Brooke and Jeffrey: Second Date Update - Second Date Update UPDATE: Bid On Me

Episode Date: October 24, 2024

Usually if you hear about someone exchanging money for a romantic time, it's something weird or illegal...But not today! In fact, it's one of the most romantic phone calls we've had all year... in a Second Date Update UPDATE!See omnystudio.com/listener for privacy information.

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. Second date update. Most of the time, if money is exchanged in return for a date, that can be viewed as kind of sketchy. I think it's kind of illegal.

Well, not for me, though. No? That's why I always walk around with seven different money clips full of many denominations in multiple types of currencies from all around the world because you never know. Just to be ready, huh? Have you ever heard of Venmo?

You're willing to do that for 800 Barbadian dollars? You're in luck, sir. I just happen to have that right here. Is that actually the currency in Barbados? I have no idea. Barbadian sounds cool.

You'll never know. And one of our listeners said in their email, a money exchange was attempted for a date with her. It might have something to do with why she's not seeing this person right now, but she definitely wants to get a hold of them. Let's talk to Mila about it. Mila, welcome to the show. Hi, thank you so much for having me. Oh my God, the setup to all of this makes it sound so sketchy. Yeah.

Well, when you say it like that, I guess, but... There's no shame in doing like a sketchy money exchange for a date. I think there is some shame in that. Don't get in your head about it. Not if you're happy with the amount. You load your head up with pride, Milo. Tell us about this person that

you met and how this money exchange happened. Okay, so I met this guy, Sam, at a charity auction. It's basically, I was trying to raise money building a new community center. Oh, that's awesome. Part of the event was auctioning off dates.

Oh, my God. I participated in something like this once, and it was so nerve-wracking. Were you being auctioned? Yes. And I'm like, please, someone just bid. This is going to be so embarrassing. Was it weird that your husband didn't even put his hand up?

That must have been pretty sad. Oh, my God. So wait, were you being auctioned off, or was he being auctioned off? Yeah, no, I was auctioned. Oh. I will say, and I maybe shouldn't, I was auctioned off once and I actually ended up getting drunk with the person on our date and we had the greatest time. But this could actually be a date.

These are supposed to not be real dates. This is a room of experienced date auction people. Yes, Bob has sold. Jeff, you've been sold before. I have not been sold, no. I'm the buyer. But Mila, how did you feel when you were being put up like that? Were you nervous?

Of course I was nervous. Especially because I met this cute guy. Part of it was a silent auction, and during that time I met Sam, and he was very sweet and he made me laugh. He made me feel less nervous about the whole thing. Okay, so you guys talked about how you were up for auction. Before that.

A date with James. Yeah, yeah. Okay. So then he asked me, like, hey, what number are you in the auction? And I was like, well, be prepared, though, because you're going to have to take out a second mortgage. I'm not cheap. That's funny. It's a little scary.

Jeff's frightened. But it's for charity too, right? Yeah, it is for a good cause. So it's not the worst thing. So he's showing interest that he wants to bid on you before it happens. That's great. Yeah, no, and it was luckily that joke landed well. So it gave me a lot of hope, but of course the worst

possible thing happened. What? Sam starts bidding on me. Great. Love that. We knew that was going to happen. But then my freaking ex-boyfriend comes into play. Shut up. And starts bidding against him.

What? Wait. Why would he do that? That's so stupid. He wants to get back together with me. Did Sam ever know that was your ex? Or was it just like a bidding war with a guy he didn't know, hopefully? I don't think he knew.

OK, that's good. I mean, honestly, it kind of hypes you up. Yeah. You know what I mean? Yeah, that's true. So did he win? Who won the date? My ex won.

Oh, he loves you. Did you actually verbally say yuck when he won? You start crying on stage. Well, it's obviously for charity, so I didn't want to seem perturbed by who won. Yeah. It wasn't like it was a bad relationship either. Like, the relationship had just run its course. Okay.

It's just bad that he can't get over it. Yeah. Can we ask how much money you went for? Is that a rude question? No, it's... No, it's not rude at all and i for the record definitely think i'm worth more than this amount okay it was two thousand dollars oh that's pretty good two thousand dollars i thought you're gonna say 20 grand but okay it's respectable

charities do you go to i'm not gonna what the Illuminati does and does not do. But the $2,000 is great. That's a good amount of cash, but it's with your ex. Did you already go out with him? No, I didn't. I'm not looking forward to it. But I'm going to make it very clear, you know, that this is just for charity. But what happened after the auction ended with Sam?

Were you able to, like, reconnect with him and be like, hey, I actually was hoping you would win? Yeah, I told him that. And I was actually able to get his phone number later on through my supervisor. There we go. And look at that. He's like, what? I get a free date? Awesome.

Yeah, well, I haven't contacted him yet. And I was hoping that maybe you guys could help me out. Oh, my God. Why? So, wait, hold on. Are we going to call him and convince him to ask you out somehow? Why don't you just ask him out? I don hoping that maybe you guys could help me out. Oh my god, why? So wait, hold on. Are we going to call him and convince him to ask you out somehow? Why don't you just ask him out? I don't know. I'm nervous and I know

he loves your show too, so I figured this might be the best way. Okay, the whole point is we need to ask out Sam for you. I just think this is going to be so easy. Like, why would he say no? I guess I'm kind of surprised that he didn't find a way to get my number, but I don't know. Maybe he didn't find a way to get my number.

