Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Spontaneous No

Episode Date: August 20, 2025

One of our listeners says his plan to impress his date and make her like him did NOT go how he wanted… in fact his night ended in physical pain! See omnystudio.com/listener for privacy information.

Hey guys, it's Janae, aka Cheekies from Cheekies and Chill Podcasts. And I'm bringing you an all new mini podcast series called Sincerely Jeannay. Sure, I'm a singer, author, businesswoman, and podcaster, but at the end of the day, I am human. And that's why I'm sharing my ups and downs with you in real time and on the go. Listen to Jikis and Chill on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. It's black business. month and black tech green money is tapping in i'm will lucas spotlighting black founders investors and innovators building the future one idea at a time let's talk legacy tech and generational wealth

i had the skill and i had the talent i didn't have the opportunity yeah we all know right genius is evenly distributed opportunity is not to hear this and more on the power of black innovation and ownership listen to black tech green money from the black effect podcast network on the high heart Radio app, Apple Podcasts, or wherever you get your podcasts. Tune in to All the Smoke Podcast, where Matt and Stacks sit down with former first lady, Michelle Obama. Folks find it hard to hate up close. And when you get to know people and you're sitting in their kitchen tables and they're

talking like we're talking, you know, you hear our story, how we grew up, how I grew up, and you get a chance for people to unpack and get beyond race. All the Smoke featuring Michelle Obama. To hear this podcast and more, open your free iHeartRadio app. Search all the smoke and listen now. If a baby is giggling in the back seat, they're probably happy. If a baby is crying in the back seat, they're probably hungry. But if a baby is sleeping in the back seat, will you remember they're even there?

When you're distracted, stressed, or not usually the one who drives them, the chances of forgetting them in the back seat are much higher. It can happen to anyone. Parked cars get hot fast. be deadly. So get in the habit of checking the back seat when you leave. The message from NHTSA and the ad council. I just normally do straight stand-up, but this is a bit different. What do you get when a true crime producer walks into a comedy club? Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story.

Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life. This is Wisecrack, coming September 2nd. Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, it's Brick and Jeffrey in the morning. And in the second date, the guy tries to impress the woman he's out with and ends up, we'll just say, in 30 straight minutes of nonstop physical pain. Oh, because of it. Talk about a backfire.

That's what's a backfire. You're going to hear what happened in just a second. But, okay, comments, Alexis. Yes, I mean, speaking of unconventional ways to meet someone, Amber commented and said, I showed up to a date two hours late And we now have a kid together The patience on the man for staying that long Oh my god

And how do he stay and it works out I have so many questions Oh that's awesome What do you eat and then eat again when they get there? I mean I could You know what I mean? It's like yes they're two hours late Fourth wheel is no joke

What about six mil? Why don't we go that far? All right we're going to start your second date right now Date Update. Text to 785.8.592, and this is for the guys out there, what is the craziest thing you ever did for a girl spontaneously on a first date? It's Brooke and Jeffrey in the morning, and I'll ask Jose. Jose, craziest spontaneous thing that you've ever done for a girl on the first date.

There was one time, you know, when you're leaving, like, a restaurant or a theater, and they have somebody selling single roses outside? I remember one time I bought all the roses. He's like, four left. And I bought all home. Like, I'll take the rest of them. I gave him to my day. Whoa.

You're dangerous, Jose. Look out street flower vendors. You're about to run out of inventory if Jose's nearby. Where the thorns on those roses? That's even more risky. I bring it up, though, because one of our listeners says he went full, spontaneous on a first date. And now he's kind of regretting it because he's not getting a call back.

She's allergic to flowers. Maybe. He's like the one thing I did. Let's welcome Patrick to the show. Patrick, how you doing, ma'am? Hey, hey, guys. Thanks for having me on. Yeah, is it normal for you to get spontaneous on a date or is, was this like a one-time sort of thing?

Not even remotely. Oh, dude, I've got to like you. I feel like I overplan, though. I don't like that this didn't turn out the way you wanted to because she's not calling you back because you need that confidence boost to do it more often. So what was it that, like, caused this feeling inside of you that night that said, I need to do something really spontaneous right now? So I basically, I met this girl named Maggie, and we're on our day.

and the topic of being spontaneous kind of came up and we both agreed that being spontaneous is a really good thing not gonna lie I don't agree but I agreed in the moment but like she caught me right away because she was like wait I thought when we were first talking you had said like

you're not the type of person who does spontaneous thing she called you out on you agreeing to call me out I had to double down I was like what are you talking about of course was spontaneous And I took one of, like, the flowers out of the vase on the table, and I just ate, I ate it. Eat it. No. Ew.

