Brooke and Jeffrey: Second Date Update - Second Date Update: Street Walker Love Story

Episode Date: May 5, 2025

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in a brand new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

You're listening to an iHeart podcast. My husband has a secret son from a past partner. Hold up, Sam. How do we know how we done the DNA test? Well, John, luckily, it's mother may have a DNA test week on the OK Storytime podcast. So we'll find out soon. And this wife writes, my husband received a Facebook message from a woman saying that he is the father of a five year old. Whoa. At first, he didn't remember her, but then he realized they had a one night stand

right before we started dating. Wait, but do we have proof he's a dad? To hear the explosive finale, listen to the OK Storytime podcast on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I want you to ask yourself right now, how am I actually doing?

Because it's a question that we rarely ask ourselves. All of May is actually Mental Health Awareness Month, and on the psychology of your 20s, we are taking a vulnerable look at why mental health is so hard to talk about. Prepare for our conversations to go deep. I spent the majority of my teenage years, my 20s just feeling absolutely terrified. I had a panic attack on a conference call. Knowing that she had six months to live, I was no longer pretending that this was my best friend. So this Mental Health Awareness Month, take that extra bit of care of your wellbeing.

Listen to the psychology of your 20s on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Yo, K-pop fans, are you ready? It's your boy, Bum-Han, and I'm bringing you the K-Factor, the podcast that takes you straight into the heart of K-pop. We're talking music, idols, exclusive interviews, and even the real behind the scenes K-pop stories.

Plus you're the fans, you're part of the show and you can get a chance to jump in, share your opinions and be part of the conversation like never before. And trust me, you never know where we might pop up next. So listen to the K-Factor starting on April 16 on iHeartRadio app, Apple Podcast, or wherever you get your podcasts. This isn't just a podcast. It's a kpop experience Are you in let's go go Hey, I'm Jay Shetty and my latest interview is with Michelle Obama to whom much is given much is expected

The guilt comes from am I doing enough me Michelle Obama to say that to a therapist? So let's unpack that having been the first lady of the entire country and representing the country and the world, I couldn't afford to have that kind of disdain. Listen to On Purpose with Jay Shetty on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. It's nostalgia overload as Wilmer Valderrama

and Freddie Rodriguez welcome another amigo to their podcast, Dos Amigos. Wilmer's friend and former That 70s Show castmate Topher Grace stops by the Speakeasy for a two-part interview to discuss his career and reminisce about old times. We were still in that place of like, what will this experience become? And you go, you're having the best time. But it was like such a perfect golden time. Listen to Dos Amigos on the iHeart Radio app,

Apple Podcasts, or wherever you get your podcasts. Hey, brand new week, brand new podcast. Welcome to the Brooke and Jeffrey second date update podcast. We're so glad you're here. Yes. And we got a wild one today, so I think there's gonna be a lot of angry people

by the end of this, at this guy. But I could be wrong, I could be reading it wrong. Let us know in the comments. And we got some great comments from our wonderful listeners Yes, this would make me laugh from Grayson who said I watch these every night to fall asleep. I love y'all Mean I feel like we're too annoying to fall asleep to Maybe it's like white noise like it hits that level where it's just like... Got it! Someone needs to explain to us on that one.

But we love it, thank you, keep the comments coming. Like, subscribe, and sit back and enjoy. The brand new podcast starts now. Second date update There's a lot of fun things in life that begin with the word street street street magic Street tacos. Okay, Jeff. I'm getting it. Yeah street walkers Right, I feel like I do that. I walked down a lot of streets Well today we're gonna talk to a street dater just like why are people giving me money Have really good hair today But again this guy says he's a street dater. He met someone while well not stereotypically, but he met somebody while out on the street

