Brooke and Jeffrey: Second Date Update - Second Date Update: Unattractive Trey Is Back

Episode Date: February 6, 2026

One of our listeners did something HEROIC for a stranger, and it got him a date! Meet our hero in today's Second Date Update!See omnystudio.com/listener for privacy information.

In the middle of the night, Saskia awoke in a haze. Her husband, Mike, was on his laptop. What was on his screen would change Saskia's life forever. I said, I need you to tell me exactly what you're doing. And immediately, the mask came off. You're supposed to be safe. That's your home. That's your husband.

Listen to Betrayal Season 5 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Black history lives in our stories, our culture, and the conversations we still having today. This Black History Month, the podcast, I didn't know. Maybe you didn't either. Digs into the moments, perspectives, and experiences that don't always make the textbook. Let me tell you about Garrett Morgan. Brough had to pretend he didn't even exist just to sell his own invention. Listen to I didn't know.

Maybe you didn't either. From the Black Effect Podcast Network on the I Heart Radio app, Apple Podcasts, or simply wherever you get your podcast. 1969, Malcolm and Martin are gone. America is in crisis. At a Morehouse college, the students make their move. These students, including a young Samuel L. Jackson, locked up the members of the board of trustees,

including Martin Luther King's senior. It's the true story of protests and rebellion in black American history that you'll never forget. I'm Hans Charles. I'm in Lick Lamuba. Listen to the A building on the I Heart Radio, Apple Podcasts, or wherever you get your podcasts. Hey, I'm Jay Shetty, host of the on-purpose podcast.

On a recent episode, I sat down with Nick Jonas, singer, songwriter, actor, and global superstar. I went blank. I hit a bad note, and then I couldn't kind of recover. And I built up this idea that music and being musician was my whole identity. I had to sort of relearn who I was if you took this thing away. Who am I? Listen to On Purpose with Jay Shetty on the I-Hattie on the I-Harty. Radio app, Apple Podcasts, or wherever you get your podcasts. What if mind control is real?

If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. Mind Games.

a new podcast exploring NLP, aka neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Ooh, here we go. Brand new episode on a Friday. Welcome to your second day podcast. And I've been warned by Alexis that she has a long comment that she really wants to read. It is a long comment, but it's a nice one.

So it was on an episode in December. okay for reference and they said oh my gosh Alexis I didn't know you listened to comments past yes I thought I was a lone traveler in the abyss of comments long gone where only travelers like myself would see comments and gain encouragement from the fact that we're not behind on the show alone I'm catching up and to those behind onward to those ahead I'm on your six and the time is coming where I'm beside you as we anxiously await the next episode keep it gangsta I love it. I love it.

And you know what? In a month, she'll hear that. Yep. Get closer. You're getting here. You're getting here. When you hear this, let us know. And when you write your next novel, also let us know because I'll buy it.

Yes, onward. Onward. Brand new episode starts right now. Brooke and Jeffrey in the morning. Second date update. You may remember a few months back, a listener we had on the show named Trey, who met his date at a singles mixer where the host was. accidentally rude

telling him, oh, you're lucky that you're here tonight because you're not that attractive. Oh, I do kind of remember that. I felt so bad for him. Right? And he was able to shake that off and score himself a date, took her out to a wine bar,

and then come to find out that woman was actually paid to be there that night. It wasn't cute, the whole thing. So again, Trey is getting roasted, being called ugly, then learning that the women at the event didn't even really want to be there in the first place.

I don't know that he needs recap, Jeff. Well, this is where our listeners. It's not Tray remembers. He lived it. Our listeners may not remember. I just feel for him. Trey came on her show. He made his case to that woman, and it came down to this moment.

So, Steph, will you go out with me again? Can we try running it back and doing it again? Aw. Wow. Yeah, I mean, I think I'm going to say yes. It's not like a pity yes or anything. like I really would like to see you now. That was so cute.

I remember it ended really well. Yeah, and then she ghosted him. What? Really? Really? When she said, yeah, I really mean it. That means she doesn't mean it. I absolutely do not want to say yes to this, but I will to save my image.

