Brooke and Jeffrey: Second Date Update - Second Date Update: 1027 Dates

Episode Date: February 16, 2024

We were SHOCKED when the woman on the phone told us HOW MANY dates she’s been on in her life in her quest to find the one. It’s not dozens, it’s not hundreds… but over a thousand! Hear her story in the Second Date podcast!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. We get a lot of email submissions for second dates on this show. Yeah, for sure. Something just jumped out about one from a woman named Bonnie.

Okay. It had nothing to do with her actual date, though. Huh. Uh-oh. What? Make sure you're sitting down for this because Bonnie says she has been on the dating apps now for almost two decades.

Decades. What? Have they been around for that? Longer than Alexis has been alive basically. Literally. The websites have been around that long.

I mean like match and stuff. Yeah. Okay. Those are the OG ones. Yeah. Like online dating has been a been around that long. I mean, like, Match and stuff. Yeah, okay. Those are the OG ones. Yeah, like, online dating has been a thing for that long. Thank you for confirming what she said. Well, he was questioning her. He was like, she's lying.

I don't know why anybody would admit to that in an email. Oh, Jeffrey, that's not a good way to introduce someone. It's kind of a quadruple red flag. Well, maybe she's had a lot of relationships from these things over the 20 years. Sure. Or she's super picky. Hopefully she didn't say that on the date to the guy, though. Oh.

I need to ask her. Bonnie, are you there? Hey, I'm here. So let me just start. The guy that you went out with, we'll get his name in a second, but did you tell him that you've been actively on the dating app since the turn of the millennia yes i i did i thought it's an interesting fun fact about me like i've actually kept count the entire time okay kept count wait like kept count of how many dates you've been on from these yeah whoa how many how I'm dying to know. How many dates can you do in 20 years?

He was my 1,027th date. 1,027 dates? That's nuts. Is your system like you count a different person gets one count or can the same person get like three counts? Do you know what I'm saying? You know, I guess I only count like... Dates. You know, because I mean, some of these guys I actually dated

for quite a long time. So that's... Right. Yeah. Okay. So every date counts as a date. First date. Wow.

Can I ask, aren't you exhausted at this point after 1,027 dates? You know, it's not all that bad. Like, I've ended up with four long-term boyfriends. Oh, okay. I've gotten engaged to two of them.

Okay. Okay. Wow. How have you not written a book on how to do these websites? I can't tell if she'd be, like, the spokesperson or make you want to delete them. Yeah. Like, I don't know which it is. She got engaged twice. I mean, like, she got two rings on her finger.

But she's not happily married. It'd be more like how to not do it. I don't think so. I think it's a success. I mean, it depends on what you're hoping for, I guess. But, like, she's doing it right enough where there's real relationships coming from this. That's a good point. Yeah, like, it's just never quite worked out all the way, you know?

Okay. Honestly, I just want to spend the rest of the time talking about your horror stories. I bet you have so many. We could have her on Battle of the Tinder Dates battling herself. Yes. But, I mean, okay, so you've been through a lot of ups and downs in your dating life. How cool would it be if after going through all of that, you finally found real love on our show? Wow.

That's sweet. That's what I'm hoping for for you today. It could be the case with this new guy that you went out with. Oh, yeah. What was his name? Did you tell us? We haven't learned it yet. What's his name?

His name's Grant. Grant. Okay. Tell us about Grant. Okay. Well, he asked me out to a restaurant and I did not want to tell him I've been there like 12 times before with guys on other dates. I did not tell him that. They are going to every restaurant in the city.

Why didn't you tell him that? Why would that be a bad thing? Oh, that's her boundary. You're wondering why she told him about the thousand dates and not that? Maybe if you told him, he would have felt like pressured to make it an even better date. No, I feel like it would just be weird

and like second guessing what he wanted to do. You know, like he mentioned the place. I'm not going to be like, oh, no, I can't go there. Right. I feel like that's what you want. You want him second guessing yourself.

