Brooke and Jeffrey: Second Date Update - Second Date Update: Double Booked Dating Fail

Episode Date: September 4, 2023

If there’s one piece of advice to take away from today’s Second Date it’s this: never have a roommate that’s hotter than you are.See omnystudio.com/listener for privacy information.

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Second date update. Sometimes with a bad first date, there's one moment that you can look back on and say, that was it. That was where I messed everything up. For me, each date has about 14 of those moments. Is it when I did the full reenactment of the movie Garden State? Was that it? Or was it when my zipper got caught in the sushi conveyor belt? I still go with Garden State for some reason. Why were you that close to the belt with the zipper? You know why.

He likes sashimi. Too much. Well, one of our listeners says that she knows that she made a huge mistake in one moment, and she's regretting it today. That's why she's asking for our help. Her name's Jessica. Jessica, welcome to the show. Hey, guys. Jessica, before you let let us know i just want to say sometimes it's good to only have one

giant bad thing go wrong because at least you can pinpoint what went wrong yeah did you have a sushi conveyor belt incident too there was no sushi involved good oh man that was sabi burns tragedy avoided what what what happened with this guy? What's his name? I went out with Vince. Vince. Okay. And how do you know Vince?

How did you guys meet? It was online. So it was kind of, you know, like our first sort of blind date online. And it was good. Oh, okay. It was nice. We had a really good vibe. All right.

Well, we'll play a song. We'll come back. Oh, we should hear more about it huh i mean were you were you shocked that it was going that well i totally was i i you know i had kind of low expectations but i don't know he was just he was humble and cool and fun and we're having a good time the problem is so because i have these low expectations, I kind of sort of accidentally double booked myself that night. Oh. Like with another date or with a party or something?

No, it was another date. Oh, girl. Oh. Oh, I like that you have options. Okay. Why two in the same night? I just figured we'd eat and be like, okay, thanks. That was fun.

Bye. And then that would be it because that's kind of been my experience. Was Vince aware that you had two dates going on that night he was not okay he was not and you know looking back i mean that's the moment like i should have canceled because i lost track of time and i when i realized i was like 20 minutes away from the second date and i was like oh shoot so i had to wrap things up really fast he was like oh we're done and i was like, oh, shoot. So I had to wrap things up really fast. He was like, oh, we're done? And I was like, yeah, I'm so sorry. I got to go. And I Venmoed him some money for the, like, half a bill, you know,

because I didn't want to just be like, thanks, bye. Wait, did you actually leave before the bill came? Well, like, it had just gotten there. Yeah. But, like, you didn't let him, like, walk you out to your car or anything like that? No, I had to run. Oh, man. Yeah. you didn't let him like walk you out to your car or anything like that no i had to run oh man oh yeah oh just as a guy having to sit there and watch your date like bolt on you yeah before you even finish like totally paying the bill and then they venmo you which is feels it like business

transactioning right yeah and i think i mean i think he could tell that something was going on because he was asking me are you okay? Like, did I do something? Oh. You know, and I was trying to tell him, no, no, no, it's not you. You're great. This is good. I just, something personal came up. I got to run.

Oh, man. I feel like I would almost prefer a girl to sneak out on me. Yeah. Rather than, like, collect herself frantically and be like, okay, sorry, I got to go. Bye. No, you just reschedule. You should have been honest and just said, look, I have something going on.

I want to give you my full attention. You know, it's like a job interview. You don't want the person interviewing you being like, okay, just tell me about yourself real quick. I got to go. I got to go. Yeah. Based on your profile picture and your interests, I had very, very low expectations of you coming

into this. I never, ever thought this was going to go like this. But yeah, sorry. Bye. And the bad thing is I'm guessing the second date went terribly because we're not calling the second date for a second date update. We're calling the first dude. Oh, yeah. What happened with guy number two?

Yeah, guy number two was a no-show. Oh! Oh, that. So stupid. I bet you felt. I would feel so foolish at that point. Oh, I did. I waited an hour at the bar for this guy,

and I just felt like a bigot's fault. And so after my hour of waiting, I texted Vince, and I was like, hey, so I cleared that up. If you're still out, I'd love to hang out some more. Kind of try to smooth it over. And he texted me back, LOL. Oh. Yeah. Oh, he is not feeling it and that's all you guys have talked since yeah i tried texting him one other time and he didn't respond so i was like okay i'm gonna leave it alone i don't want to

pester him but i'm feeling really really bad about it and i you know i i hoping it's something that i could kind of come back from i don't know if you tell him the truth it makes you sound bad like hey i'm only calling you back because this guy stood me up or i would have but i just don't i think the whole thing doesn't rub me right but you can explain it as like you made a mistake he's dating like he gets it like it's hard it's hard to make decisions it always feels like the more you date, the more options you'll have or something. I don't know. I wouldn't want a date to leave me for another date.

No, I mean, nobody would. Nobody would. But do we have to tell him that part? No, that's why I think we don't. Okay. Well, I think we're going to go in planning to not tell him. Yes. But you know what?

