Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Get Silly with Two Milly

Episode Date: November 16, 2024

One of our listeners has one of the COOLEST claims to fame ever. But he’s worried its attracting the wrong type of woman… hear what it is in the Second Date Update 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.

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For years, I had to rely on other people to tell me my story. And what I heard wasn't good. You really f***ed last night. It felt like I lived most of my life in a blackout. I was trapped in addiction. You had to grab the lamp and smash it against the walls. And then, I decided I wanted to tell my own story.

Listen to Crumbs on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Welcome to My Legacy. I'm Martin Luther King III, and together with my wife, Andrea Waters King, and our dear friends, Mark and Craig Kilberger, we explore the personal journeys that shape extraordinary lives. Join us for heartfelt conversations with remarkable guests like David Oyelowo, Mel Robbins, Martin Sheen, Dr. Sanjay Gupta, and Billy Porter. Listen to My Legacy starting January 20th on MLK Day on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey, you're here. You found the Second Date Podcast, and we love that.

Thank you so much. So happy you're here. You know what? If you want us to invade more of your life, we're on YouTube. Yeah, we are. You got that? With Brooke and us to invade more of your life, we're on YouTube. Yeah, we are. You got that? With Brooke and Jeffrey. Text in your address.

I can show up. Jose will come to your house and give you hugs. And food, or you give me food. And also, there's 45 more minutes of this dumb content that apparently you like, which we're really grateful for. You can go over the main feed for the full show, Brooke and Jeffrey. But right now, let's get into this relationship stuff. Yeah.

Second date update. We've been doing these long enough to know that people fib on their dating profiles. Yeah. And sooner or later, they're probably going to get caught. Yeah. It doesn't matter if that happens on your first date or four months into the relationship. When you say, hey, so those noises upstairs aren't actually rodents. It's my other secret family.

I just got to go back up there for dessert in like five minutes and then I'll come back down. We can go out bowling just like I promised. I thought they were going to be living with their parents, Jeffrey, not a whole other family. That came out eventually. And today our listener Ray says he's worried his lie may come back to bite him. And he wants to nip it in the bud today. We're going to figure out what's going on in a second. But first, Ray, welcome to the show.

Hey, how you doing? Oh, man, probably better than you, Ray. I mean, if you're coming on to admit that you lied about something, how are you feeling? Yeah, I just kind of have like all this guilt and i know this isn't really like the normal process are you talking in hushed tones because your secret family's in the other room and they're going to hear this yeah sorry i'm just a little nervous i guess okay it's all right this is a safe space you can be honest with us and we'll try not to judge you but before we get into the whole thing what is this girl's name that you went out with?

Why do you think she's not calling you back? Well, she's calling me back. Oh, she is? Yeah, she wants to definitely continue. Okay. What's her name? Oh, I'm sorry. Her name is Zoe.

Zoe. Okay. So you're excited about that piece, right? That she wants to see you again? Yeah. Okay. Exc excited about that piece, right? That she wants to see you again? Yeah. Okay. Excited about that. We don't do a lot of second date updates where the other person wants to go out on another date, but they're calling us anyway.

Was this like a big, big, crazy lie? Like I'm a complete different identity? Or is this like, oh, I have a sixth toe I didn't talk about? Well, I guess you'll have to be the judge of that. Okay. Maybe we're asking too many questions here. I want you to be on record that he just asked us to judge him. Okay?

So whatever happens next, you ask for it. You're safe. Okay. Let's maybe start at the beginning with how you and Zoe met and what you did for your date. So we met online. Yeah. And we started talking and we went out to this real fancy Italian restaurant. Oh, okay.

So you wanted to impress her. Was that your idea? Yeah, that was kind of the goal. But I think I made a mistake. On my online profile, I have this little section that says that I won the lottery. Oh, God. And I actually did. I won the lottery a couple years back.

How much? How much? Around $2 million. Whoa! Congratulations, man. Dude! I was expecting, like, a technicality. Like, I won the lottery, the genetic lottery.

Oh! I thought it was going to be, like, five bucks, because I won the lottery, and there's that dollar. Like a scratch ticket. Yeah, yeah, yeah. I won 50 the other day. But $2 million, that's some serious cash. Yeah, it was great. Well, it lasted. Oh. Yeah. Okay. You've already blown through $2 million, that's some serious cash. Yeah, it was great.

