Brooke and Jeffrey: Second Date Update - Second Date Update UPDATE: Marathon Date

Episode Date: March 26, 2026

One of our listeners ended up on a 10-hour long marathon first date and the only thing more shocking than that... is what happened after we hung up the phone! It’s a Second Date Update UPDATE!See omnystudio.com/listener for privacy information.

Getting ready for a game means being ready for anything. Like packing a spare stick. I like to be prepared. That's why I remember, 988, Canada's suicide crisis helpline. It's good to know, just in case. Anyone can call or text for free confidential support from a train responder anytime. 988 suicide crisis helpline is funded by the government in Canada. Ready for a different take on Formula One?

Look no further than No Grip, a new podcast tackling the culture of motor racing's most coveted series. Join me, Lily Herman, as we dive into the under-explored pockets of F-1, including the story of the woman who last participated in a Formula One race weekend, the recent uptick in F-1 romance novels, and plenty of mishap scandals and sagas that have made Formula One a delightful, decadent dumpster fire for more than 75 years. Listen to No Grip on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Bailey Taylor, and this is It Girl. This podcast is all about going deeper with the women's shaping culture right now. Yes, we will talk about the style and the success, but we are also talking about the pressure,

the expectations, and the real work behind it all. As a woman in the industry, you're always underestimated. So you have to work extra hard in a way that doesn't compromise who you are in your integrity. You know, I like to say I was kind of like a silent ninja. Listen to It Girl with Bailey Taylor on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Marsh Madness is here. And if you're trying to keep up with everything happening on and off the court, We've got you covered on the podcast, Flaigrant and Funny.

Do you want to start with the first special for the Big Ten coach of the year? Oh, whatever. Would you like to? Yes. So you're a Spartan, is that what I'm getting? On Flagrant and Funny, we're giving our unfiltered takes on the biggest moments the conversations everyone's having. So whether your bracket is busted or you just want the latest on the tournament,

we got you. Listen to Flacrint and Funny with Kerry Champion and Jamel Hill on the IHart Radio app, Apple Podcasts or wherever you get your podcast. Presented by Capital One, founding partner of IHeart Women's Sports. 10, 10 shots five, City Hall building. How could this have happened in City Hall? Somebody tell me that.

A shocking public murder. This is one of the most dramatic events that really ever happened in New York City politics. I scream, get down, get down. Those are shots. A tragedy that's now forgotten and a mystery

that may or may not have been political, that may have been about sex. Listen to Roershack, murder at City Hall on the I-Heart radio app Apple Podcasts or wherever you get your podcasts. I feel like I can't say this anymore, but I'm always shocked when we have a couple check back in that no way in hell

did I ever think that they would have contact with each other again after this show. It's wild. All right. Your second date update is happening right now. It is brand new. We are going to play you the original second date so you know what's up. And then on the third part, yes, there's a couple commercials. Okay.

You can skip through. Part three, that's when we get them back on the phone to see what's happened since. Yes. All right, comments. Yeah, Queen Alia said, listening to y'all while waiting for a colonoscopy. Oh. I'm nervous, but y'all are making me feel better. My girlfriend told me it's the best cleanse of your life.

Oh, wow. There you go. Yeah, I've heard you, like, lose weight. Hey, there's a motivation for you. There's a positive spin. Good for you. Always get those things checked out. All right.

It's Brick of Jeffrey, and your brand new second day update. Update is on now. We've all heard the phrase size matters. I feel like you guys have heard it more than us. Brooks got it as a bumper sticker on her key. I'm talking about the size of the car, Jeff. Oh, sure. Well, what about duration matters?

That should count for something. That's my second bumper stick. Because one of our listeners ended up on a 10-hour-long marathon first date that somehow just kept on going and going and going. going. And the only thing more shocking than the call that we did is what happened after we hung up the phones. You're going to hear all of that because it's time for a special second date update update.

We're going to do it next. Brooke and Jeffrey in the morning. Second date update. What's the optimal amount of time you should spend with someone when you're on a first date? If it's best case scenario, how long should that hang out last? Best case scenario means we never leave and we get married. I was going to see two hours max. I was going three to four.

