Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Burned By Beauties

Episode Date: October 9, 2026

When we offered to send this couple on another date that WE PAY for, we never expected to get the answer back that we received. Hear one of the most bizarre endings to a Second Date Update ever!See omnystudio.com/listener for privacy information.

Lisa, tell them about our new show. We have a new podcast. It's called Don't Lie to Me. I'm Lexi Youanu. We're two best friends, 22 years apart, but so close at heart. And I'm Lisa DiGulio, the old one, which means we have wildly different references, occasionally different opinions, and at this point in my 50s, I've lived it all. Now in my 30s, being the founder of new shoes, good taste is my business.

Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Lacey Mosley, author, actor, stand-up comedian, creator, and host of Scam Goddess Podcasts. The True Crime Comedy Podcasts all about robbery, fraud, and those who practice it. Each week I bring on an amazing guest. Ooh, I scammed them. What? I can talk to you for an hour. You're a generational yapper like me.

That's why I had to make yapping a job. And now you can catch full episodes of my show on YouTube. Start listening to Scam Goddess on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. I'm Hamza. And I'm Martin. And we're the hosts of Out of Character. The best podcast in the world is what they said. Wait, they said that?

Yeah, yeah, they said that. The best podcast with two best friends who jabber and talk about topical, trendy, funny stuff, give our input on it. That's what you've needed, I think up until now, listener. Listen out of character on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Sometimes I just feel like a burden. You're a bird. You fly. You're a Martin.

And we are Out of Character Podcast. Dude, he messed up the clip. Hi, this is Kylie Breakman. Angel Geratana. Jeremy Colhain. Patrick McDonald. And we're the hosts of the Artists on Artists on Artists on Artists Podcast. The Improvised Character Comedy Podcast where each week a new panel of artists discuss their craft.

Join us for a panel of Eurovision participants. And we do a little Halloween sometimes. Does the Pope dress up? He winks on Halloween. It's right up next to the microphone. I hear you can almost hear the eyelashes hit each other. You never seen Italy so quiet as when the Pope gets up to wink on Halloween. Listen to Artists on Artists on Artists every Thursday on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

What would change if you stopped letting money stress run your life, sis? I'm Mandy Money, host of Brown Ambition, The Podcast. And right now, I'm taking you through my six-part Money Reboot series. This is your chance to hit reset, break the debt cycle, get honest about where you're your money's going, build a savings plan that actually sticks, and start making financial choices that support the life you want, not just the bills you have. Because wealth building is not about being perfect. It's about having a plan, knowing your numbers, and making your next move with confidence with a community that cares like we do on Brown Ambition. Each episode gives you practical

steps, real talk, and the motivation to stop putting your financial goals on hold. So if you've been saying, I'll get serious about money next month. This is your sign. Start now. Listen to Brown Ambition. That's Brown Ambition. And begin your money reboot today. Listen to Brown Ambition on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Hey, we got your second date podcast for you. And this is Brooke and Jeffrey in the morning. And you just caught Jose and I awkwardly crying in the studio together. Oh, I got a sweet message from someone. I appreciate our listeners. I was like, what's going on? You cutting onions over here, bud? And then he reads it to me, and then I started crying.

Yeah. What do you got on the comment section, Alexis, who never cries? I cry so much. Not at work? I'm a huge cryer. You are. That's interesting. If you talk to people I'm like super close with.

Yeah. She's a different person outside of work, Brooke. It's the kid movies that always get me, too. I watched sheep detective the other day. I heard that so good. Yeah, my friend walked it on me in tears. Oh, I was upset in Cheap Detective. But anyways.

That's just because of all hot, huge action. Alexis is the onion. New layers all the time. for her. Barry Allen said, I listened to these full shows while at work and I have laughed so much. My dad wants to send me to get evaluated since he now thinks I'm crazy.

There you go. Join the crazy with us. Oh, you just reminded me. Somebody at my comedy show recently said they were at the dentist and the Dennis lets them listen to our show going and they were listening to our show and going I had to ask them to change it because they were laughing too much.