Trey, you are better than that. Thanks, guys. I really appreciate that. And Brooke totally meant it when she said it. I really do. He's a good guy. Trey has already suffered through the trifecta of humiliations. He's been through it all, but he's back.

That's what's important. He's back again. So, Trey, thank you for trusting in the only people in this world who don't care how unattractive you are. Oh, my God. We don't care. He is attractive. We haven't seen a photo of that. We don't care about your physical looks.

And also, sure, Trey, we are getting paid to be here with you. Yeah. But that's not a lot. But we want to. Yeah. Trey, I'm not going to let you talk to them anymore. How are you doing? I've been pretty good, y'all.

I really appreciate it. I'm giving love a chance. I'm hopeful. That's right, Tray. Kind of a weird situation, but I was driving home from work one day, and there was this bus that was, like, broken down. It was kind of like blocking part of the road. Okay.

So I go over because I want to check to make sure everybody, you know, is everybody okay? That is so nice. I can get out potentially. Nobody stops anymore. If you see a car on the side of the road, you do not stop for it anymore. I thought for sure you're going to say you reended the bus on accident. Oh, that's what Alexis would have done.

That's the Alexis story. I don't know. Wow. Okay. Yeah, that is true. Not a lot of people would slow down at all, let alone stop to try and like assist. That's amazing. Yeah.

So I go chat with them and they're waiting for like another bus. Come there like a tow truck. It was kind of, they weren't really sure what was going to happen next to the driver is having some issues getting a hold of anyone. So he was like, I think I'm going to run to this gas station to see if they have like a tow truck. And I suggest I was like, why don't I just go run to the gas station? Like you stay with. your bus, you're responsible for everybody.

So, okay. Dang. You've really volunteered to, like, be the superhero and swoop in to save the day for these people. You didn't even know them. It wasn't that big of a deal. I mean, the gas station was down the block. I could see it from where the bus was. And I guess the bus is blocking the road, so you need it to move so you could drive home.

So it's kind of selfish, too. Yeah. And, like, as I was walking, some of the other folks from the bus were, like, listen, we're just going to bail on the bus. We're just going to find someone to come pick us up. We don't know how long this is going to take. Totally. I'd go and call an Uber as well. But while we're walking in this group, I started chatting with one of the riders.

Hey. This girl named Julie. Okay. And she's telling me like she was really bummed if she had a long day at work. She just wanted to get home to her dog, which was crazy because I'm like, I have a dog. You have a dog. That's so cool. We talked about our dogs. What are the odds?

Yeah. Crazy. That's cute, though. It's meant to be. It sounds like. I mean, that's your opening to offer a ride, right? Exactly. Okay. There we go.

Trace saw the moment. You suddenly care less about the rest of the bus. Yeah. Peace out, everybody else. I know we met five minutes ago, but tell me where you live. I'll take you there. Well, I didn't say it like that, but I did offer. She said, you already had someone coming to pick her up, so not a big deal.

But I asked her for her number. I was like, why don't we try to get a drink sometime. Okay. And did that happen? We did go on a date a few days later. Yep, we did. You did. We finally get to a date.

Okay. I don't know if we have any time to talk about it at this point. I know. It was a long walk to get here, like literally and figuratively. So quickly, tell us about your date. The date was great. Like, what was nice was we were texting a bunch leading up to it. Like, we had tons of bus jokes and all that.

You know, ha-ha, don't take the bus to our date. Ha-ha, you know. Okay, that's funny. But when we got there, it really was just a drink. Like, really hung out for, like, less than an hour. We were just, it was great to get to know her. was really shy and honestly I understand, you know, how often do you just

meet random people that came to your bus that broke down? And we should probably just get this question out of the way. Do you know if she found you attractive or if she was paid to ride the bus that day? Paid bus driver. Yeah, I don't know. I have yet to confirm or deny that information.

Of course you found him attractive. You don't agree to a drink and give a guy your number that you don't find cute. But this is a little bit of a different scenario because it sounds like, Trey, you were the hero that moment. You stepped up and tried to save the day for her. So I don't know, maybe if she felt obligated to go on that date with you and kind of be like. But she got her own ride.

