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Jeffrey
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Brooke
Hey, you found the Second Date podcast. Thank you so much. I found it, too, Finally.
Jose
It's pretty easy, actually.
Brooke
Thanks for being here, Jose.
Jose
You're welcome.
Brooke
I love it. I love it. And, hey, just a reminder. If you want to endure or punish yourself for 45 more minutes, we've got a full show, whole hour long.
Unidentified Female Caller
I dare you to try it at
Brooke
the Brooke and Jeffrey feed. But for now, we'll get into some questionable relationship advice. Brooke and Jeffrey in the morning.
Second date update.
Jeffrey
What happens if you're on the apps and you recognize someone from your past?
Jose
Oh, swipe right, just in case. The second you match, you unmatch and act like it never happened.
Unidentified Female Caller
What type of someone?
Jeffrey
Maybe someone you had a crush on before.
Brooke
Oh, then that's good, right? And then you want that, like your
Jeffrey
friend's former stepmom or Alexis's old gym teacher.
Brooke
What?
Unidentified Female Caller
Don't remember them being hot?
Jeffrey
That's never stopped you before. But for our listener, Nathan, it was someone from a while ago, and he decided to go for it. Okay, so, Nathan, welcome to the show. Who did you recognize on the apps?
Nathan
So I recognized a girl that I had taken a class with, like, a couple of years back in college.
Brooke
Okay, that's pretty normal.
Jose
Yeah, because you, like, know her, but you don't know her.
Trish
Yeah.
Jeffrey
Well, how big is this class that we're talking about? Like, a huge, like, college course? Giant course, or, like, a small one?
Nathan
Good point. It was, like, a big lecture. So it was, like, a class of, like, 200 people, so there's no.
Brooke
Wait, did you have interactions with her in this class, or did you just stare at her from afar?
Nathan
I always, like, saw her, and I noticed her. Like, she really just stood out, but I never actually spoke to her.
Jeffrey
Okay, well, what's her name?
Nathan
Trish.
Brooke
Trish. Okay, did you tell Trish right away on the app that you knew her? Because if you'd never talked to her before, that might be.
Nathan
No, I didn't. I didn't mention it.
Jose
Okay.
Nathan
I don't think she would recognize me, and I didn't want to sound, like, creepy, so.
Jose
Yeah, well, you have to bring it up sometimes, Right?
Nathan
Well, at some point, I was planning on just, like, making it, like, oh, did you take this class?
Brooke
Or just. Yeah, be like, what, you were in that class to play dumb?
Jose
Yeah.
Nathan
Oh, yeah, you do look familiar. You know, like one of those things.
Kel Penn
Okay.
Nathan
Yeah.
Jeffrey
So if you didn't mention that you recognized her, how did you initiate conversation?
Nathan
So in her bio, on. On Hinge, she had a line that, like, really made me laugh. It said something like, hello, Sharks. I'm seeking frivolous amounts of flirting and fun, spontaneous dates in exchange for a small negotiated percentage of my heart.
Brooke
I'm a big Shark Tank fan, so I immediately thought, okay, Shark Tank.
Jose
It's his pitch to the Sharks.
Brooke
I see.
Jeffrey
Okay.
Brooke
I was waiting for, like, a fish pun at some point.
Nathan
I'm so sorry.
Jeffrey
Okay.
Brooke
Yeah, I didn't get that.
Nathan
I've watched enough of those Shark Tank presentations to know exactly what you're talking about. Okay.
Brooke
Okay. So what was your pitch?
Nathan
So my offer was endless amounts of flirting and witty banner in exchange for 5% of your heart. Offer expires at midnight.
Jose
Whoa, 5%? I'd hop on that if I was her. She has a low commitment.
Brooke
Sounds like an offer she couldn't refuse. Yeah.
Nathan
Yeah, it was a big offer and not a lot of commitment required, but there was a time limit on it.
Brooke
That's so cute.
Jeffrey
When did you get a message back?
Nathan
It was 11:57, and I think she did it on purpose.
Brooke
She made the deadline, but she was
Jeffrey
trying to purposely make you wait a little bit.
Jose
Really funny.
Brooke
Yeah. Where'd you guys go on your date?
Nathan
So we ended up going to a baseball game because we talked a lot about sports and stuff before we met up.
Brooke
This is such a great date. I love it.
