Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Age-Ja-Vu

Episode Date: October 19, 2024

What’s the opposite of a Wingman? Whatever you call it, that type of guy is what ruined our listeners date.  Now he wants our help to try and save it with a Second Date!See omnystudio.com/listener for privacy information.

Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews and more. Now this is a second term we can all get behind. Listen to The Daily Show Ears Edition on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Second date update. Brooke, imagine if you had to jump back into the dating pool. Like, for example. All right.

Let's say you were caught being unfaithful to your husband. Oh, no. With your garbage guy, Boone. That's how it would go down. Why is it always gotta be Boone? I'm just trying to be realistic here. You saw him out in front of your house heaving large bags of waste into that truck.

Oh, boy. And you just thought, God, I wish I was that trash can. I do like a dirty man. Yeah. I will say that. And the fact that she knows his name. Exactly. Already kind of sketch. That all leads to things happening I do like a dirty man. Yeah That all leads to things happening and suddenly you have to re-enter the dating scene. Oh, I think you would do

Think I would be really disappointed you You would. Oh, you would be the disappointed one. That's interesting. Okay. I think I'm a catch. I mean, the text board's always flooded with guys saying how hot Brooke is, so. Well, that's Boone's friends. Right. Oh. That makes sense.

But the only reason I ask is because one of our listeners, Mike, just had to reenter the dating pool after going through a separation. Oh, man. And it led him to us today. So, Mike, welcome to the show. Hey. Hi. after going through a separation. Oh, man. And it led him to us today. So, Mike, welcome to the show. Hey, hi, how are you? Good. Oh, man.

You don't happen to work in the waste management industry, do you? No, but I'm a huge fan. Oh. Oh. We have something in common. This is great. He's available for lunch today. I think he meant of the show, not of waste management.

You know that. He's a fan of the show not of waste management you know that he's a fan of the show not waste management gotcha yeah anyway let's talk about the uh date that you went on the other night who was it with so i guess i should start by saying that you know recently divorced a little over a year ago okay i'm a little out of practice right and i don't know with all the apps and everything, it's sort of different. Yeah, it's changed for sure. It's so quick nowadays. Everything is fast. Is this your first actual date since your divorce, or have you gone on others? The first one was online.

Oh, this is the very first one. Whoa. A lot of pressure. Oh, man. Who's the person that you met online her name is tanya and uh i don't want to get too into specifics but she is a little younger than i am let's say okay that always sounds like it's a lot younger yeah the way you said that we're talking legal here right yeah no she's legal but let's just say she's definitely younger than i am okay

i'm gonna make an assumption here that you sound like you're in your mid-30s and that's a weird No, she's legal, but let's just say she's definitely younger than I am. Okay. So she's in her 20s. I'm going to make an assumption here that you sound like you're in your mid-30s, and that's a weird age because you can date girls that are like 23, or you can date girls that are like 43. You're kind of in the middle at this point. Yeah, I'm pushing 40, but I was excited, and here's why. Because her profile, it showed her as a devoted dog mom. Cute.

So she sounds like a caring person. And, you know, having kids myself, if I'm going to try to hopefully end up with someone, that's a caring person, right? Oh. Oh, that's cute. I like that. So you weren't just going for her because she was, like, young and tight still. Whoa.

Whoa. Girl. Interesting way to describe it. What is that? She had, like, nice abs. It's just a lot of other words you couldn't use. So Tanya is young, beautiful, and loves dogs. These are all good things.

And tight. And tight, okay. Yeah, I'm not going to deny that she was easy on the eyes, you know? Okay. There you go. I want to get into the actual date with Tanya. Tell us where you went. How did it go?

So we met up for drinks just to get to know each other. Okay. And it sort of naturally came up that I've been married before. Right. But, you know, honestly, she didn't seem bothered by it. That's really good. But, but, but we were interrupted. And, uh, Someone you know?

Not your ex. No, no, it wasn't my ex. Oh, okay. But the guy that comes up is my life insurance guy. Oh. He was in the bar, too? That just made you feel really old. I'm sorry.

My life insurance guy. Yeah. I mean, it just bumped you from late 30s to late 50s. I didn't even know you had a guy for that. Late 50s. And so he, I guess he had a few dreams because he was like, I just sell me right then and there. Like, oh, you know, for $10 more a month,

you can have term life insurance and blah, blah, blah. Oh, God. Oh, man. In front of Tanya? Oh. Yeah, but she was cool. She was laughing about it. And then, you know, I said, let's get out of here.

And I asked her if she wanted to come to my place and, you know, watch a movie or something. And she was into it. She said, yeah. Okay. Oh, there you go. This first date is going quite well for you. It's like his first date back on the scene,

and he's just making it happen. Yeah, I know. I'm thinking, oh, wow, man, this is awesome. And then we get home to my place and asked her if she wanted some wine or something. But then she's like, it's like really it's a lot later than I thought, so I should probably go.

