Brooke and Jeffrey: Second Date Update - Second Date Update: Flirt and Observe

Episode Date: May 12, 2025

One of our listeners says she experienced an intimate moment with a guy she’d never met, when they were in a crowded coffee shop at the same time… and It was definitely more than just flirty eye contact. We're going to hear how that transpired into a whole afternoon together in your brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

You're listening to an iHeart podcast. Ugh, we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Geminis because you know you always like them. More of you dating with intention

because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and find them on Bumble. The Made for This Mountain podcast exists to empower listeners to rise above their inner struggles

and face the mountain in front of them. So during Mental Health Awareness Month, tune into the podcast, focus on your emotional wellbeing and then climb that mountain. You will never be able to change or grow through the thing that you refuse to identify. The thing that you refuse to say, hey, this is my mountain. This is the struggle. Listen to Made For This Mountain on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Yo, K-Pop fans, are you ready? It's your boy, Bum-Hun, and I'm bringing you the K-Factor, or wherever you get your podcasts. your opinions and be part of the conversation like never before. And trust me, you never know where we might pop up next. So listen to the K-Factor starting on April 16 on iHeartRadio app, Apple podcast, or wherever you get your podcasts. This isn't just a podcast, it's a K-pop experience. Are you in? Let's go. I want you to ask yourself right now, how am I actually doing? Because it's a question that we rarely ask ourselves. All of May is actually Mental Health Awareness Month and on the psychology of your 20s, we are taking a vulnerable look at why mental health is so hard to talk about. Prepare for our conversations to go deep. I spent the majority of my teenage years, my 20s just feeling absolutely terrified. I had a panic attack on a conference call. Knowing that she had six months to live,

I was no longer pretending that this was my best friend. So this Mental Health Awareness Month, take that extra bit of care of your wellbeing. Listen to The Psychology of Your 20s on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This week on Dear Chelsea with me, Chelsea Handler, Connie Britton is here.

I think you should encourage your friend to go ahead and not be holding out for any man to have her babies. She could be waiting another 10 years before she finds the right guy. Connie didn't meet her right guy until you were what, 50 Connie? 52, 52. I kept thinking, oh, I'm gonna meet the guy,

I'm gonna meet the guy, I'm gonna meet the guy. I finally was like, what am I waiting for? And I did it, and I'm just so glad that I did. Listen to Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. All right, starting your week with a brand new second date podcast. Thank you so much for being here. It's Brooke and Jeffrey.

Please like, subscribe, comment, do all the things because we love it. Before we start today's, we do have to put a disclaimer that we do not to put a disclaimer that we do not approve of this woman's actions. We're just gonna leave it at that. Yeah, totally, totally. We can't control the people. Yeah, thank you, Orson.

That's a great way to say it. We'll see what we mean. Yeah, you're gonna understand real quick, I'll tell you that. I think we sure did. But before we get to this brand new podcast, what are our comments? Oh, yeah, I saw one from C.Guerriera3

said, Jeffrey's intros are unmatched. He can make the most uninteresting situations into a five star story. Oh, I love it. I love it. For sure. Thanks for leaving your comments, and let's get this podcast started.

Second date update. Everybody always says, gosh, I wish I could meet someone in real life. Yes. But really, do you actually want that? Why wouldn't you? Not really. It sounds so scary.

Yeah, it really does. There's no block button in real life. That's a good point. You can't Google search them while they're standing right in front of you. And you can't work with your friends to send a message. Yeah. Oh, yeah. Or forward the rest of your conversation to voicemail.

You're out there on an island all by yourself That would be awesome if your friends were in the other room though. Yeah, you're like what did you just say hold on? I'll be right back You could ask Siri for like a flirty compliment to give to them But it is kind of awkward when they're sitting right in front of you So nobody knows that better like our listener Stacey who according to her email says she met a guy out in the real world. Was it frightening Stacey? Were you so scared? No. Well, thanks for being on the show with us today, Stacey. Tell us about this guy you met.