Well, it lasted. Oh, you've already blown through $2 million? Did you buy a house? Well, I wish I bought a house. Oh, no. So you're one of those lottery ruined my life candidates. You blew the money on something else? Yeah, I bought this really cool hovercraft.

Hovercraft? It's like a boat that can drive on land and water. Like one of those swamp boats? I've seen those things. I would show up to work in a hovercraft and feel pretty good about myself. It's very practical. I mean, no, I didn't say it was practical. I would just feel cool.

Yeah, it's flashy. But you don't have a house to store the hovercraft at. So what else did you get? So I hit another boat, and then I got sued. Oh, you crashed your hovercraft at. So what else did you get? So I, I, when I hit another boat and then I got sued. Oh, you crashed your hovercraft. Into another boat.

Okay. Okay. And I'm guessing you didn't have insurance on it. Okay. No, I didn't know that you had to have insurance.

Yeah. Oh my gosh. So you, it's kind of a vehicle thing. Yeah. A big trunk goes away like that. Oh my God.

Why would you put this on your dating profile if you don't have any money left? There's funny prompts like two truths and a lie and stuff. I think this would be away like that. Oh, my God. Why would you put this on your dating profile if you don't have any money left? There's funny prompts like two truths and a lie and stuff. I think this would be good for that. Don't you think it's sending out the message that I am rich? Maybe I'm not financially responsible. I think it's funny to see you crash something out there.

It's a good question from Brooke there. Why did you put it on your profile? It's not a lie. I mean, I did win it, and I guess maybe if I won it once before, I'd be prone to winning it again. No, I'm sure that's how it works. That's how odds go. You're a lucky guy,

and girls should know that about you. So how does all of this relate to your date or whatever happened between you and Zoe? Well, that's the thing is because we went to this bougie place and she might, you know, have this expectation that, you know. Did you guys talk about it on your date?

Well, yeah, we talked about it. But, you know, I didn't say that I'm basically broke, no. You know, I think it's a cool story. Like, how did you win it? What was your reaction? What's the first thing you bought? It's a good conversation starter for a date. Huge red flag that he spent all the money, that there's nothing left.

I mean, just that you're not very fiscally responsible. It's the cool start of a story, but with a very, very sad ending. Yeah, it is true. He could have done a lot more with that. And so now clearly you're worried that she's going to find this out about you, that you blew your $2 million. I hope he's worried that he has to tell her the truth, Jeff. Well, yeah, I'm really not worried about any of that. I'm just worried about her expectations

and more expensive dates that I really can't afford. Okay, so did you actually call in because you know we give a free gift card at the end of this? Is that what's going on? The gift card wouldn't hurt right now, that's for sure. Okay. Okay. What are we doing here, though?

Because she already wants to go out with you. So what's our question for her? Well, I'm hoping that when you ask her about the date, she likes me for me and not really my money. And if that's the case, then we can continue. That's what I'm hoping for. Just ask her questions about you. Get the vibe. You're trying to read the room here.

So we're going to call Zoe and try to get her to vastly lower her expectations on you and still want to go out with you when we come back and do your second date update right after this. Thank you. All right, man. Hold on. Second date update. If you're just joining us, we got a lottery winner on the phone with us right now who took home two million bucks a few years ago. Unfortunately, he blew pretty much all of it

on, quote, a bunch of dumb crap, including a hovercraft that he ended up crashing into a boat. Yeah, and the lawsuit that followed. Yeah, with no insurance. But look, he seems like a really good-hearted dude who met a nice woman recently named Zoe. She already wants to see him again. But he's a little bit worried that the expectations of dating a millionaire,

because she doesn't know that he blew all the money yet, that could break them before they even get started on this relationship. Well, and that's the thing. It does kind of feel like a lie. Even though he did win the lottery like the way you're portraying it isn't fully honest but brooke he shouldn't be on his profile like hey by the way i'm broke after winning the lottery i mean like how honest do you want to be funny again another funny story yeah it's funny but not romantic like no girl's

gonna swipe on that i know but don't you feel like, I mean, let's be honest. What's his name? Oh, God. I always forget. See, if you have a net worth of under $5 million, she refuses to remember who you are. No, really. That's not true. I don't think I remember either.