I thought you were going to, like, give it to her. Jose, did you not eat any of the roses that you bought? No, I didn't. Oh, okay. Is she laughing or just? She's worried at you. Druling because she's so turned on. Or she's also hungry and there was only one flower.

She's like, hey, I was going to eat that flower. Well, what's her reaction? She did laugh and she thought it was funny, but she was like, are you? sure you're not just weird. Okay, she's ribbing you. It is kind of, yeah, I can't tell if it's a joke at this point or not. It could be, you should be. It is kind of borderline between spontaneous and just really strange.

Yeah, and now even though I'm not spontaneous, now I feel like I have to prove my point. So the waiters walking by and I called him over, I took a $100 bill out of my wallet and I tipped him mid-meal. What? Whoa. What did you say to him? Oh, my God. To be spontaneous?

I said, you're doing such a. great job. I just want to give this to you now, letting you know that we really like you. I can't remember what I know. Okay. Yeah. So you tipped early because you're spontaneous. And a lot. Exactly. Was she impressed with it?

I don't know if she was impressed or... Okay. Probably because it was happening inside of a jack in the box. So she was like, that's a little unusual to do that here. You're doing a good job. They have flowers on the table, Jeff. They don't have those at jack in the box. Okay.

So was that it? Did the spontaneous proving stop there? No. No. You're still on one, huh? Okay. Okay.

There's more. So we leave after dinner and we're walking and talking and she says kind of out of nowhere. She's like, you know, it's okay if you're not spontaneous. Like that's not a bad thing. She's right though, bro. I'm sorry to interrupt you. But have you thought at any point of this just to be yourself and be like, but that's just

not how men think. No, you're right. except like, hey, you're not that cute, you're not that charming, and that's fine. You're like, what do you mean? Yeah. So reverse psychology is what we're working with. Yeah.

You guys have to prove themselves. We do. It's like a man thing. So what did you do? Well, we were walking by a tattoo shop, and I said, I'll be right back. And she was like, no. No. Don't do that. Oh, my gosh.

You robbed the tattoo store? No, Jeff. Oh, wow. That is a badass. I got a bunch of guns. I got him. Robbing a tattoo store, probably. would have been smarter.

Uh-oh. Half an hour later, and I've gotten a small, what do you call? Like an infinity symbol on my shoulder. Oh, all the things. Why did you go with that? Did you say you just left your date for a half an hour? You didn't even bring her in the shop with you? Yeah, I should let her pick it out.

I wanted to surprise her because she has the same tattoo on the same spot. Oh, no. Oh, you got a matching tattoo. Oh, you got. Oh, you know. Oh, buddy. that was endearing in your head. Hold on. What was her reaction? At first I thought it wasn't great because she was like freaking out a little bit like,

oh my God, I can't believe you did that. But then she kind of then started laughing about it and was like, you know, oh my God, you're crazy. Yeah, mission accomplished. You proved it there. So she waited for a half an hour and was still able to laugh. Yeah, it is questionable. She waited. She should have left. I mean, if I'm in that situation and I'm the girl, I would want to know how it ends. That's true. You're saying do it for the plot, save for the plot. I'm curious what's he coming back with? Yeah. I hope that's the end of your spontaneity.

Or is there more? He's like, then I cut off my hands. Okay. No, I walked her home and that was it, but like literally that was it. I haven't heard from her soon. I mean, obviously you really, really wanted to impress her. Yeah. I don't know

if you did, but like this girl must mean a lot to you. I mean, yes, I do like her, but I don't know. I feel like she was calling me out and I felt like I had to defend myself even if it wasn't she wasn't trying to bully you she was trying to tell you to just like Jose said be yourself

pick a random bar you should go to last minute that is also spontaneous you don't have to get that too I think what we're saying is we're all impressed we're all very impressed by how far you went in order to make this woman like you yeah for a girl you kind of like yeah and so now we're gonna do even more spontaneity when we spontaneously call her and ask her why she's not giving you

another chance well this is very planned we do it every day well no she's not going to expect it she's going to be like wow spontaneous phone call second date update i want to date him i think we're using the word wrong you know we all have to get matching infinity tattoos by the end of this then we will do it we will get the tattoo gun out for your second date update right after this hold on Some people get spontaneous on a date by skinny dipping or hopping a train together. Yes. Or hopping a train after skinny dipping. Close on or close off.