His name is drew Oh, okay. That's what I meant. His name is Drew. So he's a streetwalker. Yeah. Drew, you a streetwalker too? I think I walk the streets about as much as everybody else around here. Yeah. He's a humble streetwalker. You must live in Jeff's neighborhood. Okay. We should probably stop using that phrase. Apparently you met somebody while just walking out and about. How did that happen? Yeah, I was at a bookstore locally and I like to read so I'm leaving the bookstore I'm you know have my face buried in the book cuz I'm walking and I knock into this woman Oh, that's kind of a cute. You know sounds like out of a movie Bookstores involved clumsy her bag fell I helped her and then I gave her a little

Wait, did everything happen in slow motion. I think he's joking about that part I know I'm bad. Oh, I imagine the bag falling he grabbed it. He picked it up. He ran Gotcha you just knocked her bag out of her hand by accident. Yeah by accident. Oh you really did knock the bag over Yeah, we bumped into each other was pretty big bump, and you know everything just kind of flew all over the place I helped us and stuff fell out of her bag. And I said, you know, it's usually old ladies I knock over and then I just move on and she laughs. That's a really funny joke.

He's just joking. He beats them with their walker. No, I get the joke. Oh, okay. I just stop laughing. Oh, I kind of liked it. So then we started walking and we started going in the same direction.

So I just started doing a little more like joking like you following me And she's like no you following me and we laughed again trying to build like a little rapport Like you're turning like kind of a bad situation or a weird situation into like something positive What point were you able to get her name? I did ask her name, but we walked a little more her name I did ask her name but we walked a little more we'd love to know the name she's like don't tell anybody what my real name is Sonia so you and Sonia are just accidentally walking in the same direction and kind of flirting with each other it sounds like yeah we eventually get to a park and we start walking through the park when you got into the park is that when you took her bag then? That's when I knocked her over and ran

Did you really have to go to the same way or were you just pretending so you could Plants like you both just had free time to keep walking. Oh, yeah, that's true, too I walk through that park all the time. Yeah, no, this isn't like the first. I was going in that direction anyway so it's just like a very good meet-cute. Okay. Eventually we came across a sketch artist and he flagged us down. He was like hey you guys want to get a picture? I thought we were a couple. Wait did you get a character drive?, I was down There's so many like Perfect things that are happening to you along the way on this short walk. You didn't set this whole thing up It sounds like how could he do? No, I didn't set anything up

Well, you just have a friend who's like in the park with a thing and he's like, I'm just gonna take her this way I didn't say it was a friend. It just a sketch artist he wasn't a friend. That would be the most elaborate setup ever you accidentally run into somebody and then suddenly you call your buddy when she's not looking who happens to be an artist to tell him to set up quickly in the park. I really want to sit down with her for 45 minutes this stranger. I'm just saying we've heard people that have like orchestrated all sorts of weird things in order to meet people. That's true but this doesn't sound like that Jeff. How long is this walk going on? We're about 20 minutes into the walk by the time she said no to the picture

Okay, halfway through the park and we got to the end of the park. It was probably about a half an hour We were together and I got a good vibe So I asked her her number to go out and she gave her number, and the date just hasn't materialized since then. Okay. Have you guys talked via text or phone call? No, nothing. I've tried to call a few times. I've left a few messages. God, I automatically think that she gave you a fake number. Oh, if there's no response, yeah.

It was her voice on the voicemail. It's her. Oh, it was? Okay. Okay. Yeah, yeah. she gave you the number So I'm assuming she's single did you specifically ask her I didn't ask her if she was dating anyone no But I left a few me and my voicemails, and she hasn't answered how many yeah three maybe four I don't think I call the girlfriend that many times in one year.