I love it. I love it. I love it. Keep sharing those stories. It makes us so happy. and makes us cry. All right. Second date update starts right now. Brooke and Jeffrey in the morning. Second date update. When you've been single for a bit and your friends are telling you,

you need to get back out there and start dating again. Yeah. If you're a little shy about it, maybe the best thing you could do is pop on a mask and leave the house with your head held high. A mask? What kind of mask? Like a pandemic-era mask or like a full? Super Louie.

Wow, Brooks certainly is interested in getting herself back out there and wanting to know exactly which type of mask to wear. Maybe that's a question we should ask to our listener, Riley, because that's what he did. And apparently it led him to a little love connection. So, Riley, welcome to the show. Hey, guys, thanks for having me. Okay, your voice isn't muffled.

That means you must be mask-free right now. I'm Sam's mask at the moment, yeah. Okay. All right. Now, Brooke wants to know what type of mask you. wore, but I'm more curious about the girl that we're going to be calling here first. What's her name? So I met Dana while I was wearing an animal mask. Why were you wearing an animal mask? So the event we met at was an art installation and the theme was animal mask. Oh, this makes sense.

Everybody at the art installation was required to wear a mask in order to be there? Yeah, I think Encouraged is more the term. There were a few people without masks. Okay. Okay. So you're into art. Like, it was an art event that you were at. Very much so, yeah.

Cool. That's cool. And it sounds like she probably was too. Was she masked? Yeah. Her dress was beautiful and it matched her flamingo mask. Wow. Okay.

What was your mask? What were you? Wait, we don't want to know if she was standing on one leg? No? Sorry to move on. How in character was she? I'm kidding. Well, she.

was hopping around on a leg for a little bit because we had our little inside joke and the inside joke was because I had a crocodile mask on I'm her natural predator. Like I'm gonna get you. This sounds like Alexis's dream interaction. I'm joking.

Oh, okay, I was like, what? I like animals. Okay. Yeah, animals attacking each other inside of an art gallery. That's really cute and romantic. I mean, obviously it's flirting, right? Like you guys are flirting with each other.

Oh, yeah, very much. I mean, we really hit it off. The masks kind of did it, but sort of our energies matched and I think our sense of humor match too. Okay. You can't tell someone's cute with a mask on. Like, remember in COVID when people would wear them? And then as soon as they take them off, you're like, oh,

a different person. When did you guys see each other's faces? We did at the end of the night. It was both like release. You know, we were both like, oh, okay. Okay. I didn't waste my time. Okay.

All right. Interesting. That would have been awkward too. It would be like, oh. So this is just the first meetup. Was there a date after this? So I did ask her out and yes, we did go out. It was like three or four days later.

We did a little rooftop scenario. Oh, the rooftop bar or something? What was the vibe like then? Because you guys were so playful and everything the first time you met. The date was normal and I stand by that. But here's my thing. I am skeptical. of beautiful women.

And this woman is beautiful. She is so stunning. Why are you skeptical of beautiful women? Well, I've dated a couple of beautiful women. One was a damn klepto, friggin' liar. I don't know. She stole my laptop. I don't know that that speaks to all beautiful women.

It speaks to her. Or your tasting woman. Broke, why would you trigger him with a question like this? Look what you've done. to this phone call. So was she different than all the other stereotypes that you have in your head about pretty people? Well, I think I gave her the benefit of the doubt. But here's the thing, though, I feel like my skepticism kind of bit me in the butt because my approach to the gate was more like businessy and like questioning. Like, well, what do you do? What's your favorite things? And this

and that and less. Like you were basically trying to interrogate her and find out what's wrong with you. He can't be beautiful and nice. Did you ever hold your hand out with your watch on it and like see if maybe she would try and swipe it off of you? Leave your wall on the table and go the bathroom. Oh, tester. Yeah. That didn't happen?

No, she didn't steal the watch. Okay. Wow. She passed the klepto test. That's big. Really, I do, I'm honestly like I'm running this situation over my brain many times. I really feel like I wasn't like slurdy enough. I wasn't cutesy,

lovey-dovey. Okay, well, you're admitting maybe it didn't go perfectly, but how did the date end? It did end well. We had a little kiss. Oh, cute. That's great. Like a Hershey's kiss? It was a little peck, you know, like it wasn't anything outrageous, but then after that, I've asked her out a couple of times and she did at first seem keen on it, which I've also heard before,

which goes back to why I don't trust these pretty people because it's like their other options on the other side. Of course. I think everybody can have a lot of options. You're right, anybody can, but let's be real, pretty people have more. Absolutely. You feel very triggered by pretty people, it feels like. Well, you're not wrong.

