Brooke and Jeffrey: Second Date Update - Second Date Update: Baggage Claim

Episode Date: March 10, 2023

There’s something so forbidden and magical about making a romantic connection with someone your age at an airport. It happened to one of our listeners and now we’re doing an intercontinental Second Date!See omnystudio.com/listener for privacy information.

Ugh, we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and find them on Bumble.

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People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up another season of Questlove Supreme. Man, we've got some amazing guests lined up to close out the season. But, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, E., Jonathan Schechter, Billy Porter, and so many more. Look, if you haven't heard these episodes yet, hey, now's your chance. You've got to check them out. Listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. did you ever want to give up on finding love i wasn't really you didn't think you were going

to find it anyway i just i don't know if that was my goal oh i think that's actually good advice they say when you're not looking for love it finds you i really don't like i i found it and i love him and i definitely wanted to get married in my life but he was your cousin so then you had to settle for the guy michael i get it i don't know I don't know. I don't know that that was. I was in love with lots of different people, though, yeah. That checks out. Oh, wow. The reason I ask is because one of our listeners has been having kind of a tough time, not

just finding the one, but even just locking down a date. And so now he's reaching out to us for help. His name is Hunter. Hunter, have you considered giving up on love yet? I, no, not giving up. Good. Okay. Well, maybe after this, we'll push you to that point. But first, let's talk about the woman that you recently met, I guess. What's her name?

Well, I'm kind of nervous to say it. Why? Is it inappropriate? No, no, no. Her name's a swear word? No, it's not inappropriate. I don't know if you found her name out there. Well, all right. Her name's Jamie.

Okay, we're going to call her. We have to know her name. You chased it now. Do we beep it out or something? There's so many of them. That's true. Jamie is a very common name. All right.

Sorry. I got nervous for no reason. I'm sorry. This whole thing is nervous for me. That's okay, man. That's all right. We get it. You're on the radio. We're sorry. This whole thing is nervous for me. That's okay, man. That's all right. We get it. You're on the radio.

We're just trying to have a fun time with you. Tell us what makes you feel kind of down about your dating life recently. I'm getting really frustrated. I've gone on a lot of dates, and a lot of them just keep bailing on me at the last minute. Oh. Oh, no. I'm talking a couple of times I've been at the restaurant or bar drinking hand. Oh, you're talking actual last minute.

I thought you meant like day of. People are so flaky these days. Yeah, it's like a culture in dating. It really, like even in friendships, people are flaky. Yeah, no, you're right, Brooke. Did you hear that, Hunter? Brooke says it's not you, it's everyone else in the world. Yeah.

That's how everyone should live their life, right? Yeah. It's not my fault. There must be someone else to blame. I'm perfect. And there's so many flawed humans out there. It's a lot easier way to live. I'll use that line of my therapist.

That's good. So tell us, where'd you meet Jamie? Well, I met her at the airport. Oh, interesting. How? So I saw this lady. Jamie grabbed my bag off the luggage carousel, and I literally chased her down across the terminal. Oh.

Let me guess. It was a black bag? Yeah. I remember buying my first piece of luggage and going, wait a minute. Everyone has a black piece of luggage. Oh, man. Like, what's the luck that it's someone that's single and you're attracted to? Yeah, and attractive.

Yeah. That's a good strategy, though. Just keep taking bags off of the luggage carousel until a cute person walks up to you. Or keep checking bags in hopes people will steal it. Like, I'd like to check 10 bags in my flight today. She wasn't actually even flying. So, wait, did you catch her? Yeah, I finally caught up to her,

and I couldn't tell what she looked like until I did. You know, because she was running away from me. Uh-oh. Moment of truth. Okay. So she turns around. Yeah. Did you scream?

Ah, you're so pretty! Oh, my God, you're gorgeous! Oh, keep the bag. Oh, my God. I don't know. What happened? Well, I made a joke saying, you know, I would have taken your bag, but I don't think I'd look as good in your clothes as you do.

