Brooke and Jeffrey: Second Date Update - Second Date Update: Boujee and Busted

Episode Date: October 7, 2022

One of the two people in today’s Second Date got caught in a caper. (Don’t you hate when that happens?) And you can hear all about their scheme in the podcast!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 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. 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. Second date Update. Brooke, you ever feel like you married way out of your league? Oh. Like your husband is in the majors and you're still playing Little League T-Ball?

Oh, my gosh. Is that how you feel? No, I don't feel that way. I feel like we are on the same level, but I think he is amazing. Oh, you're both T-ball. You're both at coach pitch. What? I'm just saying, your husband is listening to this show right now.

You don't want to use the opportunity to compliment him? By saying he married down? That is not a compliment, Jeffrey. Well, you do not know how to woo a man. Sorry, Michael. We love you. Why'd you choose me? That's what Jeffrey wants me to ask.

Thank you. He appreciates that. I'm just saying it can be a little bit intimidating when you feel like you're dating up. But sometimes that gives you the chance to rise up to the challenge and find that smooth talking Casanova that's been hiding deep inside you this whole time. There it is. You're on the same level all of a sudden, my friend. Unfortunately, that didn't happen for our listener, Grant. He fell short, which is why he's on for a second date update

now. Why did you say all that then? No, he really likes it. The backhanded compliments are strong today. Let's see how he feels. Grant, welcome to the show. Hey, thanks for having me. You say that now. You can hang up if you want now, Grant, before all this starts. Let's hear the story about your date. Who did you go out with?

Well, I met this girl, Ashley, online. Okay. Okay. And have you been doing a lot of dating lately? You know, I've been trying out the dating apps. I've gone on a couple of first dates, but I haven't really found anyone I connected with until this girl. Oh, until this girl. Okay.

Well, it's good you're being patient, too. Yeah. You're not just going out with everyone that swipes right. If I'm being honest, a lot of uggos swipe right on me, but I don't swipe back on them. Are we still using that term? No, we're not. We still need to be honest. It's hard being everybody's type.

I know what that's like. What? Yeah, just everybody wants you, but not everybody can have you. I can say you're not my type, right? Yeah. So, I mean, Ashley is like everything that you are looking for, essentially,

is what you're saying. Yeah, she's in a different league than the other girls. Okay. I think we all know what you mean. Were you a little bit intimidated by that? A little bit, yeah. On her profile, she had

a few of these really high-class pictures. One, she was on a yacht in a beautiful trip. Another, she looked like she was in one of those owner's boxes at a sports game. That's interesting.

Got it. And I feel like those are purposely put there to say, this is what I expect. Yeah. Upper crust of society. She's either a real classy girl or really good with Photoshop. So how do you step up to the plate with a girl like that? Well, you know, I wanted to show her that I am also worthy.

I'm in that same league, you know? I am just as much a catch. Sorry, Brooke is yawning while you're telling your story, so you gotta get to the interesting part. Didn't mean to.

Sorry. Well, you know, I took her to a really nice steak restaurant. Okay. Okay. I paid for her Uber. She accepted that. Oh, that's really nice. I never thought about somebody doing that before. They. Oh, okay. I paid for her Uber. She accepted that.

Oh, that's really nice. I never thought about somebody doing that before. They don't do that. Oh, I see. Yeah, like pay for an Uber to come get you. I mean, I can see

on the way home after you spent the night. Oh. You know what? Some of us guys do. You need to change your dating profile pics, Alexis. Apparently you're on a rowboat

instead of a yacht. Yeah. Okay. Did she appreciate those gestures? She did. I mean, she accepted it and she thanked me, which was nice. Okay. So, I mean, you've got to be nervous.

What was it like when you first saw her? Well, I was nervous. She was really pretty. She was wearing this gorgeous dress. I didn't know what to say to her. And I told her straight out. I was like, I don't know what to say to her. And I told her straight out. I was like, I don't know what to say to you. You are really pretty.

Oh. That's kind of cute, though, bro. Is that a good line, Alexis? Would that work on you? I don't know. I like the guys that are a little hard to get. Not like that. You know, I like insults more than that.

She wants you to be like, you're ugly. Kind of. She likes unhealthy relationships. Yeah, all right. Yeah, I think that's sweet. It's like awkward and earnest and people like that. Yeah, I mean, how did dinner go after the disaster start? Dinner went fine.

I paid for dinner, which I totally didn't mind doing. And then when I asked if she wanted to go grab dessert or do something afterwards, she said she couldn't. She had another appointment that night. Oh, my God. She had another date. An appointment at night? It's a date.

It's a date. That's another date. Do you believe her? Or does it feel like something else is going on? It's a weird thing to say. Yeah, I didn't know what was going on. Did you offer to pay for her next whatever date was? Maybe that

would have been the gentlemanly thing to do. I mean, women like that, maybe she was on some helicopter ride around the city or something. I don't know what she was doing. Well, you should have handed her a blank check and be like, whatever it is, it's on me. I don't want to offend you here, but maybe

a steakhouse and paying for the car is too boring for someone like her. Oh, it's not classy enough. Yeah, maybe you should have taken her to a gold mine. I'm just worried he's too nice. I think you guys are putting too much pressure. I think that she just is dating a ton. Had another date that night. She said thank you.