Well, basically I was going to get a coffee and it was full and there was only one chair open. Yeah. When I went to sit in the chair, I mean, this sounds like cliche, like I'm making it up, but it really happened. Like this guy went at the same time. Oh. Oh. And he was a hot guy, huh?

Very hot. Ooh. I thought my prayers had been answered. I thought the universe heard me because I couldn't believe it. We were both like literally, we decided to share the chair He was that cool. We were sitting you did sit on his lap then is that what you're saying? Now we shared the chair next to each hips next to each other two butts one chair

Like how did you introduce yourself? Well, I don't know how it happened. It just was so natural We started talking and then I just honestly wanted to read my book So I just pulled out my book catcher in the rye and then he Turned to me and he said I read that book. I love it. Yeah, I feel like we all read that in high school Yeah, it was required reading. Yeah, like you had to do it in order to pass really. I read it book. I love it. Yeah, I feel like we all read that in high school. Yeah, it was required reading. Yeah, it's like, oh my god. Like you had to do it in order to pass. Really? I read it for fun on my own.

Oh, really? I don't think I read that one. Oh, we had to. It explains a lot about Brooke. Yeah. By the way, did you catch his name at any point during this conversation? Yes, his name was Tyler.

Okay. And I bet he was impressed with you. You're reading like a literary classic instead of some like smut romance Is the turn on to you out in the world if you see a woman reading like a really fancy book you're like Oh, yeah hot. I after you said see a woman oh sorry okay no if a girl's reading a book that is good you want a little bit of intellect right I'm dumb so I need her to be a little smart so we can balance

yeah okay all right so you guys are sitting there at the coffee table two butts one chair and what happens and then he said when he's like hey I have to go for my workout oh he's telling you where he's suddenly, he's like, hey, I have to go for my workout. Oh, he's telling you where he's going. I always feel like that's kind of a, I wanna see you again or an invite or something. Oh, that's smart. Yeah, like when I say I have to go to the bathroom, that's like an invite to let you know where I'm gonna be

and you can think about being there. Well, I mean, why would he tell a complete stranger where he's going? You know what I mean? In Weston, there was- Why wouldn't he tell her where he's going? Well, he wants her to know it's a real, yeah, like, no, I honestly have an appointment or something. Yeah. Okay. her where he's going?

Hey, it was nice meeting you I have to head to my workout It's sexy I know but how did you get his phone number like it sounds like that's the end like he doesn't you know No, I said, oh wow. I no wonder you're in such great shape. I love to work out too. And then he invited me. He said, really? You know, I do power yoga. And I said, oh my gosh, not a lot of guys do that. What's power yoga?

Will I find out soon? It doesn't matter. Okay. So wait, so you went to his workout with him? Uh-huh. Oh! You were ready on the spot to work out? Don't lie.

You never go to a coffee shop without wearing yoga pants. I mean, you're always kind of ready. No, I had him in my bag. Okay, you guys are working out together? That seems a little bit more intimate. How did that go? Let's get out of here and come by. It went great.

I mean, it wasn't that intimate. It was just a class, so I just jumped in. Okay. Did you guys get spots next to each other? Yeah, but we were just doing yoga I mean you can't talk but I love the bonding when you bring a friend and you make the eye contact like this pose is hard Yeah, you know you like give you turn the look Making out the whole class Sounds so friendly, you know Is there a big romantic moment at the end of this

Well like I got it number, and he took my number was there a talk of a date Are you his workout buddy well he talked about getting together again? Maybe but it could just be like to talk about catcher in the rye and like discuss plot points and stuff That could be really sexy. I would enjoy it. She did do it for fun. As long as there's wine involved in the discussion. Okay, so you have a point there.