Who's the old person now? That's really weird. Why would she do that? That's what I was wondering, you know, because it's like your face just it totally changed when we walked in. And then I looked around the living room and thinking, was it something embarrassing or something I left out? But everything seemed A-OK. So wait, like I'm thinking you're a recently divorced guy. Like, does the apartment look like you're a squatter or something?

You know, like a bed on the floor? I don't think that would scare a young girl off, though. That's a good point. Like an old picture. Like old pictures of me. No, I was worried about, yeah, exactly that. Pictures or, you know, no, it's clean. You don't have a cleaning person.

And so I'm racking my brain. Like, what was it? You know? I want to about, yeah, exactly that. Pictures or, you know, no, it's clean. You don't have a cleaning person. And so I'm racking my brain. Like, what was it? You know? I want to know, too. I'm curious. So she just left after that. And you have you talked to her since? No.

And I tried texting, calling, whatever. And the thing is, on this one, you need to know if there's something weird in this place. Like, you're just beginning dating. If you're going to bring other women back to your house, need to change whatever she saw that's a that's a good point i want the feedback totally maybe tanya took out her phone and googled what term life insurance was and realized how old you truly are and it scared her off but we're going to find out for sure when we call her and get your second date update right after this okay okay thank you i'm a little nervous thank you though thank you all right hold get your second date update right after this, okay? Okay, thank you. I'm a little nervous. Thank you, though.

Thank you. All right, hold on, man. Second date update. You know, during the break, Brooke pulled me aside and said she has a problem with older men dating much younger girls. I don't have a problem with it. But while she was talking to me, one of the young fit promo boys strolled by. And she looked at him like he was a giant Reese's peanut butter cup. She was licking her lips, her giant glasses fogged right up.

So to all the ladies on the text board right now at 78592 saying he shouldn't be dating someone 10 years younger. Maybe direct your advice to Brooke. I'm just saying, get you some of that peanut butter. Because even though she's married doesn't mean Brooke can't peruse the menu. Mama wants to see the special of the day. I'm just not going to order it. Gross sounding.

Maybe the early bird special. A special. The reason why we bring that up is because one of our listeners, Mike, went out with a woman who's a few years younger than him and ended up having a great time until they got back to his house where she started acting a little bit weird. We're going to try and help figure out the reason why. Mike, you ready?

Yes. Oh, my God. I've been thinking about it. Maybe it's because you offered her wine instead of Alexis' favorite. White Claw. Exactly. Too classy. Maybe she was like, this guy doesn't get me.

I'm out. That's true. I wish I knew what it is. Maybe she was worried that you were going to card her. No. She was going to get kicked out. Oh, no. But only one way to find out is by just asking her directly.

So I'm going to dial her number right now. Here we go. Okay, okay, okay. And remember, this is Mike's first online date that he's ever had since his divorce happened a few years back. A year back. Okay. Well, I'm just saying. Thank you.

Thank you for the fact check. Here we go. Let's call tanya hello hey is this tanya yes this is she hey tanya how's it going uh my name is jeff from the radio show brooke and jeffrey in the morning oh i've never been called by a radio so you might be familiar with us i do these awesome parody songs every week. Have you heard about them? Young Jeffrey's Song of the Week? I may have heard it, but I wouldn't be able to be like, yeah, totally.

Huge fan. Huge fan. I can tell. She's intimidated. Don't be intimidated. That's what it is. He's not going to sing to you if it makes you feel better, Tanya. Unless you want me to.

Okay. The real reason that we're calling is because we're doing a segment called a second date update have you ever heard of that before um no yeah all right now we're getting the honesty i like that tanya that's what we need it's where we help our listeners who've gone out on a date recently figure out the reason why they're getting ghosted. Okay. All right. And so the other day you went out with a guy named Mike. Yeah. All right. You remember Mike? Yeah, I remember Mike.

Okay. So we've spoke to Mike about the hangout that you guys had going to the bar, and we want to get your perspective on it. How was it for you? You just want me to tell you about the date or just like about your feelings about him too you know like did you have fun we could start there like okay uh yeah i had fun i mean he's very nice very personable so why aren't you dating him anymore stop jeffrey sorry getting there i I apologize. These are all good things.

I mean, yeah, there was nothing wrong with him. Like, he was fine. He really was. I would definitely have gone out with him. He thought you were very fine, too, if you just wanted. Oh, okay. That's cute. Yeah, it's a good thing.

So what changed? I mean, you're not calling him back. Why did that change? Well, like I said, it went well, and I actually went back to his place with him. We were going to watch a movie, and then everything kind of just fell apart, and I had to leave right then and there.

I was like, I got to go. Oh, no. Yeah, we heard that happen, but I don't think Mike knows the reason why. Yeah, was it him? Okay, so when we pulled up, I really didn't recognize anything. but I don't think Mike knows the reason why. Yeah. Was it him? Uh, okay. So when we pulled up, I really didn't recognize anything.

I didn't think of having been there before. Um, but we get into the house and I immediately know I've been here before. Wait, you've been in his house before? I have been in his house before. What? Are you Mike's ex-wife?

No. She's like, I have amnesia. What is this? Definitely not his ex-wife no she's like i have amnesia what is this definitely not his ex-wife but i have met his ex-wife wait you met his ex-wife what how okay about five years ago i actually used to babysit kids in that house they must have been separated because Mike didn't live there. Like, I never saw a guy. It was just the mom, just the kids. And I used to babysit them for, like, almost a year.

What? You never met him? I never met him. But as soon as I got to that house, I saw the living room. I saw the paintings on the wall, and they're, like, pictures. And I was like, oh, my God, I know these kids. That would freak me out, too. It was just so awkward because, like, how am I going to ever meet these kids and be like, and now I'm dating your dad?

Well, but that's, you know, at least you know the kids like you. That's true. I don't think it's a negative. They did like me, but it's been five years. They're all grown up. They're going to hate me. They're going to be like, what a homewrecker. And they're going to be like, you did this.

It was like the long con. I'm like, I can't. You're saying that they're going to assume that you were having an affair or something. Yes. Oh, my gosh. I didn't even think about that. That was the first thing that came into my head. I was like, oh, my God, these kids are going to hate me.

I have to get out of here. But once you you had that realization why didn't you tell mike that why did you just leave because it like it left him not knowing what happened i felt really really awkward and i felt embarrassed and i honestly didn't really know how to handle the situation so i just felt like gotta get out of here, I think I know how to handle the situation, and that's by putting you in direct contact with Mike right now, because he's on the other line listening. Oh my God. Are you serious?

I'm serious. He wants to talk to you, Mike. You there? Yeah. Oh my goodness. Uh, wow. Mike, I'm so sorry I joked to you. I really, you're a great guy.

It was nothing about you. It was just the fact that I've, like, given your kids baths. Oh, my God. That sounds weird. Yeah, this is a crazy, this is the weirdest thing that, oh, I can't believe it. You weren't living there, right? Like, I didn't just not see you because that would be probably even worse. Right.

No, no. there right like i didn't just not see you because that would be probably even worse right no no i you know basically the arrangement was that i was out of the house after we separated and uh in the final divorce i ended up getting the house so that's why i have it now so you move back in okay i mean but mike do you see this as a deal breaker because i know you're making a bunch of assumptions tanya about like what his family will think about you but you don't even know why they got divorced maybe it's his ex-wife that asked for the divorce i don't know it was just the first thing that i thought mike now that you know all this like what are your thoughts yeah i don't know i i think this is

actually uh positive i think this is great news. I mean, she already knows my kids. And, you know, you already know how to get to the house. You're already kind of like a second mother. You know where the silver drawer is, how to do the laundry. That's true. You're really familiar with the kitchen, you know. And in a few years, Mike's going to need help bathing. Stop.

You can help him out with that. You can put everyone to bed. No, no. not a turn on I mean it sounds Tanya like he's not concerned about you know his kids hating you it sounds the opposite I mean this that's cool but I was just kind of thinking this was a date or two or maybe leading to something and now I'm like a second mom because i know where the kitchen is like i don't know where to go from here yeah i could see no no no no no you gotta you take these things a little you know a day at a time i'm not saying oh move in now i'm just saying that if it ultimately gets to that point don't talk about that on the first date don't jump that far i would just focus on getting that second date.

Because I know for Mike, I bet nothing would feel better than showing up to his ex's house with their babysitter as his new girlfriend. See, that's crazy. Yeah, crazy sexy. I don't think that that's helping, Jeff. I mean, at this point, I just need to ask you, Tanya, would you like to go out on another date with Mike? Because we'll pay for it. I mean, it's definitely weird, but it's kind of cool weird and i don't know maybe this is kind of like the movie moment i let's let's try it what kind of movie i don't know not that kind of movie okay well congratulations you two it sounds like you guys are going to go out again.

Okay. All right. I was going to say the movie would be Fatal Attraction, but Tanya probably doesn't even know what that is. I've never heard of that. I know what that is. Hey, you guys can have a family movie night. I don't think that that ends well, does it?

No. People get murdered or something? I think it ends in a separation. I don't want your ex-wife to try and kill me. Let's not have it. It's a kill me. It's a long time ago. Okay. I didn't think we could get any sexier, but we did it.

Brooke and Jeffrey in the morning. Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews, and more. Now this is a second term we can all get behind.

Listen to The Daily Show, Ears Edition on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.