Okay, so are you going to be able to be calm if we get her on the phone and she doesn't want to go out with you again? Or are you going to... Honestly, I think she already doesn't want to go out with me. She keeps kind of making up things to not go out on a second date. So if I had the opportunity to just to find out what it is instead of being iced out, like I think that will go a long way, not only between her and I, but like me moving forward. Yeah, with pretty people in general.

Well, you know, let's give him a little bit of credit for putting himself out of his comfort zone and being willing to date a beautiful person. That's a big, that's a big move. Must be hard. You know, and so we're going to try to reward that by doing our best with their Second Date Update. When we come back, call Dana and trying to get you some answers right after this. Brooke and Jeffrey in the morning.

Second Date update. Ugh, beautiful people. Right? We just can't be trusted. We? I mean, yeah, sure. We look nice on the outside. But inside, well, yeah, we're still beautiful.

Yeah, it's pretty nice in there, I bet. It's genetic, yeah. But some of us, a very small percentage, I'm sure, sometimes will be. do bad stuff just because we can. No, Jeff. And ugly people let us. Say it ain't so. And it sounds like our listener, Riley, has been burned by a bombshell before.

And he's currently getting burned again by another beautiful woman who's not calling him back for a date. Yep. It happens when you go for the bombshells, brother. More than one. You guys, do not hype him up into this mindset. This is the mindset he needs to get out of. But he's not wrong. Yeah, exactly.

I'm not wrong. That's why we're going to call and look this beauty. right in the face and say what gives. Okay, wait. I thought it was like, don't judge a book by its cover. I mean, that's true for beautiful people, for ugly people. It doesn't matter. Brooke, you can't afford this book cover.

I'm definitely paperback. Riley, we're about to call Dana here. You feeling ready? As ready as I'm ever going to be. Thank you. Okay. Take deep breaths through this, okay? We're going to try and get you this bombshell back.

Yeah. Whether he wants it or not, I can't quite tell. He hates somebody loves it. Yeah. Everybody wants him. So here we are. Story of my life. Let's dial this number.

Hello. Hello. Is this Dana? Um, yes, it is. Who is this? She does have a nice voice. I really, yeah. You have a very nice, sultry voice, Dana.

My name's Jose. What? Don't know. Don't mock her. I like it. I like it. I like it. You're probably noticing a lot of people

on the phone right now. It's because you're on a radio show called Brooke and Jeffrey in the morning. Hi, good morning. Hello. Nice. Did I win something or what's going on? Besides the genetic lottery, maybe.

We heard you're beautiful. That's what Jeff said is saying. The reason that we're calling is because one of our listeners gave us your number, asked us to reach out on his behalf, a guy named Riley that you went out with. Oh, wow. Yeah, and we do this because it's part of a segment called a Second Date update, where we attempt to help out our listeners if they're not getting a call back after a solid first date,

we try to figure out the reason why. Okay. So Riley says, according to him, he's been trying to get a hold of you and he's not having any luck. So he feels like something must be up. Yeah, so, okay, sorry, just catching me off guard. That's okay.

It sounds like you guys had quite the connection before your guys' date started. Yeah, I mean, he was cool, but after our date, I found out that he snooped around my Instagram and found pictures of me and my ex. What? Yeah. Okay, so wait, hold on. You can't blame him for looking at your Instagram. How do you know he did that?

Yeah. That is a good question, actually. Yeah. accidentally hit that like, ooh, God, that's terrible, isn't it? No, actually, it's worse. He reached out to my ex in DMed him. Oh, no. Okay, that's a step farther then.

Oh, that's pretty grim. What did he say to your ex in a DM? Well, this is how I found out. My ex reached out to me and told me that apparently Riley was asking him if I was trustworthy and asking him for advice. I'm sorry. If you were what worthy? Trustworthy.

Trustworthy. Oh, no. Yeah. How does that make you feel knowing that he reached out to your ex? Well, you know, I feel like he's not trustworthy because I feel like that's a red flag. It is a lie. Yeah. You know, you don't typically ask for, like at a job application, you'd ask for references, but not necessarily a dating situation.

