Brooke and Jeffrey: Second Date Update - Second Date Update: Trust Fails (#5)

Episode Date: December 20, 2024

How long should a first date last? The couple in today’s Second Date Update had their date last much, much longer than either one of them either expected.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.

Jon 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 Jon's unique take on the biggest topics in politics, entertainment, sports, and more. 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. The forces shaping markets and the economy are often hiding behind a blur of numbers. So that's why we created The Big Take from Bloomberg Podcasts, to give you the context you need to make sense of it all. Every day in just 15 minutes,

we dive into one global business story that matters. You'll hear from Bloomberg journalists like Matt Levine. A lot of this meme stock stuff is, I think, embarrassing to the SEC. Follow the Big Take podcast on the iHeartRadio app, Apple Podcasts, or wherever you listen. $1.4 billion in NFL quarterback contracts. The untold stories behind the biggest deals in football history.

I'm A.J. Stevens, Vice President of Client Strategy at Athletes First, introducing the Athletes First Family Podcast, the Quarterback Series. My co-host Brian Murphy, Athletes First CEO, and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tua Tugnavailoa, and Jordan Love. Listen to Athletes First Family Podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What if you asked two different people the same set of questions?

Even if the questions are the same, our experiences can lead us to drastically different answers. I'm Minnie Driver, and I set out to explore this idea in my podcast, and now, Minnie Questions is returning for another season we've asked an entirely new set of guests our seven questions including jane lynch delaney rowe and cord jefferson listen to mini questions on the iheart radio app apple podcasts or wherever you get your podcasts seven questions limitless answers if you didn't know, we've been counting down our top 10 second date updates. Oh my God, it's so fun.

Appreciate all the feedback, and we have seen your requests. We do apologize that Alexis is not in the thumbnail photo for our second date update. I was in the studio that day, too. Yeah, well, someone requested that you not appear in these photos Well, it's just like there's only one blonde yeah, it's like when there's two blondes it kind of like puts people off You know what I mean, but we could go off. This is more natural Especially in the dating world like in today's five, top ten second date update countdown. This one is titled Trust Fails. Second date update.

We haven't been to a lot of off-site team bonding events at our radio station. Thankfully. Can we say thankfully? We don't want to give management any ideas, Jeff. I don't know what you're saying. I have heard that other companies do that. Yeah, they do. And one of the big events that they do is the trust fall, where you stand with your arms crossed, either on top of a desk or on a tree stump out in the woods, and you fall back and just trust that your team likes you enough to catch you.

There is no way I would trust any of you to catch me. The only good part of that is the part where you get to close your eyes for a second. I will say I do know the one person in this room that I would accidentally let slip through my fingers. Oh, is it me? I catch all of you. I guess you'll just have to fall and see. But it all comes down to trust. And unfortunately, our listener Kevin recently asked his date

to just trust him. Did he do a trust fall with his date? No, it wasn't that. Oh, okay, that'd be really awkward. But it was possibly the worst thing that could have happened when she said yes. No! Kevin, you came to the right place because we were just voted the least trusted morning

show in North America. So welcome, brother. Well, congratulations on that award, everyone. Thank you. Sounds like from Jeff's description that you should be part of our show. Exactly. Very untrustworthy, sir. I mean, it's not my fault, but I still feel terrible about what happened. Never is.

Never is. I trust you already. Let's start at the beginning. Tell us about the girl that you met and how you met her. All right. So her name is Courtney. Met her online. And it's obviously online, so I can only go off of pictures.

But in the pictures, she had a great smile. And she was sporting bangs, which to me is usually a red flag. But she rocked it well. Bangs. Brooke has bangs. Exactly. You're not trustworthy, and I'm offended. Actually, it makes sense.

I think you're reading the room right. What don't you like about bangs? Why is that a red flag? Bangs look good on certain people. It looked good on her. It's usually when a girl decides to get bangs, it's after something traumatic happened in their life. Good point. Brooke got married and then right away.

