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Brooke
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Brooke
Visit L E G E N D Z.com hey everyone, it's Kelpen.
Kelpen
I'm inviting you to join the best sounding book club you've ever heard with my podcast, Hearsay, The Audible and iHeart Audiobook Club. Every episode I nerd out with amazing guests and dive into the best new audiobooks available on Audible. It's the book club for your ears. Listen to Earsay, the Audible and I Heart Book Audiobook Club on the iHeartRadio app or wherever you get your podcasts.
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Jeffrey
All right before we get to your back to back classics, there is something that we really need to address in this room. It's Brooke and Jeffrey in the morning. Ashton, have you recovered from the Jersey Mike's fiasco?
Ashton
Oh, we heard all about it out there.
Jeffrey
I mean, they put oil on his sandwich and he did not want oil on his sandwich.
Ashton
No, I did not.
Brooke
He asked for no oil.
Ashton
I requested it specifically.
Jeffrey
Yeah. Did you eat it and the whole thing?
Ashton
Yeah, they must have.
Jeffrey
Okay, so do you want to talk to the manager now? After you've eaten the sandwich?
Ashton
You know what I think I'm entitled to?
I bet you do.
Jeffrey
I bet you do.
Ashton
Okay.
Jeffrey
Okay. I'm glad that we got that out of the air. It was uncomfortable in this room for a minute.
Ashton
Yeah, it smells a whole lot like onions in here, I'll tell you that for sure.
Jeffrey
All right, hope you're having a great day. We do have your back to back classics right now. But first comments.
Ashton
Yeah, well, Cushy Galore said cool name. It's 2026. Why can't we watch full podcast episodes
Jeffrey
with a video yet?
Ashton
Is your station poor?
Jeffrey
Well, yes.
Jeff
Yes.
Jeffrey
Yeah and yes.
Brooke
Yes and yes.
Jeffrey
Yes and yes.
Ashton
I mean, sorry, we had a lot of comments on the chair that I sit in and it is proof that we're poor.
Jeffrey
That chair, front half of it is just missing all of its fabric and the foam is fully exposed.
Sammy
Yeah, yeah.
Brooke
I mean we've got so many things in here that we talk about. Jeff's microphone. Ye my headphones people were freaking out about needed to be replaced.
Jeffrey
And Ashton happy to move back in with his mom and dad. Cause he can't afford rent. We're doing great at the radio station. Everything's fine.
Ashton
Seems like you catch a lot of strays.
Jeffrey
Nothing's burning down, I promise. All right, you're back to back classics right now.
Brooke
After many failed romantic encounters and a couple of outright scams.
Randall
Oh gosh.
Brooke
One of the most lovable and eternally optimistic listeners that we've ever had on the show is back again.
Lowe's Advertiser
Again.
Brooke
We know he's gotten himself into some weird situations before, but this time he thinks it's different.
Jeff
Okay.
Brooke
Cuz he finally executed the perfect date night.
Yay.
Well, at least for a few minutes. Until his lady friend received a text that changed everything. Once you hear it, you're you'll agree that this man definitely deserves a do over. We'll try to make it happen for him in your second date update.
Show Announcer
Next, Brooke and Jeffrey in the morning. Second date update.
Brooke
I'm gonna do a quick recap about one of my most favorite listeners we've had on the show in the past year. And I'm gonna do it because he's back today.
Jeffrey
Yeah. That's awesome. Then his name.
Brooke
Hold on. Don't get excited. He's his favorite. Not our favorite.
Well, that's fair. His name is Randall. And last time we spoke to Randall, he had met not one, but two international women on the Internet. One was from Vietnam, the other from the Philippines, and he had even flown out to meet the first one in Vietnam.
Jeffrey
Yeah. They turned up. Not at the airport.
Ryan Reynolds
Yeah.
Brooke
She never showed up.
Ryan Reynolds
So they.
Brooke
We didn't call that woman. We ended up calling a different lady. Someone that he'd met locally because his friend had suggested, why not try dating in your own area code?
Ashton
Great friends.
Jeffrey
Why try not getting scammed? Yeah.
Brooke
And that woman ended up just wanting
Ashton
to be his and help him avoid scammers. Yeah.
Brooke
The thing that we learned about Randall is that he believes in the power of true love.
Jeffrey
That's true.
Lowe's Advertiser
Yep.
Brooke
And he's just had a bad run of luck lately and needs our help. So I'm curious to hear about his latest romantic endeavor. Randall, my guy, welcome back to the show. How you been, man?
Randall
Thank you guys so much for having me back on. I really appreciate you.
Jeffrey
Please tell me, in the time between the last time we talked and now you have wired no one money?
Randall
No.
Ashton
Sweet.
Brooke
Okay, sweet doesn't count as wiring.
We're learning, we're growing. That's great. But what brings you back today?
Randall
Well, I had a few friends listen to the show the last time and they agreed with you guys that I should try dating more locally first.
Ashton
Okay.
Randall
And surprisingly, I started doing that, but it hasn't gone that great, to be honest, guys.
Jeffrey
Okay. Are you on the apps? Is that how you're finding women locally to date?
Randall
Well, I met a girl named Sammy, and we met in person.
Brooke
Okay, here we go. See, you are doing a good thing where you're looking at the past mistakes and learning and adjusting and adapting. That's all very good.
Randall
Now, you guys know me. I'm a romantic, right? So I surprised her with a very special date.
Ashton
I'm scared.
Randall
I took her on a picnic to an outdoor movie.
Jeffrey
Cute.
Brooke
Ok, that's great.