And this is one date. It's like, if they've been dating for maybe six days, he's like, all right, I'm going to ask him with my girlfriend. Still, it seems weird. It's not much worse. Yeah. That's a lot. He didn't tell us that. Yeah, we did not know that.

I bet he doesn't even know that you know that. I don't know what he knows. I mean, he's, you know, he knows a lot. We can find out exactly how much he knows because Riley is on the other line of this phone call, listening and waiting to talk to you. Oh, wow. Oh, wow. She said.

So unlike him. It's romantic. He's got a lot of surprises up his sleeve. Riley, are you there? I'm here, yep. Oh, Riley. What are you doing? You get her for ex-doc?

Why didn't you tell us that? Well, at least the good news is you pass the test. No. That's not good news for you, though. Nobody wants a test while they're dating. He wasn't supposed to find out. He promised he wouldn't say anything. He must have been a pretty person.

Can't trust them, right? Yeah. Well, he sure wasn't ugly. Okay. Okay. Oh, wow. His allegiance is obviously going to be to her, not to you. Not the random guy from the internet,

jamming him about a girl. Well, you know what? We really need to just step back so that you and Riley can talk this out because this is something between the two of you. So go ahead. Okay, so here's the deal. I've been burned before multiple times. And it just so happens that these women, also like yourself,

happen to be outrageously beautiful. Now, I'm not saying that you're going to do those things, but I've been burned. and I'm just trying to make sure that I don't get burned again. And I was looking to get some background from your ex who, by the way, seems like a pretty cool dude. Oh, you approve. It's just weird because we went on one day

and then you reached out to him behind my back and it's like, I want to get to know my friends and ask them some questions. Yeah. All right, hear me out. I reached out to him, obviously for a specific reason. and if he had said anything that was like really bad or if he was just a kind of a crazy ex, I wouldn't have, one, taken the information and two, professed it to the world on the radio station.

Right. That's honest. It was a positive review of you, Dana. Yeah, but you shouldn't have done that. Yeah, but I think I should have. And also, I think I've kind of made a new friend in the meantime. Like, he's a cool dude. That's insane.

Friend is a really strong word there, Riley. You've had one conversation with him. Yeah. It might have been maybe more than that. What do you mean? What? Well, we linked up, had a brew, had a conversation kind of about life. You had a beer with her ex.

Whoa. You did not meet with him. Come on. Like, you're joking. No, I did. We actually, like, had a really good time. And I'm kind of, like, I heard a lot about you. I heard about your first kiss.

Oh, my God. Oh, wow. First kiss with the ex. I honestly can't believe you broke up with a guy. Like, he really seems like a genuine sweetheart. Yeah. Are you? You're trying to get them back together?

Do you like him, bro? I honestly do like them. We're actually, we have plans tomorrow. We got basketball lined up. Oh, wow. Maybe a little friend no after. You all should just be friends at this point. Sounds like they are.

I don't know. We need more male friendship in this world. Yeah. Yeah, but I just met the guy. And then he's like hanging out with my ex. Like, that's weird, isn't it weird? Yeah, this did get worse. Guys, it's actually not weird.

Now I know a lot about her, and I'm actually just like your ex. Like, I really do think we'd be a good match. Aw. The ex didn't work out for a reason. Yeah. Well, it sounds like Riley ships the relationship. Dana's ex even ships it. All we need is the final sign-off from Dana to go out with Riley one more time and make this thing final.

No, and I'm thinking about deactivation. my Instagram. Like, I'm just scared he's going to reach out to somebody else and do an interview with them. Yeah. I got to say, Dana, I've been single for a while and, you know, if it doesn't work out with us, I would still think you should probably give your ex another shot. Wow. Are you wind-fanting for him? What a good friend. You know, Riley, what you should do is hang up the phone and we should never talk again. Oh, out. All right. She's not interested in Riley. But, Dana, I'm only going to offer this once. Would you consider going back out with your ex?

No. As a favor to Riley. That's a different segment we do. And we would pay for that. Everybody wants it to happen. Even Riley wants it. I'll be foolish, Dana. He's a good guy.