Brooke, you seem more convinced now. No. That part kind of checks out. So what did you and Courtney decide to do for your date? Well, you know, we were talking a little bit and, you know, it seemed like we were getting along fine and she said I get to pick where we go on the first date. Yeah.

We decided to do dinner. I love wings. It's my favorite food. Wings. It can be a questionable first date food, though, because it's so messy. Yeah. It's true. That's actually why I love wings on a first date, because it is messy.

You put your guard down. Yeah. You can tell a lot about someone by how they eat their wings. Okay. Very true. Yeah, so she tells me she doesn't normally eat wings, but I told her about this place I love, and she said she trusted me, which again, I feel really bad

that she did trust me. That's where the trust comes in. I mean, what happened? Well, you know, we sit down, we start looking at the menu, and she admits to me that she's never had bone in wings before. She's only ever eaten boneless wings.

I married a man who doesn't want to know that animals have bones for some reason. I don't get it. I think boneless is better, for sure. No way. You're just eating chicken nuggets, then. Perfect. Yeah. So did you want to end the date right there, or did you keep going? No, because, like I said, that was like red flag number two for me.

Oh, it was a red flag for you. Oh, it should be. I mean, I think it shows that she's adventurous and that she's open to try new things. Like she's never tried it before, but she's there. She's ready to do it. Well, that's what I liked about her though. She said that she's never had boneless wings.

And I said, tell you what, why don't you order some and you can have some of my bone-in wings. I can sort of show you how to eat them. Okay. That's good. That's fun. That's a green flag instead of a red flag. Actually, I think it's a you how to eat them. Oh, there you go. That's good. That's fun. That's a green flag instead of a red flag.

That takes away a red flag, so now only one red flag. But it's also showing he does compromise, right? Because she's ordering bone-free. You guys are overthinking it. That's a yellow flag. So now we have a green flag, two red flags, and a yellow flag. Which I think means we're at purple.

Oh, yeah. We'll mix them all together. Or we have a rainbow flag, which we love as well. Yeah, sure. I mean, it's all kinds of colors. All right, we approve. Bottom line so far, Kevin. What happens next? So the food gets there, and I give her one of my bone-in wains.

And she, honestly, I thought it was adorable. She, like, genuinely did not even know how to approach the thing. I think people can see that if you've never had one. How was it? She loved it. She was like, oh my God, this is so much better. And I said, I know. It does taste so much better.

So I give her a couple of my bone-in wings. I take some of her chicken nuggets. And legit, the third wing she bites into, she actually just bit into it. I don't know if, like, she forgot that the bone was in there or something. Oh, no. Oh, that just hurt my mouth.

Did she crack a tooth? She, yes, straight up chipped her front tooth. Oh! Her front tooth? Front tooth. Oh, that's so embarrassing. She sees on my face that I'm freaking out, and she starts freaking out. She, like, gets up and like, I have to leave.

I have to leave right now. Oh, it's so embarrassing. That and bangs together. Oh, stop. Could you imagine? I mean, not a good look. Who is she, Jim Carrey? Dumb and Dumber?

Just horrible. I mean, here's the thing. There's like something of a happy ending here. Really? I told her a friend of the family is like a dentist. Okay. And so I called them up and she said that she could see her right now. Oh.

So we jumped in an Uber. We went over there. Like it was after hours. So she opened up just to like see her and actually fixed it up. Like you really couldn't tell that anything had even happened. Wow. Bro, I'll give you credit. You are a problem solver.

This whole time, she throws little things at you and you just help. I like this. Maybe she's not calling you back because she got the dentist bill. Oh, yeah. That's going to be $4,000.

Is that true? Did you have to pay for it? No, no. My friend said it was free of charge. Oh, wow. You're coming off actually looking really good here. That's amazing. And he found the one nice dentist in the world.