Ashton
You can't really talk, can you? During the movie?
Jeffrey
It doesn't matter.
Ashton
Okay.
Jeffrey
And it's outdoors. People are only halfway through.
Brooke
How did it go?
Randall
Well, I think the first 30 to 45 seconds was good.
Brooke
What seconds?
Well, that's a good Start.
Randall
Yeah, just my luck. Right after we sit down, we get situated, she goes, oh, my gosh, I think my friend's here. Then she looks at me and says, do you mind if I text them where we are?
Brooke
So of course. You were like, yeah, tell your friends to come say hi, right?
Jeffrey
Yeah.
Brooke
It's a good sign that she's already wanting to introduce you to her friends.
True.
Randall
That's what I thought it sounded like. Man, I'm really in there this time.
Jeff
Yeah.
Randall
So a couple minutes later, a very good looking guy shows up. And the only face on the little blanket that we have is on the other side of me. So now I'm in the middle of them. The movie starts, and then as we're about to watch it, she whispers in my ear, this is my ex.
Jeffrey
What?
Ashton
Wait.
Brooke
Oh my God.
Jeffrey
Wait, how did she text him? Her ex boyfriend?
Randall
Yeah. So I had to watch the movie with her ex.
Jeffrey
Oh, my God.
Ashton
What?
Brooke
You stayed?
Ashton
Bro, I have so many questions.
Jeffrey
Well, they're on his blanket. What is he going to do?
Brooke
I'd be like, is my blanket.
Ashton
I'm leaving. Why the ex there alone?
Brooke
Anyway, let's hold on. Maybe it gets better from here.
Jeffrey
Oh, goodness.
Ashton
Does it?
Randall
It does not.
Jeff
Okay, okay.
Brooke
What happened?
Ashton
What?
Randall
They're laughing at parts of the movie together that I'm not laughing at because they have some history of inside jokes that I don't even understand. Oh, yeah, here's the bad part. At one point, she reached around my back and rubbed his shoulder.
Jeffrey
Oh, my God.
Brooke
Maybe there was like a spider or something. She flicked it off.
This is bad.
Jeffrey
Why are you watch wanting to call this woman. She sounds terrible.
Ashton
Somehow the woman in the Philippines sounds better.
Brooke
It doesn't sound like this girl's giving you the attention that you deserve and that you want for a day.
Jeffrey
Like respect.
Brooke
Yeah. Why would you want to reach out to her?
Randall
I really liked her. I thought she was nice. I thought we had a good chemistry. I mean, after the movie I was like, so that's your ex, huh? But she said, we'll always just be friends.
Jeffrey
So I mean, that did probably give you hope that she was still interested in you though, right? Her saying that?
Randall
Well, that's what it sounded like to me. She was trying to make sure I understood they're just friends.
Jeffrey
Okay, well, that is good.
Brooke
At least. She's like explaining like, I know this looks weird, but I want to reassure you, like, that could be nice.
Jeffrey
So nothing sense.
Randall
No. And I really would love another chance with Sammy. I like her.
Jeffrey
I think she's the one should be asking for another chance with you or her ex.
Brooke
Maybe.
Yeah, it would be probably nice to get an opportunity to a date without an ex boyfriend sitting directly next to you. That would probably help.
Randall
I prefer to sit in the non ex.
Brooke
That's a fair thing.
It's crazy. You've been on so many dates recently and none of them have just been one on one with a woman.
Yes, we gotta hook that up for you. I mean, at least get you some answers because clearly you're looking for help here.
Randall
I am. I really want to be the person that likes me. I like them. So if there's something I need to do to fix that or improve it, I want to hear it.
Jeffrey
Okay. Okay. That's a good attitude.
Brooke
You don't need to fix anything about yourself. You're perfect the way you are. Randall.
Jeffrey
Maybe he does well. We all could use growth, Jeff. Perfect.
Brooke
We're going to try to help Sammy, see how amazing you really are when we call her and try and get you your second date update. That's coming up right after Brooke reaches around Jose to scratch my shoulder. Oh, wow. Okay, never mind. We'll just do it after this.
Show Announcer
Brooke and Jeffrey in the morning second date update.
Brooke
If you're just joining us, we've got Randall on the phone, a friend of the show who's been unlucky in love lately. Yeah, he's back because his latest date was with a woman named Sammy, which also turned out to be pretty unlucky because Sammy's ex was at the outdoor movie theater where they both were at and then invited.
Jeffrey
Invited to join them.
Brooke
Right, that was the really weird part.
Randall
Oh my God.
Discover Advertiser
Randall.
Brooke
Like the cream in their Oreo sandwich
because he ended up sitting between them for the entire film.
Ashton
Which he stayed for.
Brooke
Yeah, I have no idea how.
It's not exactly your ideal first meetup and Sammy's not responding now. Is she back together with that ex boyfriend? We don't know. We might find out here in a second. Randall just wants to understand if he's doing something wrong on these dates.
Randall
Just kind of want to find out. What am I doing wrong? I just think I have a big heart and a lot to offer.
Jeffrey
Not only that, but you're putting in the work like you are trying to do different things, change the way you're dating, Even learn from this experience.
Randall
Yes, absolutely.
Jeffrey
God, I'm frustrated for you.
Brooke
This is like the good guys finish last kind of motto. It's like, you know, there's a guy out there who really does want love and really is trying. It's just. It's like helpless.
Well, not today. The good guy's gonna finish first or at least get some explanation for why he can't win.
Yeah, or we'll hang up on her.
Randall
You guys are like my best friend.