Jose
Yeah, if you're into it.
Nathan
To me, it's, like, low stakes. Like a public place. There's a lot of fun. It's easy, you know? It's an easy thing.
Jeffrey
Okay.
Brooke
All right. How'd the game go?
Nathan
Well, I mean, it was. I thought it was good, but when I picked her up, she seemed, like, a little, like, off. I was like, what? I didn't know what was wrong. Like, it's just something was wrong. And she was like, oh, yeah, we just have to hurry. I want to see the whole game. I don't want to get there late.
Jose
Okay.
Unidentified Female Caller
Were you late picking her up then?
Brooke
Like, is that what caught?
Unidentified Female Caller
Because that'd be annoying. You weren't on time.
Nathan
No, I wasn't late. I mean, there was just more traffic than I thought. We could have been there on time, but it was just, you know, that's
Brooke
out of your control. Did her mood ever lighten up?
Nathan
Well, I mean, I offered to buy her food, and she didn't really want anything, and. Whoa.
Jose
That's how you know she's mad.
Nathan
At some point, she was like, when's the seventh inning stretch? And I looked at her. I'm like, in the seventh inning.
Jose
At least she knew the answer.
Jeffrey
Maybe she's not as big of a baseball pan as we thought.
Nathan
She just seemed to be, like, not having a good time. She was kind of bored. I don't think she realized that baseball is just kind of watching people stand around most of the time.
Brooke
She probably realized it.
Jeffrey
No, but, like, was the game itself itself, like, not an exciting game.
Nathan
I mean, I thought it was good, but as a first date, you'd think it was to me. I mean, yeah, I went to see the game, but I wanted to just hang out with her. I mean, that was the whole point.
Jeffrey
So it didn't start good. It didn't seem to go super well, and it didn't seem to end very good.
Brooke
Well, maybe we didn't hear about the end. Like, how did it end?
Jeffrey
How'd you leave each other?
Nathan
Well, I don't know. Like, we went back to the car again. There was traffic going home, which was not, you know, outside my control. And she just seemed bothered. I mean, we talked a little bit, but nothing, you know, too crazy. Like, the opening Shark Tank introduction that we had, and the chemistry kind of. It seemed like it kind of fizzled out a little bit, and now she's just not responding to me.
Brooke
Why do you want to call her?
Nathan
If I did something wrong, I want to take responsibility. Like, I don't know if it was me or if it was her. It was just okay. I don't know.
Brooke
All right, that seems reasonable enough. Plus, it's like, a girl that you kind of had a crush on years ago. Like, oh, yes, you don't want this to be the end of that.
Nathan
Yeah, I've been waiting this whole time, and it's like, oh, wow. It was almost, like, meant to be that I ended up matching with her, and now it's, like, just totally fizzled out. And you think maybe she recognized me during the date and was like, oh, is that weirdo from my class?
Jeffrey
One that always stared at me across the lecture hall and drew little?
Nathan
Maybe she thinks I'm, like, stalking her now because she, like, found Out. I don't know.
Brooke
Yeah, she.
Jose
But you never talked to her back then, right? And never did anything weird to her, so.
Brooke
Except for write his and her name together over and over and over again in a piece of paper, right?
Jose
If you did that, you better tell us right now.
Jeffrey
Well, we're going to find out when we come back and we call Trish and we finally reveal that her long lost crush from college is the one that took her to the baseball game.
Brooke
We're going to reveal that.
Nathan
Please don't bring that up.
Brooke
Yeah, yeah, okay. I'll blow you up.
Jeffrey
I'll let you deliver the message when we do it in your second date update right after this.
Brooke
Brooke and Jeffrey in the morning Second date update.
Jeffrey
Going to a ball game is a great idea. Idea for a first date.
Brooke
Yeah, for sure.
Jeffrey
Even if it wasn't necessarily Nathan's idea, his date was the one that was adamant that they go to one together.
Brooke
So it's even better because then you know she likes it. Yeah, right.
Jeffrey
That's why it's so odd that their interaction was so off from the minute that he picked her up. Nathan said she just seemed to be in a bad mood.
Brooke
Dude, she didn't even want the food. Yeah, he offered to buy her food and she turned him down.
Jose
That's part of the fun of a baseball game.
Jeffrey
Brooke almost wanted to slap her off on Nathan's behalf.