Okay, so what's happened since you guys said goodbye to each other? Well, we basically texted, I'd say back and forth about three times. And it was going really good at the start super easy Texting back and forth sounded like we were going towards setting something up, and I haven't heard from him since Okay Like something else could have happened in his life, and so what do I do well we call him? in his life and so what do I do well we call him yeah that was a smart move we're gonna try and call this guy Tyler we'll see if he picks up the phone and hopefully he has an answer for why he's not setting up a second meetup for the

two of you. I hope he's not in the middle of power yoga we are going to embarrass him. He won't bring it in the studio. No pockets in power pants. Okay, we're good then. Alright, we'll do it right after this. Hold on. Second date update. What else do you need for a steamy first date besides hot coffee, power yoga, and catch her in the rye? Dang, I'm sweaty just thinking about it. Hardcover first edition? Oh, you studious stud.

Honestly, that would be worth so much money. If you had that. Oh my God, actually, yeah. That's the impromptu date that our listener, Stacey, went on recently, after randomly meeting a guy named Tyler at a coffee shop. And even though they worked out together and seemed to have a lot in common,

there didn't seem to be a ton of romantic chemistry happening. So like Jose was saying, it's possible that Tyler sees you more as a workout study buddy. But we don't know. That's the whole reason that we're about to call him. And even if that's the case, then maybe we can help turn his mind into a more romantic thing. I mean, sometimes, especially with guys, they just don't see it unless it slaps them in the face. You're so right, Brooke.

Brooke is ready to slap Tyler right across the face till he sees the sexy side of Stacey. I mean, figuratively. Yeah, but physically too if it comes to that. Okay. Stacey, are you cool with that? Do you condone that? Yeah, I just really don't meet people in real life.

Okay. That's a common sentiment. I mean, romantically, right? I mean, you're probably, most people. That's just how it is. I'll bring that up to Tyler, too. That's a good point. You don't meet people like this every day, so he shouldn't let it pass him by. He really shouldn't let this pass him by. There we go. That's the confidence we need, Stacey, going into this. First, let's see if he picks up because I'm dialing his number right now.

Okay. Hello? Hey, is this Tyler? Yes. Hey, man. How? Uh, yes? Hey, man. How you doing today? You're on a radio show right now called Brooke and Jeffrey in the morning. Welcome to the show, Tyler. What up, man? Good morning.

Uh, okay. I'm on the radio right now? Yeah. Yeah, well, yeah. Okay. Say hi to millions of people. What is this about? We wanted you to do all the shout outs for the day on the show. Yeah.

So we'll get to that in a second. Will you shout out my second cousin, Carlos? We have a lot of that. Oh yeah, okay, let's not do this then. We have a great voice for it. Before we get to that, we want to talk to you a little bit about your dating life in a segment that we do called Second Date Update. Mine?

Yeah. Yeah, you've been dating, right? Well, this isn't really a date date. Like, this may be kind of... You may not categorize it that way. We're not sure if you felt like it was a romantic hangout, but you met a woman recently named Stacy at a coffee shop? Yeah.

Yeah. The girl with the book, right? Yes. That's it. That you shared a chair with. Catch her in the ride. So we heard about you guys meeting up and you had coffee, did a little workout afterwards. Right.

Yeah, I remember her. Okay. I mean, what did you think about her? Is she cute? Yeah. She's a beautiful girl, yeah. Oh, wow. Okay.

Good! That's a start. Stacey told us that after you guys met up, you were texting about possibly hanging out a second time, but nothing happened. Right. She's just not sure where your head's at. Um...

Okay, and you want- You want me to tell you on the air? That'd be a lot better than off the air. For all the listeners. Okay, mute the phone and we're just gonna listen, okay, and you want you want me to tell you on the air? That's it'd be a lot better than off the air That's okay with you. Yeah. All right. Well, yeah, there's a reason okay, so we were Texting back and forth and scheduling a first real date mm-hmm she said and so I was suggesting we get together the following weekend,

and she comes back with, um, yeah, that's great. I'm excited, but we can't do Friday because it's your birthday. Huh? Hey! Okay. Did she mean her birthday?