It's just unprecedented on the show. Well, maybe that's a good idea because he never did anything like Riley did. So you're comparing them now. I'm open to it. Oh, my gosh. Yes. Now we're getting somewhere. Okay.

Riley, how do you feel about accidentally playing matchmaker? Yeah. You know, I don't think it was an accident. I think maybe I wanted this the whole time. I'm fine with that. Okay. He really does love your ex. Brooke and Jeffrey in the morning.

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So go see what's hiding in your closet and you might be surprised with how much you can earn. Download Vinted for free and start listing with no seller fees. Wow, what a weird turn of events. Yeah. That, I mean, wouldn't it be insane if Dana and her ex ended up getting married after all of this? All because Riley stalked their Instagrams. They brought her back together. Riley would definitely be the best man.

Oh, for you. Yeah, either the best man or maybe even the efficient of the wedding. I don't know. No, he's going to cry too much. I think Riley likes her ex more than she likes her ex. Oh, yeah. It may be. I mean, the only more bizarre than that would be if the ex-boyfriend calls.

us two weeks from now for a second date update because Dana's now not calling him back. Oh, boy. That might not be crazy. That might be expected. That may be good. She goes to. Oh, yeah. It doesn't often work out with exes.

We're still willing to try to help them out, right? We need the content. Make sure to go find all of our second dates up. They're on Spotify, Apple. Wherever you get your podcast, just search at Brooke and Jeffrey. Lisa, tell them about our new show. We have a new podcast. It's called Don't Lie to Me.

I'm Lexi Wannu. We're two best friends, 22 years apart. but so close at heart. And I'm Lisa Di Giulio, the old one, which means we have wildly different references, occasionally different opinions, and at this point in my 50s, I've lived it all. Now in my 30s, being the founder of new shoes,

good taste is my business. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Lacey Mosley, author, actor, stand-up comedian, creator, and host of Scam Goddess Podcast. The True Crime Comedy Podcasts, all about robbery, fraud, and those who practice it.

Each week I bring on an amazing guest. Ooh, I scammed them. What? I can talk to you for an hour. You're a generational yapper like me. That's why I had to make yapping a job. And now you can catch full episodes of my show on YouTube. Start listening to Scam Goddess on the IHeart Radio app, Apple Podcast, or wherever you get your podcast.

I'm GAM Goddess. And I'm Martin. And we're the hosts of Out of Character. The Best Podcasts in the World is what they said. Wait. They said that? Yeah, yeah. They said that.

The best podcast with two best friends who jabber and talk about topical, trendy, funny stuff, give our input on it. That's what you've needed, I think up until now, listener. Listen out of character on the Iheart radio app, Apple Podcasts, or wherever you get your podcast. Sometimes I just feel like a burden. You're a bird. You fly. You're a Martin.

And we are out of character. Dude, we messed up the clip. Hi, this is Kylie Breakman. Angel Geratana. Jeremy Colhain, Patrick MacDonald. And we're the hosts of the Artists on Artists on Artists Podcast. The Improvised Character Comedy Podcast where each week a new panel of artists

discuss their craft. Join us for a panel of Eurovision participants. And we do a little Halloween sometimes. Does the Pope dress up? He winks on Halloween. He gets right up next to the microphone. I hear you can almost hear the eyelashes hit each other. You never seen Italy so quiet

as when the Pope gets up to wink on Halloween. Listen to Artists on Artists on Artists every Thursday on the IHeart Radio app, Podcasts or wherever you get your podcasts. What would change if you stop letting money stress run your life, sis? I'm Mandy Money, host of Brown Ambition, The Podcast. And right now, I'm taking you through my six-part Money Reboot series. This is your chance to hit reset, break the debt cycle, get honest about where your money's

going, build a savings plan that actually sticks, and start making financial choices that support the life you want, not just the bills you have. Because wealth building is not about being perfect. It's about having a plan, knowing your numbers, and making your next move with confidence with a community that cares like we do on Brown Ambition. Each episode gives you practical steps, real talk, and the motivation to stop putting your financial goals on hold. So if you've been saying, I'll get serious about money next month.

This is your sign. Start now. Listen to Brown Ambition. That's Brown Ambition and begin your money reboot today. Listen to Brown Ambition on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.