Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Catching Feelings and Z's

Episode Date: July 4, 2025

Little mistakes are okay on a first date, but today's Second Date had one BIG mistake and we're hoping it didn't happen on purpose...See omnystudio.com/listener for privacy information.

So what happened at Chappaquiddick? Well, it really depends on who you talk to. There are many versions of what happened in 1969 when a young Ted Kennedy drove a car into a pond. And left a woman behind to drown. Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. Every week we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedy's on the iHeartRadio app, Apple podcast, or wherever you get your podcasts.

I'm Bob Crawford, host of American History Hotline, a different type of podcast. You, the listener, ask the questions. Did George Washington really cut down a cherry tree? Were JFK and Marilyn Monroe having an affair? And I find the questions. Did George Washington really cut down a cherry tree? Were JFK and Marilyn Monroe having an affair? And I find the answers. I'm so glad you asked me this question. This is such a ridiculous story.

You can listen to American History Hotline on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. On the You vs. You podcast, we welcome Polo Molina, music manager to the stars. you are podcasts. on me are not here no more, so I'm part of myself. You know, make me cry. Listen to you versus you on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Just like great shoes, great books take you places. Through unforgettable love stories and into conversations with characters you'll never forget.

I think any good romance, it gives me this feeling of like butterflies. I'm Danielle Robay, and this is Bookmarked by Reese's Book Club, the new podcast from Hello Sunshine, an I Heart podcast where we dive into the stories that shape us, on the page and off. Each week I'm joined by authors, celebs, book talk stars, and more for conversations that will make you laugh, cry, and add way too many books to your TBR pile. Listen to Bookmarked by Reese's Book Club on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What happens when we come face to face with death?

My truck was blown up by a 20-pound anti-tank mine. My parachute did not deploy. I was kidnapped by a drug cartel. When we step beyond the edge of what we know. I clinically died, the heart stopped beating. Which I was dead for 11.5 minutes. In return. It's a miracle I was brought back. Alive Again, a podcast about the strength of the human spirit.

Listen to Alive Again on the iHeart Radio app, Apple podcasts, or wherever you listen to your favorite shows. The big question today would be, could you get over this? Could you forgive this guy for what he did on this date? Let us know. Yes, it's your Second Date Update podcast with Brooke and Jeffrey in the morning.

Thank you so much for finding us. And before we start, we always love to highlight your comments because they mean a lot to us. It's awesome that you interact. And let us know how you're feeling. So what do you see, Alexis? Oh, I saw one from TJ Luxembourg who said, your comments because they mean a lot to us. It's awesome that you interact and let us know how you're feeling. So what do you see, Alexis? Oh, I saw one from TJ Luxenberg who said,

"'I like to listen to you guys in the morning "'on my way to work and all I have to say "'is sometimes I think my past dates were weird, "'but due to your second date updates, "'I think they might be normal.'" I know, seriously. Honestly. So true.

I will say that online dating has given us endless supply of People with crazy stories. Oh, yeah Someone on my stream yesterday mentioned the whole reason they listen is cuz one time they were flipping the channels and they heard about the Guy using dress like a dinosaur on his date stomping on Legos. Yeah They were like I was hooked on your show after Thanks for having awful dating lives. Yeah And if you ever want help you can go to our website. It's brick and Jeffrey calm There's a little submit button there share away, and let's get your second date started

Second date update We really need to get a victory today. Not just for our listener, but for ourselves too. I'll always take a victory. Brooke's going through some deep-ish right now with her life. Jose and I tried to high five in the break room and missed. That's embarrassing. Bad hand-eye coordination. It was a sad moment.

And then Alexis' spray tan only covered three quarters of her body this week. Okay guys, it get my back on my own. Yeah it's a mess and we're all a little down and out right now including Tiffany who's on the phone because she's having trouble getting a guy to ask her out again. Tiffany if you could describe your mood right now using one emoji. What emoji would it be? Oh, I like this question. Probably that one that's like the dejected sad face. Oh. With the little squinty eyes. Oh.

With the droopy eyes? The one that's drooling? Not that one. Like the puppy dog eyes? Okay. You guys, this is a visual thing. Maybe asking emojis wasn't the best way to start this. Tiffany, but maybe instead tell us about the guy that you want us to contact.