But I don't know. Maybe he felt like it wouldn't have been the right time since I was literally bought by somebody else. Well, I wonder if he somehow could just vibe and tell that was your ex or something. And he's just like, look, I'm going to let them do their thing. Or somebody else from the foundation that you work with. Oh, yeah. Like, let it slip. Because I'm sure some of your coworkers knew what was going on. Yeah, and then he's like, oh, they're probably getting back together.

These are all questions that we can ask him when we come back. Call him and try and get the second date update and ask why he didn't think you were worth more than $2,000. We're going to do it right after this. Second date update. You're in the middle of a second date update update. And we're going to find out how the couple is doing right after you hear part two. Coming up to the auction stage, she's a 5'6 brunette, but 5'9 in heels. She's got a sharp sense of humor with limited baggage,

except for the ex-boyfriend who follows her around to charity events and tries to win her back. Her name is Mila. Now let's start the bidding at $14 million. Do I hear $14 million? $14 million? Nope, nope. No takers. I'm going to bid on it.

Sold! Yay, Jeffrey! I think that was actually official, Mila. Good for you. You just won a lot of money. More like four Bitcoin. I know you're worth, Mila. How are you feeling, Mila?

I feel really good now that you guys just gave me a proper bid. That's right. That is right. I know I'm joking around, but Mila's actual day really wasn't too far off from what just happened there because Mila was trying to help raise money for her local community center. She was in an auction, wanted a guy named Sam who was there to win her because they had a little flirtation before the event started. Unfortunately, Mila's ex would not let that happen. He showed up and stole her away for the price of two grand. He sucks.

Wow. But he has money. Yeah, so he doesn't suck that much. And wants to support the local community. But the good news is Mila was able to get Sam's number. That's the guy she really wanted to go out with. So we're about to call him here. And I was thinking we probably, when we get him on the phone,

should not tell him that the guy that he was bidding against was his ex. Did you have to say that part out loud? What is duh, Jeffrey? Like, who was going to mention it? Yeah, I was thinking the same thing. Let's not mention it. We're all in agreement. It was all my idea. Now we're going to call

this guy Sam for you. Okay. Dial his number right now. Hello. Hi. We're looking to speak with Sam. Hello? Hi, we're looking to speak with Sam. This is Sam. Hey, Sam. Nice to meet you.

What up? You're on a radio show right now called Brooke and Jeffrey in the Morning. Okay. What an experience. We often auction this type of experience off at charity events. That wasn't as smooth as it is in your head. I thought it sounded pretty good. I'm pretty sure Sam has no idea what you're talking about.

Sam, sorry for the confusion here. We're doing a segment with you called Second Date Update. Okay. And the reason that my co-host eloquently spilled something about auction stuff is because one of our listeners met you recently at a charity auction for a local community center. Do you remember meeting? Oh, right. Yeah, I was there. Cool, yeah.

Yeah, you're big into charities, huh? Did you meet any cute ladies there? Yes, I did, actually. There was one in particular I really liked. What a coincidence. Okay. We're talking about a girl named Mila. Is that the one you're thinking of? That is the one I'm thinking of.

That's so cute. She just was super serious and I just heard your smile when we said her name. Yeah. What did you like about Mila? Mila was just breathtaking. She stood out from the crowd. She's really cute. I don't know.

We just had a really good chemistry. That's awesome. She was just sweet. Just really relatable, you know? So sweet and so relatable and so breathtaking, but not breathtaking enough to spend more than $2,000 on her. Shame on you guys. I'm just saying.

Hey, we're a comedy show. That was a joke. Even Jeff kept talking. Well, I mean, we heard that you didn't win when it came time for her to be bid on. No. For the date with her. Yeah, there was another guy out. He outbid me, so.

You realize she's not actually a thing, an item. You can just ask her out afterwards. Yeah, I know. But right after somebody bid on her, I don't think that was the right time to go up and ask her. No, it was the perfect time. Well, you don't want to do it in front of the person that just spent all this money trying to get her. But these things are actual romance. I mean, they're just like fun things.

They are, yeah. They're not supposed to be. Did you have any plans, though, like maybe after the event to try and reach out to her or something like that? Yes, definitely. It was on my mind. though like maybe after the event to try and reach out to her something like that yes definitely it was on my mind so uh funny thing happened was after the auction was over i went over and talked to the guy that outbid me oh you did oh you talked to him oh wow yeah did you roll up your sleeves and say best man wins yeah now it's time for fisticuffs let's throw hands oh i mean like i said i really had a connection with mila. I went and talked to the guy.

And it turns out he was her ex-boyfriend. Oh, no. No way. What? Wow. Whoa, that is news. Blindsided. Come on.