Is this the nude car? Oh, close off. There's no plastic on the seats here. I don't like it. And you're just naked and wet. Why does it take so long for you to get kicked off the train? He's talking to people. They like what they see here.

But not for our listener, Patrick. He proved that he was spontaneous. Oh, he did. By eating a flour off their dinner table, tipping $100 before the bill came. That's a good one. And then getting a shoulder tattoo all mid-date. How small is it? Can we ask?

It's an infinity sign. Brooke is asking how small are you? Patrick, she wants to know how small is it. It may be like an inch and a half. Okay, that's not that big. That's not very big. Big enough to see. Too big.

But the whole reason that he did it is because Maggie kept doubting his spontaneous nature, so he had to step up and prove himself to her. Yeah. Patrick, you're not going to try and prove your spontaneous again over the phone while we call her, right? Just a tattoo gun in the background. I'm getting her name. Trust me, I'm so over

trying to be spontaneous. I just want to be myself. There it is. I'm boring, and that's okay. You're not boring. You're not boring. Don't say that because I was going to prove how boring he is. Don't say that Just accept you are who you are

And we love it Patrick She probably prefer a guy Who doesn't eat flowers anyways Yeah I don't think it's It's very fun Let's see what Maggie has to say

It may have had nothing to do With the spontaneous stuff It could be something else Wait to hear her side of this date All right And her story from it Has to do with the spontaneous There's no way it's not

Well let's find out I'm gonna call her right now We'll see what she has to say If she answers Let's do it Hello. Hey, is this Maggie? Yes, who is speeches?

My name is Jeff from a radio show called Brooke and Jeffrey in the morning. Hi, Maggie. The whole show's here. Good morning, Maggie. Hi, guys. What is this about? Okay, you're smiling, you're laughing. This is about your love life, actually. Okay.

I wouldn't use love in there. Jeff. It's not your like life. Your dating life, because rumor has it, you recently went out with a guy named Patrick and had a really fun time. Oh, okay, if you say that, does he say so?

I do say so. Interesting. I can't wait to hear how you describe this date. Yeah, because we're doing a segment called Second Date Update. We're trying to help Patrick out and figure out if there was something weird about the date, if there was something that you didn't like, because he's a little bit confused.

why you haven't met up again. He's confused why we haven't met up again. Well, yeah, he did tell us a little bit. Did he talk about a date went? Yeah, there was some highlights that were brought up. Some that confused. Some lights, that's for sure. Some spontaneous moments that happened, it sounds like.

Yeah, I mean, I don't even know how to go about starting talking about this. Can we start with a flower at the table? Yeah, it was like a fun, slurty banter, and then he just eats a flower off the table. Like a man Like shocked and appalled I'm confused I don't know what to do So all I do is laugh

That he thinks That's like permission to keep going Oh is it because Is it because he didn't put ketchup On the flower Is that what it was? No but you're saying Your nervous laughter

Kind of opened the door He thought oh she's laughing I can do that I should do this It's like my seven year old I was uncomfortable I was uncomfortable Okay

Okay But it was pretty impressive When he tipped $100 It was strange to say the least why was that strange it was strange because it's like that's not how you act in a restaurant that's not I mean

I wasn't impressed because somebody like showed how much money they had all right okay fair we can say that but you're still there like you I mean you guys are still going on the day it's not like you left or you said I mean there had to be something good happening

right well I mean how do you even like how would you leave that situation get up and walk out the door Would you, though, Alexa? No. Yeah. Okay. I mean, call my friend to come get me, walk out the door. Pull the fire over.

But let's talk about the tattoo that he got at the end of the date. Can we skip to that? We're all dying. We want to know, on a scale of 1 to 10, how badly did you want to say I love you, right when he came outside? Literally negative infinity. That was just, like, actually insane. You didn't like it. It's funny you said that because we heard it was an infinity tattoo.