Who's he? Yeah, so Mike, we met on an app and I thought he was really funny. Like one thing I remember from his profile was that he liked to take the scenic route, you know. That's what he wrote as his, like, bio? Just like his little tagline. Yeah, I thought that was kind of cute. All right. Okay, so he takes a long time to do stuff

that most people get done in a short amount of time. Stop and smell the roses kind of guy. I feel like he's just late to everything. That's what it sounds like to me. Just let him know. Yeah. Well, I mean, it left room for discovery. Like, is he late or is he more just, like,

a really present, soak up time with people? You know? Maybe he has ADD like me. Yeah, okay. So what'd you guys do on your date? Well, so we talked a lot before our date. Like, I'm not someone who just like dates a lot of people.

I'm a one at a time kind of person and I wanted to really get to know him before we went out. So we talked a lot. He takes the scen scenic route, even setting up a first date. It just takes a long time. Maybe I'm a scenic route kind of person myself. Oh, OK. So what'd you guys talk about? We talked about all sorts of things.

And we had really good conversation. And then he asked me out. And I didn't tell you guys this, because I know it's like technically second date update. But we actually have been out twice. So the first time was happy hour, and I just wanted to talk to him more. So when he asked me out a second time,

I went and he asked me to go back to his place and watch a movie, and I did. And I stayed the night. And then- You did stay the night? Yeah. Nice. It was just one of those things where

when we were at his place it just felt like we had known each other for a really long time like it was comfortable we were cozy it felt good it didn't feel like oh this is the first time I met your place it felt it felt very like I don't know with a family member like a younger brother I mean a distant family member like someone you've been in a relationship with yeah that's what I said do you think you said anything to scare him like you talked too much about wanting to be in a relationship or something I mean honestly anything is possible like I don't claim to be the perfect date or anything like that.

This just felt good and I'm confused. It was natural and easy. That's amazing. Yeah it was easy. Maybe too natural and easy is a red flag though. Sometimes people get scared by that. I need more effort. There should be more problems here.

Yeah I just I don't know. I didn't see any problems. And then since then, it's just been like friends. It's been very much like the techs aren't as common or as frequent. And I don't know something. He is just like friendly. And I don't know, like, if he met someone else or if something went wrong. OK, it seems a little bit odd, especially because you've been out with him twice and spent the night

I mean Alexis talk so much if that ever happened to you like what's your read on the situation? You better text me the next day What do you think you that you did wrong Alexis? Nothing. Never me. Oh, it's not your problem? Something's wrong with the guy. What a dumb question, Jeffrey. Tiffany, do you think that there's anything that you could have done wrong? I don't think so. I mean, I'm sure it's possible, but that's kind of what I need help with. I just don't know.

It may be, like, I know you're a date-only-one-person-at-a a time type of person, but maybe he's not. Did you guys discuss that? Yeah, like on his dating profile, it said he was looking for a long term relationship and marriage. So he lied about that. I thought we were kind of on the same page. So he does. I mean, like even that is setting the vibe where he's not like a one night only type of guy. The vibe where he's not like a one-night-only type of guy well some guys may be embarrassed by their performance Or something or maybe he's a little shy and he's like is okay wasn't my best. I think we get it No, I think we get it, but Brooke said what so I'm gonna go like it. She's calling him back. Yeah enough affirmation Tiffany doesn't have anything to be embarrassed about right no But sometimes when somebody likes the scenic route

I mean you just want to see the scenes one time and then you're good You don't keep driving back down that same road over and over again Maybe you've seen it before movie yeah maybe he's seen it before I don't know that analogy I've ever heard we're trying to find answers here and hopefully we already kissed one yeah we'll see what he has to say though when we come back and try and get your second date update right after this all right sounds good okay hold on we've been talking to Tiffany about her dates plural because she went on two of them With the same guy. With a guy named Mike the second one ended in a sleepover over at his place

No Another flex I don't know if I've ever called it a sleepover Jeff That's what it was an adult sleepover and Tiffany I feel like we've gotten close enough over the last few minutes for me to call you a nickname at this Point is it cool if I call you T dog or should I just stick with Tiff? No, I prefer Tiffany my friend. Oh the full Tiffany. Okay That's how you know that I'm cool with you if I put a dog

That's how you know that I'm cool with you if I put a dog afterwards, but Okay, J-dog, let's move forward Tiffany is confused because after having this great connection with Mike who maybe I should call Michael to not offend her at this point He's not calling her back and she wants some answers. Luckily Brooke knows exactly what went wrong Brooke. Go ahead tell her I actually have no idea Oh Why would I know? I mean it sounds lovely Brooke always knows everything No You have the answers No What. Why would I know? I mean it sounds lovely. I know. You have the answers.

