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A
Welcome to the Second Date podcast. And we are counting down the top second dates of 2025.
B
Oh, yeah.
A
Number seven.
C
That's right. And I think there's fewer and fewer rom com movies that are being made now because people just don't meet in real life anymore.
A
Oh, that's kind of point like a meet cute. Swiping isn't cute. She only makes so many movies.
D
Yeah, right.
C
Just not even believable to see it on the screen. And you can't have a realistic romantic scene with a drunk dude at 2am sliding into a hot girl's DM.
A
That's just.
C
They just don't make those film.
D
Ryan Reynolds.
A
Yeah.
C
That's why today's call was so rare. One of our listeners turned a super awkward moment into an actual meet cute that seemed almost too perfect. You're gonna hear it in your second date update, number seven of the year right now. Second date update. There's a lot of fun things in life that begin with the word street.
A
Street.
C
Street magic. Street tacos.
A
Okay, Jeff, now I'm getting it.
D
Street meat.
C
Yeah. Street walkers.
D
Whoa, wait a minute.
C
Right? I feel like I do that. I. I walk down a lot of streets.
A
Yeah.
C
Well, today we're gonna talk to a street dater.
A
Jeff's like, why are people giving me money?
C
Must 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.
A
Oh. Oh, okay.
C
That's what I meant. His name is Drew.
D
Drew. He's a street walker.
A
Yeah, technically.
C
Drew, you a street walker too?
B
I think I walk the streets about as much as everybody else around here.
C
Yeah. Okay. He's a humble street walker.
A
Jeff's neighborhood.
D
Okay, we should probably stop using that phrase.
C
Apparently you met somebody while just walking out and about. How did that happen?
B
Yeah, I was at a bookstore locally, and I like to read. So I'm leaving the bookstore and I have my face buried in the book as I'm walking, and I knock into this woman.
A
Oh, that's kind of a cute. You know, it sounds like out of a movie, a bookstore is involved.
D
A little clumsy.
B
Her bag fell, I helped her, and then I gave her a little flirt.
D
Wait, wait, did everything happen in slow motion?
A
I think he's joking about that part.
D
I know.
C
I imagine the bag falling. He grabbed it, he picked it up, he ran.
D
No, that's a mugging.
B
No.
C
Gotcha. You just knocked her bag out of her hand by accident.
B
Yeah, by accident.
A
Oh, you really did knock the bag over.
B
Yeah, we bumped into each other. It was a pretty big bump, and, you know, everything just kind of flew all over the place. I helped her. Some 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.
A
That's a really funny joke. He's just joking. He beats him with their. Oh, I get the joke.
E
Okay, stop laughing.
A
I kind of liked it.
B
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, trying to build, like, a little rapport.
D
This sounds cute, bro. Like, you're turning, like, kind of a bad situation or a weird situation into, like, something positive.
A
At what point were you able to get her name?
B
I did ask her name, but we walked a little more.
C
We would love to know the name.
D
She's like, don't tell anybody what my real name is.
B
Oh, her name is Sonia. Her name is Sonia.
C
So you and Sonia are just accidentally walking in the same direction and kind of flirting with each other? It sounds like.
B
Yeah. We eventually get to a park, and we start walking through the park.
C
What, when you got into the park? Is that when you took her bag?
B
Then that's when I knocked her over and ran.
C
Okay.
A
Yes.
D
Gotcha.
C
More escape routes in here.
D
Climbs up a tree.
A
Did you really have to go to the same way, or were you just pretending so you could be with her plants? Like, you both just had free time to keep walking.
D
Oh, yeah, that's true, too.
B
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.
C
Okay, okay.
B
Eventually, we came across a sketch artist, and he flagged us down. He was like, hey, you guys want to get a picture? But we were a couple.
A
Wait, did you get a character drawing?
B
Well, I was down, but she wasn't. I think she was a little freaked out.
C
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.
B
No, I didn't set anything up.
C
Well, you just have a friend who's, like, in the park with a thing, and he's like, I'm just going to take her this way.
B
I didn't say it was a friend. It was just a sketch artist. He wasn't a friend.
A
That would be the most. 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 real quickly in the park.