Brooke
Well, I mean, I'll eat your hot dog if you're not going to.
Jeffrey
Look, it didn't really improve the entire game no matter what they did. Yeah, it seemed like Trish just couldn't get out of her funk and now she's not even talking to him. So what's going on? Nathan needs to find out for his old college crush.
Brooke
Yeah, yeah, for sure. Have you. We didn't ask, like, how many times have you contacted her post date?
Nathan
I sent her a couple texts and I left her a voicemail and that was it. I haven't heard back.
Brooke
Well, I'm really hoping when we call her, she's in a better mood.
Jeffrey
Yeah, me too.
Nathan
She's like, hello.
Jeffrey
I'm just hoping that it's all sunshine and butterflies. A total misunderstanding. Let's find out. We're gonna dial her number.
Jose
Baseballs and butterflies.
Brooke
Yeah, okay.
Jeffrey
Yeah, okay. Let's just dial her number.
Kel Penn
Here we go.
Trish
Hello?
Jeffrey
Hey, is this Trish?
Trish
Who's calling?
Jeffrey
Oh, she's.
Brooke
Maybe she's just a short person.
Kel Penn
Hey.
Jeffrey
Yeah, Trish, this is a radio show. We're called Brooke and Jeffrey in the Morning.
Jose
We're really. I'm so sorry if we upset you.
Trish
I'm sorry.
Brooke
We're laughing because. Just because of a conversation we just had, Trish. That's all.
Jeffrey
We hope you're having a good day.
Jose
Yeah. Are ya?
Trish
Who is this?
Jose
Sorry.
Jeffrey
Yeah, let's just get to it.
Jose
Yeah, we're.
Jeffrey
We're a show called Brooke and Jeffrey in the Morning, and we do a segment here called the Second Date Update.
Trish
Okay.
Jeffrey
And it's something where we're trying to help out one of our listeners, a guy that seemed pretty cool when we talked to him. And you went on a date recently with him. His name's Nathan.
Brooke
Oh, my God.
Jose
Did you just.
Jeffrey
Or did you get something in your throat
Jose
that's not even an egg.
Jeffrey
Wait, that was in response to Nathan.
Trish
Well,
Brooke
again, a second one. Okay, let's. Let's slow down a little bit.
Nathan
Yeah.
Brooke
Because he seemed lovely.
Jeffrey
At least when we spoke to him.
Trish
He was fine. It was fine.
Brooke
Okay.
Geico Gecko
Just fine.
Brooke
Okay.
Trish
Okay.
Brooke
He told us about the fun interaction, the Shark Tank humor you guys had on the app when you first met. That was like a highlight, right?
Trish
Yeah, that was very clever.
Jeffrey
Okay, that's good. So the goal of this segment is to try and help Nathan figure out if there's a reason there hasn't been a second date.
Brooke
Yeah. Like, where you went from clever to like.
Jeffrey
And we're kind of invested in this because we heard the story of the baseball game and you guys hanging out. We're just curious how it was for you.
Trish
Look, I'll probably never see him again, so I. I don't mind telling you, I was. I was just a little bit frustrated.
Brooke
What were you frustrated by?
Trish
Well, I wanted to get there for the national anthem and we missed it.
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Jeffrey
Yeah.
Brooke
That was traffic, right? He said that he didn't expect traffic from your house to the stadium.
Trish
Yeah, yeah, whatever. It wasn't. It wasn't his fault. It's not that, but.
Jeffrey
So the national anthem is really. That's an important thing for you?
Brooke
I mean, everybody has a tradition at a ballpark, right? Like, when you want to get there, how you enjoy the game.
Trish
No, it had nothing to do with that. I mean, it was important for me to get there because on the dating app and all the pictures, he has his hat on, and I just wanted to see him without his hat. Okay. And so I was like, I don't want to tell him why. So I was like, okay, so we'll just get there for the national anthem. He'll take his hat Off. And then we missed it.
Unidentified Female Caller
That's so smart.
Jose
He has to take off his hat, put it over.
Jeffrey
So that was just to figure out what his hairline is.
Unidentified Female Caller
Yeah.
Trish
And so I'm like, I just want to see what it looks like without hat.
Brooke
Why is the hairline important? Wait, hold on.
Jeffrey
No, no, no.