I don't think my mom calls me in the morning. You felt the connection, so... But everyone's different. Some people love being on the phone, so... I'm glad you take a break from your extensive book reading in order to help reach out to the show, and we're gonna try and help you call this girl. What's her name? Sonja? Sonja, yeah. Sonja, yeah. Sonja, okay, we'll reach out to Sonja, and we'll do your second date update right after this. Hold on

Second date update If I hadn't read it on the back of a blockbuster movie sleeve, I still wouldn't believe it But an accidental sidewalk bumping turned into your classic Hallmark Streetwalker love story That's the wrong use We're trying to make it sound better than it is classic hallmark streetwalker love story Hallmark movie I'll tell you that one it fits in this scenario cuz our listener drew Accidentally ran into a woman outside of a bookstore Knocked over her bag and then turned that awkward moment into a 25 minute stroll through a local park 30 I believe I mean those five minutes are gonna be precious when it's only a short amount of time you have together.

That's fair. And it all seemed too perfect to be true. And maybe it was because she's not responding to any of his messages. It's always the park scene that ruins it. Something in the park. I mean, he left, okay, here's the thing. You left four voicemails.

Yeah, that's a lot. We have not asked what was in the voicemails? I just told her hey, it's me drew by the park You need a lot of guys by the park. I mean, it's true Maybe she thinks you live in the park There's a chance though that if she's not responding to anything maybe she wasn't even real Are you sure that would make me crazy exactly? Were you micro dosing that day no mark hasn't done that yet a micro dosing Christmas Well if you over micro

Kids still the dare program Microdosing would lead to this. Well, if you over-microdose. No wonder everything was in slow motion. Jeff is one of those kids still in the D.A.R.E. program. Anyway, I signed that contract. Let's have all the Streetwalkers unite because we're going to call and we're going to get an answer from this woman to figure out what actually happened, if she's real, and hopefully if there's an explanation. A lot of kids listening who use that term wrong for the next couple weeks. A microdosing Christmas? No, the Streetwalkers. This is the education you get here. listening who use that term wrong for the next microdosing Christmas education you get here I'm gonna dial the number right now here we go hello it sounds

like a person is this Sonia um yes this is Sonia sounds like a person. Is this Sonia? Yes, this is Sonia. Who's this? Hi, Sonia. Hey, Sonia. We're a radio show called Brooke and Jeffrey in the morning. Good morning. Hi. Hi.

Hey. What's this about? This is a segment that we do on our show. It's called a second date update. And we're trying to help out one of our listeners. His name is Drew, who you met the help out one of our listeners. His name is Drew who you met the other day outside of a bookstore. Did you just laugh. Are you sorry. I just I can't believe that you're calling about him. What you remember. You remember Drew. The guy who

knocked you over on accident outside the bookstore. Yeah. Yeah. I remember Drew. OK. Well that's great because he said there was like a meet-cute type of Situation that happened on the street and then you guys went through a park for a bit. He's left a few messages Yeah, I mean that did happen and I was actually open to seeing him again Except for the messages the messages are the problem Well, we asked him about the messages and he based according to him he said it was basically hey this is drew from the park remember I'm drew is that what he said yeah interesting oh no not true he is like he left me one message that was so

ridiculous I actually my roommate and I have been like dying laughing about it. I actually, I wrote it down. Wait, you wrote down the message because it was that funny to you? Wow. Would it be okay if we know what the message said? Oh, absolutely. I'd love to read it to you. Because we haven't heard anything about it. We just know there was a bunch of messages. She is delighted to share. She is so friendly. And so he told me, he said, I left you a message you didn't respond to. And I don't like leaving second messages, but I like you. You're very elegant. You're very attractive attractive I don't play that game if I don't hear back by 3 p.m. tomorrow longer interested then she goes on to explain why I should call him. Why you should call him. Okay. Some positives, that's good.

He says, I'm very smart. Oh, okay. I'm great in bed. Okay. And I've made a lot of money. Alexis sold. Those are three good things. But also it's not something everybody says.

