maybe talk with you about our last date.

Okay. Well, what do you want to talk about? Well, I think you maybe got the wrong impression about the book that I made. Well, why do you feel like I felt that way? Well, I mean, your general reaction to it and demeanor afterwards seemed very scared, creeped out. You're not far off. I was a little weirded out. So here's the thing, like I'm a, I'm a big nerd and a lot of my nerd friends who work at my nerd place had done stuff like this with their girlfriends and I may have jumped the gun again, I know you weren't my

girlfriend but they thought it was very funny with them and I thought it might be funny for us and I might have nerded a little too hard. When you first showed me the book and we were looking through it, I initially thought it was creepy and thinking about it days later, still creepy. Yeah, but I'm kind of like a tech nerd type thing and one of those ways to show it to you was to make that for you. And I mean, I appreciate that that but I didn't really know how to take it so I would home and ask my girlfriends about it okay what did your friends say what was their feedback um I've got really big and they start saying things like no way why are you dating Hannibal Lecter? Did you throw the book at him and run?

I feel like that is a fair response after I got to relook at everything. But at the same time, I feel like you could also say I'm very confident to have shown that to you. I just couldn't get that image out of my mind, just about how ugly our future children will be. Wait, wait what? How ugly the AI fake children were? With that picture you showed me it put fear in my mind that this is what my actual kids is gonna look like, like monsters. Obviously I'm not a mom, I don't have kids But if I did I would not be able to look at my daughter

That's a sound effect that we played off of our board here because Much older technology because you're on the radio right now with a show called Broken Jeffrey in the morning. Davis, you've got to be kidding me. You got me on a radio show? Oh, no. OK, so I mean, you weren't answering any of my messages. And to go back to that, like, this is an AI program.

It's not 100% accurate. Oh. That's fair. I'm hoping it's a lot less than a hundred percent I know that it's AI and that I just personally do not think that I would be able To live with the fact of that image in my mind thing. This is what my kids are going to look like Okay, okay What you're missing because you're not a mom yet is that mothers are blind to how cute their babies are we all think our own? Children are cute. It's just like it's biology.

It's just how it works. You didn't see these children like I did. These little monster children. They are ugly. Gorgeous babies. But I kind of understand where you're coming from. Like it would be a hard image to erase. It's like I never tried on a wedding dress before I actually was engaged, because I didn't want to see what it looked like. It freaked me out.

See, I take it as a mission. I'm like, we're going to try our hardest to make kids that aren't looking like that. You just keep making kids until they don't look like that. Oh, yeah. You have a lot of choice over it, from what I understand. Did he show you the pictures? Did he show you the whole book?

No. And I'm kind of glad that he didn't. I say the freakiest thing was, was my six-year-old son's creepy looking smile. Oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh,

oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh, oh them. Okay, that was a joke that he was making, right? Davis, did you just name your AI children? Okay, I mean, I did name them, but they're not real. Oh, wow. Is the teeth something an orthodontist could fix? An AI orthodontist?

That's a good idea. I think at the end of the day, we all think that Davis seems like a sweet guy. Who was really into you the gesture fell flat He admits that he knows he had one thing bad if you think about it other than that Right Davis. Yeah, that's it Okay And when i'm not sure during these segments what should happen next? I always go to our expert alex Alexis on what she would do in this situation

Lexus Great idea what if I make you a new book of just us going on AI dates Samantha what do you think about that idea? Would be willing to go on another date if you just leave AI out of it That should be a good theme for all dates yeah, and we normally don't promote book burning on this show We can make an exception for this one time. The only book that should be banned. Yeah, just this one, you guys destroy it and make new dreams for your future.

Oh! I like it. I'm in. I'm all in. We know you're in. Davis says, yeah, we know. So what do you think about talking this out with Davis off the air? We'll end this call and you two can hash it out. Yeah. We can have a conversation.

Yay! That's so sad. That's all we care about. And Samantha, I didn't tell you some of the best parts about me. I can tickle myself. Oh, no. We didn't need that. I mean, I'm intrigued. I got a few secret talents of my own. Oh, okay. Maybe they are perfect. That might be the most shocking part. Yeah, better than we thought.

All right, well, let us know how that conversation goes. She's like, well, I can whistle by myself. Wow. Okay, here it's all together. Brooke and Jeffrey in the morning. Hey, all you Women's Supes fans, and folks who just don't know yet that they're Women's Supes fans. We've got a big week over at Good Game with Sarah Spain as we near the end of one of the most exciting women's college basketball seasons ever. The most parody we've seen in years,

with games coming down to the wire and everyone wondering which team will be crowned national champions this weekend in Tampa. Listen to Good Game with Sarah Spayne on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Imagine you're scrolling through TikTok. You come across a video of a teenage girl and then a photo of the person suspected of killing her. It was shocking. It was very shocking.

Like that could have been my daughter. Like you never know. I'm Jen Swan. I'm the host of a new podcast called My Friend Daisy. It's the story of how and why a group of teenagers turn to social media to help track down their friend's killer. Listen to My Friend Daisy on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. In 2020, a group of young women found themselves in an AI-fueled nightmare. Someone was posting photos. It was just me naked.

Well, not me, but me with someone else's body parts. This is Levittown, a new podcast from iHeart Podcasts, Bloomberg, and Kaleidoscope, about the rise of deepfake pornography and the battle to stop it. Listen to Levittown on Bloomberg's Big Take podcast. Find it on the iHeartRadio app, Apple podcasts or wherever you get your podcasts. What's up? I'm Laura, host of the podcast Courtside with Laura Corenti, a masterclass case study of the business of women's sports. I'll be chatting with leaders like tennis

icon Alana Kloss. I don't do what I do only for women. I do it for everyone. And I want the whole market. And innovators like Jenny Nguyen. I would say 50 percent of the people that come visit the Sports Bra aren't sports fans. They come to be in community. They come to be part of this culture. Quartzside with Laura Karenty is an I Heart Women's Sports Production in partnership with Deep Blue Sports and Entertainment.

Listen to Quartzside with Laura Karenty on the I Heart Radio app, Apple Podcasts or wherever you get your podcasts. and entertainment. Listen to Quartzside with Laura Karenty on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Presented by Elf Beauty, founding partner of iHeart Women's Sports. Welcome to Pod of Rebellion, our new Star Wars Rebels Rewatch podcast. I'm Vanessa Marshall, voice of Harrison Dula Spectre II.

I'm Tia Zirkhar, Sabine Ren, Spectre V. I'm Taylor Gray, Ezra Bridger, Spectre 6. And I'm John Le Brody, the Ghost Crew Stowaway moderator. Each week, we're going to rewatch and discuss an episode from the series and share some fun behind the scenes stories. Sometimes we'll be visited by special guests like Steve Bloom, voice of Zabarelio, Spectre 4, or Dante Bosco, voice of Jaiquel, and many others. So hang on, because it's going to be a fun ride.

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