You want to have the upper hand in the dating. But that whole conflict, he's like, what about here? What about there? She's like, no, no, like that no i mean after 20 years of doing these this online dating she's still positive she's still kind like that says something about who she is we haven't even called the guy yet brooke so yeah that's true he's like she hurt me so uh tell us sorry if we're just joking with you but tell us i, I mean, how did the actual date with Grant go?

Run us through it. Well, he showed up with a bouquet of flowers, and I thought that was a really sweet gesture. Like, not everybody does that. Hardly anybody does that. Okay, so he obviously wanted to impress you. He was impressed by you. What was your initial thought of him? Well, honestly, it was kind of like you guys.

Like, once I told him I'd been on the apps for that long he he also had a lot of questions yeah naturally so we talked about that we talked about our job histories and yeah i thought it was good like i don't know the thing i've learned from all of these dates is that i've learned like most good first dates won't blow you away like it's just finding sort of common ground and a baseline of friendship. And I feel like the ones that do blow you away, they often end up having red flags that

show up later. Alexis, how do you feel about that? You're supposed to establish friendship on the first date. She didn't say you couldn't sleep with them. She didn't say you're not going to date a friend. That's right. I'm glad we figured out where the lines are. I'm backing you figured out where the lines are.

I'm backing you on that one. So overall, how do you feel about the date? Like, how do you rate it? I mean, overall, I think we had a nice time. It was like probably an eight. At the end, he kissed me on the cheek. Okay. So what has happened since this date with Grant?

We texted a little, but I think he's hesitant to ask me out. Why? I don't know. I don't know exactly. And I'm a little worried that if you get him on the line, he's going to say something that I should have changed

about myself like 20 years ago or something, you know? Well, I mean, if he says that, too late, right? You don't need to worry about it. Like you've had a piece of spinach stuck in your teeth

for the last 20 years and nobody said anything? From that restaurant. Yeah, we go, spinach roll? Oh, yeah, yeah, yeah. Even the two guys you were engaged to never brought it up the entire time. Oh, that's so funny. That's why I dumped them, yes.

I mean, we can change food into teeth. Hopefully it's as simple as that, but we need to call this guy first when we do your second date update right after this. Hold on, okay? All right. All right, hold on. Second date update. Today we're on the phone with Bonnie, who's been doing online dating since the websites ran on dial-up. You got mail.

Oh, my God. Is that true? Is that an AOL match? No, it's not true. I bet. It could be true. Dang it! That's the sound of love.

My mom's on the phone again. I can't get online. Oh no! Bonnie told us that in her email. And she even said it to her date when they met up in person at a restaurant. That she's been at this for two decades. But it didn't seem to affect him. Like, it sounds like they just continued on with conversation.

Yeah, that guy seems to be really nice guy named Grant, who, even though he sat through the entire date with her, has been hesitant about going out with her again. It seems like we're going to try and nudge him back in the right direction. Kind of worried about you, Bonnie, Because it's the... I am! Why? Because at the end, she's like, what if it was something I did that I need to change from 20 years ago? I mean, that's a normal reaction, Brooke, isn't it?

It is? It is for somebody who's been dating for two decades. Is that usually how you feel after a date's gone wrong, Bonnie? I mean, the date didn't go wrong. Like, it was a really good first date, so I guess that's why I'm thinking that. That's why you're thinking that?

Yeah, Brooks, stop trying to spin her magical first date into some disaster or horrible story. It was just such a sad statement to me. I thought it was

a really beautiful sentiment, personally, Bonnie. You did? Yeah. I'm on your side, unlike some people in this room, Bonnie. Yeah.

That's a good way to spin it. You're a Hall of Fame... How does Bonnie not have her own app? Like, hey, this room, Bonnie. That's a good way to spin it. You're an Hall of Fame. How does Bonnie not have her own app? Like, hey, we met on Bonnie. Bonnie match. Does that sound good? Yeah, bonding on Bonnie.