So is that where the date ended, I'm assuming? You said goodbye after that? I mean, if you want to call it a date, I feel like we were on a date for about 20-something minutes. Yeah. Another like two to three hours together. We were more on a medical emergency. Exactly. And I've been in contact with her.

You know, it's like we still talk, but whenever I ask, like, if she's busy or if she wants to hang out again, that's when she doesn't respond. Oh, interesting. All right. We're going to pin her down and make her answer. We're at an orange flag with her right now. We've got to get to the green again. So we're going to play a song, come back and try and get your second date update right after this. All right. All right. Thanks. All right. Hold on. Second date update. You this, alright? Alright, thanks. Alright, hold on. Second date update. You know, there's that famous saying, ain't no

thang but a chicken wang. Yes. Love that saying. Turns out chicken wings are a little more dangerous than we originally thought. Yeah. Because one of our listeners, Kevin, encouraged his date, Courtney, to taste a bone in chicken wing for the very first time in her life,

which was great, except for the part where she chipped her front tooth on the bone. Not worth it. I mean, she was eating boneless and bone-in at the same time, so I could see when she bit down, she just wasn't thinking. Totally. Get a little confused. Luckily, Kevin had a family connection with a dentist and got it fixed for her that night, free of charge. That's amazing.

Impressive. Still, though, she's been acting a little bit different. He's still cordial between them, but not much else going on. And he wants a redo. Kevin, the one thing I didn't ask you, was she like super grateful for the dentist or was she kind of blaming you for having to go get her tooth fixed? No, she was super duper nice about it. She said, I can't believe I did that, but thank God you do someone good help. So she seemed like she was in good spirits.

That's hard for me to believe. No one's in good spirits after visiting the dentist. I don't care how nice they are. Maybe they got laughing gas. Oh, yeah, she was high, yeah, for sure. Well, let's just call her. I mean, we'll see if she even picks up, but hopefully she does and we can get a little bit more of an explanation from her. All right. Yeah. OK. Hopefully she's not like whistling through her teeth a little bit.

I'm going to dial her number right now. Here we go. Hello. Hey, is this Courtneyney yeah speaking hey courtney my name is jeff from the radio show brooke and jeffrey in the morning um okay i can't gauge her yeah just say hi just continue the conversation hi yeah i'm jeff i'm sorry who is this yep je Jeff from the radio show Brooke and Jeffrey in the Morning, as per mentioned previously. And we're all here too. I'm Brooke. Oh, okay.

It's like a conference call. Kind of. We're all in a radio studio just calling you. Got it. Why? Because one of our listeners went out on a date with you recently. And afterwards, things have cooled down between the two of you. He's hoping that it

could heat back up what like a chicken wing oh my god you know who we're talking about after he said chicken wing yeah for sure okay okay we're talking about kevin just to be clear he sounds darling i mean when we talk to him yeah no he's he's a nice person um yeah totally just that whole date was just like pretty much like the worst date of my life but not his fault you know what i mean yeah oh my god i thought we assume that he agrees i mean it was out of his control but obviously getting rushed to the dentist is not like your dream date. No, no. And I don't really know exactly what you told you guys, but yeah, it just didn't leave me, you know, feeling too comfortable about. Well, I can fill you in on the parts that we do know, which is that you guys went to a chicken wing place.

He encouraged you to try a bone-in chicken for the first time, which caused you to chip your tooth. But then he said he had a family connection. Yeah, well, that part was really wonderful. And he was really awesome to do that. But there was like a whole situation at the dentist. Did you not like the doctor? No, she was really sweet. It's just, it felt like it took longer than it should have, you know? It's a chipped tooth. I couldn't believe, honestly, I couldn't believe they could even just fix it in one visit. Yeah.