I want to know what does it mean when a first date lasts four times that amount. Oh, cute. It means it's cute. Goes on for 10 full hours. Maybe they're lost in the woods. A lot of people go hiking. Okay, but we all agree this is something wrong. I feel like it's not normal, but one of our listeners said that happened to him.

Unless this is a typo or something. Chad. Oh, it's one hour? Is this a typo? It can't be 10 hours. No, this was a marathon date that started early in the day. It literally kept going. Oh, really?

Yeah, it wasn't even planned. Wait, wait, wait. What's her name? Her name's Samantha. Samantha, okay. So we met on a dating app, and we were just supposed to get some coffee and pastries. I thought that was kind of where it was going to end,

and then, you know, I was complaining on going to the gym. Yeah. And she just seemed like she kind of wanted to keep going. Well, yeah, she's got all that coffee energy now. She's got to burn it off and do something else. Yeah. Did she suggest, like, an activity or something? She could be like, I'd go to the gym with you.

She wanted to go to the wine bar. Yeah, yeah, yeah, yeah. That sounds way more fun. Yeah. You get a gym clothes and sweaty and that's just too rough. So you skip Glute Day, Jeff. Wow. I know you're disappointed.

I know. I mean, you must have felt the connection, too, if you're willing to skip the gym for it. How was the white bar? Well, things are going pretty well. she kept asking like tons of questions she was super into me I could tell she definitely liked me and again I liked her too and then we're about four hours in at this point wow you're drinking four hours worth of wine

well we got coffee first and then wine yeah we're trying to make our heart stop your stomach's upset what's going through your mind at the four hour mark I mean I'm just thinking like when is this ending like I like her but yeah because it's like what's next But it's so fun to get kind of day drunk, and then you just say, like, one thing leads to another, and suddenly you're at some house party at night, and you're like, whoa, today was awesome. Yeah.

So we actually, we took some wine to go, and then she wanted to go to the park, and I was like, well, I don't know, we're already here this far. Let's go hang out of a park. Yeah. Let's put some public intoxication on this first day. That's cool. I want to be lunchtime soon. I know. I feel like they need to eat, too.

You need to get something in your stomach. Right. So we're up to like maybe five hours here. And she asked if she wants to go get some dinner. Yeah. So we went to another bar before the dinner. Oh, okay. Are you seeing this as an issue at all?

Are you having fun? A little bit of column A, a little bit of column B. Okay. The buzz is kicking in and I'm having fun, but it's also like, if this is a long time, but again, I like her, he likes me. At the same time, you were saying at hour four, you were wondering when this date was going to end. So it sounds like you just don't know how to politely be like, I need this to be over.

Yeah. So I did say at one point, hey, I've had such a great time. I'm sorry to take up your entire day. Okay. All right. So you gave her an out. I mean, because maybe she was doing the same thing. Maybe both of you don't know how to end the day.

Yeah. Right. Just passive aggressive. What did she say? And she goes, are you kidding? The day has just begun. Hey. Oh, no.

No, but I go in to kiss her and she pulled away. I thought for sure after 10 hours, four different location changes, I thought she wanted me to kiss her. How many signs can you get from one person that they like being around you and like hanging out with you? I would have been making out an hour too. Brooke makes out to say hi. At the wine bar for sure. It's weird that she pulled away from the kiss, though. And where did that happen?

Was that in the restaurant? Is that? No, we were actually, yeah, we walked back to her place. It was right in front of her place. She pulled away and she hasn't returned my phone call since. Had she sobered up any, maybe she was just more intoxicated than you thought. Yeah. She didn't want your first kiss to be a super sloppy drunk kiss.

Or actually a good thing. Or she didn't pull away. She just lost her balance. Oh, yeah. I mean, all could be true, but then that doesn't explain why she won't return my calls. Yeah. Okay. Great point.

So would you be disappointed if after a great 10-hour date, You find out you messed up at the 945 mark. And his last 15 minutes just absolutely killed it for you. Or she blocked out an hour two. I'd be very upset. Okay. All right. She's like everything was perfect until he tried to kiss me.

Yeah. Did you like her more at the end of the 10 hours or less? I kind of just was Carpe Diem season of day and it felt right. So I still just can't explain it. I liked her very much. He was just relieved that it was over. he can go home and take a nap, probably. But let's come back.