Someone who would just mindlessly do that, would expect it, wouldn't probably even say thank you. Like someone who, who would just mindlessly do that, like would expect it. Wouldn't probably even say thank you. You know what I mean? That's true. She seemed very nice. You know, very few people like that are genuine on those apps. So she seemed pretty genuine. That's a great sign then. Do you feel like looking back on the night, there was any mistakes that you made or something that would have scared her off? No. Honestly, I think I was kind of perfect. Oh, well.

Wow. That is quite the bold statement, sir, because you're on the phone with us. Yeah. Well, that's why I'm on the phone with you guys. I don't know what the issue was. You can't think of it. I like the confidence. I do.

Let's call Ashley in just a second here and ask her, why would you turn down Mr. Perfect? Yes. We're going to do it with your second date update right after this. Hold on. Second date update. We're in the middle of a second date update with Grant, who isn't really a man of words. He's a man of action. Yeah! I mean, it's good to be one.

I'm neither. I'm just a man. But he's a man of action. That's why he paid for everything at the steakhouse with his date with Ashley. He even covered her Uber costs and complimented her appearance by saying, I don't know what to say, because you're

so gosh darn beautiful. It makes my mouth not work. I mean, he is kind of, you know. Jose whispers that to me every single day. It does. But Grant, we never really asked you about your dinner conversation while you sat down with Ashley. What would you guys talk about? We just talked about different kinds of things, you know,

like fighting experiences we both had, trying to impress her with my bougie life. Do you really have a bougie life? Aren't you just making this all up? He talked about things.

Can't get any fancier than that. I mean, she may not be calling you back because you just weren't yourself. She can tell. Yes. I mean, you can't fake all of this. I was just spicing up things I actually do and making them sound a little bit more exciting and extravagant. Okay. You say so.

For your information, I do have a bougie piece of furniture. Oh, really? Yeah, it's a footstool from Neiman Marcus. Oh! Wow. I hope that's not a thing you talked about. I mean, what woman could turn that down? Ready to leave my husband right now.

I think we've heard enough from Mr. Perfect Date. Yeah. We just need to call Ashley and see why she's not calling you back. I'm going to dial it right now. I think we've heard enough from Mr. Perfect Date. We just need to call Ashley and see why she's not calling you back. I'm going to dial it right now. Here we go. Hello? Is this Ashley?

This is Ashley. Who's this? Well, if you couldn't tell, it's the Jeffrey from the Brooke and Jeffrey in the Morning radio show. In the morning. In the morning. Yeah, there it is. You can recognize like once and it goes to your head. What is this about?

Yeah, there it is. There it is, Jeffrey, always. Okay, never mind. I am lowly Jeff, and we do a very questionable segment on our show trying to help out our listeners in the dating pool. Yeah. Okay. Okay. You were swimming in the same pool as one of our listeners named Grant. You had to look down and read his name.

Well, I know him as Mr. Perfect, so I forgot his real name. Wait, so you talked to Grant about our date? Mr. Perfect, yeah. We talked about the date. It's weird that he would talk to you about that. What was your first impression of Grant? Well, I... Well, first

impression was good, but like, I don't know. He's a little strange. Oh, he's a little strange. Oh, he's strange. You're intimidated by his perfection? Is that what it is? Wow. Strange because nothing was wrong. I don't know. I don't want someone perfect, but it's like someone that can

at least carry a conversation, you know? Okay. So you weren't enjoying the conversation with Grant? No, he would do this thing where we'd be talking, and he would just go silent. I didn't really understand. What do you mean? Well, he mentioned that you were really beautiful, and he wasn't sure how to accurately describe your beauty.

So he was at a loss for words. In the middle of a conversation, he was at a loss for words? Is that what you're saying? It happens, Brooke. It happens. Sometimes you catch a glimpse of somebody gorgeous, and was at the loss for words? Is that what you're saying? It happens, Brooke. It happens. Sometimes you catch a glimpse of somebody gorgeous, and it takes the words right out of your mouth. Why do you think I haven't talked in 30 seconds?

I keep looking at Jeff. Did it feel like he was nervous, and that's why he was struggling a little bit? No, it just, he would go quiet. Like, there was a really weird moment where, like, it got really awkward, and we were just staring at each other. Oh, my God. I hate that. I could feel that.

Doesn't it just make you, like, crazy a little bit? I don't know. He pulls out his phone and goes, I have to double check my bank. My bank? And then he, like, dials a number. And then there's, like, a robot voice and you can hear it he put it on speaker it seemed like he did it on purpose what and like check his bank account yeah and then like it was it was a lot of money i i don't know if he thought he was it would impress me but

like this really loud robot voice echoed throughout the restaurant. And it was like, your current balance is something like $57,000 or something. That sounds like a good thing. It sounds like she's not into him for money, Jeff. And on speaker so everyone can hear. Yes. I don't know. He was acting like he was trying really hard to pick it off speaker,

but it didn't look like he was trying that hard. Oh, where's the button? I can't find it. Oh, the giant speaker button. I turned the volume up louder by accident. Well, actually, he didn't tell us about any of that stuff with the bank and the voice. And, you know, maybe technology, you know, it's crazy right now. Sometimes it's hard to figure out.