No. What are we going to do now? I'm bummed out for her. You know, it's a guy who says he's looking for a serious relationship, makes an amazing connection with a woman. Yeah, that great time. Yeah, totally. And then nothing.

Does that make you feel better, Tiffany? There's no reason for him to not be calling you back, but he's still not doing better Hmm, I guess not really Depressed her even more. Maybe there's a reasonable explanation. Yeah, I mean I just I thought he was really lovely It felt really easy. It felt right. I I would really like to see where it goes because I don't feel that like comfort and Natural feeling on stage very often you know I'm really hoping this works out for you well let's find out for sure we're gonna call him

and see what he has to say thank you all right let's get m dog up on the line here we go Jeff don't do that Hello? Hey, what's up? Is this Mike? Uh, yep, this is he. Who's this? Hey, my name is Jeff, but all my friends call me Jay Dog. We don't.

Do they really? I'm sorry. How can I help you? I have a lot of friends, so yeah. Hey, I'm in... I'm sorry, what's going on? Yeah, you're on a radio show right now called Brooke and Jeffrey in the Morning. Hey, Mike.

Hey. Oh, what up, man? Okay, I've kind of heard of you guys. Oh, nice. Kind of. I'm sorry. I'm sorry. I'm sorry.

I'm sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry. I'm sorry what's going on? Yeah, you're on a radio show right now called Brooke and Jeffrey in the morning Okay, I've kind of heard you guys oh nice kind of why am I on this show well You're on this show for a segment We do call the second date update because you went out on a couple hot dates with one of our listeners named Tiffany oh Tiffany huh yeah Sounds like you two had a lot of fun together. I don't know if they were hot dates, but yeah, we went on a few dates. They were interesting.

Wait, did you say that they weren't hot? I didn't find them to be that great. I don't know, maybe insulting a little, depressing a little, let down. She's a nice girl and all, but. What? Oh, no. Didn't she stay the night at your house? This will be depressing.

Yeah. Wow. So cry. I don't know how much you talk to Tiffany, but. So we we did speak to her a little bit from what we've learned. There were two separate dates that you guys went on. Yeah. One was a happy hour. And the second one was I think dinner and then back to your place. Then you watch a movie and she stayed the night.

I mean, dinner was fine. I think here's the thing. Uh, she repeatedly fell asleep during kind of serious conversation about. No way. What do you mean? Well, let me give you an example. Kind of like nail in the coffin for me was I was talking about time I almost died once. I'm like a big outdoor wreck guy. I hike, I climb, I ski.

So I- So wait, wait, wait. Are you sitting at dinner talking about this? Are you back at the house, like on the couch? Where are you? That moment was back at the couch after the dinner. Okay. Yeah.

So I'm, you know, I'm whitewater rafting. I went the wrong way, almost about to go over a falls and was bad And it's kind of the exciting interesting part when I don't die Oh my god, and I look over and I thought maybe she's closing her eyes cuz like ah, it's dress Oh, no. No, she was she was out like a light And you know, I get it we all work like busy she might have been tired But yeah, you fall asleep on like two other phone calls at night when we've just been chatting,

trying to get to know each other. Oh, wow. Oh, jeez. I'm kinda jealous she can do that. Maybe I bore her, I don't know, my life's boring to her, she just likes to hear herself. Can I ask, was she drunk during all of these times that she fell asleep?