Yeah, no, they were, this woman was like, I think her name was like Claire. She was really nice. So that's not the issue. And I don't know if he told you, but like, she's really beautiful. Hot. Okay. Let's just, she's really beautiful hot okay let's just she's a really hot dentist i need a new dentist can i get the number that's a bad is it a bad thing no except for the fact that kevin was just openly flirting with her the whole time like right in front of me just like saying like all this you didn't need to how nice she looks how

she's so sweet and all this like family from who knows when yeah but she was doing him a favor right like she's staying late she he's probably just trying to compliment her i was there i know what it was she's flirting back and there was a lot of chemistry and don't get me wrong there was chemistry between me and him too but but you're just sitting there with a broken front tooth seriously like i couldn't even open my mouth i mean forget about talking and he's over there talking about how great she looks okay is that why is that why you say that it took so long that he was just flirting with her the whole time yes yes literally she would stop and they would talk and laugh. And then she'd be like, oh, let me change my gloves and blah, blah, blah. And I'm just there, you know,

like he went to get her coffee. They drank it. Sounds like you kind of felt like you were watching another date happen on your date. That is exactly right. That is exactly right. They came in with martinis. It's like, where did you get those from? Are you remembering this correctly? Were you on any anesthesia or anything? No, I didn't have any anesthesia. No. Are you sure you didn't hallucinate that whole thing?

I'm just saying. Obviously, she's really cool, and it was great that she did this, but I just felt like maybe they have some emotions there that they need to kind of figure out you're making a lot of assumptions like it to me it's just like it's a family friend i would assume she's older because she's no she is not older she's not she is his age and he couldn't like keep his eyes or his attention off of her like he literally didn't talk to me until we were leaving okay well i don't. I mean, I can understand why

you may have felt that way that night, but I would love to hear how Kevin actually felt, because he's actually on the other line listening right now. And wants to talk to you. Unless, I don't know, he's on a second call with Claire. Oh, stop it, doctor.

You're joking. I'm not. Kevin? Oh my god. Hey, Courtney, I'm sorry to surprise you. You're joking. I'm not. Kevin? Oh, my God. Hey, Courtney, I'm sorry to surprise you. Is it okay if I ask you a few things about this? Oh. Well, sure. What do you want to ask me? I just, I don't even know where to begin.

Like, this is just very weird to me. That's how you saw it. I just want to let you know the bad sort of meme player she's literally my mom's best friend's daughter so she's like my god sister essentially that doesn't make it yeah that doesn't really but like here's the thing like we were literally just catching up i hadn't seen her yeah but i get that but like catching up about how you have the most amazing eyes. Oh, and that smile. What? It's just like when you complimented her smile, and I literally wasn't sure if I was going to have a front tooth. It just wasn't the right time, you know?

Look, I didn't mean to be inconsiderate, but it's just like she is beautiful, you know? Like she has literally competed. We know. We established that. Okay. But, like, I feel like just because she's beautiful, you can't hold that against me.

I feel like that's your... No, it wasn't hold that against me. I feel like that's you. No, it wasn't how she looked. No, it wasn't how she looked. It's how you gave her so much attention during a really difficult moment for me. Can I just ask, Kevin, why would you compliment her eyes? You know, like, I could even say smile because she's a dentist. I could maybe see that, but like the eyes. Have you ever sat in one of those dentist chairs with those

bright lights shining on you? It makes your eyes pop. She wasn't sitting in the chair. The whole room. The whole room. Everybody in the room is instantly gorgeous. That's not like a friendly compliment. It's a flirty compliment. I feel like I need to ask this question.

Kevin, have you ever hooked up with claire before do we want this answer i don't know that i think we do i'll tell you straight up no we never have and look yes we have like some sort of like vibe or chemistry or whatever but here's the thing like i heard you ask like you didn't know if she was single she is single she's been single for a while i just never wanted to go down that road with her because, like I said, I see her almost like a family member, but not really. This is so hard. I can understand both their points. I really can.