How would she know your birthday? Yeah, that is true. How does she know your birthday? Or maybe it came up when you guys were talking at coffee. Did you mention that to her? No, I never did. And I was racking my brain to see if I could figure out where she would have learned my birthday.

The yoga studio would never say that. But isn't that, like Alexis, isn't that normal if you meet a guy that you like you like immediately stalk him online everywhere you stalk him on you probably would see someone's birthday but you don't mention it yeah messed up okay what is like Facebook yeah yeah are you sure you're not like misremembering that like maybe somehow you mentioned it in conversation I don't think so I mean we didn't have a lot of deep talks that's why we were gonna get together for another date. Well, but she's not trying to date you on your birthday, which is a good sign But just her knowing when my birthday was kind of freaked me out. So I just stopped responding to her I mean, yeah, like if you stalk a guy and you know, he has two brothers, you don't mention the brothers

He's still a siblings. You know,, Alexa, she maybe did it on accident. Yeah. On accident. It's possible, and we can find out, because Tyler, I mean, this isn't gonna be a great look for her when I tell you this, but Stacey is quietly listening on the other line to this conversation, waiting for her chance to talk to you.

It's not what it looks like, dude. Not like a stalker. Oh, man. No. That's not creepy at all. No, we helped her. Yeah. Wait, that's not creepy at all. No, we know. Yeah. It's just how the segment works. That's our bad. Yeah. Stacey, are you there? Hi, Tyler. Oh, God. Okay, I just want to say I missed your birthday. So happy birthday. Oh, doubling down. That's kind of funny. You mean that is a joke

No, it's not a joke. I really did miss his birthday and they hide a little buster for me your dog Wait, how do you how do you know my dog's name? I never told you busters name. I Have a confession to make what are you inside his house right now? have a confession to make. Are you inside his house right now? You are the dog, you're buster. No. This whole meeting of ours was not an accident. What?

Oh no. Yo, this is getting worse. Dude, what are you, wait, explain. Yeah. What's going on right now? I did run across your dating profile about a week ago and I saw the logo for the coffee shop behind you when you're receiving and I went to the coffee shop and waited until I would run

into you and I just hope that you can respect a girl who does her homework Suddenly all make sense now, okay You said that it was like a chance in real life me what was a chance that I would meet him She didn't know what day he was gonna be in the coffee shop worse if she went every day This is not normal behavior. I don't know what to say right now. I'm kind of weirded out. I don't blame you.

And how do you know his dog's name? It wasn't on my dating profile. That is nuts. Stacey, you can't do that. I can do that and I did. He just gave me the information on the app and I put myself in a situation to run into him. Dude.

Oh my God. I trust nothing that you're saying right now like what was the book were you actually reading that book? Yes, I mean after I saw that he liked it Isn't it the thought that counts behind the dude you stop it you stop it. You stop it. If we would have known this, we would have not called for Stacey, Tyler. Yeah, this is the more we don't like to be around. Well then who was gonna call for me? He had blocked me. You didn't tell us that either! And I'm sure you know his best friend's names. Don't lie.

You guys are really funny. I saw the guy on the dating profile and I just went the extra mile to meet him You clearly still want to go out with Tyler here, but before we do I do but I have a problem with something I have to clear up first You have a problem. I noticed you paid someone named Trish three times last week And on a Venmo and I'm hoping she's a dog walker Venmo is kind of like public knowledge. No, you can switch it to private I'm switching it to private right now That's not very nice it's not polite I don't like that Tyler Why is that the creepiest thing?

But it's still a yes as far as I understood that From Stacy, are you actually going to ask Tyler? It's kind to ask Are you actually going to ask Tyler? It's kind to ask. Don't put him in that position, Jeff! Well, Tyler, we would pay for your guys to meet up again if she's not already waiting for you in your apartment. Oh, no. Or at the yoga studio. Dude, check your closets. I'm not even lying.