So negative infinity. Wow, that's like matching soulmates. Not really. Yeah, not really. So, okay, wait. You're waiting outside a tattoo parlor for 30 minutes. Like, did you know that's what he was doing inside? I, honestly, I had no idea what was happening.

You weren't sure. And when he came outside with the tattoo that I had, I, like, wanted to scream because he even asked me what it was. I'm actually in the process of getting it removed because that's a matching tattoo I had with my ex. Because it was a matching tattoo that you had with your ex. ex. Is that what you just said? Yes. Dude.

Oh my gosh. Oh my God. Well, now you don't have to get it removed because it matches with your new boyfriend. No. That's going to move our appointment sooner. Oh, God. Isn't it crazy to think that two men in your life has a... I'm not saying tattoo?

We're willing to get an infinity tattoo? They're not both in my life. Okay. That's like your exit mark. Every time you're done with one, you give infinity. Well, they're not totally out. of your life yet either because here's something that's kind of spontaneous and fun patrick has been waiting on the other line listening wanting to talk to you oh my gosh really yeah i think he's still there

patrick yeah hey hey god as if that tattoo story could i thought it was already bad i thought it couldn't get worse yeah and it did patrick how do you feel about your tattoo now uh not not so great uh i'm nice sure what to say that is who but you know what I hate you're a bet your ex was not as spontaneous as I am nope right oh gosh still he goes he keep going with that whole thing it's like it's not a joke anymore it's kind of just annoying at this point that was some okay try and be boring now be yourself bro yeah be boring that's what you said you were gonna do right like that's what your goal was to be yourself yeah and show her who you really are. No, absolutely. I was, I was, that was a really, a real bad joke. Okay. He's a jokester. We know

that. She doesn't like jokes. I think he's uncomfortable. I feel bad for him. I do too. So, Maggie, I got to ask, like, was your ex-foring? What was he like? Oh, I don't even have to tell you. You, like, didn't even talk to me on the date. It was all about how you felt. I'm like, I don't need to tell you anything about myself. That's true. Do you know You literally went on a date and sat down and just witnessed a lot of weird stuff. When we talked to him before we were on the phone with you, he understands how dumb he was. And he said he just wanted to be himself and get a do-over with you, you know? Yeah, he should have just admitted.

Maybe he's not missed for spontaneity. I'm not. I swear. You don't have to convince her. I mean, I think he's a really nice guy. I think he is trying too hard. It needs to get a little bit more grounded with who he is. Okay.

And I don't know. I think there are a lot of assumptions that were made, and I didn't like it. And I don't have time to give other people chances. Okay. So you're selfish. That's okay. Oh, my God, Jeffrey, no. She has boundaries.

Boundaries are what those are called. Brooke, the point is we're trying to help our listener, Patrick, get together with this woman that he really liked and made a lot of effort to try and impress. He did do that. Maggie, we're all in agreement, and even Patrick is that he went too far with it. Yeah. We want to reel it back so much so. What do you think about getting your tattoos removed together?

And we will pay for that. Maybe you could add on, though, and make it something else. Oh, even better, like little butterfly. Let's erase all of the past and start a happy, brand new future with Patrick. Do I have to pay for both of those two? Patrick, don't come off as cheap right now. No. Well, Brooke, he already spent his $100 bill on the waiter already, so we probably should step in.

Maggie, what do you think? No. Okay. Wow. all of the effort, but it's going to be a no for me. I kind of know why her ex-boyfriend left her now after hearing this. Oh, my God, Jeffrey! You assume he left.

He's fun. He's spontaneous. He tried. Patrick, do you and me want to get a beer with me sometime, dude? Yeah. Oh, magic tattoos, you guys. I can't wait to see Jeffrey's Infinity symbol when he comes to work next week. We're going to get the tattoos that you have to, like, press your

bodies together in order for them to make one giant thing. One giant flower. Yeah. One cheek, each. Okay. Patrick? That might be a little weird, a little like too much for me. Oh, okay. I'm the weird one now. Who are on, Jeffrey? I thought that for a long time. Brooke and Jeffrey in the morning.

