Brooke and Jeffrey: Second Date Update - Second Date Update: She Got It Off Her Chest

Episode Date: July 31, 2023

One of our listeners says she accidentally OVERSHARED about her ex and she’s certain it’s what blew her spot on her date. We’ll try to help earn her another one in a brand new Second Date podcast! See omnystudio.com/listener for privacy information.

Catch Jon Stewart back in action on The Daily Show and in your ears with The Daily Show Ears Edition podcast. From his hilarious satirical takes on today's politics and entertainment to the unique voices of correspondents and contributors, it's your perfect companion to stay on top of what's happening now. Plus, you'll get special content just for podcast listeners, like in-depth interviews and a roundup of the week's top headlines. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Being a woman on a dating app must be like going to the Cheesecake Factory and looking at the menu. You just have so many options and pages to choose. You don't even know where to start. It's like, ooh, do I want something that's tart and 6'4", or something with a little more in the middle, but he's got chocolate chips in his teeth. Okay, but Alexis's reaction, I don't think the menu items look that good for him. Yeah, it's just a subpar menu.

Did I say the Cheesecake Factory had a great menu? I said there's a lot of options. A lot of options, not rave reviews on all of them. I bring it up because one of our listeners, Morgan, says she met a guy recently on a dating app. And so I want to hear about it. Morgan, welcome to the show. Hi. Was he the Snickers cheesecake of your life?

That's the good one. I mean, honestly. That's what it is. The Adam's peanut butter one is really good. I am curious, as a woman, how do you decide who you want to go out with if you're getting tons and tons of swipes? I mean, you kind of pick one that maybe has something that stands out to you. You know, you kind of go with your gut. All right.

Okay. And how did your gut do for you this time? What was your gut craving? What's it saying? Well, I wasn't craving this, but I saw a picture and he was really good looking and then I realized

he had taken this picture of himself on a toilet. Oh, no. What? And he's like, it's in a funny way and he's like surrounded by toilet paper

and he's got like a toilet brush in one hand. Oh, no. Oh, no. So your gut was craving toilet boy? Yeah. I just thought it was hysterical. Oh, you thought it was funny. Oh, no. So your gut was craving toilet boy? Yeah. I just thought it was hysterical.

Oh, you thought it was funny. Oh, God. What was his name? Aiden. Aiden. Aiden. Okay. I thought I was sure it was going to be like Ed or Rupert.

All right. You swiped on toilet guy Aiden. He must be hot to be able to pull off a toilet picture. I'm confident, right? Yeah. It's the only way you can do it. Yeah. That makes sense.

So what did you and Aiden do when you went out? Well, we met up and went to a bar and we were having like a pretty good time, a little fun. We were drinking a little bit. And as we drank, we talked more. And at one point, we kind of bonded about like our most memorable date. Oh, interesting. Yeah. So I told him about mine and I was like, it we kind of bonded about like our most memorable date. Oh, interesting. Yeah, so I told him about mine and I was like, it was kind of a normal date. And he was like,

well, why was it so memorable? And I was like, well, I was engaged to a different person at the time. Oh, God. You just threw that out there? Yeah, he was like, oh, gosh. That's a bomb. Wait, so you were cheating on your fiance? Well, I mean, I was kind of on the way out.

Oh, that's not an excuse. Just checking the field out one more time. Yeah. As a guy, if you're sitting across from somebody and you hear them say that, that would be kind of a red flag. I mean, not kind of. That's a big red flag. I can't believe you said kind of. Yeah.

Excuse me. The giant red flag. What did he say? What was his reaction to that? Well, he was like, you're not engaged now, right? And I was like, oh, no, no, no. We just, we laughed about it. And, you know, like looking back, I realized it was probably a really bad thing to do.

And I shouldn't have done that, you know. But I hope he doesn't think I'm an unfaithful person. Well, he probably does. Yeah. That's how you guys meet. He's going to think one day if I'm engaged to you, you may go on dates with other guys. That's kind of intense. What was his most memorable date?

I honestly don't even remember. Yeah, I probably changed the momentum. She was just shame spiraling, realizing what she had done. Oh, my gosh, girl. Yeah, I was kind of, my mind was elsewhere. But, like, we kind of got over and started like talking kind of flirty again you did how do you what do you talk flirty about after admitting to dating other people on your fiance quick change the subject right and at one point like i asked him are you

a boob guy or butt guy he was a boob guy and i had mentioned like oh i was thinking maybe about getting an enhancement oh okay that's a You're just throwing it all out there. That's a smart strategy, though. Two of my three husbands are butt guys. Why is it a smart strategy? Just because boobs are going to distract him that much? Totally. He's going to forget everything that happened before that moment. I don't know, man.

Trust me, I know. You said boob enhancement. I haven't heard anything else she said. Oh my god. Maybe at this point I haven't heard anything else she said. Yeah. Oh, my God. Maybe at this point I'm getting a little too tipsy. The night kind of ends a little faster than I thought it would. But like I said, I'm kind of glad it did end because the alcohol was really starting to kick in. Who knows what else you would have shared? My God.