Brooke
Try not to think that's a sad thing.
Jeffrey
But hey, just move on. Let's call it.
Brooke
You know what, best buddy? We're in this together. I'm gonn to dial her number right now.
Randall
Here we go. Okay.
Tara
Hello?
Brooke
Hey, is this Sammy?
Sammy
Yes.
Brooke
Hey, Sammy. We're calling from a radio show. We're called Brooke and Jeffrey in the Morning.
Jeffrey
Hi, Sammy. The whole show's here.
Brooke
I was hoping nobody would talk and Jeff would look crazy, like we are from a morning show.
Thank you for speaking.
Sammy
I really do radio shows.
Jeffrey
Sorry, you don't do radio shows.
Sammy
I don't like to talk on radio shows.
Jeffrey
We've never gotten that.
Brooke
Oh, yeah, that is.
Jeffrey
That is a stance.
Brooke
Look, I totally understand that. And listen, we won't air this unless we have your permission to do it. Yeah, but this is a segment. It's called a Second Date Update.
Sammy
I've heard about that before.
Brooke
Yeah, they're pretty popular.
Jeffrey
Yeah, thanks. Maybe you saw it on TikTok or something.
Sammy
Yeah, yeah, yeah, that's us.
Randall
Interesting.
Sammy
Definitely interesting.
T-Mobile Advertiser
It is.
Brooke
And you should take it as a compliment because it means somebody out there is trying to get ahold of you.
Sammy
I want to know. I'll play along.
Brooke
Okay, well, I'll just tell you. It's a guy that you went out with recently named Randall.
Tara
Oh, my God.
Jeffrey
Okay, is that. I'm going to take that as a fun excited laugh. Like, yay, Randall.
Sammy
It was like.
Tara
It was the weirdest date I've had.
Brooke
Really weird.
Okay, could you tell us how you felt? It was weird because we've heard a little bit from Randall Sandals side. We'd like to get, like, your perspective on the night.
Jeffrey
Yeah, we know. Outdoor movie, picnic. Super fun.
Sammy
Yeah, it was actually, like, a really sweet idea. I was like, wow, this guy really put a lot into the effort. But my ex was there and he texted me. I'm over near the lemonade stand.
Jeffrey
Wait, how did he know you were there?
Sammy
He saw me. I guess from across the way.
Brooke
Okay, so he's the one who initiated the conversation with you.
Jeffrey
Dude, how rude. You were obviously on a date. Like you're showing up with a guy.
Sammy
Well, you know, I don't really think my ex knew I was on a date. And Randall is such a sweetheart. He's like, why don't you just invite him over?
Brooke
But when we spoke to Randall, he told us that he was under the impression it was just a friend of yours.
Jeffrey
Yeah, you didn't specify.
Sammy
Oh, well, he was a friend, but he was my ex friend.
Jeffrey
Okay, so you didn't tell him?
Sammy
I wanted to tell him, but it all happened so fast, and the movie just started and he sat down right next to us.
Jeffrey
Oh, my God.
Brooke
All right.
Jeffrey
Oh, that makes me feel better, though, because it sounds like you weren't trying for this interaction to happen.
Sammy
Absolutely not. I thought he would leave, but he didn't.
Ashton
Too many nice people that can't say no is what's happening.
Brooke
Okay, so clearly that wasn't a malicious move on your part, Sammy. But I think what Randall's confused about is if you liked him so much and you're trying to be so sweet to him, why aren't you calling him back for another date?
Sammy
Well, it was kind of weird because he told me that it was a movie, but he wouldn't tell me the name of it.
Tara
Okay.
Sammy
And he said it was a historical piece, but guess what movie it was.
Jeff
What?
Brooke
Why?
Sammy
Fast and Furious. That's not historical.
Brooke
Wait, was that a joke?
Jeffrey
Are you saying that you're not calling him back because he misrepresented what film was being shown?
Sammy
No, I just. I thought it was, like, weird. Like, my ex and I were just laughing.
Jeffrey
Wait, you had told your ex, like, oh, my God, this guy thinks it's a historical piece and we're joking about him?
Sammy
No, he told us both at the same time, and he was backing it
Tara
up with all these facts.
Jeffrey
Randall told you both that it was historical?
Sammy
Okay, my ex is looking at me like, who is this guy?
Jeffrey
Oh, he's not your type?
Brooke
Okay, well, Sammy, thank you for telling us your side of the story.
Randall
Wait, hold on, hold on. I need to. Let me speak my piece, please.
Brooke
Yeah.
Tara
Who is that?
Brooke
Yeah, that's Randall.
Randall
It's me. It's Randall. Listen, it's actually based on a true story. You guys do know that, right?
Jeff
No.
Brooke
It was a street race.
Is it?
Randall
Yes. The movies are actually based on street crimes that were happening in LA in the 90s. 90s. Do you guys think Vin Diesel was the very first person to rob a semi truck going that fast on the freeway?
Sammy
So, sorry, but I did not know that.
Randall
Yes, if you read the forums that I'm a part of the movie ones on Facebook, we all know it's true. We talk about it all the time.
Jeffrey
Forums on Facebook?
Brooke
Hey, they have Tokyo Drift, Right?
Randall
That's true. Yes. It happened in Tokyo as well. That's why they made a movie about it. Street CR were rampant everywhere.
Jeffrey
Oh, goodness.
Ashton
I think.
Brooke
I think what you need to do, Randall, is actually talk to Sammy here.
Jeffrey
That's exactly not about.
Brooke
Yeah, like don't. You don't have to convince us. You have to talk to Sam.
