Brooke and Jeffrey: Second Date Update - Second Date Update: Let's Chalk About It

Episode Date: February 19, 2024

The guy in today’s Second Date has been out of the dating pool for a few years, and now that his first hangout isn’t calling him back, he wants our help of all things!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. Dating is a lot like riding a bike. First, you do it with dad's help. Wait, what?

He's right behind you, making sure that you don't get hurt, because it's scary the first few times. Yeah, the first dates are a little weird. Why is your dad there? While mom's holding the camera shouting positive things. Don't close your eyes. Stop crying. You have a really close family. But then eventually, dad lets go.

And suddenly, look at that. You're doing it all by yourself. But why is mom still there with a video camera? I asked her to be there. But I bring the metaphor up because one of our listeners, Dennis, emailed the show. And Dennis, it says this was your first date that you've gone on in quite a while.

Were you in a relationship before that? Yeah, I was in a long-term relationship for a little while. I've been single for two years now. But you've been single for two years, but you just haven't dated. Yeah, I kind of gave up on dating for a while. I mean, I was just down on myself.

You know, I just had some self-esteem issues, some things I needed to work on. And I kind of got into a pity party sort of thing for a little while and had to come back out of it. So I love that you did you, Dennis. And it looks like it turned out pretty good. You're back up on the top. I love hearing those type of stories. I love that. You did you, Dennis, and it looks like it turned out pretty good because you're back up on the top. I love hearing those type of stories. We all do. Yeah.

I got into a gym, got back into racquetball. I'm rock climbing now, and I'm even on an adult kickball team. That's fun. We don't need a second date update with him. We're going to do self-help with Dennis. Yeah. I mean, this is great. Who needs women?

Just play racquetball until you die. Yeah, you got mountains to climb, not ladies, bro. Well, I mean, this is great. Who needs women? Just play racquetball until you die. Yeah, you got mountains to climb, not ladies, bro. Well, I mean, that's great that you came out the other end and it sounds like you're in a better place.

So you ended up meeting somebody? A young lady named Stephanie. Okay. Real smart and a great sense of humor. We hooked up after work. Even nicer.

Whoa, wait, whoa. That was quick. I mean, you sound confident, but I didn't realize. When I say hooked up after work. Whoa, wait, whoa. That was quick. I mean, you sound confident, but I didn't realize. When I say hooked up, I just mean we got together. Oh, you should probably clarify that. I told you guys, I haven't been dating for a while. I don't know what all the lingo is. Okay.

I need to know what that is. Okay. Hooking up, just so you know, Dennis, tends to be like you get intimate like romantic with somebody I hope you didn't say that's like too many women I wonder if you haven't dated in two years bro I want to know like you haven't done this in two years how are you feeling

like what's going through your head when you're going to meet her? Very excited extremely excited a little anxious. Yeah. So what did you and Stephanie end up doing for your date? We ended up doing

what I like to do and I wanted to share with her, which is a passion of mine. It's rock climbing. Cool. Oh, nice. That's a sexy date. I like it.

I like it. Had she ever climbed before? Was it brand new to her? No, she'd never done it before, but she was really open-minded to the idea, which was totally a turn-on. You hooked up with her, with the cables.

Hooked the cables. Showing the ropes, baby. Show me your carabiner. Did she seem like she was having fun? Not sexy. She was totally into it. I was totally into her. And even during the thing, some of my friends from class came over. They were really cool, so it actually made me look good made me look like i

had some sort of popularity there yeah i think it's such a smart thing too like it's a way to bond together she's trying something new a lot of adrenaline is going on when you're climbing like it's awesome yeah so is rock climbing the only thing that you did for the day or was there more yeah we went to a bar afterwards, had a few drinks. I'm a tequila guy, so I had a couple of pops, you know what I'm saying? A couple of what? Shots? A couple of pops.

Pops? What's a pop? I don't know that either. Yeah, it's old school lingo. You know, pops, like soda pop, like a can of pop, that sort of thing. Oh, you went to a bar to have some soda? With tequila? Yeah, exactly. Okay.

Wow. Tequila sodas, guys. Got it. We figured it out, though. Oh, like soda and butter is something else, too. I was thinking Coca-Cola and tequila. I'm all over the board. Yeah, got it.

Tequila soda. Okay. I'm very popular in dating right now. You can say that. Yes, all right. I just thought to have a good time with her. It was really great enjoying her company. She's a great conversationalist, captivating almost to the point of just other people were walking by and looking at the two of us like, wow, those people must really like each other.

Aw, that's sweet. That's awesome. I mean, she's not calling you back, so there must be something going on. Did you get a chance to really learn about her? Because it sounds like this was a lot about your interests, your activities. It was. She did a lot of talking, but mostly it was about her work and her job. I mean, she's got like a high-pressure job.