If it slips out, then it slips out. No. No. You do this sometimes. Don't let it come about, Jeff. Every once in a while, somebody wants what they can't have. And if he thinks that she's wanted by a lot of other people, that's not necessarily that thing.

So we're going to play some games? I don't know. Maybe we should say it wasn't just one extra date. Maybe it was 20 extra dates. And none of the other guys could match up to Vince. And they were all rich and famous. That's right. And Vince was better than all of them.

We're going to play a song. We'll come back. We'll call Vince and we'll try and get you your second date update. Okay, Jessica? Alright. Alright, hold on. Second date update. The saying is, nice guys finish last. But that's not always true. Sometimes

they don't even get to finish dinner before their date ducks out on you for a hotter guy. Sorry for the low blow there, Jessica. But that is what she did to a great dude that she was with named Vince. She had to leave early to go meet up with another

guy. And what happened? Other guy no-showed. And the thing is, Jeffrey, if you liked Vince more, you would have booked his date second. Yeah. Do you know what I mean? My initial, like, you wouldn't have put him first.

Because you could have ended the night no matter what. But she went in with those low expectations. So, Jessica, I want you to know we are going to try our very best here. But even though we're enjoying ourselves, we have another phone call book with a possibly better hotter listener in 10 minutes so we're gonna try and make this quick okay all right but really really please if we can not tell him about the other date okay okay so why did you leave then i mean we're gonna have to tell him something family emergency right like it made it the family emergency and we just met he doesn't have to know those details yeah okay well what's the detail grandpa's sick like she said she didn't have to just met, he doesn't have to know those details. Yeah. Okay. Well, what's the detail?

Grandpa's sick? She said she didn't have to know the details. He doesn't need to know. What if he asks? Like, oh, my God, family emergency. Is everyone okay? What do we say? None of your business.

Oh, wow. Okay. Don't you talk about my family. Yeah. Okay. All right. All right. We'll get defensive.

Let's do it. Aggressive and vague. Aggressive and vague. I like it. It's going to go well, Jessica. All right. So, we're gonna aggressive and vague aggressive and big i like it it's gonna go well jessica all right so we're ready we're gonna dial vince's phone number try and get your second date update here we go hello hey is this vince This is him. Who's this? Hey, Vince, my name's Jeff. I'm from a morning radio show called Brooke and Jeffrey in the Morning.

What's up? Uh, okay. Awkward. There was awkward silence. I freaked out. Say hello. Just say hello. Hey, Vince, we're all here. What's going on? Is it awkward?

It's a segment. It is an awkward segment that we do. It's called a second date update. We're calling on behalf of one of our listeners who went out on a date with you. Her name's Jessica. Yeah, Jessica. Okay. She really liked you.

Really? Yeah. I know it doesn't seem like she liked you because she left the date in such a hurry, but that's just one of the things that she does when she really likes a guy. She gets nervous and panics and leaves. Freaked out. It's a problem. Oh, so she told you guys what happened?

Yeah. She gave us a little recap of it. And she actually felt bad about it. Yeah. She gave us a little recap of it. And she actually felt bad about it. Yeah. I mean, she told us she didn't want to have to leave, but she didn't really have a choice. Family emergency. Okay. Yeah.

I don't know. I just kind of doubt that's really the case. What? I mean, she texted you later, she said, just to let you know that she was still interested. Yeah. Yeah, yeah, she did. She did text me later. She wanted to like meet back up. Right.

And we heard you texted back kind of snarky, just LOL. Yeah, I mean, I said that because she really seemed like she had better things to do and she had somewhere else more important to be. Like we were having a great time. We were eating and she pretty much ended it in the middle of us eating and left. Yeah, but that's not really fair to her because it could have been something that was totally out of her control. Oh, really? So, I mean, you guys talked to her.

So what did she say was out of her control? She, no. She made a commitment that she had to follow through on. Yep. Okay. Yeah, this sounds really general and vague, but vague but yeah do you have a problem with that yeah families vague and aggressive i don't know i just mean it's kind of hard to believe considering the way that it sort of ended like i don't know i just feel like so you say that

you think she's lying yeah 100 well i mean this is the thing like and you know I'll be completely honest with you guys but I've had some trust issues from the past and everything when we were talking seemed pretty good the way that everything sounded and she seemed pretty straightforward but uh my trust issues kind of came into play and I just wanted to sort of see like where her head was at so I actually had one of my closest friends who is you know he's basically a model but he is a model and looks you know really good looking dude and so he actually matched with her and I had asked him like you know why don't you schedule sort of like a date for the same day what oh my gosh i know this is crazy and you know this is like putting it all

out there but this is kind of why i feel so this really disappointed hold on a second so you already knew about the other date that you had scheduled yeah so he reached out and she already had a date scheduled with me and okay dude you set a trap for her well i didn't know that to be honest she would be that thirsty to hop on it the same day come on if you had a model that matched with you and wanted to go out the same night you're not telling me that you wouldn't book her still i actually would have just canceled the other date and gone out with the model or you two dates i mean i don't want to like yeah because then it kind of just felt like a pity date you know yeah i don't like this that's low man i just think that you're missing an opportunity

like if you could give her some grace here Like you may actually find somebody who you really connect with and like. The reason why I put the test out there was because she put on her profile, she's tired of the game, she's looking for something really meaningful, and I felt like we were aligning really well. I did, and that was why I was like, before I even, how serious are you?

