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

Episode Date: April 24, 2024

One of our listeners had TWO hunky men fighting over her.. but what should be a total dream ended in the worst way possible and now she wants our help repairing damage with a new Second Date 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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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. Second date update. Most of the time, if money is exchanged in return for a date. Oh, God, Jeff. That can be viewed as kind of sketchy. I think it's kind of illegal. 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 of 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 hang your head about it. Not if you're happy with the amount. Yeah. You hold your head up with pride, Mila, okay? Tell us about this person that you met and how this money exchange happened or almost 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. Good for you. So 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. Is 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, though. This is a room of experienced date auction people. I've been 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 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 it. You talked about how you were up for auction. Before a date. 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 frickin' 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.

Okay, that's good. I mean, honestly, it kind of hypes you up. You know what I mean? Yeah, that's true. But it also could have been good if he knew that it was the ex, because it's like she was so amazing all the exes want her back Did he win who won the date my ex one Did you actually 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. It wasn't like it was a bad relationship either. The relationship had just run its course. It's just bad that he can't get over it. Can we ask how much money you went for? Is that

a rude question? 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 say what the illuminati does and does not do. The $2,000 is great. That's a good amount of cash, but it's with your ex. Yeah, but it sucks because then

you have to go out 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 that this is just for charity. But what happened after the auction ended with Sam? Were you able to reconnect with him and be like, hey, I like 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 i was hoping that maybe you guys could help me out oh my god my God. Why? So, wait. Hold on. Are we going to call him and, like, convince him to ask you out somehow? Why don't you just ask him out? I don't know. I'm nervous.

It's a crazy night, and I love you guys so much, and I know he loves your show, too. So, I figured this might be the best way. Maybe we could frame it like the other date fell through, and so he can, like, step in if he wants to. It'll be more, like, official. I don't know. Because then he's going to think that he still owes $2,000. Yeah, he's a backup. Well, then we'll take the

$2,000. Now we're talking. To the Brooke and Jeffrey charity? Yeah. We have needs, but the whole point is we need to ask out Sam for you. I just think this is going to be so easy. 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 felt like it wouldn't have been the right time since I was literally bought by somebody else. I don't know. 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. Like, let it slip.

Because I'm sure some of your coworkers knew what was going on. 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. So weird. Yeah.

We're going to do it right after this. Second date update. 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. Or 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? Well, okay. Like, who was going to mention it? Yeah. That's true. Are you going to blow up her spot?

Sometimes, you know, I like to brainstorm with everybody in the room. It may come up. Don't do that. Mila, is that good with you? Yeah, I was thinking the same thing. Let's not mention it. All right, good. We're all in agreement. It was all my idea.

So now we're going to call this guy Sam for you, okay? Oh, my God. Here we go. Okay. Dial his number right now. 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. So, Sam, sorry for the confusion here. We're doing a segment with you called a second date update. Okay. in a segment with you called a second date update um 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 me oh right yeah i was there yeah did you meet any

cute ladies there? Yes, I did, actually. There was one in particular I really liked. What a coincidence. Oh, okay. Was her name Brooke? Brooke does do a lot of charities. She likes to snatch up as many gentlemen as she can. He didn't say

drunk lady. He said cute lady. Yeah, 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's just super serious and I just heard your smile when we said her name.

What did you like about Mila? Mila was just breathtaking. She stood out from the crowd. She's really cute. We just had a really good chemistry. That's awesome. She 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. Really relatable, you know?

So sweet and so relatable and so breathtaking but not breathtaking enough to spend more than $2,000 on her. I'm just saying. Hey, we're a comedy show. That was a joke. 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. Bummer. What were you feeling when that was happening? It was kind of intense. I mean, I didn't have tens of thousands of dollars to spend on a date. Yeah. Sounds like that guy had a lot of money.

You realize she's not actually a thing an item you can just ask her out afterwards yeah i know but right after somebody bit on her i don't think that was the right time to go up and ask her yeah 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 they are 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. So 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. 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. Yeah. Oh, no. Oh. No way. What? Alexis. We, 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, you know, 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 on. I mean, obviously it's over. It's over. 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. 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. Wait, what? To buy the date of Mila off of him. No way, hold on. Wait.

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, sorry dude the reason why we're reacting this way we had no idea that this plan was gonna 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 but oh man well are you there it going to be a nice surprise. I was looking forward to seeing it. Hey, twist 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.

She's cute. 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 guys are so sweet. Like, I know you feel bad for, like, ruining the surprise, but I'm so happy right now. I'm speechless. Are you sure? Oh, that is the kid! Oh, that's awesome. 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. Hey! I feel like you need to start calling more exes of just other random people if you're able to convince them so you can move on. No, no, no. Not unless they're Mila's ex.

Or like a couple's counseling. I mean, honestly, if he can help me move over my ex... How were you planning on telling her? I was going to just come to the date. I mean, it was all... You were just going to be like 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'll actually care 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.

Aw, man, you're great. This is making me sick. Yeah, now I'm getting a little nauseous. I love it. Well, what we normally do is we offer to send you guys out on a date that we would pay for. Well, we could 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. Oh my god, he is so into you.

He's already planning the next date. 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 okay that's a spirit so cute brook and jeffrey in the morning and the award for the cutest couple in a second date update for this entire year goes to Mila and Sam. Yay! Well deserved. If they do not polish back in an update, I am going to be so upset. Seriously. You can hear the chemistry. So many texts in to 78592.

A lot of awws with like 20 W's afterwards. One said, best ruined surprise ever. We didn't know. And he wasn't even mad that he spent the two grand. You know what I mean? He could have been like, what? She was going to go out with me anyway. Why did I spend all that money? We totally should have sold him for more than that. I knew we could.

But anyway, I can't wait to hear from them again as long as their update isn't that the ex showed up to the date anyway and decided to fight for her. I mean, that could be entertaining. He doesn't sound like a fighter. He sounds like more of a crier. that the ex showed up to the date anyway and decided to fight for her. Oh, boy. I mean, that could be entertaining. Oh, yeah, you're right. Actually, I would like to hear that. He doesn't sound like a fighter.

He sounds like more of a crier. Yeah. He's like, I'm on the check bounce. But we can always try and help you with your love life if you ever need a little bit of assistance. Email the show. We'll call that person who's not calling you back. And go check out all of our second dates

wherever you get your podcasts at Brooke and Jeffrey. 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. 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.