Randall
Yeah, I know that.
Jeff
I'm a good guy.
Brooke
Yeah.
Randall
I didn't get jealous when the guy came over your ex. I found it weird. But I totally understand that you're a nice person too. And I'm just going to be honest and straightforward to Sammy when we're sitting there watching that movie. You may not have believed me, but your ex sure did. You could be with a man like that that believes the truth. Then I think you should be with me as well. Me a chance.
Brooke
Oh, wow.
Jeffrey
Wait, the pitch is if you can date your ex, you can date me.
Brooke
Don't look into it too much.
Two fellow truth finders. Hey.
Sammy
Yeah, no, I'm sorry to break it to you, Randall, but he did not buy it either. We talked to each other over text.
Jeffrey
Okay?
Ashton
Oh, they're texting again.
Randall
Well, now, you know what? He probably just trying to make you feel better because you didn't believe it.
Sammy
Oh.
Brooke
It's like when you talk to those people that believe the earth is flat and you're like, you know what? You're right, it is.
Jeffrey
I mean, he's a good guy. He has some funny quirks. We'll say that. This could be a cute story you guys tell later or something that you make fun of him for in a relationship.
Randall
You know, I'm going to tell you what, man. Nobody else that I know is making fun of Fast and the Furious.
Show Announcer
Okay?
Brooke
Yeah, well, maybe the benefit is you'll actually learn some interesting things by giving him another chance.
His best friends.
Randall
I could send you guys nice documents. So many.
Brooke
Honestly, we need to stop talking about the true crimes that have happened on the streets of LA and focus on true love. Because that's what you're here to do. Sammy, we're here to. To attempt to connect you and Randall one more time. Movies aside.
Jeffrey
And you deserve to give him another chance. I mean, your ex hung out the entire time like this guy. Like he deserves one more shot.
Brooke
Yeah, a one on one shot. And we would pay for it.
Sammy
I would ask. Absolutely. Love to go out with Randall.
Jeff
Yes.
Brooke
Oh my God.
Ashton
Good.
Sammy
As a friend.
Jeffrey
Not again, Sammy.
Brooke
You got the big buildup.
Jeffrey
But maybe she means friend in quotes like she did about her ex?
Sammy
No.
Ryan Reynolds
Maybe.
Brooke
Good to be a friend of hers.
Sammy
All right, now there's just not any potential. It's more of a friend friend thing.
Brooke
Friend friend.
Ashton
Doubling down on the friend.
Brooke
Yeah, Randall, that's okay.
Randall
Because you know what? You have to be friends before you can be romantic. So I still have hope.
Jeffrey
Okay, well, you were romantic in hers. Well, actually, you were one of those one in a million moments.
Brooke
Vin Diesel and Michelle Rodriguez were friends in the movie before they had gone.
Jeffrey
Based on a true story.
Brooke
Real events.
Tara
That's not gonna happen.
Sammy
But Randall, I would love to hang out with you as a buddy.
Ally Bank Advertiser
Buddy.
Ashton
Oh God.
Brooke
We're downgrading even more as an acquaintance.
Just don't call him a pals.
Randall
Randall.
Brooke
Well, Randall, man, I'm sorry. So we've done now two second dates with you and you've gotten two friends out of it.
Randall
I'm not feeling down about this, guys. Like you said, I just earned another friend.
Brooke
That's a good attitude.
Ashton
And you have us, your four best friends.
Show Announcer
My BFFs, Brooke and Jeffrey in the morning.
Brooke
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Brooke
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Brooke
Man, we should be so lucky to be like Randall, who's just collecting friends left and right in his life. Not on purpose, but he's doing it. Collecting friends.
Jeffrey
I like that dude.
Brooke
You know, this guy is so good at self Improvement. That one day, and maybe when he's 100, he's gonna be the perfect man.
Ashton
Oh, he will be.
Brooke
Think about it.
Jeffrey
Hurt my soul when she called him buddy.
Brooke
Yeah, I know. Now you see how we feel, Brooke.
But how, friend zone, how cool would it be if Randall does finally find love with us here on the show and we're there to witness it?
Wow. Or better yet, we're calling someone who's like, I went on a date with this guy Randall. He won't call me that.
Jeffrey
That would be even better, dude.
Brooke
Although it is like Brooke always says, almost everyone deserves love.
Jeffrey
I don't say that. Everyone does.
Brooke
She keeps a list of people who don't. So if you're not on that list, feel free to email us for help with your dating list life. And remember, you can listen to all of our second dates on our podcast at Brooke and Jeffrey, wherever you listen to them, and on our YouTube page. Check it out.
Show Announcer
Brooke and Jeffrey in the morning.
Brooke
They say trends are cyclical. All the old stuff that went out of style years ago is suddenly back and cool again. Baggy jeans, mid calf compression socks, blazers with shoulder pack hat.
Discover Advertiser
Wait.
Brooke
Damn it, Brooke, did you get a
hold of my notes again? Nobody likes shoulder pads.
Lowe's Advertiser
Nobody.
Brooke
I don't care how hard you try,
they're never going to be cool again.
Jeffrey
They are not.
Brooke
But I will tell you one thing that's becoming hot in the dating world all of a sudden. Yeah, and it's math.
Jeffrey
No, even you said that with a question.
Brooke
I'm surprised. But that's what one of our listeners says, and it helped. It helped her to meet the perfect guy. You're gonna hear how in your second date update. Date next.
Show Announcer
Brooke and Jeffrey in the morning. Second date update.