No, not drunk at all, absolutely not. I'm wide awake for her stories and she's telling hers and then she Zonks out. I mean, I don't know Interesting because when we talked her Tiffany didn't mention anything about falling asleep probably because she didn't remember falling asleep. That's During the movie because some people you turn a movie on instantly out but the phone conversation I mean I could go to sleep right now And maybe it's a good idea to bring Tiffany on the line right now before she falls asleep Just listening to this because I need to tell you Mike. She's been on the other line this entire time

Oh, wait, what I mean, she's on the line now like listening to our conversation. Yeah, that's how the segment works We have them waiting to jump in. Tiffany, are you awake? Yes, I'm awake. There was a moment there. Wait, you sound mad. Yeah, I'm I'm frustrated because really, I mean, I remember you telling me about the story that you died or whatever.

Like, I remember that every time I was talking about important things in my life that weren't boring and were interesting and full of climax you were not there you were sleeping you were snoozing off. Maybe your life isn't as interesting as you think it is Mike and you need to have more crazy experiences to hold her attention. I mean I guess that's the message but I'm looking for like long-term love and marriage and a partnership. Oh wait though. I don't want someone who falls asleep.

Listen, Mike. Can you imagine the middle of the wedding, like do you take this man? And she's like, how long are his stories? Like, let's be real. I mean, you guys, I mean, it doesn't matter if we think they're boring or not, because Tiffany said to us, Mike,

like when you were on the phone, how amazing you were and how interesting you were and how connected she felt to you. Yeah, I mean, I just felt very at ease and comfortable and I guess You know, it was a Thursday. It was the end of the week I was at peace and I just dozed off a little bit like it's not an insult God, it sounds like he has such a nice couch Yeah, you're the human version of a sleeping

I mean I guess I maybe I get being comfortable around me, but I'm just not into that. Sorry. But you say that you're looking for long-term relationships in marriage. That's kind of what happens when you get married. You kind of just start to tune each other out and fall asleep in the middle of conversations. Am I right Brooke? I don't know that that's how it goes. But not at the beginning. Not at the beginning, hopefully. Yeah. You got a welcome before you were born.

You don't want your marriage to last that long apparently no the next morning she's kind of she was be like I fell asleep so like can you finish the story and you know it's just like what that's even more off-putting to me I thought you guys like had a night together together I never thought I just said I spent the night there Perverts over here that we Fell asleep in the middle of the story and the couch I mean, what do you want like we made out it was like my first time going over there I'm not doing that in first grade. It doesn't impress her It's hard to think of like making out and then getting so tired immediately after the oh god

I think we're kind of losing the point of the problem here Which is her falling asleep while he's trying to talk to her Yeah, you know Tiffany. I really don't think you're as into me as you say you are It's like if you were you wouldn't be falling asleep. Yeah, I really don't think you're as into me as you say you are, because like, if you were, you wouldn't be falling asleep. Yeah. I don't know, I just, I would at least have a better vibe about if you fall asleep once or something, but so many times during, I don't know. I mean, I can't convince you that I had a good time. Like I've told you, I like you, I thought it was natural. I can't convince you of that if you've decided that you bore me, you know? The fact that she reached out to a radio station

to get in touch with you is a pretty good hint that she has feelings, some sort of feelings. I also fell asleep three times. Like actions are louder than words. Yeah, not yet. Alexis is right, not yet. I know, but those feelings aren't mutual. Oh.

Oh, really? That was to the point. You don't even want to give her at least a chance to stay awake for an entire day. We'll send you out at noon to really, and we'll pump her full of seven Red Bulls right before. To a coffee shop.

Yeah. No, that wouldn't do it either. Sorry guys. Well, I'm sorry. It sounds like Tiffany, we're not gonna be able to get you out another time with Mike. You know though, I mean, I'm not hitting on him or anything or anything Jeff, but I got two kids that will not go to sleep

So if he wants to pop by my house Mike if you want a baby we only need you for like 30 minutes In the morning So what happened at Chappaquiddick? Well, it really depends on who you talk to there are many versions of what happened at Chappaquiddick? Well, it really depends on who you talk to. There are many versions of what happened in 1969 when a young Ted Kennedy drove a car into a pond. And left a woman behind to drown.

There's a famous headline, I think, in the New York Daily News. It's, Teddy escapes, blonde drowns. And in a strange way, right, that sort of tells you. The story really became about Ted's political future, Ted's political hopes. Will Ted become president? Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. And he's not the only Kennedy to survive a scandal. The Kennedys have lived through disgrace, affairs, violence, you name it.

