Brooke and Jeffrey: Second Date Update - Second Date Update: Getting Silly With Two Milly

Episode Date: March 18, 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 a brand new Second Date podcast!See omnystudio.com/listener for privacy information.

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, 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.

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 secret family so i just gotta 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 gonna be living with their parents jeffrey not a whole nother

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 is in the other room and they're going to hear this? Yeah, sorry. I'm just a little nervous,

I guess. Okay. It's alright. 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, 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. I'm 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. We'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. 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 you know 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 two million dollars

congratulations man i was expecting like a technicality. Like I won the lottery, the genetic lottery. I thought it was going to be like five bucks. Like a scratch ticket. But $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. You're one of those lottery ruin 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. That's very practical. I mean, no, I didn't say it was practical. I would just feel to work in a hovercraft and feel pretty good about myself. That's very practical. 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? I hid in another boat

and then I got sued. You crashed your hovercraft. Into another boat. And I'm guessing you didn't have insurance on it. No, I didn't know that you had to have insurance. 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.

This is kind of a vehicle thing. A vehicle. Don't go 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. Oh. Don't you think it's sending out the message that I am rich? I don't know. Maybe I'm not financially responsible because I think it's funny to the message that I am rich? Maybe I'm not financially responsible. I think it's funny to say you crashed something. 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 like be prone to winning it again. 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 have this expectation. Did you guys talk about it on your date? Yeah, we talked about it, but 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. I think it's a huge red flag that he spent all the money, that there's nothing left. Yeah. I mean, just that you're not very fiscally responsible.

It's a 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 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 $2 million 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 so 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, 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.

How honest do you want him to be? Then again, another funny story. But Brooke, he shouldn't be on his profile like, hey, by the way, I'm broke after winning the lottery. Like, how honest do you want him to be? Then again, another funny story. Funny, but not romantic. Like, no girl's going to 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. That's not true. I don't think I remember either. What is it? remember no it's uh i got this it's ray i wrote it down right right i heard lottery winner and everything else went blank ray yeah that happens to most people that's all they could think about. Yeah. 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. 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? Hi, we're looking for Zoe. This is Zoe. Hey, Zoe. I'm calling from a radio show called Brooke and. This is Zoe. Hey, Zoe. I'm calling from a radio show called Brooke and Jeffrey in the Morning. Hey, Zoe.

Hey, good morning. You're on the air with us. You might see my face up on a billboard in a city near you. We have been on billboards a lot. Weren't we upside down on a billboard one time? Yeah. It was an accident. But, you know what?

I thought it got more attention than when we were right side up. Everyone remembers that one. But Brooke and Jeffrey in the Morning, and we're good friends with a guy that you know what? I thought it got more attention than when we were right side up. 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 Ray. 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.

Oh, I see. 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. Yeah, he pays us more than our own job.

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. So what do you think about Ray? I mean, 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 he was unique in that way. Oh, like what? 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 yeah 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 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. I think what Jeffrey's asking is if the lottery wasn't involved at all,

would you still want to go on another date with him? So are you telling me that he didn't win a lottery? No. No, that's totally true. He won the lottery. A while ago. It was a long time 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. Zoe, how you doing? Oh, 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 in liking me.

Oh, that came out kind of weird. Yeah. Okay. You know, so it's true. I did win the lottery, but 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 of it at all 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's fun money anyway 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. 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, 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 right you took me out to a beautiful restaurant and acted like you had a bunch of money and i'm not 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. Oh, 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. Like, what do you want? Him to take you to Chipotle? 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 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 i play i want to know it's a fun game to play even when you don't win guys like if you want that's not what it's about though well hey you know i'm just letting you know i'm not i'm not done playing the lottery i mean there's a chance that i still really could win again oh wait a minute wait that's'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,

a couple hundred bucks a week or something. What? 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 sure, that's what any financial advisor would tell you. 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 the gift cards, too, so we don't have to worry about that. Yeah. It'll be all on us. 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. Ow. 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. You're an idiot. You don't have any gold to dig. Yeah, my bad. That's not it. Brooke and Jeffrey in the morning.

Man, I feel really bad for Ray and for all of the listeners who have reached out for help lately because this is the fourth listener in a row Brooke's called a liar. I didn't say he's a liar. I never said that. He told the truth. He just misrepresented himself. That is different, Jeffrey. How did he misrepresent himself?

Honey, he pretended like he was rich. No, he didn't. Yes, he did. He took her out to a nice restaurant. He bragged that he won the lottery. He didn't brag. He told the truth that he won the lottery once. The app is meant to tell funny,

like a captivating story to catch somebody's interest to get the party started. That's how it works. But the thing is, he just wanted a genuine call to gauge like how this woman really felt about him as a person. And she didn't really care about him as a person. She just cared. No, she didn't. I guarantee if we had called her and said that he took his two million dollars and invested it wisely so he's not worth $2 million, he's worth $10 million. Wait.

That would be a different type of lie. I thought she was okay with it until he said he gambles every day. Yes. I don't know why you're sticking up for him so much. Because somebody needs to stand up for our listeners on this show. Whether or not they're in the right, nobody's perfect, and we understand that. At least three-fourths of us do. So come on the show if you

need help with your dating life. Hey, listen. I won the lottery once. I got two bucks off a scratcher. She's a liar, Jeff! So now I can claim that as well, right, Jeffrey? Under your rules. It doesn't work for you because you are kind of rich. Yeah, I agree.

But we promise we'll help you. Email the show. We'll call that person who's not calling you back. Brooke and Jeffrey in the morning. 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