D
I really want to sit down with her for 45 minutes, this stranger.
C
I'm just saying, we've heard people that have, like, orchestrated all sorts of weird things in order to make people.
D
That's true, but this doesn't sound like that.
A
Jeff, how long is this walk going on?
B
We were about 20 minutes into the walk by the time she said no to the picture. That's like 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 number to go out, and she gave me her number. And the date just hasn't materialized since then.
A
Okay, have you guys talked via text or phone call?
B
No, nothing. I've tried to call a few times. I've left a few messages.
A
I automatically think that she gave you a fake number.
C
Oh, if there's no response.
B
Yeah, it was her voice on the voicemail. It's her.
C
Okay.
E
Okay.
B
Yeah, yeah.
A
She gave you the number, so I'm assuming she's single. Did you specifically ask her?
B
I didn't ask her if she was dating anyone. No. But I left a few meme voicemails, and she hasn't answered.
A
How many?
B
Yeah, three, maybe four. Oh, geez.
C
I don't even.
D
Like. I don't think I called a girlfriend that many times in one year.
A
I think my mom calls me on my voice.
C
You felt the connection, so.
D
But everyone's different. Some people love being on telephone.
C
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 going to try and help you call this girl. What's her name? Sonia. Sonia.
B
Yeah.
C
Sonia. Okay, we'll reach. We'll reach out to Sonier, 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 bump in turned into your classic Hallmark streetwalker love story.
A
Okay, again with the term. Yeah, that's the wrong use.
D
We're trying to make it sound better than it.
C
Than it is.
A
That's not a Hallmark movie. I'll tell you that one.
C
It fits in this scenario because 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.
A
30, I believe. I mean, those five minutes are gonna be precious when it's only a short amount of time you have together.
C
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.
D
It's always the park scene. Yeah, that ruins it. Something in the park.
A
I mean, he left. Okay, here's the thing. You left four voicemails.
D
Yeah.
A
We have not asked what was in the voicemails.
B
I just told her. Hey, it's me, Drew. By the park. You meet a lot of guys by the park. I mean, it's true.
D
Not even from the park. Like the guy that's adjacent to the park.
C
Maybe she thinks you live in the park after that one.
D
That would be awful.
A
That seems innocent.
C
There's a chance, though, that if she's not responding to anything, maybe she wasn't even real.
B
She was real.
C
Are you sure?
B
That would make me crazy.
D
Exactly.
A
It could just mean you have a bad drug habit.
D
Yeah, from the park.
C
Were you microdosing that day? Because Hallmark hasn't done that yet. I'm microdosing Christmas.
A
I don't think microdosing would lead to this.
C
Well, if you over microdose.
A
Yeah.
D
No wonder everything was in slow motion.
A
Jeff, is one of those kids still in the DARE program?
D
I signed that contract.
C
Let's have all the street walkers unite, because we're gonna call and we're gonna get an answer from this woman out what actually happened. If she's real, and hopefully if there's an explanation, a lot of kids listening.
A
Who use that term wrong.
C
For the next microdosing Christmas, none of these should be. This is the education you get here. I'm gonna dial the number right now. Here we go.
E
Hello?
A
It sounds real, Jeff.
C
It sounds like a person. Is this Sonia?
E
Yes, this is Sonia. Who's this?
A
Hi, Sonia.
C
Hey, Sonia. We're a radio show called Brooke and Jeffrey in the Morning.
D
Good morning.
E
Hi. Hi. Hey, what's this about?
C
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 other day outside of a bookstore.
A
Did you just laugh?
E
Sorry, I just. I can't believe that you're calling about him.
A
Well, you remember Drew, the guy who knocked you over on accident outside the bookstore.
E
Yeah, yeah. I remember Drew.
C
Okay, well, that's great. Cuz 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.
E
Yeah, I mean, that did happen and I was actually open to seeing him again. Except for the messages. The messages are the problem.
C
Well, we asked him about the messages and he basically. According to him, he said it was basically, hey, this is Drew from the park.
E
Remember?
C
I'm Drew.
E
Is that what he said?
A
Yeah, well, yeah.
E
Summary, Interesting.
B
Something like that.
A
Oh, now I'm so curious.
E
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.
