Brooke and Jeffrey: Second Date Update - Second Date Update: First Time Tinderer

Episode Date: June 20, 2022

The woman in today’s Second Date is trying online dating for the first time after leaving a long term relationship. Her first try went so well she’s reaching out to us for help!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. You know, we've talked about people getting back into the dating game after being out of it for a while. But we don't normally speak to people on this segment who are using dating apps for the very first time. Like ever?

Ever. Oh, cool. It's like a time warp. Yeah. time like ever ever it's like a time warp yeah like if you haven't dated since 2010 and you met somebody at a grocery store nowadays you're getting an eggplant all right oh but it's a digital one and i don't know if you even wanted it in the first place but that's what happened with rachel recently she emailed us saying this is her very first time being on a dating app and she actually met a great guy who's somehow not calling her back.

So, Rachel, welcome. Hey, thanks for having me. I'm just curious because I've never been on dating apps, right? Because I met my husband, like, before they were huge. Like, what is it like for your first time? It made me feel kind of old, too, though. I mean, I had been in a relationship since college so like 2007 you know what I mean so like I just completely knew for me and um when I got flooded with all these guys

it was exciting it kind of it boosted my ego but it took me about like two and a half weeks to find someone that actually fit all of my criteria and that was jack yeah so you messaged him so he reached out to me okay uh so i thought that was vulnerable you know what i mean like that's pretty hardcore. Not at all. But it's literally what thousands of other guys did. But it's okay. He said, hey. She's like, oh, my God, he's so formal. So confident. I mean, how long did it take you to go out with him?

Like, between talking to him on the app and then the actual date? Actually, about five days. So we started kind of like Sunday, Monday talking. And then that weekend, he was free and I was free. So I feel like a weekend date is a big commitment date. I don't know. Like using your weekend for that. I'll take a date any day of the week.

I think single people think any time is a good time. Marry people like my weekend is my only time. So what did you guys end up doing rachel so we ended up going to dinner okay it was really really sweet we we met there so i took an uber and what what was that like for you because it's like your first dating an uber ride you've never been in an uber it's done nothing technology is amazing they can deliver food now? What the? It's her first dating app.

It's the first guy she's met on this. I would be so nervous if I were you. Just because, God, that's a lot. I'm a huge fan of Broad City, and I felt like I was in Broad City. What was the actual date like? Oh, well, he was just such a gentleman. Like, he was dreamy. He was such a good listener to you guys.

Oh, that's important. He was what? Yeah. Yeah, it's important. Did your ex come up a lot? Because, I mean, you did mention to us that you were together for a really, really long time. It did. Because, like I said, it was over a decade.

And each thing that came up, he seemed to roll with it and it didn't seem to bother him. I mean, because here's the thing. I was up front with him from the get-go and I told him straight forward that I'm not going to go home with him. Oh. This is like immediately after the handshake? Yeah.

Or when is this? This was like after the first appetizer because i wanted to kind of loosen things up but i just didn't want to get too loose if you know what i mean okay but that also sounds good you want to set boundaries and he should respect it could also come across as rude though like you're also assuming that that's all that he's looking for you know like brooke's only saying that because she never would have said that to a guy. Those words have never crossed her lips. She's like, I'm surprised we haven't slept together yet.

So we finished the first nap. Is it time? No, but seriously, he could have been insulted by that. What was his reaction? Were you able to gauge it? He was taken aback, but he said he wasn't expecting anything. So maybe, like you said, it just kind of threw him off or whatever. And I mean, here's the thing.

When you talked about bringing out my ex, for the first time, I didn't cry, guys. You know, I was... On the date? Oh, honey. I'm glad. Well, I mean, I get teared up whenever I think of Dylan, you know? That's my ex. Sister, I'm with you.

It's been five years since I've been broken up. I hear Rachel crying right now. You've been just mentioning him. That's hard. You probably were still emotional then, if you're just like just now not crying, talking about him. I think maybe that the drinks didn't help, you know? It always enhances. Do you think that that's why Jack isn't calling you back? I don't think so, no.