I mean, it's one of those things where you say it's hard to believe. Yeah, it's like you need to discover those things. then he says believe it or not. I'm a complete cat Oh, I'm one of the only men in the city that has no issues I have yet to find a person that doesn't have issues Yeah, this is like yeah, I'll trying to do reverse psychology on you is that finally the end of the message No To find a person that doesn't have issues Finally the end of the message So I don't know what your situation is if you're just insecure or if you're on medication

Halfway psychologically normal, and you haven't called me because something bad happened in your life, and you just needed a few days Okay, so clearly there was a lot happening in that message and it could help to get insight into what he meant by because so embarrassed right now Maybe because Sonya is on the other line listening. We've got drew waiting to talk to you Something that I said that wasn't true was it something that I said on that voice now that wasn't that was a lie I said on that voice now that wasn't, that was a lie. What? Yeah, you can't say that, right? Dude, hold on, you're coming in kinda hot now. Yeah.

Let's chill a little bit. I think- Defensive. No apology. Well, I'm sorry, Drew. I just like, we met for 30 minutes. We didn't even go on a real date. And then all of this, you're going on

about how great you are. And then you start to come for me and like, blame me for not calling you back. I just found it all to be a little much for someone that like, I'm- Okay, So you agree that I'm right. What? So what was the problem? You don't you don't appreciate being direct. You don't like guys who are direct. I'm direct. When did she say that? I make a lot of money. I'm smart and I'm good in bed. That's all being direct. It's becoming more and more doubtful. You know you're all laughing now but you won't

be you'll be crying later when I'm out of your life. That's what's gonna happen if you don't make the right move. I mean I gotta find out how good you are in bed bro so I'll be quiet. You didn't call me back was really stupid I mean come on people like me who are good in bed and smart and stuff, you know. Why do you lead with that? Oh, okay. Stupid person is gonna give that up. I think he's making some good points. I think so, yeah.

He's a champ, too. You know, you know in this city, there are no men and I'm a total catch. You know there's no men. I kind of agree with him on that. I don't know. I don't know, Drew. I feel like the people who are actually good in bed

don't go around talking about how good they are in bed. I'm not getting the best vibes from you, to be honest. It just feels like a lot. Well, I know that you haven't bragged about being good in bed. Yeah. You're not supposed to. That's stupid.

What are you talking about? Listen to any hip hop music. They're all about that. Are we going to ignore the rest of the text? Yeah. About her being on meds? I did. What?

What was that? I saw her bag, her bag, everything fell everywhere. I saw her meds. What? The bottle fell out. You read? Everyone's on medication. Yeah.

He's concerned about her health. You guys know what you are on medication. You sound crazy. I sound smart and well-read. I really thought you were gonna come to Drew, this is honestly, this is shocking to me, I thought we were gonna come to Drew and you were gonna be humiliated

that this voicemail was out there. But like- Only somebody who's addicted to meds would be humiliated. He's perfect, bro. Yeah, with no narcissistic tendencies at all. No, Sonja. Thank you, I don't, clearly. Good.

Thank you. Sonja, was he right? Are you on the verge of tears right now? Oh, I'm just really heartbroken that I can't be with this perfect guy. Oh, man. I'm glad that you can finally admit it. Sonja, don't give up yet because I'm going to give you a second chance right now by offering to send you out with the only perfect man in the entire city. With no issues.

With no issues. She would do that if she went on a date if she called me back like a normal person I wouldn't have to do. What happened? But she just called me back like a normal person. Sonya it's up to you if you'd like to see him again or not. Would you have to go get yelled at a little bit? It's your choice. I appreciate the I really I'm really not into the narcissist She's talking about me though there like and I get that but what about drew I say no to Drew also Really Sonya True if this woman can't see how perfect you are then she doesn't deserve you. Thank you. Thank you very much