A
Wait, you wrote down the message because it was that funny to you?
E
Yes.
B
Wow.
C
Would it be okay if we know what the message said?
E
Oh, absolutely. I'd love to read it to you because we.
C
We haven't. We haven't heard anything about it. We just know there was a bunch of messages.
A
She is delighted to share. She is so friendly and.
E
Okay, 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. But I don't play that game.
A
What?
B
Huh?
E
If I don't hear back by 3pm tomorrow.
A
What are you doing?
E
I'm no longer interested.
D
Give her an ultimatum.
A
Obviously, he just lied because he called us. Yeah, he didn't even mean.
E
Then he goes on to explain why I should call him.
A
Why you should call him. Okay, some positives. That's good.
E
He says, I'm very smart. I'm great in bed.
C
Okay.
E
And I make a lot of money.
C
Alexis. Sold.
A
Those are three good things.
D
But also, is that something everybody says?
A
I mean, it's one of those things when you say it, it's hard to believe.
D
Yeah, it's like he needed to discover those things.
E
So then he says, believe it or not, I'm a complete catch.
A
Oh.
E
I'm one of the only men in the city that has no issues.
A
That's a bold.
D
Well, name every man in the city, bro.
E
Yeah, exactly.
D
I'm the best one I have yet.
A
To find a person that doesn't have issues.
D
Is this like a child trying to do reverse psychology on you?
A
Is that finally the end of the message?
E
No, he goes on and he says, 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.
D
Heck is he projected that got a little unhinged.
A
So started unhinged. Then he got a little better. Now we're back.
D
Now we're unhinged again.
C
Okay, so clearly there was a lot happening in that message, and it could help to get insight into what he meant by it, because.
A
Pretty embarrassed right now, maybe, because.
C
Sonia, he is on the other line listening. We've got Drew waiting to talk to you.
B
Hey. Hey. Hey, Sonia. Hey. Hey. Is there something that I said that wasn't true? Was there something that I said on that voicemail that wasn't. That was a lie.
E
What?
B
Yeah. You can't say that, dude.
D
Hold on. You're coming in kind of hot. Yeah, a little bit, I think.
A
Defensive, no apology.
E
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.
B
You agree that I'm right? 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.
A
When did she say that?
B
I make a lot of money, I'm smart, and I'm good in bed to talk.
E
Being direct, it's becoming more and more doubtful talking about.
B
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 going to happen if you don't make the right move.
D
I mean, I got to find out how good you are in bed, bro. So I'll be quiet.
B
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.
A
Why do you lead with that?
B
Stupid person is going to give that up.
C
I think he's making some good points.
A
I think so.
B
He's a chance here, you know? You know, in this city, there are no men, and I'm a total catch. You know this.
C
I kind of agree with him on that.
A
I don't know.
E
I. 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?
A
Yeah.
E
I'm not getting the best vibes from you, to be honest. Like, it just feels like I know.
B
That you haven't bragged about being good in bed.
D
Yeah, you're not supposed to.
A
What are you talking about?
C
Listen to any hip hop music. They're all about that.
A
Are we going to ignore the rest of the text?
C
Yeah.
A
About her being on meds.
E
What was that?
B
I saw her bag. Her bag? Everything fell everywhere. I saw her meds.
A
You read. Everyone's on medication.
D
My man, he's concerned about her health.
B
You guys are on medication. You sound crazy. I sound smart and well read.
C
Sonia.
A
Wow. 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.
C
But, like, only somebody who's addicted to meds would be humiliated. He's perfect.
A
With no narcissistic tendencies at all.
B
No, I don't. Clearly.
C
Good. Sonia, was he right? Are you on the verge of tears right now?
E
I'm just really heartbroken that it can't be with this perfect guy.
C
You know what?
B
I'm glad that you can finally admit it.
C
Well, Sonia, 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?
E
None.
B
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 it. Wouldn't happen. But here, she just called me back like a normal person.
C
Sonia, it's up to you if you'd like to see him again or not.
D
Would you have to go get yelled.
B
At a little bit?
C
It's your choice.
E
I appreciate the offer, but I really. I'm really not into the narcissism.
A
That's shocking.