We will call Samantha for you and hopefully get some answers about why after a 10-hour marathon date, she is suddenly ghosting you. We'll do it right after this. Hold on. Brooke and Jeffrey in the morning. Second date update.

You're in the middle of a second date update update, and we're going to find out how the couple is doing right after you hear, part two. If you're just joining us for the second date update, our listener Chad went on a first date that lasted longer than most relationships. Ten full hours. It wasn't planned that way.

It just happened naturally where they kept rolling from one activity into the next, to the next, to the next, until 10 hours later, he's finally standing in front of her place, going in for the kiss, and she pulled away. Yes.

Hasn't heard from her after that. Yeah, it sounds like it was an awkward moment for sure. Yeah, but they were both. drinking the whole day, so who knows what the moment was really like. But just to be clear, Chad, you still want to try to get another date with Samantha here? Are you just doing this to figure out why? I wouldn't know both. I want to know why, and I would love to go on another date with her. We had a good time.

But it's interesting, too, because every new activity you guys did was her idea. Right. Not one of them was your idea. That's true. Maybe in her life, 10 hours is a really short date. And she's like, he can only last 10 hours. She's like the opposite of dog lives. She does sound like the type that would have gone out after it.

He left that night. She was up until three in the morning after that. But I don't know. Let's call her. We'll see if she picks up. And I'm dying to know what she has to say about this. Just remember when we get her on the phone, we don't have 10 hours to talk to her. Oh, okay.

We'll do a quick question. Oh, my gosh. What if that's it? She just doesn't stop talking. All right. We might need some help with it. But I'm calling her right now. Here we go.

Hi, is this Samantha? Yeah, who's calling, please? This is a radio show calling you called Brooke and Jeffrey in the morning. Not fun. Hi. Good morning. Oh, okay. That's weird.

Why are you calling me? Did I win something? Yeah. Kind of at the end, you kind of do. Yeah, depending on what happens over the next few minutes here, because this is a segment we do called the Second Date Update. Oh, I think I've heard. this before.

Okay. It's pretty popular. Yeah, some of them go viral in TikTok and stuff. Oh, okay. So you're calling me. So who is the person that I went out on a date with? Oh, we're helping Jeff. Yeah, I really appreciate you doing my job because I'm not great at it.

But there's a guy you should definitely remember because you spent 10 full hours with him, a guy named Chad. I can't tell him that's good or bad. Incredible, incredible. Wow. You think he's incredible? I think it's incredible you're calling me about him. Why would it be so unbelievable?

It sounds like you had a great time all day long. Yeah. Yeah, yeah. How do you spend 10 hours ongoing with somebody if there's not some sort of vibe happening if there's no feelings? I'll tell you. I'll tell you. So he went out with my best girlfriend. Wait, wait, wait, wait, wait, wait, when.

Wait, when? After you went out with him? No, no. Before, months ago, he went out with my best girlfriend. Okay, wait. Did you know this before you went on a date with Chad? I sure did. You knew Chad before you went out with him as having dated your friend.

Yeah. Oh, that's weird. He didn't mention that. Yeah. Well, he didn't know this, but he spent many, many hours with her. Then ghosted her. He was very intimate, liked him so much. He totally, I feel like he.

He led her on. He even took her to spend time with his grandma. Wait. He took your best friend to spend time with his grandma, and then he ghosted your best friend? Yeah. Introduced her. He spent all this time with her, basically, you know, half a day. And then he just ghosted her.

Never replied to her, never called her. Nothing. I know she didn't do anything wrong. She's adorable. She's sweet. Complete ghost. She showed me pictures of him. and I matched with him months later on a dating app

and I ran to her and I was like oh my god you're never going to believe this I matched with him she goes oh you got to go out with him and get him back what oh wait a day your whole 10 hour date was just revenge for him ghosting your best friend yeah we girls gotta stick together yeah give him the message now you know how it feels

give him that message well you know I don't have to tell him that because he's actually been listening to this phone call on the other line quietly this whole time. So he's kind of already heard it. Great. This gets even better. I love it. Okay, you're enjoying this. I feel bad about it. She's like loading now. I mean. Chad, are you there? I don't even know what to say right now. That's really what was going on