He was, like I said, he didn't see it, like he didn't seem like he was weirded out by it at all. That's good. No, it seemed fine. We all know you obviously didn't hook up, but did you guys like kiss or hug or like do anything else that's like intimate? No, he was a gentleman, so we did like this side hug thing the side hug like i do with all my friends like a one-armed hug okay i don't know that that's a good sign it was my first date like i haven't been

in an real in-person date in over a decade like give me a break. It was like a backward tongue. We used to side tongue on this. We've heard a lot of dating stories, but yours sounds very nice, especially for your first time back into the dating pool. First time on a dating app. So let's play a song. We'll give, not Dylan. Jack.

Don't do that. I am so sorry. I promise you, Rachel, I will not call him Dylan. In fact, this is going to be the last time I ever say Dylan on this show. You just said it again. Okay. Sorry all the Dylans out there. We'll play a song, we'll come back, and we'll call Jack for you, not Dylan.

Okay, don't say it. Right after this. Second date. We'll be Dylan's number, dialing his number. Yeah, sorry. Coming up. Second date update. We'll be dialing his number. Yeah, sorry. Coming up. Second date update. If you're just joining us for the second date, we're talking to Rachel, who went on her first first date in a very long time.

Yeah. She said it's been more than a decade since she's gone on one. And she's never been on a dating app before. This was her first time on a dating app. And that was a little bit overwhelming which is understandable in fact i'm gonna do an impression right now of a guy seeing fresh meat on a dating let's take the music down oh yeah oh a newbie we're gonna stay at applebee's for 20 minutes and then go back to my mom's house and she's gonna watch me play mario kart oh man so it's like she was dating in college all over again but Jack who she met wasn't like that he

was different he was a gentleman and how do I know that they were a good match because Rachel said she didn't cry once during their entire date cry about her ex. Well, cry in general. Still, yeah. No tears, that's love. Yeah. So, Rachel, we're about to give Jack a call. How are you feeling? Honestly, I'm hoping for the best. There was nothing but positive vibes. So I feel like something happened maybe at his job or family.

I don't know. I hope everything's okay. But he's just perfect. And also, it's like, you know, this is new to you. There's a lot of options out there that you haven't even explored. I knew this was coming. I mean. Here it is.

Here's Brooke's pep talk to go out on the town and sleep around. That's how you get over people, Jeff. There is one thing that doesn't change in dating, and that's vibes. Like, you can tell if something happened on the date. You can pinpoint a moment usually. So if you don't feel like there was something, then maybe there wasn't. She hasn't even really dated in her adult life. I mean, you've had the same boyfriend since you were in college.

You know, like, just want you to make up for lost time. But okay, let's call Jack. You know what? We're just going to stop projecting our feelings and our failed relationships onto you. We're just going to dial Jack and see what he has to say, okay? Okay. Okay. Here we go.

Hello? Hey, is this Jack? Yeah, this is Jack. Who's this? Hey, Jack. My name is Jeff from the radio show Brooke and Jeffrey in the Morning. Hello. That's my co-host, Brooke, who just jumped in with a weird voice. No, it just sounded like how he was hitting on us

when he answered the phone. So I was, like, returning the favor, Jack. Oh, yeah. I just think it's interesting because, like, it was an unknown number, right? Were you expecting someone else on the phone, Jack? I'm sorry. What is this all about?

Yeah, no, i'm sure you're very confused this lady is talking at you and kind of hitting on you at the same time no we're a morning radio show and we're doing a segment called the second date update where we're trying to help one of our listeners get in touch with you after you went out oh geez um sounds like fun right all right um what do you what do you need from me well we heard a lot of good things about you Sounds like fun, right? All right. What do you need from me? Well, we heard a lot of good things about you, so that's a good start.

And we heard them from one of our listeners named Rachel. Oh, okay. Yeah. Yeah, so tell us what you thought about Rachel. I mean, Rachel was, she's cool, she's nice. Were you attracted to her? Did you feel like you guys had some chemistry yeah you know uh i think she's beautiful she's really cool and i think maybe she's just going through a lot right now and working through stuff but what do you mean

i was not prepared to talk about this. It's okay. I mean, she told us some stuff about, like, her ex and maybe how she talked about that on the date. She said a lot of really nice things about you, about how you're a great guy. And a good listener. She said you're a great listener.

Well, that's super nice of her. She was just really specific about what she wants in a guy and kind of went on and on about how I fit those things. And that wasn't good to you? I mean, it's nice. It is nice. I think it was just like a little much at some point. What was much?