Brooke
I don't know why, but in the last year or so on the show, it seems like people are trying to hack the dating system more.
Jeffrey
Oh, yeah.
Brooke
They're not just trying to meet people and let things happen the way that they happen. They're. They're actually strategizing beforehand.
Jeffrey
Well, because the other way wasn't working, Jeff. I don't know if you realize that.
Brooke
Yeah, well, yeah, but I'm just surprised that the lengths people go to. They're setting up more unique dates.
Ashton
Dates.
Brooke
They're trying new online techniques, even laying down first date traps to catch the perfect person.
Jeffrey
Traps?
Brooke
Like, oh, did I say this was a modeling job interview? Oops, sorry. I meant first date. Stupid autocorrect.
I thought you meant physical trap, like a net drop.
Jeffrey
Yeah, yeah, I was picturing the same thing. I was totally going with one of those bear traps, the giant claws. Like, from the comments, your caveman runs out.
Brooke
Got her.
Guys, no wrong way to find your soulmate. And one of our listeners emailed us saying she tested out a new dating theory that she found online called Optimal Stopping Math, which immediately sounds sexy. Oh, yeah. Optimal stopping math.
Jeffrey
What is that?
Brooke
Down for a little OSM girl?
I mean, that sounds way better.
Nothing hotter than dividing the variable angles of an isolation. Oscill's dry.
Jeffrey
Can we get to her before you get too turned on?
Brooke
Oh, you don't want to solve for why with me, bro?
Jeffrey
I don't. Okay? I don't. I'm not into Pythagorean's theorem or whatever.
Brooke
Oh, wow. Some dirty talk from Brooke over there. Let's hear how it actually works, though. And talk to Tara. She's the one who emailed. Tara, I know this is a dating segment, but I would absolutely love to hear more about optimal math.
Jeff
How.
Brooke
How does that work?
Tara
Okay, I know it sounds boring, but hear me out.
Brooke
What. What are you talking about?
Tara
This is for people who basically are tired of playing games and, like, texting forever, okay? And it just basically cuts right to finding the right person for you.
Brooke
How?
Jeffrey
Okay, are you making your own algorithm right now?
Tara
I mean, the theory is you go on 25 first dates as fast as
Brooke
you can with the same person, different people.
Jeffrey
It's a first date.
Brooke
Okay?
Jeffrey
This is exactly how Jose did in math. Yeah, word problem.
Brooke
I know.
Jeffrey
We already lost him.
Brooke
Okay, 25 different. Different first dates as quickly as you can.
Jeffrey
That's hard.
Tara
Yeah. So you basically have 25 candidates to choose between, and you end up picking the one that's best for you to continue with.
Jeffrey
1 out of 25.
Ashton
Yeah, 25. Good. To start with
Jeffrey
a big wide net.
Brooke
Well, I think that's probably the point. Like, you date a bunch of people as quickly as you can, and then you get a big selection to choose from.
Jeffrey
Right? It sounds just like what the apps are already doing. Doing to me.
Brooke
It sounds like your college days. Right?
Jeffrey
I wasn't looking for the one. I was looking for the many.
Tara
But it's. It is different from the app, though, because the thing is, you need to meet all 25 guys really quickly, like, pretty much within a week.
Jeff
Whoa.
Brooke
Wow. So how we really like. Well, I guess any girl.
Jeffrey
How are you doing? Do you work?
Sammy
Yeah, so I do work, but here's
Tara
how I do it.
Brooke
They're just coming to our office.
Jeffrey
Okay, wait, listen, listen. Why?
Tara
What the Purpose of meeting them all so quickly is that basically if you don't do that, then the one you like is probably going to move on. Because we know in these online dating situations, it's fast, it's quick.
Jeffrey
Okay, okay.
Tara
You can miss out on somebody. Great.
Jeffrey
So how did you manage to go out with 25 people in one week?
Tara
Okay, so this is what we did. Me and my girlfriend, we decided we're going to do this together. So we knocked out 20 first dates in one day. How?
Brooke
Oh, my God.
Yeah, that sounds like you'd have to plan like, you have like a spreadsheet for that.
Jeffrey
Yeah, that's a lot of.
Tara
So what we did was we found a location that had two cafes across the street from one another.
Brooke
Okay.
Tara
So my girlfriend, she had my Tinder and she was swiping for me. She knows my type. She was setting up basically 15 to 20 minute long coffee dates with these guys back to back to back.
Jeffrey
So you were just bouncing between cafes and you did two different cafes so that the guys never overlapped into the same place.
Tara
Right.
Brooke
That's better than like sitting in one cafe and letting them roll through one after the other.
That's like speed dating at that point.
Jeffrey
Dude, did you get caught? I mean, there's got to be one guy who lingered later or, you know, early.
Tara
No, it was. It worked out great. Like, I actually met a ton of guys. Some of them did cancel. Some of them were kind of like duds.
Brooke
Okay.
Ashton
Okay.
Tara
There was one that I liked the most.
Brooke
Okay, who is that?
Tara
His name was lol.
Ashton
Lol.
Jeffrey
Lol. Like lol, Like a Lowell in the conversation or.
Brooke
L O W E, L L. Lowell.
Tara
Yeah.
Jeffrey
Oh, yeah, you got it, Jose.
Brooke
Instead of an S. Lowell in your life.
No, not. Not under the age of 70.
I don't think I knew. Was also very old.
Okay, what made you. What made you drawn to him out of 20 different guys?
Tara
So basically what was sweet about him was he arrived with a cookie, which I thought was really cute because in my profile I say that I really love chocolate.