This is kind of a train wreck. Not going to lie. It feels like an overshare but again remember this is a guy who takes pictures of himself on the toilet and posts them online but that's funny cheating on your fiance not really well i didn't cheat i mean technically i went on a date i had a free meal that's full cheating you can't date someone Wait, did you tell him that too? Did you tell him that? No, I said nothing happened. It was just dinner and, you know, some social time. What? Okay.

She answered the question honestly. It was a memorable date night for her. She didn't say it was the best date night for her. It was a memorable one. And all relationships are different. I do think like 99% of them would consider cheating, but maybe you have a really cool fiance. Well, no, they're not together anymore.

I think that, yeah. Well, we haven't asked that. Are you still with your fiance? No, her date asked that. No, no, I'm single. Yeah. Okay. Her date even asked to make sure.

Yeah. Well, that's a smart guy, I guess. Yeah. I remember. I stopped listening. So we need to help you come back from this, because I'm guessing that you have not heard from him. Well, I have. Oh. I remember. I stopped listening. So we need to help you come back from this because I'm guessing that you have not heard from him. Well, I have.

Oh. Wrong again, Brooke. How does that feel? Okay. So why are you calling us then? Why don't you guys just go out? Well, he's like kind of aloof. Like he's not getting back to me right away.

Sometimes it's an energy shift or like when you ask specifically about dating. Oh my God. They all of a sudden don't answer Would it be amazing if we call him and we find out he has a fiance? Why is that funny now? It wasn't funny when the girl did it It's just the irony of it all Well let's find out how funny it really is We're going to come back

We're going to call Aiden for you Toilet boy himself And we'll see what he has to say. Try and get you a second date update right after this, all right? Okay. Okay, hold on. We've always said on this show, talking about exes on a first date is a big no-no. Yeah.

But we've never said anything about bringing up past behavior when you were engaged and you accidentally went on a date with somebody else. I don't think she was an accident. Whoopsies! I got a free dinner and a funny story out of it. Oh, wow. Oh, no. If we don't want our listeners to do that, we need to explicitly tell them not to.

Well, I mean, that's actually true. I mean, this woman doesn't even think that was cheating. It wasn't. It's not cheating until parts touch. No. That's not emotional cheating. If my husband went on a date with someone, you better, yes,

bet your butt that it was cheating. Can you imagine him coming home from work right back? I've been on four dates this week, and they're all been so bad, honey. So do I have to cancel dinner with them later? Yes. Jeffrey. He's going to be really upset about this.

Jeff and Michael. All right. But see, this is something that happened to one of our listeners, Morgan, on her date, who told a story about how she went out with a different guy while she was betrothed to another. They're no longer betrothed. Okay. She made that clear. Engaged.

Well, I didn't want to keep saying engaged. So I had to dig into my, you know, the source. She's single. Yes. She is single and trying to mingle once again with Aiden. That's the guy that she went out with. Yep. So, Morgan, how are we doing? I'm doing good.

Really? Even after hearing all that? Okay. Okay, I apologize. I like your attitude, though, Morgan. I think you have a good attitude. It sounds like you can take a good joke. That's me. She means that in the most demeaning way possible.

I don't. I don't. Imagine her saying this talking down to you. That's where it's coming from. But we're all on your side, at least for now, Morgan. We'll see if it changes when we call Eden, okay? Don't laugh evilly every time I say things like that okay here we go good luck let's do it hello hey is this Aiden? Yeah.

Sorry, who's this? My name is Jeff from Brooke and Jeffrey in the Morning. We're a radio show. Hey, Aiden. I won't even tell you who that is. Yo! Okay. Why are you doing this?

Jeff's like, don't talk to her. Just, yeah, don't ask questions. Let me talk to you for a second, Aiden, because we're doing something called the Second Date Update on our show here. You ever heard of that before? Okay. Yeah, I think I've heard it before. Okay.

Okay, that's cool. Yeah, it's where we help out our listeners and try and hook them up on a second date after they've gone out with somebody. So you recently went out with a woman who listens to our show named Morgan. And it doesn't sound like you're ghosting Morgan or anything. I guess you guys have been texting and stuff. Yeah, you know, I'm trying to be nice a little bit. You know, like, she's been fine.

She's definitely unique. She's unique? Is that good to you? Is unique good? Nice, fine, unique. Those aren't usually glowing reviews. I'm trying, Jeff. Did she tell you, like like how the date went we got some details from it we heard you were out at a bar together

and uh you guys talked about some interesting things yeah after after having some drinks of course well truth serum yeah yeah a little discussion about Some of your most memorable dates Right So Oh my gosh So she told you that About that story Yeah

Are you talking about Her story you mean Yeah Yeah what'd you What How'd you hear it I just So she said

Her most memorable date Was that she Went on a date While she was still engaged to a guy. Yeah. Had that say. Yeah, that definitely was pretty weird to me. Did you say progressive of her? Progressive.