Like, I don't know. First dates are supposed to be a little much at some point. What was much? Like, I don't know. First dates are supposed to be a little more chill and steer the conversation toward things that are maybe more fun and getting to know each other. And it was just basically at one point, I was like, look, I just want to get to know you. You know, and she smiled

and she reached into her purse and handed me an index card. Okay. What was on an index card. Okay. What was on the index card? Index cards are sexy. Who has index cards? Was it a recipe from her grandma or something? I kind of wish it was.

On top it said physical boundaries and kind of listed all these physical things that she would allow. And she also listed them by date. Oh, like you mean like like first kiss three dates in you can touch my butt four dates that's exactly it wow really oh my gosh a lot of planning do you have the card yeah oh yeah uh date one fist bump, side hug, and high five. Oh, my God. I wouldn't have even shown up. Send me the card before the date. From what we heard, it sounded like you did that side hug on the first date. Oh, yeah, yeah. We definitely did. Actually, we did do the side hug.

Yeah, how was it? It was exactly what you'd expect from a five-five. Okay, all right. So it wasn't necessarily her boundaries. It was the way they were presented. Is that what you're saying? I think it's cool. Like, her therapist says always create boundaries, which she told me, you know.

And I think it's super healthy. That's great. But it's just not what I'm looking for. It's just a little much to me, and especially talking about on the first date like that, you know. Maybe there's a more organic way to work in your boundaries. Yeah. Rather than a five by seven. Like what's more organic than having her be on the radio with you and tell her her boundaries right now?

Because she's been on the other line listening, Jack, and she wants to talk to you. No. Yeah. No. She's not respecting your boundary in that way. Rachel? Oh, no. Jack. Jack. Oh, my God. yeah no she's not respecting your boundary in that way no no jack we had such a great time i mean you you're such a sweetheart you just told me that

you you like like you think i'm attractive you know like i'm trying to be a great communicator you know what i mean like no gray areas i thought you would appreciate to know exactly what i want what i needed you know like i'm i'm not i'm not trying to play games yeah that's a hot pitch right there i liked it jack feel free to respond rachel rachel okay look this is a i can't believe you're on we're on the radio right now this is ridiculous um ridiculous is a little offensive to me that's okay yeah i think it's very offensive it's just even though i think you're a great person you are clearly physically attractive and it's just like the chemistry was just not there you know and like the way this this whole boundary note card thing was was brought up it

just kind of killed the vibe and i know maybe dude do you know how many times a note card thing was brought up, it just kind of killed the vibe. And I know maybe... Dude, do you know how many times a note card would have saved me on one of my Craigslist meetups? Whether or not... Like, you think it's... If it's going too far or it's, like,

taking the spontaneity out of it. She's just trying to show you what she's comfortable with doing before things get awkward. But your cards go by the hour, Jeff. I think she is. The first hour, the second hour. I'm just saying, it's her first day in a really really long

time so she's just trying to get her feet back under her it doesn't mean you need to be a robot it's like when i walk into your car i have to pull out the note card and check what i can do if it's like side hog or small fish you said we didn't have any chemistry but i guarantee that server would have told you different and to be, it's your loss because after date number five, things really open up. Oh. Was that on the card? Yeah. No, I mean, the thing about Rachel, she sounds like someone who's very organized and maybe

very different from you and could really bring some other aspects to your life that you don't have right now. Let's get to the second date on your note card so we can get to some of that other stuff because we'd like to pay for that. What do you say, Jack? Give it another shot. A lot could happen. Rachel, I think it's cool that you think we had chemistry.

I just think that a lot of the fun was kind of drained out of it as soon as those boundaries came up. Give her a second chance. On the second date, she knows that already. She doesn't have a second note card. Do you, Rachel? Do you have another note card? Not anymore, no. See? Look at that. Maybe you could just change a few things. She's funny.

She's funny, Jack. Alright, you know, if we can start over. If we can start over. You want to go back to date one? That's fist bump, man. It's like a punch card. You're going to get a free latte. So are you just saying yes? Is that what you're saying, Jack?

I mean, yeah. Okay. I'll say yes, but I'll pretend like the card never happened. Okay. She still wants you to remember. Still respect her. Jack, I'm actually excited and I'm really happy that I was vulnerable and called the station. Thank you, guys.

You barely cried once during this entire call. That must mean it was a positive experience. Yeah, just don't say that code word that makes her cry. It's Dylan. Oh, God. Brooke and Jeffrey in the morning. John Stewart is back in the morning.