C
She's talking about me, though, there, like. And I get that, but what about Drew?
A
That was really shocking.
E
I say no to Drew also.
C
Wow.
D
Jeff was kidding me. Wow.
C
Really, Sonia?
D
He wasn't asking you out. Tell her, Drew.
C
I'm with you.
A
Jeff was. I don't think he was very sarcastic at all.
C
Drew, if this woman can't see how perfect you are, then she doesn't deserve you.
D
Wow.
B
Thank you. Thank you very much.
A
Drew can't read sarcasm.
D
Yeah, he's really thanking you, Jeff.
C
Oh, wow.
B
You don't read sarcasm.
C
Yeah, you hear it, Brooke. Exactly. Thank you, Drew. You're my dad.
A
Thank you.
D
He really Is perfect.
C
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? One to ten.
A
Oh, my God.
C
Because I felt like maybe he was a four going into it. He would have said he, like, 30.
A
Yeah. Here's the thing. He acts so confident, but we never brought up the fact that on message, too, he said he'd never be interested again if she didn't call him back. And yet he was still on the phone.
C
Yeah.
A
Still left her more voicemails.
D
Yeah, still.
A
I mean, all of what he was saying is it's not believable.
D
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. And then you tried it.
A
They love ultimatums.
C
Yeah.
A
Yeah.
C
Didn't work. And he was totally shocked that she wouldn't take him up on the opportunity.
A
To be with him.
C
I'm sure he is the perfect man.
A
So many other options.
D
Dude, when is anyone.
A
He'll be fine.
D
Ever said they were perfect and turned out to be, like, perfect? Like, when has George Clooney been like.
A
Guys, oh, my God, do you know what he said this week that was so annoying to me?
C
No, let's not go into it.
D
Let's not go.
C
I don't want to go into it. Want to go into it. But look, if our listeners.
A
I kind of do.
C
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 them.
A
Oh, really? Okay, listen, text in if you want to know about the George Clooney dirt. Okay, I do. I'll share.
C
We'll talk about it off air. But go check out our podcast wherever you get yours. Online at Brooke and Jeffrey.
Theme:
This episode, "Street Walker Love Story," from Brooke and Jeffrey's Second Date Update series, features the #7 most entertaining second date call of 2025. The premise involves Drew, a listener who experienced what he thought was a rom-com-worthy "meet-cute" with a woman named Sonia—an accidental collision outside a bookstore led to a 30-minute stroll through a park, playful banter, and an exchange of numbers. Yet, after the encounter, Sonia never returned Drew's calls, prompting the show to step in, reveal what really happened, and try to broker a second date.
On unrealistic meet-cutes:
“You can’t have a realistic romantic scene with a drunk dude at 2AM sliding into a hot girl's DMs.” – Host (00:21)
On the initial encounter:
“It's usually old ladies I knock over, and then I just move on.” – Drew (02:30)
On the ultimatum voicemail:
“If I don't hear back by 3PM tomorrow, I'm no longer interested.” – Sonia reading Drew’s message (10:37)
Drew’s claim to perfection:
“Believe it or not, I'm a complete catch. I'm one of the only men in the city that has no issues.” – Drew (as quoted by Sonia, 11:16)
Sonia’s pointed response:
“I feel like the people who are actually good in bed don't go around talking about how good they are in bed.” – Sonia (13:49)
On seeing her medication:
“I saw her bag. Her bag? Everything fell everywhere. I saw her meds.” – Drew (14:16).
“My man, he's concerned about her health.” – Host (14:25, sarcastic)
On the failed second date offer:
“I appreciate the offer, but I really—I’m really not into the narcissism.” – Sonia (15:30)
"Street Walker Love Story" is a hilarious cautionary tale about mistaking initial chemistry for destiny and how overconfidence and poor communication can kill a potential relationship before it starts. Drew’s inability to read the situation—exaggerated bravado, unsolicited self-praise, and misplaced ultimatums—served as a vivid demonstration of "what not to do." Sonia’s reactions and the hosts' banter made it highly entertaining, if not uplifting for the would-be Romeo.
For anyone seeking real-world dating advice: skip the ultimatums, tone down the self-praise, and remember self-awareness is key!