Unidentified Female Caller
Not hairline. But people look so different with a hat. It's like when we all wear masks in Covid. You look so different with it on and off.
Trish
Like, totally.
Brooke
So you were angry that you missed the national anthem because you didn't know what his head looked like?
Trish
It's just like, don't you want to know what somebody looks like? Completely.
Brooke
You could have pulled that obnoxious girl. I'm going to steal hat move.
Unidentified Female Caller
So drunk.
Trish
It's so obnoxious. And I was like, I don't want to. I don't want to be rude. Right? So I was like, okay, how about for maybe they take their hats off for the seventh inning stretch? Right? I mean, like, don't you have to, like, stand up and, like, do stuff?
Jeffrey
Yeah, I don't. I don't think the hat is part of the.
Jose
It's not formal.
Jeffrey
You sound like a true baseball fan. The more that we talked.
Brooke
The baseball game only for the national anthem.
Trish
Yeah.
Jeffrey
So do you.
Trish
Do you.
Jeffrey
You enjoy baseball itself?
Trish
Not really.
Brooke
Oh, I'm sorry. This is, like, so dumb to me. Were you attracted to him with his hat on?
Trish
Yeah, it was very cute with a hat on, but if I'm gonna marry somebody, they can't wear a hat 24 7. Right.
Jose
Okay. You're worried. Yeah.
Jeffrey
But it's crazy that you would just give up on the idea after not seeing him with his hat off. Like, you could get together one more time and there would be an opportunity there.
Jose
Yeah. Book a nice restaurant that doesn't allow.
Jeffrey
Or take them through TSA at the airport. They force you to take your hat off.
Trish
That's the little soon, little soon.
Brooke
Did you realize that you weren't, like, very fun during the baseball game? Like he said, it felt like you were angry the whole time.
Trish
I was just pissed at myself. And then the fact that it was forever. And you know what it's like when it's like you want to ask something, but then it keeps going forever, and so you end up not asking because it just.
Jeffrey
I know exactly what that feeling is like because I've been waiting forever to tell you that Nathan is on the other line of this phone call, listening,
Brooke
wanting to talk to you.
Jeffrey
Careful. Don't Turn her on too much.
Trish
That is just embarrassing and really dumb.
Jeffrey
But I don't know if he's still there.
Nathan
Yeah, I'm just totally in shock. Like, I. I don't even know how to respond. Like, what?
Brooke
Yeah.
Nathan
This is just the strangest thing I've ever heard. Why didn't you just ask me?
Trish
I guess I didn't want to seem so superficial that I would be like, well, I would date you if you look one way without a hat and not with another way. So it just became like a thing. I started to get into my head and then it was just like I was putting all this pressure on myself and on you, and it was just like. And I thought baseball game would be more fun, and then it wasn't, and it was just taking forever. And like, when we're stuck in traffic and I don't know what to do, and it was just like, you need
Brooke
to take a deep breath. Yeah, that was a lot.
Nathan
Why have you been, like, ghosting me? Like, we had a good conversation and just. Because you didn't get to see my head. Like, honestly, we could have, like, come back to my place if we had a good time and we could have had a romantic dinner and. Oh, you could have gotten some whole head or something, you know? I don't know.
Jeffrey
Did you just say you could have gotten some whole head?
Brooke
Yeah. A vision. I like it. You're kind of at tease. That's good. Yeah. You want to see it? No, you don't get.
Jose
You want to see my bowling ball girl.
Jeffrey
I mean, if you're still curious. There is. It sounds like a window of opportunity to make that happen.
Trish
Yeah, I don't. I don't know how I feel. That whole head.
Brooke
That's what you've been asking for.
Jeffrey
That was the whole goal.
Brooke
And wait, do you care if he's bald? Is that an emphasis for you because.
Jose
Or if it's receding?
Trish
I like a guy with a head of hair. I mean, that might be superficial, but, I mean, I do prefer that.
Brooke
You can't predict how that's going to end up. Just going to let you know.
Jeffrey
But you still have a chance to actually see him in person one more time and get another shot to peek
Brooke
at his dome if he still wants to even go out with you.
Jeffrey
That's good point. Nathan, are. Are you turned off by this? Totally. Or are you still willing to give Trish a chance?
Nathan
I'm very confused. I wouldn't say I'm turned off. I'm a little bit confused why you went this particular route to try to accomplish this, I would be open to a non hat date, but I wish you would have just told me that in your shark tank requirements because it wasn't really listed.