Your entire identity has been fabricated. Your beloved brother goes missing without a trace. You discover the depths of your mother's illness, the way it has echoed and reverberated throughout your life, impacting your very legacy. Hi, I'm Danny Shapiro. And these are just a few. of the profound and powerful stories I'll be mining on our 12th season of Family Secrets. With over 37 million downloads,

we continue to be moved and inspired by our guests and their courageously told stories. I can't wait to share 10 powerful new episodes with you, stories of tangled up identities, concealed truths, and the way in which family secrets almost always need to be told.

I hope you'll join me and my extraordinary guests for this new season of Family Secrets. Listen to Family Secrets Season 12 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Noah. I'm 13. And as you might have seen from the news, I got a podcast. And I explain those fake headlines like your uncle would, like your cousin would if he actually did the research. Honestly, adults don't ask the right questions.

Now you know with Noah de Barroso is a show about influence. Who's got it, how they use it, and what it means for the rest of you. It's not the news. It's what the news should be if someone Gen Z or Gen Alpha made it. When I'm watching everything. The majority of the youth, 18 through 24, say they trust Republicans more than Democrats to from the economy. You kidding. Politics is wild and I'm definitely not here to pay it, but I'm here to make sense of it.

Just what's happening, why it matters, and what it means for us. Bring your brain Listen to Now You Know With Noah Debarossa on the IHeart Radio app Apple Podcast or wherever you get your podcast Man I am so disappointed

Honestly You really thought that was going to turn out differently I just feel like men are constantly trying to put in extra effort To show that they care about these women They want to stand out And they get roasted for it on our show Every single time

Here's the thing All she wanted him to do was be himself, Jeffrey. She didn't say that. Yes, she did. She did. She did tell him. She said that. Not before the date.

After the fact, she said it. She said it during the date. She said you're trying too hard. Just be you. Honestly. She gave him a chance. Do you not listen to anything people say? Really, I blame myself for this.

It's all about you. I am not being wild and spontaneous enough in these calls to make the other men appear more normal. I see. That's my job. Although I did ask the guy to grab a beer and get matching butt tattoos with me. at the end. So maybe I am growing. Yeah. You got turned down, though. Yeah, it's a rough day for everybody.

So, I don't know. We're still willing to help you out, but let's give guys some credit for effort. Yeah. Ladies? Sure. Oof. Yeah. Okay. Half the room is based. We will call the person we'll put in the effort by calling that person who's not calling you back. So email the show if you feel like you need a little bit of help and go check out all of our second dates, wherever you get your podcast at Brooke and Jeffrey.

Hey guys, it's Janae, aka Cheekies from Cheekies and Chill Podcasts. And I'm bringing you an all new mini podcast series called Sincerely Jeanne. Sure, I'm a singer, author, businesswoman, and podcaster, but at the end of the day, I am human. And that's why I'm sharing my ups and downs with you in real time and on the go. Listen to Jikis and Chill on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. It's Black Business. month and black tech green money is tapping in i'm will lucas spotlighting black founders investors and innovators building the future one idea at a time let's talk legacy tech and generational wealth

i had the skill and i had the talent i didn't have the opportunity yeah we all know right genius is evenly distributed opportunity is not to hear this and more on the power of black innovation and ownership listen to black tech green money from the black effect podcast network on the eye heart Radio app, Apple Podcasts, or wherever you get your podcasts. If a baby is giggling in the back seat, they're probably happy. If a baby is crying in the back seat, they're probably hungry. But if a baby is sleeping in the back seat, will you remember they're even there? When you're distracted, stressed, or not usually the one who drives them, the chances of

forgetting them in the back seat are much higher. It can happen to anyone. Parked cars get hot fast and can be deadly. So get in the habit of checking the back seat when you leave. The message from NHTSA and the ad council. Tune in to All the Smoke Podcast, where Matt and Stacks sit down with former first lady, Michelle Obama. Folks find it hard to hate up close. And when you get to know people and you're sitting in their kitchen tables and they're talking like we're talking.

You know, you hear our story, how we grew up, how I grew up. And you get a chance for people to unpack and get beyond race. All the Smoke featuring Michelle Obama. To hear this podcast and more, open your free iHeartRadio app. Search all the smoke and listen now. I just normally do straight stand-up, but this is a bit different. What do you get when a true crime producer walks into a comedy club? Answer, a new podcast called Wisecrack,

where a comedian finds himself at the center of a chilling true crime story. Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life. This is Wisecrack, coming September 2nd. Listen to Wisecrack on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.