We knew that. Okay, yeah. To be honest, we heard that that was the case. And she was super disappointed. Yeah. Yeah, well, I mean, I felt really bad. I mean, he was like really trying to get back to her. He was getting all teary-eyed talking about how much he missed

her and I kind of just, I felt bad for him. So I kind of consoled him a little bit and I told him let's move on. I mean, obviously it's over. It's over. So. Well, we've all been there. So you're kind of being a bro at this point. That was a good message. Post-relationship therapy.

Did he listen to you as he moved on? Yeah, he needs to. Well, I mean, it took a little bit of a bribe, so I actually ended up paying him for the date. So I reimbursed him plus a little bit extra. What? Wait, what? To buy the date of Mila off of him.

No way. Hold on. Why does Mila not know this? Well, it's going to be a surprise. Like, he's supposed to go on a date, so I'm going to show up instead. Oh, no. Oh, my God. Hang up all the phones right now.

Are you kidding me? Oh, dude. By not saying one thing, we ruined something else. That's actually really cute and really sweet. Oh, my gosh. And I'm sorry, dude. The reason why we're reacting this way, we had no idea that this plan was going to happen, and we actually have Mila waiting on the other line listening, wanting to talk to you.

Oh, no. That's our surprise. Dude, I'm so sorry. Oh, man. Well, Mila. Mila, are you there? It was going to be a nice surprise. I was looking forward to seeing it.

Hey. Oh, no. It was the knife. We feel bad already. Dude. Mila. Mila? No, I'm still surprised.

I'm so surprised. That's so sweet. Oh, yay! Okay. Yeah. Did you hear her? I don't get to see your reaction in person, but... Wait, wait, hold on.

Mila, Mila? Are you okay with this? Are you sure you want this to happen? You guys are so sweet. I know you feel bad for ruining the surprise, but I'm so happy right now. I'm speechless. Are you sure? Oh, that is the kiss!

Are you sure, Mila? Because we can get your ex on the phone and convince him to up it even more. Let's see how high we can go with this, like $2,500? Oh, he's going to have to pay me a lot if he wants that date back. How were you planning on telling her? I was going to just come to the date. I mean, it was all...

Yeah, that's the perfect setup. You were just going to be sitting at the table and she was going to walk in and instead of the ex, it was going to be you. But this is good because now she can get more ready because she actually cares about the date. That's what I was thinking too, Alexis. What she would have worn before. Because Mila, you weren't going to try if it was going to be the ex at all, right? That's a great point. Oh, yeah.

No, not at all. Oh, my gosh. I'm sure Mila would have looked amazing no matter what she was wearing. Oh, man, you're great. This is making me sick. Yeah, now I'm getting a little nauseous. I love it. So what we normally do is we offer to send you guys out on a date that we would pay for.

Well, we can do that. We don't have the money. We do not have $2,000. They're going to go on two dates now. After the date that you've already paid for, would you like to go on another date after that? And we'll pay for that. I would love to. Okay, great.

Oh, my God. He is so into you. He's already planning the next date. That's so cute. Well, Brooke, technically, I planned this, so I get ownership of it. Well, technically, the ex planned the first one. So, I mean, what has he done? You really have to step up your game here, okay, Sam?

You're not doing a whole lot over there. I'll try my best. That's a spirit. So cute. Brooke and Jeffrey in the morning. Well, that call happened six months ago where we blew the surprise. Typical us. But it was so cute, I still can't get over it.

But now we've got them both back on the phone to get a very quick update update hey sam and mila welcome back thank you for having us and you two are not together right now just hang up the phone yeah you better be married well fill us in on what's happened since you guys were talking to us last so basically after the last call with you on your show, we went on our very first date. And of course, there was drama. Wow. Don't tell me that ex showed up. Yes. So predictable.

Exes suck. I know. Brooke, you shouldn't have told him where the date was. That was a bad idea. It is Sam on the phone, right? Not your ex. No, it's me. Yes.

Okay. Sam, were you freaking out? Yeah, it was pretty crazy. I didn't expect him to show up, but eventually I just ended up just paying him to leave. You paid him again? Wait, what? Dude, you are just a baller. Is that why he showed up? Is he now just showing up for Sam's money? He knows he'll

get paid to leave. How much did you have to pay? Well, I gave him another $300. $300? What? Which is kind of insulting that he's only in love with you up to $300. I mean, the ex is only obsessed. Well, I tried to pay him less, but I would have paid

a lot more just to have her. That's amazing. Have you guys gotten rid of that dude hopefully you'll never we'll never see him again okay that doesn't sound very yeah no it was definitely a weird moment but ever since then it's been really great oh okay i could just imagine though you two are on the couch like at home watching a movie and you get a call from her ex he's like hey i'm coming over unless you venmo me a hundred bucks right now it's like okay oh i wouldn't coming over unless you Venmo me $100 right now. It's like, okay. Oh, I wouldn't doubt it. I wouldn't doubt it. You're a good guy, dude.

Keep us updated on your guys' relationship. You're so cute. Thanks, man. Yeah, make sure you keep that location secret, okay? Will do. Brooke and Jeffrey in the morning. 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.