Brooke
Oh, okay. When you made the deal, we might.
Nathan
We might have to renegotiate because I'm not sure if I'm going to fully commit.
Brooke
I see.
Nathan
I need at least 10% of your heart if you want to see me without a hat on.
Jeffrey
Cards are on the table there, Trish.
Trish
He's a hard negotiator and so we're
Jeffrey
just going to throw it out there. If you're willing to meet up with Nate one more time, we would pay for that date. Whatever happened? Oh, you're in.
Brooke
Oh, look at that.
Jeffrey
Okay, looks like a deal has been struck. In exchange for 10% of Trish's heart, Nathan will show up and show 100% of his head.
Brooke
That was an intense negotiation.
Nathan
That's awesome. I'm so looking forward to it. Trish.
Brooke
Maybe if she asks for the pants off, cease negotiations.
Discover Advertiser
Okay.
Trish
Brooke and Jeffrey in the morning.
Geico Gecko
And now for a bit of breaking news. Between your breaking news with me, the Geico gecko, here are some things you ought to know today. People who switch their car insurance to Geico save about $900 a year. Experts are calling that nice to know. Also, plants can hear when bees buzz. My ficus just heard that. And finally, animal experts have confirmed that goats have regional accents. I'm getting a hint of Irish there.
Jeffrey
It feels good to get good news. It feels good to gecko.
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Jeffrey
man, what a deal. We just struck 10% of her heart for a hundred percent of his head.
Jose
Yeah, I mean, I don't. I think he got the bad end of the deal.
Brooke
If a guy was upset that I didn't, like, take off my coat the entire date or something, I would not go back out with him.
Nathan
Oh,
Brooke
I don't know why that guy is so cool with it.
Unidentified Female Caller
He's got a good head of hair under there, that's why.
Jose
Yeah, I didn't want to tell him, but if he is, like in the middle of a receding hairline, he should just shave it. All right now. This is a good time.
Jeffrey
So he's fully bald before hit that reset button. This whole thing does make me curious, though, to think about Brooke. If you had a heart, how much would you be willing to give to your husband?
Brooke
Oh, I'll give him all of it, but all those idiots that I dated before, they got less than 1% and then I took it back back after I was done with them.
Jeffrey
Okay, same question with the head.
Brooke
What?
Jeffrey
They never even got to mention Nathan and his crush in college, so I wonder if that's going to come up during their next meetup.
Brooke
I hope not.
Jose
I totally forgot about that.
Brooke
I think that's more of a like three months in conversation.
Jeffrey
Yeah, maybe we'll find out down the road in an update.
Kel Penn
Update.
Jeffrey
We'll see. And if you're new to the show, we do do those all the time. You can hear them on our podcast, do Brooke and Jeffrey in the morning where we show full head in the thumbnail. So you are welcome. I'm U.S. transportation Secretary Sean Duffy. We all get distracted when we drive, but how we handle these distractions can be a matter of life or death. Please put your phones on silent and take a mental note to focus on driving. Paid for by nhtsa.
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Kel Penn
Hey everyone, it's Kel Penn. I'm inviting you to join the best sounding book club you've ever heard with my podcast, Hearsay The Audible and iHeart Audio. Every episode I nerd out with amazing guests and dive into the best new
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Release Date: June 15, 2026
Podcast: Brooke and Jeffrey (iHeartPodcasts)
Host(s): Brooke, Jeffrey, Jose
Segment: Second Date Update
This episode of "Second Date Update" centers around Nathan, who reached out to the show after being ghosted by his date, Trish. The twist: Nathan matched with Trish on a dating app, recognizing her from a college class years prior. Their lighthearted Shark Tank-themed banter quickly turned into a real-life negotiation over a first date at a baseball game—but things went awkwardly off-base after Trish seemed distant the entire evening. The hosts help Nathan get answers directly from Trish, leading to a hilarious, revealing, and surprisingly tender exchange.
[11:11–18:59]
Nathan's Pitch:
Trish’s Real Reason:
The Big Reveal:
Nathan’s Counter-Offer:
Perfect for fans of lighthearted dating stories, this episode delivers amusement, a surprising twist, and a hopeful outcome for two people who just want to see (and be seen) a little bit more clearly.