And what did he do? Walker to the gas station? You know, it's not like, he wasn't really. We don't know what part of the neighborhood they were in. It could have been a very dangerous area of town. So we're about to call Julie here. The good news is you've already been humiliated on this show so many times. How could it possibly get any worse, right?

I think this is going to go fine. That's exactly what I said, just in a different way. The way matters. Okay. You feel good about this, right, Trey? I trust you guys 100%. Famous last words. That's a fatal flaw.

Before we make that tragic call for your second date update and hopefully get you another meetup. We'll do it right after this. Hold on. Brooke and Jeffrey in the morning. Second date update. If you missed it earlier, it's the glorious return. of our listener, Trey.

Yes. And I don't care what the rest of the room says. I am not afraid to call him the H word right to his face. Really? Hero. Oh. True story. He is a good guy, for sure.

See, Brooks hesitant to use it. I'm not afraid because he unselfishly pulled over while driving to help a broken down city bus full of random people. One of whom was Julie. Yeah. Who, if you could believe it, owns a dog. What are the odds?

Ended up getting her number, taking her out to drinks, where even though she was a little shy, he says they did have a really nice time together. Yeah. I mean, maybe that's just why she's not calling you back right now. Just being a shy girl? Yeah. It's possible. Some people have a hard time with that.

It is true. No second date has materialized, so that's why he's come to us. But I don't think we really got the full picture of what's going on with her right now. Is she texting you? Have you called her? or snapped her or DM? Like, what are we working with? So I sent a few texts weren't responded.

I, you know, I'm smart enough to know not to completely double text. And then I also called her, but left the voicemail and I haven't heard back. Oh, okay. Voicemails can really backfire. Yeah. It was a short voicemail, right? Yeah, I was sweetened to the point. Okay.

See, I trust, Tray. You're going to hear him on the loser line next week. He knows. Yeah. This guy's got emotional intelligence. He knows what's up. All right. I'm going to dial, Julie, here. We'll see if she picks up the phone, and hopefully we can hook you two up for one more.

Hopefully we don't scare her is really what it is. She's a shy girl. Okay, we'll be very delicate with the shy girl. Gentle. Here we go. Hi, is this Julie? Yep, that's not what I mean. I hear you.

Hi, Julie. Hi, this is Julie. Sorry for yelling. Thank you for picking up. We're on the radio right now with a show called Brooke and Jeffrey in the morning. What we're doing is a dating segment that we have on. our show. It's called the second date update. Okay. Okay. It's a good thing. It means you met somebody recently who had a really nice time with you,

thought very highly of you, and wants to see you again. What? Did you drop something as you said. She faked in the show. Oh, God. We joke a lot, Julie, just so you know. Okay. But this is a guy named Trey that you met right after. after your bus broke down on the side of the road? Yes, I know exactly who you're talking about. Okay.

I mean, he told us that he's been texting you and calling you and trying to meet up, and for some reason that's not happening. He's a little bit confused. Why? Listen, as far as Tray goes, he's fantastic. And I would almost say, from what I could tell, from the day we had, Like, he's consistent. He's a very what you see is what you get.

Good person. That's so great. What a wonderful thing to find out. That feels like if that's a good thing, that you would want to see him again. Yes, but the thing is it's complicated. Like, he's very uncomplicated. I'm in a little bit of a complicated situation.

Oh, no. What situation? Complicated always means you're not single. Yeah. Well, I, so I'm not in a relationship. but I am in a situation ship. Okay. Okay.

So I felt a little curious, like, oh, go on the date. You know, like, how is it going to be? And to be honest, I expected it not to go as well as it did. So when it did, I kind of, yeah, I cut short a little bit because I was just starting to feel guilty. Because here's this person who's really great, open, ready. And I would like those things, love those things, but I have this situation ship kind of in the background. So just break it off. Why can't you just break off the situation ship?