Oh, nice. Damn. That's pretty smooth. And it's funny. Really smooth. I would have taken your bag, but I don't think I'd look as good in your clothes as you do. Oh, nice. That's pretty smooth. And it's funny. Really smooth. Obviously, she had a good response to that. Yeah. I mean, it's all downhill from there.

Oh, no. That was a good moment. That's when the screaming started happening. No, she laughed. And we just stood and waited for our Ubers on the corner. We talked. And I took a risk and asked for her number. Oh, nice. So you made friends real quick.

So you guys, where'd you go for your date? I asked her to grab just a coffee. I wanted to keep it casual, you know. Okay, nice. And, yeah, we were texting the entire week leading up to it. And she was just saying, like, she was excited to meet me. And then, like, clockwork, day of, she canceled. No, she canceled on you yeah you know it's risky

with coffee though because it's easy to cancel on coffee because you're like if it's early in the morning like what's 30 minutes it's true alexis how many times have you done this to guys before canceled at the last second i don't even say yes to coffee dates just saying i could see alexis canceling after she gets her drink i could see her like thanks bye canceling before they even ask god was she sorry yeah did she give you an excuse no i i didn't even hear from her and at this point it's happened so many times like i need to understand what's going on because this can't just be a coincidence i mean i hear you i'm like canceling on coffee but this has just happened so many times.

It's weird you can get dates. You seem charming. You're obviously attractive enough. Yeah, you're not even catfishing people because you're meeting people in person. But why cancel every time? I think that there's other people that want this exact same answer. I want the answer.

Well, I think you need to stop screaming at people jeff and that'll probably help call her there yeah we're gonna we're gonna call jamie for you and in a very even keel voice i'm gonna ask her why she's not going out with you i'm gonna be super chill about it all right hunter her situation could be different from from the other ones i don't know but i'd at least like to hear from her what happened. Right. Is that someone you met in person and actually had a connection with?

Yeah. Or we can call every girl that's canceled. Yeah. Really get to the bottom of it. Just a 25-minute segment. Yeah, we may not have time for that. Or threaten to steal her luggage because now you know what it looks like. I don't know if threats are good.

Yeah. I got your back. We'll avoid the threats. We'll just stick with the questions and get your second date update right after this. Second date update. We just learned one of the best places to meet someone is at the airport,

specifically the baggage claim area. You just stand in front of the carousel, wait for a really attractive guy or girl to walk up to a bag, and then run up and nab it right before they do and say, Oops, I thought that was mine. Now that we have our bags in common, maybe we should hook up. It's pretty good.

I mean, honestly. That's almost how one of our listeners, Hunter, met Jamie the other day. She accidentally took his bag, thinking it was hers, so he had to go chase her down. And they ended up vibing at the airport. Then she canceled the day of their coffee date. Which has been happening to him over and over again. It's gotta be so frustrating. We agree that

that's kind of become the new dating culture where people are just flaking out all the time. In fact, I'm kind of thinking of flaking on my lunch with Brooke tomorrow. Unless she buys again. Right. Yeah. In fact, I'm kind of thinking of flaking on my lunch with Brooke tomorrow. Oh. Unless she buys again. I always buy. Then I'll be there.

I always buy, Jeffrey. Then maybe I'll come. Yeah. Maybe. Hunter, how are you feeling? Nervous, but excited to get an answer. Yeah. Maybe get some truth out of this.

Figure out if it's something you've been doing wrong and you can fix it. I disagree. I think you're perfect, Hunter. Don't listen to what my hosts say. There's nothing wrong with you. Oh. Well, you know, if only I wasn't interested in women. I don't think that's where I was going with it,

but I appreciate that, Hunter. Well, Jeffrey, you started this. Yeah. He may be free for lunch tomorrow, bro. That is true. We'll see what happens with Brooke. You actually blushed for a second. Will you buy?

Are you going to pay, Hunter? Sure. All right. I got a backup date. I got a solid plan B. Good. Take him, Hunter. Let's call your plan A, though, Jamie, here.