Jeffrey
Oh, that's cute.
Brooke
He had bribes. That's a good idea.
Jeffrey
Must have been buzzing on so much caffeine. It just dawned on me.
Brooke
Do you drink a latte every single time?
Ashton
Yeah. You can't go to a coffee shop
Jeffrey
and not buy something, right?
Tara
I. I bought things other than the coffee. You know, I had, you know, treats and.
Jeffrey
Okay, lemonades and tea.
Brooke
Limping across the street by date number
Jeffrey
19 for cutting you off, he shows up with a little gift for you. I Mean, obviously, that makes him stand out from the crowd.
Tara
Exactly. And I think going back, I think he was date number 17.
Brooke
Oh, wow.
Tara
So I was really glad that I could honestly, like, still focus by that point, because, honest, the day was super exhausting.
Randall
Zachary.
Brooke
I know one date sounds exhausting to me, let alone 17 in a row. Back to back to back to back.
Tara
Terrible interviews.
Jeffrey
I mean, were you able to hold a conversation?
Sammy
Oh, yeah.
Tara
We had a really great, like, 15 minute hangout. We've been texting afterwards and I tried to set something else up, but then in the last week, I don't know, he kind of cooled off or whatever.
Jeffrey
Wait, when we get him on the phone, you don't want us to mention that he was the best of 20, do you? Because, I mean, some guys.
Tara
No, no, no.
Jeffrey
Honestly though, some guys may be flattered by that.
Brooke
Yeah, guys are competitive. We want to know that we' the best out of a big group.
There you go. Yeah.
Ashton
Yeah.
Brooke
Tell me after I was the best. Not in the middle of it.
Ashton
I feel good knowing.
Yeah.
Tara
I really just don't want him to know because I feel like he might find it really cringy.
Brooke
I mean, it's way different. So.
Randall
Yeah.
Brooke
Okay, well, we'll keep it a secret then, when we call Lowell for you and try and get you your.
We have the right number, right? Because you have numbers.
Jeffrey
No, it just dawned on me. What if his name is wrong?
Show Announcer
What if we're calling him the wrong name?
Jeffrey
So many things. That's what I would do, but he's
Tara
the only one I've been texting.
Jeffrey
Okay, that's good to know.
Brooke
This is really interesting. An optimal stopping math experiment where Tara met 20 guys in one day. Back to back to back to back. We're gonna call the one that she actually liked when we do your second date update right after this.
Show Announcer
Brooke and Jeffrey in the morning. Second date update.
Brooke
Going on 20 dates with 20 dudes all in one day.
Sammy
Wow.
Brooke
Wow. That's a big statement.
Jeffrey
It sounds like a Kate Hudson movie, doesn't it?
Brooke
Yeah, sounds like an episode of Bachelorette, but it's actually a dating theory called optimal stopping math. And it's what one of our listeners, Tara, set up for herself the other night. With the help of her friend, she bounced between two coffee shops back and forth, meeting 20 different guys over the course of a few hours to pick the one that she liked the best. And who was that? It was a guy named LOL L O W E L L. Spelling it for himself. I know because I will have A whole fit about it. But he came with a chocolate cookie for her. So Brook is going to steal this guy if he doesn't agree to a date?
Jeffrey
He's actually going to take his cookies.
Brooke
Yeah, okay, rob him, whatever.
Where's the rest of them?
Jeffrey
I do not need another man, Jeffrey. I just need more cookies in my life.
Brooke
More chocolate. But we're trying to hook her up with Lol one more time because they've been texting but hasn't been able to lock down a date. How you feeling?
Tara
Before we call him tonight, I'm interested to see what he's gonna say. I mean, curious, I guess.
Jeffrey
Okay, if. If this doesn't work out, are you gonna call us back tomorrow for number two?
Brooke
Dude, second best option.
Tara
No, he's the only one I clicked with.
Brooke
Honestly, all or nothing here.
Jeffrey
Not good when you have 20 guys.
Discover Advertiser
Wow.
Jeffrey
It's just one in 20.
Brooke
Well, let's call this guy and we'll see if he picks up. Good luck to me. Here we go.
Good luck to you.
Yeah. To get through Just to say his name.
T-Mobile Advertiser
Here we go.
Jeff
Hello?
Brooke
Hey, is this Lol?
Jeff
Yeah, speaking.
Brooke
Good job, Jeff. I did it. Okay, so you are Lol and we are a radio show.
Jeffrey
Hey, Lol.
Tara
Hey.
Brooke
We're called Brooke and Jeffrey in the morning.
What's up?
Jeff
Yeah, I know you guys. What's up.
Brooke
Oh, you do?
Jeffrey
Yeah.
Brooke
Well, welcome onto our show here. We're doing a second date update today.
Randall
Oh.
Jeff
Oh, okay.
Brooke
Yeah, that's a good thing. You know that somebody's trying to get a hold of you and you're not calling them back.
Jeff
Yeah, I guess I'm just thinking about it.
Randall
All right.
Jeffrey
This would be so crazy to get like you're just trying to process everything that makes sense.
Brooke
It's a weird call.
Don't hurt yourself thinking. We'll just tell you who it is. Her name is Tara.
Jeff
Oh, yeah. Okay.
Jeffrey
Yeah, you guys had a. Well, that's okay.
Brooke
I feel like the smile left his voice when I said that.
Excited doesn't sound sad.
Jeffrey
I mean, he only had like a 15, 20 minute date. Like, it's not like you guys had a big, long connection.