What is it? No, it's, I got this. It's Ray. Yeah! He had to look at his notes. I wrote it down, Ray. Ray, I'm sorry, Ray. We remember you. notes. I wrote it down, Ray. We remember you.

Ray, I heard lottery winner and everything else went blank, Ray. Yeah, that happens to most people. That's all they could think about. Just for the record, I never lied. I know. I'm just saying you kind of misrepresented the finances. Maybe she thought he only won $10 like we did when he first called. Let's hope. Let's stop doubling down on Ray here and call Zoe.

Okay. And remember, we're trying to figure out if she really likes Ray for Ray or if she was just mesmerized by the lottery winner thing. If she thought she won the dating lottery. There you go. By meeting a lottery winner. All right. Here we go. I'm going to dial her number right now.

Hello? right now hello hi we're looking for zoe this is zoe hey zoe i'm calling from a radio show called brooke and jeffrey in the morning hey zoe hey you're on the air with us you might see my face up on a billboard in a city near you. Oh. We have been on billboards. Were we upside down on a billboard one time? Yeah. It was an accident, but yes, they fixed it. But you know what?

I thought it got more attention than when we were right-sided. Everyone remembers that one. But Brooke and Jeffrey in the morning and we're good friends with a guy that you know named Ray.

Okay, hi. Yeah. Hello. Hi. I know Ray. Cute Ray that you went out on a date with brooke calls him cute yeah yeah he was fun right and we heard a little bit about the date ray said he had a

blast with you at dinner the other night and wants to see you again well that's great but he's not showing it because i've been trying to hang out with him again and he's not responding i see okay yeah no he actually had a really good time yeah and he knows that you've been wanting to see him ray is just kind of like a reserved type of guy though and he needs like a third party to come and help him gauge like what you really think about him so you guys are like his assistants like for him he pays us more than our own i mean this is free but yeah yeah we're unpaid we're doing this out of the kindness of our hearts he just seems like a nice guy who's interested in you and so what do you think about ray i mean i i had a good time i've been wanting

to get together with him again okay can i ask what did you like about him yeah he just like was nice and normal and he had some really interesting things about himself that you know other people don't have and so it was he was unique in that way well it was cool he told me that he won the lottery at some point and you know i play scratch off like every week and i was just like oh that's so cool that someone actually won like you exist i didn't find that part very interesting about him i was more focused on like his personality personally oh i can see why like if him and i were like best friends that wouldn't be the first thing that i would mention about ray really i feel like it'd come up when i'm drunk if i had a friend that doesn't make money that just, no, drunk men don't make money.

That just speaks to the type of person that Alexis is. That's honest. That's all right, Alexis. The thing is, Zoe, Ray has had some bad experiences before with women who maybe were in it for the wrong reasons. Yeah, I mean, at this age in our lives, we've all had bad experiences with people. Sure. So let's say that Ray was the same exact guy that you went out with to dinner the other night, but he did not have the lottery attached. Would you still like him? I mean, that's like part of who he is. And that's like part of his story. Like I.

True. That's a small part though if you cut that part out would you still love ray for ray well i don't love anyone yet let's just be clear i enjoyed getting to know him and i wanted to go on another date with him so but if you took i think what jeffrey's asking is if the lottery wasn't involved at all, would you still want to go out another day with him? So are you telling me that he didn't win the lottery? No, no, no, that's totally true. He won the lottery a while ago. Some of the expectations that come with winning aren't what I know.

It's complicated. It's kind of hard for us to tell you. It'd be easier to just let ray explain it himself because he's on the other line listening right now what in the world is going on this is like super weird yeah these second date calls do get kind of weird sometimes but ray really is there and he wants to speak with you ray joey how you doing oh uh super confused how are you doing right i'm sorry for all this you know i just wanted to really just try to you know understand how genuine you are and and liking me oh i came out kind of weird yeah okay you know so it's true i did win the lottery but um

i also you know i don't have any of the money left over. I blew it. Not a lot. We're just going to drop that. Yeah, no, I don't have any of it at all. Oh, man. Let's try to help a little. There's the truth.