You know, if this call doesn't work out, we'll hook you up with some people to set that app up for you. Okay, all right. Let's work on Grant first here. I'm going to dial his number right now. Here we go. Hello? Hey, we're looking for somebody named Grant.

Hoping that's you. That's me. All right. Hey, Grant. We win. Good work, team. Press the numbers correctly. I did it. Hey, Grant. Hey, man. You win. Good work, team. You pressed the numbers correctly. I did it.

Hey, Graham. Hey, man. You're on a radio show right now called Broken Jeffrey in the morning. What's up, bro? Hi. Hi, Graham. I can sense you're starting to hang up already. Please don't. Come on, man.

We're doing a segment called a second date update here, and we really could use your help. Sorry, what is happening? Oh, this is fun. It's actually pretty fun. It's all about you, Will. Well, it's about one of our listeners and you, a girl that you went on a date with recently named Bonnie. A woman.

What was that emphasize? We're not trying to hook you up with underage women here. When you say girl, I mean, she's definitely a woman. I don't think anybody thinks that. This is a of-age woman named Bonnie. Yes. You went to dinner with her the other night. Yeah, she even told us that you showed up with a bouquet of flowers, which was really sweet.

Yeah, she loved that. Heard a lot of good stuff. We're just trying to figure out, how did you feel about Bonnie? I liked Bonnie. She had a like Bonnie. She had a nice smile. She was really easygoing. Good. Those are nice compliments. I thought she was a nice lady.

We had fun. Nice lady. Did I age her too much? Yeah. That hit the ear wrong. Sorry. Nice lady. Did you feel any chemistry with her? I guess, yeah. I guess. Okay. There's definitely

a little hesitation every time before you answer. That's so confusing. You said all these positives. Now, I will tell you this. She did mention that she brought something up to you during the date

that she was worried may have been a red flag to you. She wasn't sure that she's been going out on these dates via the apps for almost two decades. Yeah.

With breaks, with breaks. Yeah, well, that was shocking, definitely. I mean, I've been on them for a year, and I'm ready to jump off a cliff. Oh, you're only a year in. Oh, you're a newbie. Oh, did you get some good advice from her, I would assume, right? Oh, that's what you should have done. You don't want advice to be like, hey, so I'm going to go back on the apps now and meet some other people.

If anything, you should feel like a lot of respect for her for like being able to push through all of the ups and downs of online dating. And still be positive. Exactly. She still is. Yeah. I mean, I thought it was a little weird, but I didn't make a big thing of it. I still was enjoying her company. I thought it was good.

OK, because we were assuming that the reason you might not be calling her back is because that could be a turnoff for some men. Yeah. So you weren't scared off by that information? Honestly, it wasn't the dating history. It was her job history. Her job history? Oh.

Jobs. Would she have like 1,500 jobs? Oh. That's interesting. We didn't even ask her what she does for work. Did she do something weird? No, jobs. We have like 1500 jobs. That's interesting. We didn't even ask her what she does for work. Did she do something weird? No, it's not that we were just talking about what she's done,

what's letter to here and all the jobs she's had. And it turns out that when she was younger, she interviewed for like a stream job that she wanted to, and she still seemed to kind of feel bad about it. And I was going through the dates in my head and i realized i i'm pretty sure i was the hiring manager at the time rejected her and didn't take her for the job wait what wait wait she she applied for a job at the company you worked for and you turned her down i mean mean, I didn't know it was her, obviously,

but yeah, like at the time. I mean, it's so vague. Clearly, I don't have a good memory of the interview or why I even turned her down. But I definitely rejected her from this job. Did you tell her that during the date that you were the guy? I hope not.

No, once I realized, I figured, oh, she's going gonna hate me if she figures this out. Were you able to remember anything about her? Like, did you interview her? No. I want to know why you didn't hire her. Yeah, you remembered her resume? That's what I figured. I figured she would want to know that too, and I just don't have

any answers for her, so I figured it's probably just safest to end this now, because I guess I ruined her, like, dream job. Oh, my gosh. You're not calling her because you're afraid that in the future that information would come out and make things weird between you two. But I have good news because that information is not coming out in the future. It already came out to her because she's on the line right now listening to this.