Who cares about those? I thought that's the beauty of a situation ship is that there's less strings attached. It's easier to move on to the next. Well, this has been going on for several months now, and it's just kind of been. And I think the biggest thing is at its long distance. Oh, girl, what are you doing? Everything's working against you with that other guy. I mean, Trey's right here, like right in front of you.

You are standing in your own way right now. I know. It's intimidating. He's even listening to this phone call quietly. right now waiting to jump in and speak to you. Wait, you're kidding, right? No, that part I'm actually not kidding about because he's on the other line.

Oh, God. Hey, how's it going? Trey. Hey. Wait, you just heard all of that? I did, yeah. And listen, like, I appreciate, like, if you just be honest,

my feelings never hurt knowing information. I think I just, it's not that I didn't want to. I think under all different types of circumstances, you're definitely someone that I would consider. It's just, I don't know, I feel like you deserve to do with someone who's on your level of openness and uncomplicatedness. And like, that's just not me right now. Well, I understand sometimes things get complicated and they get uncomplicated. Life is messy. I get it. If there's any chance that you might be interested, I I'd love to go out again and show you really that maybe I'm better than the other situation.

Not maybe. You are, Trey. There's no way that you're not. So that's what I mean. Like, you're such a sweet guy. Like, just that response. And there's just something else. And it just makes it really difficult.

That's all. Something else. I mean, lay it on me. I don't mind. I like being open and honest. And I like you. So I'm sure we all have our flaws. Oh, wow.

Yes. Um, so my situation ship is actually long distance because he is locked up. He's locked up? Oh, locked up? Yeah. How does this get worse? She likes bad boys. Actually, he does sound kind of sexy now that she's described with him.

Not for anything like super like murder or anything. Like, no, I would never. Oh, that's your life. It's good to have a bar. I guess I'm a little confused. I mean, how does a situation should happen? happen while someone's in prison? Well, I mean, to be fair, we had met, like, the week before he got locked up.

Just a week. And we kept talking, but I get to go visit him every three months. Oh. And we get to have, like, those visits that we get to be intimate, you know? Oh, okay. We need all those details. You kept talking to a guy, and you only knew him a week before he was. went to prison? Well, we kept talking

and it just developed over time, and then in the three months that he was in there and I got to go and we kind of feel the deal physically, and I can't, unfortunately, I feel like I can't emotionally untangle myself from it. Okay. I mean, it sounds like a real Romeo and Juliet sort of situation there. They knew each other for one night and look what happened in that story.

And they were like 12 and 14, right? Yeah. Turned out great. Trey, this is a lot of information coming at you now. Where's your head at? I wasn't expecting that, honestly. I mean, I really enjoyed our time together. I think it'd be

crazy not to at least maybe try to hang out again because again, I think I'm not going to say can. I know I will. There it is. You better fit for you. Yeah. What a bold statement. Look at that confidence. Okay. So, despite what Julie is

telling you, you're willing to give her another chance. I mean, think about it, Julie. How long is this other guy locked up for? Three more years. Same. Yeah. Do not waste all your pretty on that. A long situation. I'm serious.

Trey, are you willing to fight this guy after three years when he's released and proved that you're the one for Julie? If I can see a mug shop before it, so I can better assess it. See, emotional intelligence. That's smart thinking. Look at this, Julie. This man is willing to literally fight a criminal for you. Depending on the tats.

Yeah. So, with all of that said and everything you've just heard, would you be willing to meet up with Trey one more time, and if you are, we would pay for that date. Do yourself a favor, Julian, say yes. I mean, if you're okay knowing all of this and that this is still happening in the background while I figure this out, yeah, I mean. You won't even be thinking about jail guy, okay? We won't even think about chocolate bars.

That's how much. No, bar. Yeah. Jail cells. I get it. Okay. Well, that means, Trey, congratulations, man. You got another second date.

Yay. You guys are the best. Okay. This time with a woman who's in a situation ship with a different man who's serving a prison sentence for three more years. Yeah. But still, pretty good. Hey.