We'll see what she has to say. Let's do it. Hello? Hey, is this Jamie? Yeah. Hey, Jamie. I know this is going to sound a little bit weird, but you're talking to a morning radio show right now. Hey, Jamie.

Hi. Hi. Hey. I'm sorry. Why am I talking to a morning show right now? Oh, good question, Jamie. The answer to that is we're doing a segment called a second date update. Okay.

Okay. Yeah. I don't think she knows what that is. I've gotten a lot of dates, though. Oh, you've been on a lot of dates. That's fine. You've been dating. No, well, we hear that you're a very attractive, fun lady.

Socialite, even. Yeah. Maybe even an entrepreneur. Thank you. Flying a lot. Oh, well, yeah, I travel a lot for work. I know. I'm sorry.

I don't know what this is about. Well, we heard that information from one of our listeners named Hunter, who you met the other day at the airport. Ah, yeah. You remember Hunter? Because you didn't have a long interaction with him. Yeah, I grabbed his bag by accident.

And then we exchanged bags. That was kind of like funny, cute coincidence, huh? Yeah, yeah. I mean, sure. What was your first impression of Hunter? He's like, you know, just kind of normal guy. But he's cute. Yeah, marriage material sort of thing oh jeffrey i mean i don't know if i felt that right off the bat but um i think he was a little

ramped up because um i had his bag yeah well it's good yeah it's awesome you know somewhere between nice and marriage material that's a good you know happy medium in there so it's a weird scale somewhere but the the weird part that we heard is that the two of you were supposed to go out to coffee and then yeah something happened and you had to cancel yeah it didn't feel like maybe you were going to reschedule with him is that true uh i don't think so I think we kind of are a little different in how we approach things. So maybe it just wasn't like the best fit. How would you know that though? How would you know that if you hadn't even hung out with them? Well, they texted for a week, right?

Yeah, we texted for a week beforehand. And two days before he texted me and said, are we still on? I said, yeah, I'm excited to see you and then after that like 24 hours before he was like hey we're 24 hours out I just want to make sure we're still on I was like at that point I was like that's a little weird I was like yeah we're still on and then he sent me like text leading up to the next day it was like hey i'm excited to see i just want to make sure we're still on i'm like uh yeah i'm like really busy with work and stuff so like like respond to these texts like over and over again do you have one of those limited text plans

where you can only text so often so it's not for you no but i have one of those limited life plans where i don't have a lot of time to deal with, like something really high maintenance right off the bat when I haven't even met you. Girls don't like that. It's called making yourself too available. How many times did he text you asking if you were still on? Let me see. It was like, yeah, it was like 10.

Oh. Whoa. He was excited. Yeah, on the bright side, it means he was really, really looking forward to seeing you again. I mean, that's great if, like, you've met somebody. But, like, I feel like the initial meeting should be really just kind of, like, short to the point. And then maybe after. Yeah.

And then after, if it goes well, maybe then a little more text. But just, like like that was well if the initial meeting went well maybe the second meeting will go even better which is going to happen in three two one because he's on the phone right now he wants to talk to you are you available to talk to him okay are you excited to meet him i mean again i guess hey hunter look i i gotta admit i'm a little embarrassed hearing it all aired out like that but i i do want to i just want to give you some context it's not so much a high maintenance thing i just i've been canceled on last minute a lot on dates by a lot of women and it's just i wouldn't be putting that sort of information out there, Hunter.

It doesn't sound great. Do you do this with all those girls, too? Yeah, I mean, this may be the reason, buddy. No, no, no, that's why I was doing it with Jamie. I wasn't doing this before, but after so many times, I guess it's affected me more than I thought. Oh, it's kind of scarred you. You didn't even realize it? Wow.

I mean, do you see where he's coming from, Jamie? I mean, I do. But like when I don't know him at all, like to come off like that, that's like my only reference point for who this person is. It just seems like a little much. Yeah, I didn't mean to come off that way. I just I was excited to go on a date with you. And I just wanted to make sure it wasn't going to be another last minute cancellation. And I get it.

I mean, it's like that's just what you deal with in this dating world. So like I've been canceled on two and it sucks, but I don't think that I would like. So, you know, the feeling that he has. Yeah, I definitely know the same thing, but it's I wouldn't just then send 10 texts to somebody making sure they weren't canceling. I find a middle ground. You know, it's just a middle ground. But it sounds like, Hunter, you're hearing her, right?

Like, you're hearing what she's saying. I do hear what she's saying, and I've heard this segment before. I know normally we ask if there's another date opportunity. I mean, Jamie, would you be interested? I promise I won't text you. Wow. Oh, my God.

That breath was not good. Yeah, Jamie, I think he sounds sweet. You know, he's a little jaded, a little hurt from the dating scene. And, Jamie, look, I'll text you the proper amount this time around. I mean, I'll go three to six, two to four. What's your sweet spot? Let's get this down in writing. How many texts per day exactly are we going to be sending back and forth? It feels like we're at an auction right now. Yeah. Who wants three texts? Who wants three texts? I want a four text. I got a seven text. Four texts a day. Sold. Yeah. And

here's the deal. Like if I commit to something, I will show up. Well, actually, you didn't show up when you committed to the last date with him. That's a point. Well, I mean, she was going to until all the texts came in. But she didn't follow through with her commitment. That's not following through. But look, Jamie, I'm going to forgive you for that. That's what she's looking for. Not only do I forgive you, I'm going to pay for your next date.

As long as it's with Hunter. Three texts a day, max, one text minimum. We're negotiating. What is this, a contract? It's making it sound really unattractive. It should be a casual vibe. It shouldn't be written on paper. I do think you should give him another chance.

Yeah, Jamie, give me another chance. I want to communicate with you the proper amount. The proper... I mean, the proper amount. That sounds so like... Romantic. You're right. Yeah, I guess. Yeah, why not? Alright. Okay.

Look at that. I love it. We're doing two texts. We're doing three texts. Where are we agreeing on? Let them text each other. I love it. We're doing two texts. We're doing three texts. Jeff, stop. Where are we agreeing on? Let them text each other. Jamie said two. Yeah. Lock it in.

Two texts a day or you guys are done. Yeah. He's going to be like, oh, no, I forgot to ask directions to the restaurant. Too late. I love that. Hit my limit. Brooke and Jeffrey in the morning. I just got a text from Hunter saying, do you think it's okay to text her right now?

I knew it. Someone needs to take his phone away from him. Until the date, don't you think? Hunter, we just finished, so I would give it a few hours before you finally reach out to her. His first text to her is going to be like, do you mind if I text you? And there's one text, gone.

And the second one is, you sure, right? I can stop if you want. Yeah. Well, I mean, I think she did bring up a good point where she said the pendulum swung too far the other way. Because she was probably right. He was trying to overcorrect because he felt bad about getting ditched so many times. It's all understandable. It really is.

From both sides here. But I think what Hunter needs is he needs like a dummy texter. Like a buddy who he can text instead of her every time he's feeling the urge. It's kind of like a, you know, a sponsor or something and other systems.

Maybe he can text our text board, 785-922-7885. Yeah, Brooke, if you want to volunteer to be his sponsor text person and get texts from him all night, what, can you give out your phone number? No, 785-922-7885. Oh, okay.

I guess just the text board, 785-922-7885. But remember remember if you ever want to listen to any of our second dates you can find the podcasts of them up online wherever you get your podcasts we put them on youtube now we're everywhere we are you can't avoid us you can't avoid us that's your second date update brooke and jeffrey in the morning we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists,

especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and find them on bumble john stewart is back at the daily show and he's bringing his signature wit and insight straight to your ears with the daily show ears edition podcast dive into john's unique

take on the biggest topics in politics entertainment sports. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up

another season of Questlove Supreme. Man, we've got some amazing guests lined up to close out the season, but, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. We talked to A. Marie, Johnny Marr, E. Jonathan Schechter, Billy Porter,

and so many more. If you haven't heard these episodes yet, now's your chance. You've got to check them out. Listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.