Okay. And did you hook up in the modern sense? If you mean, did we do anything that somebody would be saying we should have done on our first date or anything like that? No, we did not. Nobody on this show would say you should have done that on your first date. You're talking about the wrong show. It was a nice little goodbye, just a hug, a little peck in the cheek, nothing out of the ordinary. Well, overall, it sounds like it's a pretty solid date.

How long has it been since you last talked to her? It's been a couple of months. What? Months? Months. It's been a couple of months. What? Months? Months? It's been a couple of months. What? Have you dated since?

Or you did the one date after two years and we've done nothing since then? You're just playing the really slow game? I've gone out a couple of times with other people. It hasn't felt the same. Okay. Okay. It was fun still. I mean, I had fun.

We didn't do the rock climbing thing. We pretty much just did a couple times with a bar. Okay. We didn't focus on rock climbing thing. We pretty much just did a couple times with a bar. Okay, we need to focus on them. Let's focus on Stephanie. And we're going to play a song. We'll come back. We'll call and see if she remembers you. Because two months in the modern dating world is forever.

She could be married by now. It's possible. We're going to come back. We'll call her and try and get you a second date update, all right? Sounds great. All right, hold on, man. Second date update all right sounds great all right hold on second date update dennis i know you've been telling us that you just got back into the dating scene and you didn't know what you were doing yeah but i'm guessing that stephanie thought

you were a player you know just into the rock climbing place with your extra large harness on acting like a boss fist bumping all your friends, talking about your new clubs and activities. I bet she thought you were some type of smooth talker that gets around town. No way. There's no way she could have thought that. I put it with you, Dennis.

I would like you to prove right now that you're not. Pretend that Brooke is single, and you just saw her out on the street. Give us your best pickup line to get her interested. Go ahead, Dennis. Hey, Brooke. Yeah. What you doing?

I'm doing radio, my job right now, Dennis. What are you doing? Why don't you come on over here and sit on Daddy's lap? What? Dennis. Dennis. You're proving me right, Dennis. That was really your first line?

How did you go to daddy so quickly? I thought of you as a different person. I haven't been out in a while. Oh, sure, sure. Anyway, you say that you went out with Stephanie two months ago, and now we're going to be reaching back out to her again. I'm not sure if she's even going to remember going out with you, dude. Maybe the rock climbing part she'll remember.

Yeah. I think she'll remember. I think she'll remember. Have you tried calling or texting in that period in between? Oh, yeah. We didn't ask that. I did. I just never heard anything back from her.

Okay. And you have no idea why? No. No idea whatsoever. All right. Well, we're going to try and get you some answers here. Okay. Sit down. Sit, we're going to try and get you some answers here. Okay, sit down. Sit down, Daddy.

Okay? She's going to tell you where to sit in just a second. But I'm going to dial Stephanie's number, and let's see what she has to say. All right? All right. Sounds good. Here we go. Hello?

Hey, is this Stephanie? Yes. Hey, Stephanie, my name's Jeff from the radio show Brooke and Jeffrey in the Morning. How are you doing today? Really? Yeah. I'm good.

Hi, Stephanie. Yeah, the whole show's here. Brooke, Jose, Alexis. Hi. Me. Hi. Cool. It sounds like you listen. That's awesome's awesome yeah i've heard the show before but it's been a little bit well you can always catch up on our podcast

available anywhere you get your podcast spotify apple we're not desperate yeah yeah we'll just hang out and we'll call you periodically you listen to whatever you want to listen to stephanie but we're calling you today because we're trying to get a second date update for one of our listeners. Okay. It's a guy that you went out with a little while ago. His name's Dennis. Do you remember a couple months

back? Dennis? Yeah. That's quite a while ago. That's the reaction we had when he told us how long it had been. Yeah, it's been a while, so I have to think for a minute. Well, it's a good sign that he's reaching out to you. I know it's a little bit late, but he told us about your date and said he had a really good time with you.

And afterwards, he said he tried texting and calling you, but he hasn't gotten any response. Oh. Have you been seeing those? Yeah those yeah you know he was a really nice guy i just i feel like he was just looking for something else that i oh but yeah can you explain well i mean i just have different expectations at this point in my life and he just seemed to we just seem to be out of alignment i guess okay well i mean he told us a little bit about your date that you guys went rock climbing and went to a bar and got to talking a lot about your lives is something come up yeah i mean things

were great we were vibing and we had a couple beers and you kind of get to be more a little bit of like yourself yeah and he threw in a line where he said something like he was just kind of get to be more a little bit of like yourself. Yeah. And he threw in a line where he said something like he was just kind of looking for a hookup buddy. What? Yeah. He did? Wow, that's really honest. He didn't say anything like that to us.