Yeah, that's interesting. Yeah, she isn't owned by anybody. Yeah, that was definitely one way to push right yeah i'm not gonna lie we got some red flags in this room when we heard that too oh my gosh and we told her that you know but she took it well right so i mean that was the first thing that was the first thing was there more well if you like got super flirty and was asking questions that were a little, I don't know, maybe for later in the date or for a second date. Like what? She was asking me if I was a butt or a boob guy.

You don't like that? I wasn't ready to be talking about that yet. See, Jeff? It wasn't a good move. Do you remember you told her, oh, that's a great move, talking about how you want to get breast enhancements. I don't know why you're bashing me right now. It wasn't a good move.

He didn't like it. Everybody's different, Brooke. It's okay. I think the majority of guys would agree, and you can always just say both, brother. Well, and what it sounds like is she was just trying to set it up so that she could brag about maybe getting a boob job at some point. She was kind of leading.

Yeah. So was that like inappropriate to you? It was definitely on the line. And she immediately like mentioned, oh, I'm getting breast enhancements. And I was like kind of caught off guard. And I said like, well, you don't seem like the type. Just because like she didn't seem like she needed that. She was so confident in herself anyway.

There's a lot of confident women that still get plastic surgery. Yeah, that's about how it makes them feel. I mean, do you think that that was off-putting to her when you said that she wasn't the type? She seemed excited about it to prove me wrong because then she

reaches into her shirt and whips out this jelly-type thing and pops it down on the table. It's a cutlet. Yeah. Is that what they're called? She said it's like the saline bag, and I guess they give them to

you at the medical center to pry it out. It's like a pro-water balloon. Yeah, I mean, she just whipped him out and put it on the table and said i'm taking these babies for a test run oh my god i'm sorry i love her did you not laugh like that's pretty funny i think i laughed but i was definitely uncomfortable it was you know i like somebody who's fun and outgoing and she's definitely that but this looks like insane i'm not insane that's not gonna help yeah she's supposed to wait till we call her in but uh aiden morgan's been on the other line

wanted to talk to you oh my god uh i was Well, I was a little tipsy, and, you know, I had a little problem controlling what I was saying. At that point, I was kind of doing damage control, but I think I was doing a lot more damage. You're that type of guy who took your picture on a toilet, you know? Oh, yeah. All right. One of your profile pics or whatever in your dating app

was you on a toilet, she said. We heard about that. It's not like my pants were down. I was just making fun of bathroom selfies. Like, come on. Well, I know, but it kind of sets the tone, right, for your type of humor. Sounds like maybe you were trying to match each other's energy. Maybe I was kind of going into the date, like, a bit more serious,

and I just was not ready to dive in the deep end. Yeah. Like Morgan was. You were a lifeguard by the end of that date. Yeah. Morgan slapped you in the face. You probably just have to get used to me. Like I'm an acquired taste.

Oh, okay. That's. Say that. Anytime someone says you'll get used to them or you'll get used to me, that's always good. It's the same of like, if you can't stand me at my worst, you don't deserve me at my best. Unapologetically me. I see that one a lot.

Which I think is sexy, by the way. Yeah, yeah, yeah. Me too, Jeff. I'm just trying here, okay? I mean, I'll say Morgan sounds fun. She sounds like you know what you're getting, okay? That's a good point. You know, she's laid it out there.

She's very, very brutally honest. Yeah, I will say, Morgan, you did good by, like, telling me about that story. You know, I feel like even though it wasn't a good light on you, you still told the story, so I guess that's good to be, like, to show your skeleton. Look at that. Jeff, we're making some progress.

The guarantee for you, Aiden, is if you go out with her, there will be no shortage of excitement. Yeah. I guess I could go with a little bit less anxiety on a date. I'm hearing that you're at least thinking about it, so we'd like to offer to send you on a date that we would pay for. Yeah.

You know, once you go on like three or four dates with me, all that stuff I do is normal, you know? Okay. Yeah. Yeah. It's like you. I'm a very awkward person and I like to laugh at myself, though. That's true.

She has been such a good sport and we have given her a hard time. It's hard to turn that down, Aiden. We need an answer, Aiden. Yes or no, you want to see her again? Yeah, dude. You know what? Let's give it a shot. All right. There you go. Just make sure you don't get engaged to her.

That's kind of the first thing. Hey, maybe you can try out her saline bags, huh? I would want to put them under my shirt. Oh, you want him to wear them? Yeah. What did you think? Let's not talk about it. Okay.

Brooke and Jeffrey in the morning. Catch Jon Stewart back in action on The Daily Show and In Your Ears with The Daily Show Ears Edition podcast. From his hilarious satirical takes on today's politics and entertainment to the unique voices of correspondents and contributors, it's your perfect companion to stay on top of what's happening now. Plus, you'll get special content just for podcast listeners, like in-depth interviews and a roundup of the week's top headlines. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.