So is there a curse? Every week we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedy on the iHeartRadio app, Apple podcast, or wherever you get your podcasts. Don't miss a You vs. You podcast. Join Lex Borrero every week as he sits down

with some of the biggest names in entertainment to talk about the real stuff, the struggles, the doubts, and the breakthroughs that made them who they are. They go deep, covering childhood trauma, family, overcoming loss, and the moments that shaped their journey. These honest conversations are meant to take the cape off our heroes with the hope that their humanity inspires you to become a better you and therefore set you free to live the life of your dreams. Here's a sneak peek. I'm trained to go compete. I'm trained to be like harder but sometimes that mentality stops you from stopping and smelling the flowers in your own garden.

Is it wrong to want more? We migrated, our family migrated here. I'm like second generation. Listen to You Versus You as part of MyCultura podcast network. Available on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. I might be alone on this, but I feel like it is a compliment

when somebody falls asleep while you're talking because they're so comfortable with your voice and your presence No, it's like a warm blanket coming over. That's not how you show you're excited Well, it gives me a great excuse for when Brooke tells me another story about her kids More about the art project Fell asleep because I'm just so comfortable with you and your family that they were doing last night. Sorry, I fell asleep because I'm just so comfortable with you and your family.

So dumb. Yeah. Yeah. Actually, you know, after hearing that, it does sound kind of bad. It is bad. I'm going to switch sides. It's bad.

It's not a good thing to fall asleep during a date ever. No. Especially if someone's mid-story about how they almost died. Yeah, exactly. He must be the worst storyteller ever. Yeah. It must be a long story.

Yeah, long, or maybe it would be more exciting if he did die that'd be a great story to tell be hard I guess I'd be forever asleep. Yeah But you know what if you ever want to get some help getting another date we can be that help for you Yeah, we promise to do better than we did today. Just email the show We'll call that person who isn't calling you back and find any any of our second day podcasts up online, wherever you get your podcast at Brooke and Jeffrey. Like, subscribe, like, subscribe, like, subscribe. Yeah, yeah. It'll help you not fall asleep. So what happened at Chappaquiddick?

Well, it really depends on who you talk to. There are many versions of what happened in 1969 when a young Ted Kennedy drove a car into a pond. And left a woman behind to drown. Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. Every week, we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedy

on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Bob Crawford, host of American History Hotline, Apple podcasts or wherever you get your podcasts. I'm Bob Crawford, host of American History Hotline, a different type of podcast. You the listener, ask the questions. Did George Washington really cut down a cherry tree? Were JFK and Marilyn Monroe having an affair? And I find the answers.

I'm so glad you asked me this question. This is such a ridiculous story. You can listen to American History Hotline on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. On the You Versus You podcast, we welcome Polo Molina, music manager to the stars. From Will.i.am and the Black Eyed Peas,

Ty Dolla $y, YG and Fergie. Here's a sneak peek. Are you so hard on yourself? That's the way I was raised. And the people that were hard on me are not here no more. So I'm hard on myself. You know, make me cry. Listen to you versus you on the iHeartRadio app,

Apple podcasts, or wherever you get your podcasts. podcasts wherever you get your podcasts. Just like great shoes, great books take you places through unforgettable love stories and into conversations with characters you'll never forget. I think any good romance, it gives me this feeling of like butterflies. I'm Danielle Robay and this is Bookmarked by Reese's Book Club, the new podcast from Hello Sunshine and iHeart Podcasts where we dive into the stories that shape us on the page and off. Each week I'm joined by authors, celebs, book talk stars, and more for conversations

that will make you laugh, cry, and add way too many books to your TBR pile. Listen to Bookmarked by Reese's Book Club on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What happens when we come face to face with death? My truck was blown up by a 20 pound anti-tank mine. My parachute did not deploy. I was kidnapped by a drug cartel. When we step beyond the edge of what we know.

I clinically died. The heart stopped beating. Which I was dead for 11.5 minutes. And returned. It's a miracle I was brought back. Alive Again, a podcast about the strength of the human spirit. Listen to Alive Again on the iHeartRadio app, Apple podcasts, or wherever you listen to your favorite shows.