Isn't that right, Brooke? Like phone calls are hard to figure out? I don't. Because Grant's actually on the other line right now. And if I could figure out this stupid phone, I would put them on so that you two could talk to each other. Which button is it? Oh, man. I think it's just in on hold.

Yeah. Hey, it worked. I'm here. Yeah. Hey, it worked. I'm here. Hey, buddy. Hey, Ashley, that's Grant. Wait, he's on the phone right now? Yeah. Oh, my God. Yeah, I'm on the phone. I'm a little taken aback by what I'm hearing, though. Were we even

on the same date? Whoa. Did you not do that, Grant? Did you not call the bank? Okay, that was taken a little bit out of context. Like, the bank called me. What contact? That's the whole contact.

You know, like, the bank called me, and I... Did it tell you your total? I, you know, I tried to turn off the phone, and I put it on speakerphone by accident. Those are totally different.

You were trying to hang up. You were pushing the volume up button. I couldn't figure out how to hang it up, so I was pushing the volume up button to try and turn it off. Panic pushing. I'm with you. Whenever they took the home button off the iPhone, I've been completely lost. You don't know how many times I emergency dial. Grant, she's telling you the best thing ever.

She's like, hey, I didn't care what was in your bank account. Like, why don't you just own up to what you did? Or it wasn't enough, Brooke. You know, when it was announced, you know, not that I meant for it to be at all, but when it was announced, people looked kind of intrigued I meant for it to be at all, but when it was announced, people looked kind of intrigued. They're like, oh, cool, yeah,

he has a lot of money. This guy's a baller. I am a baller. And you say people were intrigued. Ashley, were you one of those people? No, you looked ridiculous. I don't know what you were trying to do.

Grant, I think you have to be honest with Ashley and with all of us. Did you bring up the bank statement on purpose or was that really an accident? It's like, duh. Okay, fine. Yeah, I kind of brought it up on purpose, but that's not, that's irrelevant. That doesn't matter to the situation. Grant, why though? Do you feel like you don't have enough to bring to the table unless it's money?

Like she liked you. She wanted to know who you are, not how much money you have. You know, she just emanated this like glorious beauty and class. And I wanted to show that I was in that range. That's actually kind of cute. Yeah. I think what it really comes down to is Grant really likes you and is really nervous and kind of intimidated by you.

So he doesn't know what to say. And may have transferred his entire savings into his checking just for you. Oh, wait a minute now. That's not completely true. Completely had to keep a ten dollar balance in the savings to make sure they wouldn't close it yeah but uh oh man ashley we would like to send you and grant out on another date and you don't have to worry about money at all because we'll pay for it yeah and if you're wondering're wondering, Ashley, what I'm going to use that money on, I'm actually saving up for a Porsche right now.

Pretty nice one. Oh, nice. I don't know if she cared. She doesn't. You still don't get it. But Jeff and I care. Yeah. Ashley, if you don't say yes to this date,

some people in this room are going to steal it from you. Yeah, we are. I mean, he's going to have zero money in the bank, but he'll be driving a nice car. Ashley, what do you say? First of all, I wasn't wondering. I don't know. You just don't seem to understand, so it's going to be a no for me. Yeah.

I mean, I should repeat, it's a really nice Porsche. Okay. What Porsche is it? Did the second time win you over, Ashley? No. You could be at a Porsche with a bunch of gift cards that we give you. No one would have any money for gas, but I guess who cares? You'd get some cute pics in it. That's true.

If you're driving around a Porsche, it doesn't matter how far you go. Like, you own a Porsche. That should be their new tagline. Just a Porsche, throw it on a trailer. Brooke and Jeffrey in the morning. Man, how sad of a world that we live in now, where if you're bad at dating, money can't even get you a second date. Okay. I thought you were just going to say that everyone assumes that women want money,

which isn't true, Jeffrey. Back in our day, they would. What happened to the early 2000s where money could buy you anything and anyone that you wanted? Yeah, money equals power, bro. Even my Aunt Pat has an OnlyFans account, so I can't even get her a decent Hanukkah gift anymore. She can afford it herself? Is that what you're saying? Or you could subscribe to her channel.

That'd be a nice gift. I can't even afford that. It's sad that you can't buy people's love anymore. That's the true but depressing lesson that at least I've learned. I think you're being sarcastic, but sometimes I wonder. I don't know. I'm pretty sad. I wonder, too. I wonder. I don't know. I'm pretty sad. I wonder too.

I wonder, are people getting too principled now? Or is everybody rich except me? Oh, well. Questions. We'll probably mix them up. Alexis is definitely not as rich as you. Yeah, that's for sure.

No, but you can also still buy my love. All right. Well, maybe there is hope out there. And if you want a little bit of hope, 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. 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. People, my people, what's up, or wherever you listen. 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 gotta check them out. Listen to Questlove Supreme on the iHeartRadio app,

Apple Podcasts, or wherever you get your podcasts.