Okay. We put it all out there for you, Zoe. Okay. Which is admirable. That he lost all his money? I guess, yeah. That he there for you, Zoe. Okay. Which is admirable. That he lost all his money? I guess, yeah. That he's coming clean, Zoe. He's coming clean.

You guys, let her say something. That's nice. Like, I appreciate that he's coming clean, but, like, why did you lie to me? Yeah. It's like if I put a profile picture up of me weighing 50 extra pounds than I do now. Like, at one point point i was that skinny you mean less should he have sent you a picture of his wallet before you guys met up just to prove with nothing in it i think she's saying he's representing himself wrong yeah i mean it's

more of like a fun story that i have you know i never once said that I still had the money. Ray, you took me out to a beautiful restaurant and acted like you had a bunch of money. I'm not trying to say that I'm after your money, but when you sweep a woman off of her feet, you're giving her an expectation.

Well, you can't be after my money because I don't have any. He knows that now. I think she said she wasn't after your money. I'm being honest. I'm more concerned about your character. Why? I think he's a liar. Why?

Are you serious? What? Because he's a former millionaire and not a current millionaire? Because he's representing himself as a millionaire and he's not. It's misleading. He's got a nice first date. What do you want? Him to take you to Chipotle? and he's not. It's misleading. He's got a nice first date. Like, what do you want? Well, like,

him to take you to Chipotle? Like, how much of the conversation was about the lottery? It wasn't, like, the first thing that we talked about, but, you know, you talk about things that are on the profile.

So it was like, how did you win? What game did you play? Like, what were your numbers? Like, I play. I want to know. It's a fun game to play even when you don't win, guys.

Like, if you won, what's the first thing? Well, hey, you know, I'm just letting you know I want to know. It's a fun game to play even when you don't win, guys. Like, if you won. That's not what it's about, though. Well, hey, you know, I'm just letting you know I'm not done playing the lottery. I mean, there's a chance that I still really could win again. Oh, no. Whoa, wait a minute. Wait, that's your selling point, Ray? You think you're going to win again, bro?

Well, I mean, you know, I'm in a couple hundred bucks a week or something. Oh, my gosh, bro. That's so many lines. You told us you were broke. Well, I'm broke after I buy the tickets, but not before. You're putting all of your financial future into the lotto.

Yeah, like I said before, I got lucky once. It'll happen again. That's what they say. Lightning always strikes in the same place two times. Always, every time. And I'm sure that's what any financial advisor would tell you.

You're right. This is just like your first date. It's going to strike a second time as soon as we offer to send you guys out on another date. And they promise us gift cards, too, so we don't have to worry about that. Yeah. Look at that, Zoe. He knew it. If I'm being honest, like, Ray, I would want you to become an adult

before we ever want on a second date again. Ouch. Okay. Well, Ray, I'm sorry, man. Looks like she doesn't want to go out with you after all. That's what I called. I kind of figured she'd be a gold digger. Oh, my gosh. You're an idiot.

Yeah, my bad. That's not it. 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. I'm Tomer Cohen, LinkedIn's Chief Product Officer. If you're just as curious as I am about the way things are built, then tune in to my podcast, Building One. I speak with some of the best product builders out there. I've always been inspired by frustration. It came back to my own personal pinpoint. So we had to go out to farmers and convince them.

Following that curiosity is a superpower. You have to be obsessed with the human condition. Listen to Building One on the iHeartRadio app, Apple, or wherever you get your podcasts. I'm Emi Olea, host of the podcast Crumbs. For years, I had to rely on other people to tell me my story. And what I heard wasn't good. You really f***ed last night. It felt like I lived most of my life in a blackout.

I was trapped in addiction. You had to grab the lamp and smash it against the walls. And then I decided I wanted to tell my own story. Listen to Crumbs on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Welcome to My Legacy. I'm Martin of the Kingdom III, and together with my wife, Andrea Waters King, and our dear friends, Mark and Craig Kilberger, we explore the personal journeys that shape extraordinary lives. Join us for heartfelt

conversations with remarkable guests like David Oyelowo, Mel Robbins, Martin Sheen, Dr. Sanjay Gupta, and Billy Porter. Listen to My Legacy starting January 20th on MLK Day 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.

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