Yeah, I mean, Courtney, I don't want to invalidate your feelings, but they've known each other going way, way back. There's already, like, just an established friendship there, and I don't think it's fair to have a beauty contest in the middle of your oral exam. I don't think that's it. I think it's about the way he made her feel. He promises to call you beautiful at least 100 times on your next date that we will send you on and pay for. If you're still up for it. What do you think, Courtney? Guys, I'm just enjoying my new tooth.

Okay. I think I'm going to chill out. You got a free tooth. I like it. New tooth life. It's a gorgeous tooth, my new tooth. Okay. I think I'm going to chill out. You got a free tooth. I like it. New tooth life. It's a gorgeous tooth, by the way. Yeah. Is that no?

Sexiest tooth I've ever seen. Yeah. Good job, Jeff. Kevin, would you like to throw in some compliments about her pretty teeth? I mean, I literally said I thought you had a great smile when they asked me about you. Yeah, he did. You still do. I'm happy about that.

I'm just disappointed that apparently we're not going to go out again. Oh, man. I don't blame you, buddy. You know what you learn? Never be friends with women. That's right. That's not the lesson.

I feel you, man. I support that, actually. Yeah. Brooke and Jeffrey in the morning. I think the part of the second date that I just can't

wrap my head around is, like, I get she felt a little ignored, you know, but what is a guy supposed to say to a girl who's propped up in a dentist chair for two hours to make her feel special? Anything but complimenting another girl. I mean, honestly, he could find memes. He could find YouTube videos to show where he could get on TikTok and be like, look at this. This is funny. Like, he actually doesn't even have to say anything.

He just has to feign interest in her. That was good, bro. Just sit there and shut up for two hours while you comp this. I mean, are you serious that you would actually compliment a family friend by telling her she has beautiful eyes? If they looked beautiful. I think people like compliments. No, that's not a thing.

It's just not. I don't think it's fair. No, that's not a thing. It's just not. I don't think it's fair. Like, if you went somewhere, you wouldn't be allowed to talk to a family friend in front of your husband? I mean, he admitted they had a thing. Like, they had a vibe, right? Him and the dentist. It's just he hadn't acted on it. I mean, I could see his side.

I understand why he wants a date and he's still interested in Kourtney. I don't know. You can? I can. I can see both sides. Yeah, same here. I can see both sides. He put effort into going out with Courtney again.

I think she should have said yes. I think he said too many compliments. Maybe three too many. I was going to tell Brooke what I thought about her eyes, but forget it. You can't even see him behind these glasses. All right, never mind then. I won't say anything.

I'll just say, if you ever want to get a second date update, email the show. We'll call the person who isn't calling you back. Brooke and Jeffrey in the morning. 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. Jon 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 Jon's unique take on the biggest topics in politics,

entertainment, sports, and more. 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. 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. The forces shaping markets and the economy are often hiding behind a blur of numbers. So that's why we created The Big Take from Bloomberg Podcasts, to give you the context you need to make sense of it all.

Every day in just 15 minutes, we dive into one global business story that matters. You'll hear from Bloomberg journalists like Matt Levine. A lot of this meme stock stuff is, I think, embarrassing to the SEC. Follow The Big Take Podcast on the iHeartRadio app, Apple Podcasts, or wherever you listen. What if you asked two different people the same set of questions? Even if the questions are the same, our experiences can lead us to drastically different answers. I'm Minnie Driver, and I set out to explore this idea in my podcast. And now, Minnie questions is returning for

another season we've asked an entirely new set of guests our seven questions including jane lynch delaney rowe and cord jefferson listen to mini questions on the iheart radio app apple podcasts or wherever you get your podcasts. Seven questions, limitless answers. $1.4 billion in NFL quarterback contracts. The untold stories behind the biggest deals in football history. I'm AJ Stephens, Vice President of Client Strategy at Athletes First, introducing the Athletes First Family Podcast, the quarterback series. My co-host Brian Murphy, Athletes First CEO, and I are sitting down with

the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tua Tugnavailoa, and Jordan Love. Listen to Athletes First Family Podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.