Jeff
Well, I mean, there was some talking, I guess you could say beforehand, but yeah, you're right. More or less. What does she want to know?
Brooke
Well, basically, she wants to know why she hasn't seen you again.
Jeffrey
Yeah.
Jeff
Oh, well, I mean, I don't know what to say to her.
Jeffrey
Oh, really?
Randall
To be honest,
Brooke
you guys have good chemistry. Like, easy to talk to.
Jeff
No, I mean, she. She Was definitely cool. It's just. I guess you could tell her I know about everything. That would be a way to put it.
Jeffrey
Wait, wait, wait.
Brooke
What do you mean?
Tara
Yeah.
Jeffrey
No, no, no. Let him explain. What do you mean you know about everything? What do you know about.
Jeff
I mean, I know. I know about the speed dating or the. The whatever.
Jeffrey
How'd you find out?
Brooke
Oh, no.
Jeff
Terrorist friends told me.
Brooke
What?
Why would they do that?
Jeffrey
How do you know Tara's friends?
Jeff
I mean, she texted me. I mean, it's. It's weird. Like, apparently she's been texting me kind of the whole time.
Jeffrey
Wait, who. Who's she?
Jeff
Tara's friend was texting me in advance of us meeting up for this coffee date thing.
Tara
Why?
Ashton
She said her friend had.
Jeff
She set up the date. That's the point. Like, okay, it's like a half catfish thing. Like, I met the real Tara in person, but the person who I was was texting and emailing back and forth with somebody totally different.
Jeffrey
So. Wait, but how did you know it wasn't the real Tara that you were texting with?
Jeff
Well, because Tara's friend told me after the date.
Brooke
Oh, that's not a good.
She just came out and was like, hey, by the way, I was the one that reached out to you, not Tara.
Ashton
You have to be two different phone numbers.
Jeff
No, it was stranger than that. It was more like, hey, guess what? Tara liked you the most. Which was confusing because I didn't know who was texting me at first. And then we got into it. I found out that there was 20 guys, 25 people, speed dating thing.
Brooke
Oh, my God. She told you the whole thing?
Jeffrey
So what are you saying? You like Tara's friend, or you're freaked out about the speed dating sitch?
Jeff
I mean, the speed dating thing, whatever. There's weirder things that happen in life.
Brooke
And you, you were the best guy out of all 20 guys, so you should feel good about it. If anything, lead with that now that he knows.
Jeff
I mean, sure, I get that, but, I mean, that's not really how I think of it. It's more just the deceitful nature of it.
Jeffrey
Yeah, but you wouldn't have showed up if she said, hey, I'm going to try to line up 25 dates. You want to be one to 25?
Jeff
Probably not.
Brooke
No, she got you there.
Jeff
I mean, yeah, sure. I don't know anybody who would say yes to that.
Brooke
Okay, good point.
Jeffrey
That's what dating is. I mean, sure, she would have gone on 25 dates in a month, and you would have been okay with that, but just because she did it in an afternoon, it's like the timeline.
Jeff
Okay, no, no, no.
Randall
That's not what I mean.
Jeff
It's more. Okay, look, to put it in simplest terms, I like the.
Jeffrey
Oh, okay.
Ashton
Okay.
Jeffrey
That's the real stuff right there.
Jeff
I mean, Tara was fine. Tara's a good person. Whatever. Like, nothing against Tara. It's just she's not the one I thought I was talking to and.
Brooke
But you don't even know.
Randall
What.
Brooke
We don't even know what Tara's friend looks like. Right?
Jeff
I mean, no, but I'd still take somebody I haven't met in person who's at least admitting they are who they are.
Brooke
Some type of guy that likes women for their personalities. What?
What the heck?
Jeffrey
Jeffrey's like, loser.
Brooke
What is going on with you?
Lord.
Jeffrey
Really nice. Lol. But I don't think that Tara's gonna like that.
Brooke
Yeah, because if you listen, then you know that Tara's on the other line right now hearing this whole thing.
The real terror.
Jeff
Oh, yeah, right.
Brooke
I don't know if she's gonna be laughing, though, Terry.
Tara
There.
Ashton
Yikes.
Tara
Yeah, I'm here. And I'm just so confused because we had such a great connection when we met in person.
Brooke
Yeah. What about your. Your friend, though, going behind your back and revealing the whole plan to him?
The heck?
Tara
That's messed up. I'm definitely gonna talk to her about that. But, like, she's not interested in you like that. Like you were.
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Tara
What did she say then?
Jeff
Just that she'd like to see me for real. That's all.
Brooke
Oh, my gosh.
So this is cut and tear out of it.
Jeffrey
Yeah.
Tara
I just don't believe it.
Ashton
You don't?
Tara
I felt like we really connected. I'm just shocked.
Jeff
I mean, you're a very nice person. Don't get me wrong. It's just the heart wants what it wants. Something like that.
Brooke
Oh, my God. I guess.
Discover Advertiser
Mumble.
Ashton
Mumble. Whatever.
Jeffrey
I gotta say, I'm gonna paraphrase here.
Brooke
Yeah, I guess it's just the highs and the lulls of the dating world.
Jeffrey
You like his name now, don't you?
Kelpen
Yeah.
Jeffrey
That was a low point in your career.
Brooke
That really was.
Yeah.
Jeff
So now that we've reached, I'm gonna use that, though. I'm definitely gonna use that.
Brooke
Feel free to use it, terrorist friend, because we're supposed to offer to send you and Tara out on another date.
Jeffrey
I mean, you can at least give Tara one more try. You only had 15 to 20 minutes with her. You haven't even met the friend in person.
Brooke
But if Tara goes out with him, that's gonna make her friend upset.
Jeff
Look, the bottom line is, at the end of the day, I had a stronger connection with the roommate who I was talking to for what, like a week and a half? Two weeks? Tara. I was like. It was 15 minutes. It was basically hello, goodbye. Goodbye. I mean, it's just that simple. I'd rather date her.
Jeffrey
Oh, I hope that's okay, Tara. I mean, your girlfriend was an amazing wing woman. Like, that's a lot of work.
Ashton
She honestly should get a reward for that.
Brooke
So the wing woman ended up taking over the whole plane, though, so.
Jeffrey
Well, now we're wing women in her. Like, now it's like, back and forth. You know, you wing the wing and
Brooke
there's too many wings.
Discover Advertiser
Yeah.
Brooke
There's literally no one in the cockpit at this point.
So I guess we need to get a answer from you.
Tara
Lol.
Brooke
Yes or no on dating Tara one more time. And we would pay for it if you met up with her. With her again.
Jeff
I just feel like it would be disingenuous. I'm gonna say no.
Jeffrey
Oh, wow. But you'll see him at your apartment this weekend, it sounds like.
Brooke
Oh, God.
Jeffrey
Not with you.
Kelpen
No.
Jeffrey
You okay?
Tara
Yeah, I'm okay. I'm just upset.
Ashton
Yeah.
Brooke
Tara, we're sorry. I know you probably feel really, really bad about how this ended, but at least that joke that I said earlier was really, really funny.
Yeah.
Randall
Remember it?
Brooke
That'll keep you laughing for like a month.
Jeffrey
Wow.
Brooke
The highs and the LS of your life.
Jeff
Yeah.
Jeffrey
You need to repeat it.
Brooke
No, this is a low moment.
Ashton
Yeah.
Brooke
Okay, we're ending it on.
Tara
I'm hanging up now.
Jeffrey
Yeah, okay. I would too, if I wasn't. Jeffrey.
Show Announcer
Brooke and Jeffrey in the morning.
Brooke
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Yeah, no, I don't need.
Ashton
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Brooke
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Brooke
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Whoa, I don't trust my carrier that much.
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Brooke
mobile.com Man, Tara was really put in a tough position there, finding out simultaneously that the one guy she actually liked out of 20 was not only interested in another person, but that other person happens to be her friend who went behind her back to reveal the big plan to him.
Jeffrey
Awkward conversation because it sounds like the girls live together too.
Brooke
Yeah, I heard the word roommate.
Jeffrey
Yeah, I did too.
Brooke
I believe that's called double jeopardy. And it's worth twice as many points.
Jeffrey
Oh, are we still going on the math nerdy angle on all this?
Brooke
I don't really know, okay?
I just know it's doubly awkward for that friend situation.
Jeffrey
I know, but it's one of those things where it sucks in the moment. But you know, 10 years down the line when the roommate's married to Lol.
Ashton
Funny story.
Jeffrey
Yeah, that's true.
Brooke
Yeah, no pressure.
Commercial Announcer
Lol.
Brooke
You better marry her. And if you ever want help with your dating life, we can always try to do it. Email the show, we'll call that person who's not calling you back and go check out all of our second dates. Wherever you get your podcasts at Brooke
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Visit l e g e n d
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Host: iHeartPodcasts
Date: July 11, 2026
Episode Theme:
This episode features back-to-back "Second Date Update" classics, centering on two dramatically different stories: the return of eternally optimistic Randall and the wild results of a mathematical approach to dating known as "Optimal Stopping." Both segments blend humor with heartbreak and highlight the unpredictable nature of modern dating.
Brooke and Jeffrey revisit two wildly entertaining Second Date Updates. The first features Randall, a show regular known for his romantic struggles and undying optimism, as he attempts to secure a second chance with a new local woman after experiencing comical and harsh rejection. The second "classic" follows Tara, who experiments with a viral dating strategy to maximize her chances of finding the right partner, only for the plan to backfire spectacularly. Both stories explore the highs and lows (and Lowells) of dating misadventures, driven by quirky personalities, awkward moments, and much laughter from the co-hosts.
| Time | Segment | |------------|--------------------------------------------------------------------| | 02:32 | Main show banter, introduction to “back to back classics” | | 04:17 | Randall’s introduction and recap | | 05:03 | Full recap of Randall’s earlier Second Date attempts | | 06:37 | Randall describes his ill-fated movie picnic with Sammy | | 08:12 | Ex-boyfriend arrives—awkwardness ensues | | 12:41 | Calling Sammy for the Second Date Update | | 15:43 | Sammy reveals movie confusion ("Fast & Furious" anecdote) | | 18:31 | Randall’s impassioned, quirky plea and “friend zone” outcome | | 23:39 | Setup for “Optimal Stopping” theory segment | | 25:36 | Tara outlines her “25 date” plan with her friend | | 27:48 | Tara highlights how she managed scheduling, picks Lowell | | 29:50 | Tara discusses brief spark with Lowell, but confusion follows | | 34:01 | Lowell reveals he was texting Tara’s friend, not Tara | | 38:09 | Lowell declares preference for friend/roommate | | 39:26 | Lowell definitively declines a second date with Tara | | 38:12 & others | Hosts punctuate with wordplay/puns: "The highs and Lowells..." |
Quick Reference:
This episode is a perfect comedic case study in why there's no magic formula for finding love, and why sometimes being the “best” doesn’t get you the date—but might just earn you a new friend or a great story.