That is wild. Yeah. She's been secretly listening on the other line. Bonnie,nie you there yeah i'm here yeah you can't do that work settings but you can't do it in this setting uh hi hi um well i guess i i just i want to know like why um like i guess i heard you say you don't remember why you rejected me for that job like it was a long time ago um yeah i mean we're i i interviewed so many people this was 17 years ago i mean i obviously i'm sorry if i knew it was gonna be you i would have given you the job but i

i don't feel like i have anything good to tell you. Please tell me the job was like Blockbuster and they're like not a thing anymore. It was her dream job. Do you remember who you did hire? I hired a bunch of people. I really have no idea. Oh, jeez. So you hired a bunch of people and I wasn't one of them.

That's a good point. This is what I was trying to avoid. Oh, yeah. Well, think about it this way. You're so special. He remembered your resume. Maybe he was too attracted to you, and he believed that it was going to cause an issue in the workplace.

Grant, that's a good chance. Try and say that to her right now. Yeah. You were too beautiful. Go ahead. Go ahead. Clearly, I made a mistake. I really am sorry. I can't go back 70 years ago.

I am sorry you didn't get hired. I'm sorry. I don't think that she's upset about that still, are you? Are you still upset about it, Bonnie? I mean, it's something I brought up in our date. So it was one of those jobs that i just it was my only chance at it and whatever but like at the same time i would not be the person to let that get in the way of this either she swears she won't hold it over your head when

you're in a relationship five years from now i'm kidding i'm kidding grant how does it feel to reject someone Not only professionally But personally And romantically Years and years later Oh Jeff Does that feel good Honestly no

There you go I'm trying to guilt you Into the answer For my next question Which is Would you like to go out With Bonnie one more time And we would pay for it

They say third time's the charm. Yes. Or in Bonnie's case, the 1028th time's the charm. I'm sorry, I'm not supposed to say that. But I personally think that, I feel the vibes going on here, we'd like to send you guys out on another date, my friend. Yeah, we are.

100% on us if you'll see Bonnie one more time. And Bonnie, I'm assuming that is still a yes from you, right? Yeah. That way you can grill him and find out why he didn't hire you in person. But let's just get you on a date together, okay? I'm over it. What job?

Okay. I just want to see if this is going to work out. I don't want to live in the past. All right. That's right. Dream job to dream guy. She forgives you. Give her one more chance on us.

Look, I mean, if she's okay with it, yeah let's go out again oh man yeah thank you thank you guys yeah you're welcome that's really cute and like a sad i lost my dream job way brook and jeffrey in the morning gosh i sure hope he didn't feel pressured into saying yes to another date. Really, Jeffrey? Or feel guilt-shamed for crushing her dreams. We would never want to make him feel anything like that on the show. We don't want to manipulate people. No, we don't do that over here.

Oh, I think that they could end up cute, you know? Well, yeah. She wasn't still angry about it. No, he was the one upset about it still. She wasn't at all. I'm just hoping that we get an update update out of this where date number 1027 stops forever. Oh, boy.

Not that she killed him. I'm just like, that's the last date. She should work it into the vows when they get married. Like, you were my 1027 that I knew. I knew once I saw you after those radio segments. She's the only one that could play that song at last, and it really means it. You know what I mean? Like, whenever I see couples dancing to at last, and I'm like, you're 22.

What do you mean? She's been thank you next Ariana Grande for too long. But if you ever need help with your second date, we will try and do that for you. You can email the show. We'll call that person who's not calling you back. Even if we have to manipulate them. Yeah, well, no, we don't like to do that.

Oh, no, never mind. That's not our style. Weird. Okay. It's Brooke and Jeffrey in the morning. 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 at The Daily Show, which means he's also

back in our ears on The Daily Show Ears Edition podcast. Join late night legend John 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.