It wasn't murder. Brooke and Jeffrey in the morning. Celebrate your pride with the station that's as bold, vibrant, and diverse as you are. I heart pride, China. From dance anthems to pop icons and hits from 2SLGBTQ plus Canadian artists. It's the soundtrack that keeps life loud and proud. Just ask your smart speaker to play IHeart Pride Canada. Stream us on your phone or listen now at iHeartRadio.com.

Come together, celebrate love. Pride. Pride. With IHeart Pride Canada. Welcome to the A building. I'm Hans Charles. I'm Inaleck Lamouba. It's 1969.

Malcolm X and Martin Luther King Jr. been assassinated, and Black America was out of breaking point. Writing and protests broke out on an unprecedented scale. In Atlanta, Georgia, at Martin's Almermata, Moore House College, the students had their own protest. It featured two prominent figures in black history, Martin Luther King's senior, and a young student, Samuel L. Jackson. To be in what we really thought was a revolution.

I mean, people would die. In 1968, the murder of Dr. King, which tried to be in a revolution. traumatized everyone. The FBI had a role in the murder of a Black Panther leader in Chicago. This story is about protest. It echoes in today's world far more than it should, and it will blow your mind. Listen to the A-building on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm not sure if Trey fully realizes what he's saying yes to here.

Because I know that he's a positive. guy, but he just agreed to go out with a woman who is actively hooking up with a guy in prison every three months and says she's not quite ready to stop. Yeah. And Trey was like, you know

what, it's fine. Let her have her conjugal. I'm up for it. And I've already. Cheered it on the whole way. Because I want her to come out of it. Like, I'm sorry, but every female has a friend just like this woman. Despite all proper logic, we'll

choose the worst possible choice for herself. Yeah. Even though she deserves more. But she could change him, Brooke. And that's the happily ever after every woman wants. I don't even think she wants that. I think she just wants him to like her. I mean, honestly, I think that's all she wants.

She'll take him felonies in all. Yeah. But, you know, bless Trey's heart for being willing to, like, give it a shot and try to win her over for the next three years. Yeah. Hey, good luck. And we better get an update. I hope so.

If she actually goes out. just a letter from prison from whoever she's dating. That one works for us too. We have a lot of prison listeners. Yeah, we do. I didn't even think about that. What if he hears this while listening to our show behind bars? I mean, it's a situation ship. He's got to know, right?

You think that's his own visitor? They only do each other a week before that guy got in. Oh, my God. I'm nervous, but I do hope we hear from Trey again, whether it's an update on this situation or if he needs help with a future girl down the road. We'll always be here for Trey. And for all of our listeners, reach out to us, email the show. We can call that person who's not calling you back. In the middle of the night, Saskia awoke in a haze.

Her husband, Mike, was on his laptop. What was on his screen would change Saskia's life forever. I said, I need you to tell me exactly what you're doing. And immediately, the mask came off. You're supposed to be safe. That's your home. That's your husband. Listen to Betrayal Season 5 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Black history lives in our stories, our culture, and the conversations we still having today. This Black History Month, the podcast, I didn't know. Maybe you didn't either. Digs into the moments, perspectives, and experiences that don't always make the textbook. Let me tell you about Garrett Morgan. Brough had to pretend he didn't even exist just to sell his own invention. Listen to I Didn't Know. Maybe you didn't either from the Black Effect Podcast Network on the I Heart Radio app, Apple Podcasts, or simply wherever you get your podcast.

1969, Malcolm and Martin are gone. America is in crisis. At a Morehouse college, the students make their move. These students, including a young Samuel L. Jackson, locked up the members of the board of trustees, including Martin Luther King's senior. It's the true story of protests and rebellion in black American history that you'll never forget. I'm Hans Charles. I'm in a lick Lamouba. Listen to the A-building on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcasts.

Hey, I'm Jay Shetty, host of the unpurposed podcast. On a recent episode, I sat down with Nick Jonas, singer, songwriter, actor, and global superstar. I went blank. I hit a bad note, and then I couldn't kind of recover. And I had built up this idea that music and being musician was my whole identity. I had to sort of relearn who I was if you took this thing away. Who am I? Listen to On Purpose with Jay Chetty on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious.

Mind Games, a new podcast exploring NLP, aka neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts.