Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Red Flaggy Much?

Episode Date: November 24, 2025

One of our listeners said he made a restaurant faux pas RIGHT AWAY on his date before he even put down the menu. We’ll talk to him and see if it derailed his chances in your Second Date Update!See omnystudio.com/listener for privacy information.

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Start your love story on Bumble. Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc and send me the link. Thanks. Hey, just finished drawing up that quick one page business plan for you. Here's the link. But there was no link. There was no business plan. I hadn't programmed Kyle to be able to do that yet. I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people. Check out the second season of my podcast, Shell Game, on the IHeart Radio app or wherever you get your podcasts. On this week's episode of Next Chapter, I, T.D. Jake, sit down with Denzel Washington, a two-time Academy Award-winning actor and cultural icon.

I don't take any credit for it. I just didn't put me first. I just put God first and he's carried me. Listen to the next chapter podcast on the I Heart Radio app, Apple Podcast, or wherever you get your podcast. New episodes drop weekly. On the podcast Health Stuff, we are tackling all the health questions that keep you up at night. I'm Dr. Priyanko Wally, a double board certified physician.

And I'm Hurricane de Bolo, a comedian and someone who once Googled, Do I have scurvy at 3 a.m? And on our show, we're talking about health in a different way, like our episode where we look at diabetes. In the United States, I mean, 50% of Americans are pre-diabetic. How preventable is type 2? Extremely.

Listen to Health Stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas, and destructive companies in the history of business. First episode, How Southwest Airlines Use Cheap Seats and Free Whiskey to fight its way in the airline is. The most Texas story ever. Listen to business history on the I-Heart radio app, Apple Podcasts, or wherever

you get your podcasts. Welcome to your second day podcast. It's Brooke and Jeffrey in the morning, and I know someone who has a lot of opinions about restaurants in this room. I'm looking at him. Oh, is it me? It's you. It's sure if it was like he's getting taken on day time. No, no, no.

I mean, would someone screwing up at a restaurant be a huge red flag for you? What do you mean by that? Hold on. Well, like, screwing. ring up like what do you mean the order I can't tell you exactly because it's coming up in the second okay it's gonna happen while he's still holding the menu at the beginning okay well you should know how to go on a date at a restaurant so obviously this would be a red flag okay Jose's not dating you but you know what I don't think that's what he's asking for anyway you're gonna hear what's going on in this second date

but we love to start with your comments because you mean so much to us that's true that's true we're thankful for you we are and Mersian comments a lot but I like this one they said I might be weird but I like spoilers or teasers, so I read the comments before I listen. Oh, I actually know someone like, wait, you do that. Alexis, don't you watch movies or like, she loves the story. I know, and I skip to the end of the books first, and I read what happens at the end before I go.

I get too much anxiety. I was like, somebody in my life does this too. What is wrong with you? I need to know what happens so that I can read in peace or watch in peace. So you relate to Marijian? Yeah. Yeah. Anyways. Thanks to leave in the comment and for adding to Lexus. I love it. Your second date starts right now.

Second date update. The results are in. It's Brooke and Jeffrey in the morning. Because recent studies have shown about 50% of couples now meet online compared to just 22% only five years ago. That's crazy. That's a huge job. Yeah. It's like the pandemic like super. Yeah. It made it really normal, really quick. Yeah. So now going forward, Brooke, if you want to spice up the relationship with your husband, you're going to have to make him a dating profile. Oh. Okay.

At least you can depict his, you know. I think I could make him a really good one. I mean, to be honest. Well, I think jokes on you. He already has one. Wait, what? Apparently, you guys are, you're looking for a third right now, according to him. And we're not going to go into that because I want to talk right now.

I'm excited for that day. To Jordie, the listener who wrote into our show, because apparently he met a girl out in real life, bucking all of the latest trends. Dude, you're in the minority now. IRL. Jordy, good work. Welcome to the show.

Hey, guys. Hey, so where'd you meet this woman? So I met Harper at this German bar, actually. You know, I was playing bocce ball. Do you guys know what that is? Bocci ball? I don't forget. I've heard of it.

We have botchie ball on my rooftop, on my apartment complex. It's like you toss big, these like big colorful balls onto like a field, and then you try to toss other balls towards the ball. One goes farther and quicker. It's an Italian game playing at a German bar, but whatever. Yeah, whatever. Yeah, okay. So you said her name was Harper?

Yeah, yeah. She was actually a waitress there. Oh. Oh. I assume that she was going to be like playing in the stall next to you or something like that. Right. No, no, no, no. No.

She was super cute. And, I mean, she was super helpful, too, because I actually had to have this, like, long talk with her to tell her to cut off one of my drunk friends. Oh. Yeah. Cut off your friend, lame. You had to do it like nicely. Like, don't tell them, I told you.

I'm sure that's happened to you and you just don't. Yeah, totally. If you have good friends. If anything, it probably makes you look kind of good dirt because you seem like a responsible guy. Oh, yeah. Exactly. It's like watching Jerry Springer. It's like you look better than those people.

Oh. Can I ask real quick, was there an indication that she was interested in you because cute waitresses get hit on all the time? And they smile and they do their jobs and everyone thinks they're getting hit. I know. Brooke tries to get them to be the third in her relationship. shit, and then it's so annoyed. Harper, you're so smiling. I mean, Harper is a hot name.

But again, sorry, that is a conversation for another day. Jory, tell us how did you work Harper? That's not the right way. How did you get Harper to agree to a date? There it is. Well, I just simply asked her on the way out. I was like, look, are you single? And she said, who's asking?

And I said, I am. Good response. I like that. I'm 40. Yeah, and I just said, I love to take you out some time. And she actually gave me her number. Oh. Hey.

Dude, if we dial us and it's our loser line. Oh. We are on the loser line. That's awesome. Is that your only meetup or did you guys actually have a date? No, no, we had a date. Oh, good. Okay.

So it is her number. Because we all thought, oh, she probably just gave you your number to get ready. Right. So what did you do? We went out for drinks, little food. You know, she looked amazing. I mean, when she was like out of her. waiter outfit.

You didn't need to mention the second part. She knows. I mean, I did have one embarrassing moment on the date. We tried to order some Kish Lorraine

and I said Quicky Loran. I didn't take French in high school. Like, excuse me. Yeah. Well, you're also clashing with

Sabachi ball and the German well French. Don't want to be elitist by being able to say Kish. Cuisher. That's a tough word. What was her reaction?

She totally laughed it off. It was It was a little embarrassing, but after that, like, I think you kind of lighten the mood a little bit. And from there, like, the day was great. Especially if you can be self-deprecating about it. Yeah. You know what I mean? Like, it could almost even turn into, like, your inside joke together.

Yeah. Oh, let me go over the next thing. I speak German. And then you just ruin it. Yeah, yeah, yeah. So we actually, like, kissed at the end of the day. So that was nice. And she was the one who texted me that night saying that she got home safe and let she

couldn't wait to see me. So. What? Like, it seems super clear, right? Are you sure you didn't read that wrong, too? There's no way to read that wrong. No, no, it was in English, I think. Okay, so you've had a solid first date.

You kissed her at the end of it. She's the one saying, I can't wait to hang out again. And how long has it been? It's been, like, 10 days or so. Well, something must have happened in her life. Like, I already have a feeling this is not your fault. Oh, I can see that. like where, I don't know, maybe work got crazy or there's a family emergency or something.

Well, she rekindled something and was just like, oh, who knows? But what's happened in those 10 days? That's a long time. Have you asked her? Like, what have you done? Yeah, I mean, there was one time where I thought one date was going to work, but then she asked about a different date. So I don't know. Okay.

A hot bouchy ball player came into her work. Watch out. It's a story. Might be. Okay. Well, we can reach out to Harper for you and see if she agrees to going out with you one more time. If not, then you. You might have a backup option because Brooke and her husband, you know.

Hey. In the meantime, Jeffrey is not online. Oh, that's right. Yeah, we only like the online one. Yeah, you need to be able to keep some distance. Yeah. Sorry. But you know what?

We'll work on Harper first and try and get you your second date update right after this. Second date update. We're in the middle of a second date update with our listener, Jordy. And Jordy likes cute waitresses at German Batchie Ball bars. he likes to mispronounce Kish Lorraine just to seem vulnerable and flawed. How did he say it?

Kiki somehow? Yeah, something. You said Quicky? What did you say, Jordy? I said Quicky Loran. I like that quick Loran. And he really likes to receive texts saying,

I can't wait to see you again. Because that's exactly what his date Harper said to him after they went out. So why is she not jumping at the chance to hang out again? Yeah, she's the one that said she wanted to. Jorda, you think there's another guy who mispronounces French words even worse than you do? Maybe that's her thing.

Yeah, maybe. Yeah. Yeah, he tried to order me a quaburnette, Savangone. Oh, yeah. That's hot, yeah. And a soup, dude, I don't even know how you have mispronounced to Jor. Yeah, how do you... You can't mispronounce it, Brooke.

I mean, look, Harper's a really cute waitress. She probably has a lot of guys asking her out. Oh, my God. God, I bet she's saying no 50 times a day. Like every other table. It's so annoying. But that's why you're so special is that she said yes to you and you guys had a great date. And she went out and she said she liked it.

Yeah, but like, look, guys, if that's it, if that's the thing where she has another guy, like, just convince her that I'm a good guy. Oh. Hopefully she thinks that already. You know what? In the five minutes we've spent with you, totally will vouch for you. Thank you. You're welcome.

You're like a good guy. I mean, honestly, not even kidding. Yeah. A lot of good guys. assist how good they are. Okay, maybe that is a little red flag. So we're just going to trust you on that, and we're going to call Harper. Let's see if she answers, okay?

I don't know you. I mean, you seem nice from a little bit what we've spoken. You just stay where you're at, though, buddy. We don't know you that well. Yeah, let's get her on the phone. Here we go. Hello? Hey, is this Harper?

Yeah, who's calling? a radio show calling called Brooke and Jeffrey in the morning. Hi, good morning. Hi, Harper. That half of the room isn't very excited to talk to you, obviously, but I don't think she's excited to talk to us.

This half of the room is. She's very confused. She just don't want to come in too hot, Jeff. What are you calling for? See? Yeah, we're working. Yeah, this is something we do called the second date update,

and one of our listeners named Jordy asked us to reach out to you. Ooh. ringing in the bells? I said, ooh. What do you want me to say? You remember Jordy? Okay.

We're just trying to help him out because according to Jordy, he says he's been putting in a lot of effort trying to figure out a good time that would work for you to meet up just because he felt like you guys bonded, connected. Is it just something where the schedules aren't aligning? No, there was just like a lot of effort that's kind of a problem. What? Too much effort. What do you mean? Yeah, can you elaborate? I mean, like on the surface, when I met.

him like I was working and then we went and hung out and like he was a good guy and well that's what I was looking for yeah like he's what you were looking for I mean yeah like I thought so okay so what changed so we hung out and it it wasn't until after that I realized something was off what like I had every intention to go out again okay okay what's the problem is this something about him? Yeah, he gave me three options to hang out all in a row, like Friday, Saturday, Sunday. Like, why is he so available? What?

Wait, what do you, hold on? Did he want a three-day date, or he was just like, pick a day and we can do that one night? No, he was like, these are all the days that I'm available. And I have this belief, me and my friends do, that there's a guy between the age 24 and 32-ish, if they have that much time to hang out, it really means that he's a loser. Oh, wow. Wait, are a loser?

Yikes. Wow. You're calling him a loser because he gave you multiple options of times where he wants to hang out because he likes you? Yeah, because like they're all in a row. And it's like, okay, he should be grinding away, planning for his future. Like, if he's not working or like working on a promotion or getting somewhere,

Maybe he may be, though. Maybe he is. Like, in my mind, you're a waitress, so he's probably just trying to give you options because it's probably hard to align schedules. Like, he probably figures you work on the weekends. I mean, that sounds like an excuse he'd use, I guess. It sounds like he's doing it for you because nowadays, we hear from a lot of women who tell us, guys don't put in enough effort.

They want the easy thing. They don't really care. But Jordy sounds like the total opposite, like he's willing to do whatever, just to see you. And then maybe he'll make plans the other days that you say you can't. Yeah, but he didn't say that. He was like, I'm wide open. And I'm like, well, what else are you doing with your life just pursuing me? Okay.

What? Okay, sadly, this makes sense. But doesn't mean we agree with it. I don't know that it does make sense to me. He's not a loser. Like, you liked him. You liked everything about him. You said that he tracked all your boxes, basically.

Yeah, I mean, he did. He actually had decent hygiene, which... Okay. But he's too available for you. Maybe that's why his hygiene is so good. He has got time for it. He showers daily. I mean, you don't want to date someone who wants to hang out every single day.

Sometimes, like, they need to have a life. Well, sure. Oh, God. Yeah. And especially in the beginning, getting to know who they are, and it just seems like he's just wide open to do whatever. And I'm like, but we're trying to build who we are as people. What would you want his response to be?

When you say, hey, I can't wait to see you again, what should he have written back to you? He shouldn't have. He should have just let me hang for a bit. That was a red flag. Okay. Well, that feels kind of like a game. I don't, I don't want to tell you this because it's not that he's like super available to talk to you at any time. That's not what this is.

He was so busy. It's like we had to call him so many times. Yeah. Just in the middle of his extremely hectic day, he's taken a little bit of time to jump on the phone right now to talk to. you because Jordy's there. Hey, Harper. Oh. So you've been on the phone?

Just a little bit. Yeah. Just a little bit? It's like barely. I heard you call me a loser who has too much time on his hands. Well, yeah, they asked me to be honest and I was honest. We actually didn't say that. They asked me what was that.

I mean, that's what Jordy wanted. He wanted to know. He did want honesty. So you think I'm a loser because I want to go out a second time? Like, that part doesn't make any sense. No, no, no, it's just a little red flaggy to be able to hang out three nights in a row. And, like, my perfect guy would never do that. He shouldn't have all the time in the world for me, you know?

I'm sorry, my perfect guy shouldn't have all the time in the world for me. To be totally clear, I didn't want to hang out with you three nights and a row. I gave you three options. Okay. You're just being a little way too chill at this time of your life. You know, now's the time I'm to work hard and we're going to chill later. Yeah, well, no. Girl, your servant Steins in a German bar.

Like, I mean... She's grinding. I'm just saying, like, pot kettle. She probably makes more than I do here. Yeah. Well, it's just like, what are you doing to do the same thing? Well, you don't even know me, so how about you shut your mouth? Yeah, bro, shut your mouth.

Who are you complaining about people bringing you alcohol? No, I'm glad with it. I think being a server is a great job, but she's, like, expecting him to, like, do all these big great things. Like, multiple jobs. What are you doing to plan for? your future. Brooke, stay in your lane and keep not tipping people after they'll give you great service. Just shut up and talk on the radio, lady.

I just like, I hate when people do that. This is about Jordy. Jordy, she's concerned that you're too free and you're too available. Prove to her that that's not true. Tell her you're busy. Show her how much you got going on. Tell her you don't want to date. Yeah, I mean, it sounds like that would be more attractive to you.

I mean, I just don't understand why you want to play these games. Like, we met in real life. I thought you were a good person. Okay. Oh, that's actually a point. And how busy are you right now? I mean, I'm kind of busy. I'm not totally busy.

I mean, I... Jet, ask him again. Ask him again, Jeff. You're super busy, right? You slammed. Like, look, I'm looking to get busier. I'm looking at the right. They go.

It's close. All right. See, red flaggy muck? Oh, God. I think he sounds like a nice guy. That's not what she wants. She doesn't want that, Brooke. But you did want it that night.

Look, look, Harper. Let's rewind and pretend I didn't call you for two weeks. Are you turned on now? It has been two weeks. It's only been 10 days. Yeah, we're going to pretend. We're imagining. Harper.

I mean, the reality is you sent me a lot of freaking texts with, like, a lot of freaking dates, and now you have me on a radio show. Yeah. It does look bad. Gives her the it, huh? It's pretty bad. You know what? The thing is, we made him do it.

Yeah, we got all the time in the world. He didn't even want to be here. We didn't have time to. No. But he was kind enough to take a little bit of time out to do this with us, just so that I could ask you if you would like. like to see Jordy one more time, and we would pay for that date. I don't even know if he's free, honestly.

Jordy, are you even free? Not anymore. I'm all booked up for a while now. Finally, he got it. I'm sorry. She's like, so I'll see you next weekend? I mean, I'm not really into these games that he's playing with me, and I'm not going to fall. Oh, wait.

Now you don't like the game. Look in the mirror, sweetie. Oh, my God. Talking like Brooke now. This is not good. Okay. You know what? No second date.

All right. We are not tipping them either. This is going bad. Brooke and Jeffrey in the morning. We often think we know our type in dating. Tall, funny, a certain job. But the research shows we're usually not the best predictors of who will actually make us the happiest. As we often say on the happiness lab, our minds lie to us about all kinds of stuff.