Or are you just another girl who puts it on her profile but really just wants to you know i feel like maybe there is some truth to what she's saying there because she clearly wants to connect with you because she's actually on the other line listening this entire time that doesn't help trust issues oh man she wants to talk to you right now man wait she's listening to this whole thing yeah don't you trust her now she's right there jessica hi awkward oh yeah how's it going jessica uh not great i feel really bad that i couldn't figure out like what i needed to do in that moment and make a better choice but i feel really bad for you and those trust issues and the mind games and that's wow that's a lot oh there's so much on both

sides like I think you both just hang up before we even get into it I'm not embarrassed at all what I did if anything I feel like it gave me clarity on sort of what you're where you stand and what you're looking for and I I, I mean, I get it. I get why you're, you're feeling bad, but like at the end of the day, like you could have easily just not gone on that date or you could have canceled it or whatever. You chose to do that. That's totally fine.

You were set up. I know that's a little embarrassing, but I just, I'm like, we don't have to waste each other's time. I don't think that you can gauge in one day like what someone's all about and if they're really serious like i i i owed you nothing like and i felt bad that i couldn't make the choice because i i don't know i wish i'd been more decisive but i can be decisive right now and tell you that absolutely we don't need to bother with it because those mind games i'm not interested you're already cutting it off now i can totally appreciate that and to be honest

if it wasn't for the fact that you texted me back after you were stood up asking to hang out again like that same night i totally would have met up for a second date because you know i did feel a little about it but the fact that you texted me back right away just kind of showed like how it felt how it felt that i was into you it felt that i was into you yeah i mean i didn't want to be the one not showing up i didn't want to be the no show because that sucks and i know what that feels like so for whoever the other guy was i didn't want to be that person and when he didn't show up i was relieved and i was like cool maybe vince is still down. Maybe I can fix this. This is messy.

You guys are both making good points. That's a valid point on Jessica's part. I can see where she's coming from. She's probably obviously like she said, not interested, which is totally fine. I honestly don't have any hard feelings toward her. If I saw Jessica in the street and we said hello and talked, great. You just sound a little aggressive still. You guys should just

go out and let your guards down a little bit. Jessica, are you not going to apologize to Vince for ditching out in the middle of the date? Why would she need to apologize? She already bailed him. She ended the date, paid for half the dinner. It was the end of it. It's not like she left in the middle. He should apologize for her.

Vince did apologize. He was like, I'm sorry if I set you up for the trap, but you were the one that scheduled another date right after me. Oh, it's not a real enough apology? No. Not good enough. Not even at all. He said, I'm proud of what I did. What's this male model friend up to anyway?

I haven't heard a Jessica apologize once. I don't feel like I need to apologize. I did not lie to him. I told him I needed to go. I didn't owe him anything. Yeah, and it's not your fault, Jessica, that his friend was hotter. It wasn't about the friend being hotter, you guys.

Kidding. It sounds like we're not going to be able to get another date out of this for anybody, but did we at least learn an important life lesson from it all? Yeah, online dating is a waste of time. Oh! No, close. This show is a waste of time. Oh! No, close. This show is a waste of time.

Oh! But you know what? Thanks for playing. That one hurt. Brooke and Jeffrey in the morning. You know, sometimes in these second date updates, you can feel the ship starting to sink. Yeah.

And we can try and bail it out and try and save it. Grab a life vest! Or sometimes it doesn't really matter. It's going full Titanic. This is going to sink no matter what. And we just have to chalk it up to a bad day. That was definitely this second date update. There was no chance.

But I'm pretty sure she's going to hit up his hot roommate again. Oh, absolutely. Why not? Because, you know, the buddy did him a favor for a second. But, I mean, he didn't want to date her. I know. I mean, she's going to do that just to spite him. Maybe.

Maybe. But it'll still be good for her. She may even play the long game, like just marry her friend. Oh, wow. Sorry, marry his friend. Go all the way up to there just to rub it in his face up on the altar. That's kind of weird how specific you're thinking of this. Is the ship sinking again?

Yeah. Get off the ship, Jeff. I'm jumping overboard. Anyway, if you ever want to get a second date update, you can always email the show. We'll call the person who isn't calling you back.

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. Had enough of this country? Ever dreamt about starting your own? I planted the flag. This is mine.

I own this. It's surprisingly easy. Here's 55 gallons of water, 500 pounds of concrete. Or maybe not. No country willingly gives up their territory. Oh my God. What is that? Bullets.

Listen to Escape from Zakistan. That's Escape from Z-A-Q-istan. Binge the whole season on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.