You can't read sarcasm. Yeah, he's really thanking you. Oh, I don't read sarcasm. Yeah, you hear it Brooke Thank you, Brooke. Exactly. Thank you, Drew. You're my guy. Thank you. He really is perfect. Brooke and Jeffrey in the morning. I feel like we should have asked that guy in part one,

how confident are you in getting a date 1 to 10? Oh my god. Because I felt like maybe he was a 4 going into it. He would have said he'd like 30. Yeah, here's the thing. He acts so confident, but we never brought up the fact maybe he was a four going into it, he would have said he'd like 30. Yeah. So here's the thing, he acts so confident, but we never brought up the fact that on message two, he said he'd never be interested again

if she didn't call him back and yet he was still on the phone with us. I know. Yeah. Still left her more voicemails. Yeah. Still, I mean, all of what he was saying is not believable. It's like a guy who doesn't know how to play the game,

but someone told him, Right. Like, hey, if you ignore a girl or if you're just this they love ultimatum yeah didn't work and he was totally shocked that she wouldn't take him up on the opportunity the perfect man so many other options he'll be fine ever said they were perfect and turned out to be like perfect like when is George Clooney been like oh my god do you know he said this week that was so annoying to me? No, let's not go into it I don't want to go into it

But look if our listeners I kind of do if our listeners want to take advantage of the perfect man You can go check out our second date podcast and listen to me host Text in if you want to know about the George Clooney dirt, okay? Yeah, I do, I'm a text in. I'll share. We'll talk about it off air, but go check out our podcast wherever you get yours, online at Brooke and Jeffrey. Brooke and Jeffrey in the morning.

My husband has a secret son from a past partner. Hold up Sam, how do we know how we've done the DNA test? Well John, luckily it's Mother May I Have a DNA Test Week on the OK Storytime podcast, so we'll find out soon. And this wife writes, My husband received a Facebook message from a woman saying that he is the father of a five-year-old. At first, he didn't remember her, but then he realized they had a one-night stand right before we started dating.

Wait, but do we have proof he's a dad? To hear the explosive finale, listen to the OK Storytime Podcast on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I want you to ask yourself right now, how am I actually doing? Because it's a question that we rarely ask ourselves. All of May is actually Mental Health Awareness Month. And on the psychology of your 20s, we are taking a vulnerable look at why mental health is so hard to talk about. Prepare for our conversations to go deep.

I spent the majority of my teenage years, of my twenties, just feeling absolutely terrified. I had a panic attack on a conference call. Knowing that she had six months to live, I was no longer pretending that this was my best friend. So this Mental Health Awareness Month, take that extra bit of care of your wellbeing. Listen to the psychology of your 20s

on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Yo, K-Pop fans, are you ready? It's your boy, Bom Han, and I'm bringing you the K-Factor, the podcast that takes you straight into the heart of K-Pop. We're talking music, idols, exclusive interviews, and even the real behind the scenes K-Pop stories. Plus, you're the fans, you're part of the show, and you can get a chance to jump in,

share your opinions, and be part of the conversation like never before. And trust me, you never know where we might pop up next. So listen to the K-Factor starting on April 16 on iHeartRadio app, Apple Podcasts or wherever you get your podcasts. This isn't just a podcast, it's a K-pop experience. Are you in? Let's go.

Hey, I'm Jay Shetty and my latest interview is with Michelle Obama. To whom much is given, much is expected. The guilt comes from, am I doing enough? Hey, I'm Jay Shetty and my latest interview is with Michelle Obama. To whom much is given, much is expected. The guilt comes from am I doing enough? Me, Michelle Obama, to say that to a therapist. So let's unpack that. Having been the first lady of the entire country and representing the country in the world,

I couldn't afford to have that kind of disdain. Listen to On Purpose with Jay Shetty on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. It's nostalgia overload as Wilmer Valderrama and Freddy Rodriguez welcome another amigo to their podcast Dos Amigos. Wilmer's friend and former That 70's Show castmate Tofer Grace stops by the speakeasy for a two part interview to discuss his career and reminisce about old times. We were still in that place of like, what will this experience become?

And you go, you're having the best time. But it was like such a perfect golden time. Listen to Dos Amigos on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. You're listening to an iHeart Podcast.