It sounded like to us that he was looking for a long-term relationship. I mean, we talked to him about how he had spent two years single, working on himself, and that he was finally ready to see what was out there because he felt like he had something to offer someone. No, no. That's not the vibe I got. He said he was happy that he had a friend with benefits now. Friends with benefits?

That's what he said? Yeah. Oh, no. You can't really just say that. Does he know what that means? Like, as in you are his friend with benefits, even though you haven't given him any benefits yet. Yeah. Right.

Like I had been assigned the title all of a sudden. What? Hey, you're friends. And that's not how that works. Like friends with benefits is like somebody you already know. And then you're like, okay, maybe on the side we'll hook up because I'm in a dry spell. Yeah, I think that's why he was insinuating

he wanted things to be that way. And I'm not anyone's sidekick. But no wonder you didn't call him back. Yeah. At least he was honest with you. There's some sort of miscommunication here. Either Dennis isn't telling the truth or she misheard something. So let's just get Dennis on the phone right now.

Because, Stephanie, I need to tell you, he's been there the entire time listening. Stephanie. Stephanie. Oh, wow. you, he's been there the entire time listening. Stephanie. Stephanie. Oh, wow. Okay, that's different. Are you serious? That's different, she says. Oh, my goodness.

I have such an apology to make to you. What? That's good. You heard what I said, but that's not at all what I meant. What? Oh, I said to you friends with benefits, I meant the fact that you have a great job and you have medical benefits.

Shut up, Dennis. Really? Shut up. Come on. The last girl I was with, part of the reason why we ended up going our separate ways is because she didn't have any and she only wanted to be with me

because she thought I could get her benefits. Oh, my gosh. That is so much. You're telling me that you didn't know what friends with benefits meant? I'm talking about benefits. Actual benefits. Come on, Dennis.

Like you haven't seen a movie or listened to, like... I don't know nothing about that stuff. Okay, are you understanding what it means, like, now? Now I understand why she felt the way she felt also told her that you just wanted to hook up you what you said hook up buddy or something like that right stephanie isn't that what he said he said he wanted friends with benefits and i guess i assumed he meant a hook right? That's what it is. Yeah, right. That is what it is. Next time say buddy with dental. All right. Well, I mean, it sounds like you guys just didn't understand what each other were saying and you're actually looking for the same thing.

Dude, and he messed up on a bunch of phrases with us before she even got on the phone. It's true. Stephanie, he told us that he hooked up with you when you guys first met. When you just linked up. Yeah. I've been saying the wrong thing the whole with you when you guys first met. When you just linked up. Yeah. I've been saying the wrong thing the whole time, but you guys can tell I don't know what I'm talking about. I mean, Dennis, are you like AARP age? Like, Brooke, don't ask that.

I have been. No, I've just been out of the loop. I don't have a lot of young people around me. What do you want me to do? Watch MTV? Nobody watches MTV anymore.tv anymore people watch mtv not even watching what i know okay get a tiktok account okay i mean what exactly i gotta watch he did not stephanie i mean i gotta watch you can hear dennis he sounds like a pretty nice, genuine guy. He needs a little bit of updating in terms of dating terminology,

but we'd like to send you out on another date and maybe you can help teach him some of those things and we'll pay for the date. Oh, it sounds like fun. Stephanie, will you go with me? It's a misunderstanding. We'll go out. It'll be great. Oh, wow.

That's good. So see, now I have a true friend with benefits just make sure you go to the urban dictionary before you go on this date okay dennis look up mexican brooke and jeff Jeffrey in the morning. I feel kind of happy for Dennis. You know, he's a likable guy. Sure.

Kind of stuck in a time warp and apparently hasn't watched TV or listened to radio or watched the news in 30 years. Yeah. Participated in society, even. Because he doesn't know anything. God, even my mom would know what friends with benefits meant. Isn't that kind of a good thing? Like you get the chance to be with a guy

who's basically a baby. That sounds terrible. Maybe not like that. He's pure. He's untouched. Unworn. None of those sound nice. Brand new to dating. Yuck. I'm just saying, he's not scarred and he's not jaded by the dating world.

He's not going to play games on you. You don't even know how. He might accidentally, I guess. Or he's just going to claim dumb every time he gets caught doing something wrong. Am I too jaded? You're one of the jaded ones.

I don't want a baby man. I want a man man, not a baby man. Yeah. You want one that's been with thousands and thousands of people. Yeah, he knows all the slang. He's got paperwork that checks out things are still good. Yeah, we're good. But text into 78592.

Tell us if you think these two are going to make it. That's what we're looking at. That's a good sound coming from us. And remember, if you ever want to get a second date update, you can always email our show. We can call the person who isn't calling you back. 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.