Seriously. I think I'm gonna respectfully pass. Oh, man. I did not see this coming. Stacy, you do understand that's a no, right? I maybe just have to work harder. Oh, my God. I'm gonna see this happening. Stacy, you do understand that's a no, right? I maybe just have to work harder. Oh my god. I will see this happening one day, guys.

Don't do that, guys. We're gonna get to it again. If it's against our will or not, something's gonna happen. Brooke and Jeffrey in the morning. See, this is why we've always said, you can't trust anybody who reads a book in public It's the literacy that was the problem It's a gateway activity Brooke first you're reading Ernest Hemingway next thing You know you're reading a stranger's Venmo log and monitoring who is sending them money I mean reading is the enemy the guy in the TV show you own the bookstore

The guy in the TV show you owns a bookstore Lot of people say that a lot of psychos have come out of catcher in the ride Why do I feel like this isn't gonna be the last time that we hear from this Stacy lady though Too much yeah, I think we're gonna we're gonna hear from her again during a laser story where she's being featured in it Didn't work out this time probably for the best But if you want some help with your dating life, you can email the show We'll call that person who's not calling you back. Yeah, go check out all of our second dates wherever you get your podcasts They're up at Brooke and Jeffrey the made for this mountain podcast Exists to empower listeners to rise above their inner struggles and face

the mountain in front of them. So during Mental Health Awareness Month, tune into the podcast, focus on your emotional well-being and then climb that mountain. You will never be able to change or grow through the thing that you refuse to identify, the thing that you refuse to say, hey, this is my mountain, this is the struggle. Listen to Made for This Mountain on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Yo, K-pop fans, are you ready?

It's your boy, Bom Han, and I'm bringing you the K-Factor, the podcast that takes you straight into the heart of K-pop. We're talking music, idols, exclusive interviews, and even the real behind the scenes K-pop stories. Plus, you're the fans, you're part of the show, and you can get a chance to jump in, share your opinions, and be part of the conversation like never before. And trust me, you never know where we might pop up next.

So listen to the K-Factor starting on April 16 on iHeartRadio Apple Podcast, or wherever you get your podcasts. This isn't just a podcast, it's a K-pop experience. Are you in? Let's go. Let's go. Let's go.

Let's go. I want you to ask yourself right now, how am I actually doing? Because it's a question that we rarely ask ourselves. All of May is actually Mental Health Awareness Month, and on the psychology of your 20s, we are taking a vulnerable look at why mental health is so hard to talk about. Prepare for our conversations to go deep. I spent the majority of my teenage years and my twenties just feeling absolutely terrified. I had a panic attack on a conference call.

Knowing that she had six months to live, I was no longer pretending that this was my best friend. So this Mental Health Awareness Month, take that extra bit of care of your well-being. Listen to the psychology of your 20s on the iHeart Radio app, Apple Podcasts or wherever you get your podcasts. Hey, I'm Jay Shetty and I'm the host of the On Purpose podcast. And I'm excited for my next episode with Khloe Kardashian. God, I've been through so many things that at this point, I would rather not feel than feel because feeling is too much for me to handle. I am Khloe Kardashian.

Khloe Kardashian, everybody. Khloe Kardashian. No one understands how it's, I'm not just a TV show. Listen to On Purpose with Jay Shetty on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I found out I was related to the guy that I was dating. I don't feel emotions correctly.

I collect my roommates' toenails and fingernails. Those were some callers from my call-in podcast, Therapy Gecko. It's a show where I take phone calls from anonymous strangers as a fake gecko therapist and try to learn a little bit about their lives. I know that's a weird concept, but I promise it's very interesting. Check it out for yourself by searching for Therapy Gecko

on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. You're listening to the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. You're listening to an iHeart podcast. ["I'm On My Way To You"]