And that definitely includes the kinds of things we need to be happy in a relationship. That's why it has. helps to stay curious. On Bumble, features like shared interests and prompts, make it easy to notice right on someone's profile initial sparks of compatibility, like a shared love of cooking or the same nostalgic TV shows. Shared interests and prompts let you showcase your personality right on your profile and connect with people who get your vibe. And with photo and ID verification, you can feel confident the person you're talking to is real, so you can date with a bit more confidence. When you treat dating as exploration, instead of sticking to a rigid type,

you open yourself up to happier, more meaningful connections. So maybe your type isn't tall, dark, and mysterious. Maybe it's loves podcast as much as you do. Stay open, stay curious, and let yourself be surprised. Download Bumble today. Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc and send me the link. Thanks. Hey, just finished drawing up that quick one-page business. plan for you. Here's the link. But there was no link. There was no business plan. It's not his fault. I hadn't programmed Kyle to be able to do that yet. My name is Evan Ratliff. I decided to create Kyle, my AI co-founder, after hearing a lot of stuff like this from OpenAI CEO Sam Aldman.

There's this betting pool for the first year that there's a one person, billion dollar company, which would have been like unimaginable without AI and now will happen. I got to thinking, could I be that one person? I'd made AI agents before for my award. award-winning podcast, Shell Game. This season on Shell Game, I'm trying to build a real company with a real product run by fake people. Oh, hey, Evan. Good to have you join us.

I found some really interesting data on adoption rates for AI agents and small to medium businesses. Listen to Shell Game on the IHeart Radio app or wherever you get your podcasts. Got a text in to 785.992 that says, with that outlook, I hope she's ready to die alone. Oh, my gosh. I mean, honestly, I think she just doesn't actually.

want a boyfriend. Yeah. You know, like, everybody's saying that she's, like, looking, she says she's looking for something, but she found it. Because,

like, what? She just wants to be wanted. And the outlook that I think they're referring to is the theory that if a guy says he's available to hang out with you multiple nights in a row, that means he's a loser and must have absolutely nothing going on. You know what I'm correct that? Because when girls try to hang out with me and I tell him,

I'm sorry, I got two jobs. I'm streaming video games every single night. It also deters that. Don't you. A busy guy cannot deter women. It also matters what you're busy doing. I got my D&D club on Friday and Saturday night, so I can't hang out.

But I make tons of money. Hello? Hello? You know what, guys, just give up. It's going to be easier to be just quick because actually they're going to feel more attracted to you that you've given up on that. Really hard to get. Can we not define all women based on her? I mean, just.

Too late. She speaks for all women and now we know how it works. Check in and offend yourself. Hey, I just got canceled on by two guys. Oh, Alexis. Who saw that coming? But you know what? If you need help with your dating life, go ahead, email the show.

We'll call that person who isn't calling you back. And go check out all of our podcast. We are the home of the second date update. Wherever you get yours at Brooke and Jeffrey in the morning. Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc. And send me the link.

Thanks. Hey, just finish drawing up that quick one-page business plan for you. Here's the link. But there was no link. There was no business plan. I hadn't programmed Kyle to be able to do that yet. I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people.

Check out the second season of my podcast, Shell Game, on the IHeart Radio app or wherever you get your podcasts. On this week's episode of Next Chapter, I, TDJ, sit down. with Denzel Washington, a two-time Academy Award-winning actor and cultural icon. I don't take any credit for it. I just didn't put me first. I just put God first, and he's carried me.

Listen to the next chapter podcast on the I Heart Radio app, Apple Podcast, or wherever you get your podcast. New episodes drop weekly. On the podcast Health Stuff, we are tackling all the health questions that keep you up at night. I'm Dr. Priyank Gwala.

a double board certified physician. And I'm Hurricane Dibolu, a comedian and someone who once Googled, Do I Have Scurvy at 3 a.m? And on our show, we're talking about health in a different way, like our episode where we look at diabetes. In the United States, I mean, 50% of Americans are pre-diabetic. How preventable is type 2? Extremely.

Listen to health stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith. And this is Jacob Goldstein. and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas and destructive companies in the history of business.

First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever. Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA, and I want to tell you about my new podcast called The Mail Room. And I'm Jordan, the show's producer. And like most guys, I haven't been to the doctor in way too long.

I'll be asking the questions we probably should be asking, but aren't. Every week, we're breaking down the world of men's health from testosterone and fitness to diets and fertility. We'll talk science without the jargon and get your real answers to the stuff you actually wonder about. So check out the Mailroom on the iHeart Radio app, Apple Podcasts, or wherever you get. your favorite shows.