the whole time. Yeah, I'm not interested in you. Oh, wow. Wait, wait, wait, wait, wait, wait. I heard everything. you said, but we spent 10 hours, you mean at hour eight, hour nine, when we've had Chardonnay, coffee, all types of food, we've had the most fun all day. You mean to tell me you didn't feel anything? Because I felt something and I'm pretty sure you felt something. Five hours with you and then you go to her. So now you know how it feels. Okay. So you doubled a okay. So it was a little tip for tat. No, there wasn't even a moment in that 10 hour period that you felt like a tinge of guilt, Samantha?

Like he might be a decent guy a little bit? I was enjoying myself so much. Oh, God. And to top it off, you know who else had a great time? Sarah. We laughed for hours. Oh, my God. We're still laughing about it.

I don't even want to tell you that Chad skipped his glute day at the gym in order to extend his date with you. I hope you don't hear that to Sarah. And he really needed that day. I'll tell you what. Oh, wow. Wait. Flat movie. Okay.

Oh, Chad. I mean, do you feel bad about ghosting Sarah? I guess that's what she wanted. Yeah, I mean, it was just a tough time. You know, with my grandma not doing so well. I just didn't feel like I could be dating. I am curious, Chad. Why did you introduce the other date to your grandma?

I was honestly just dropping off medication. It was just a quick errand. It wasn't really like I was introducing it to her. You be quiet, you monster. I mean, okay, listen, Samantha, I know that your friend Sarah was really hurt, but, like, we deal with so much dating on this show that ghosting just seems like the normal way that people get out of things these days. I don't think she should have maybe taken it so personally.

Guys are just playing us all the time and they're playing games and they, you know, so we just felt like, oh, let's get this one back already. I'm scared about Sarah and you have done, but I'm also interested. Yeah. Chad just happened to be wrong. place at the wrong time. I don't know. I can kind of see what Samantha is saying here because I kind of would like to play a little bit of a game

with you. A game of would you like to go out with Chad one more time. I would rather slit my eyelids with razor blade. What? We can see. That is so dark, Samantha. Chad, are you into that?

Yeah, honestly, it just seems like she's so really angry because of what happened with Sarah. and honestly at this point, it doesn't seem like it's going to work out. Okay, man. Oh, you think? Yeah, think. Oh, okay. Right.

Yeah, he didn't answer like he's the one being asked. Yeah. I never know who you're ghosting, too, I guess. Seriously, Chad, now you know if a girl in the future ever says that she wants to hang out with you more and really likes you, red flag. Someone's trying to get revenge on you. We're on our three of this date. It must be awful. Yeah, and you know what else?

Don't say you're going to call the person. Don't say that you like them and you had a great time. She's still mad. Oh, no. She's trying to drag us into hour 10 of this phone call. We appreciate your time, Samantha. We'll let you go. Thank you.

Yeah, all right. Brooke and Jeffrey in the morning. Getting ready for a game means being ready for anything. Like packing a spare stick. I like to be prepared. That's why I remember 988, Canada's suicide crisis hubline. It's good to know. Just in case.

Anyone can call or text for free confidential support from a train responder anytime. 988 suicide crisis helpline is funded by the government in Canada. I'm Bailey Taylor and this is It Girl. You may know me from my It Girl series I've done on the streets of New York over the years. Well, I've got good news. I am bringing those interviews and many more to this podcast. Yes, we will talk about the style and the success, but we are also talking about the pressure, the expectations,

and the real work with the women's shaping culture right now. now. As a woman in the industry, you're always underestimated. So you have to work extra hard, and you have to push the narrative in a way that doesn't compromise who you are in your integrity. You know, I like to say I was kind of like a silent ninja. Each week, I have unfiltered conversations with female founders, creatives, and leaders to talk about ambition, visibility, and what it really takes to build something meaningful in the public eye. Because being a Nick Girl isn't about the spotlight, it's about owning it. I think the negatives need to be discussed and they need to be told to people who maybe don't do this every day just so they know what's really going on.

I feel like pulling the curtain back is important. Listen to It Girl with Bailey Taylor on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I don't know what's going on here. How could there be an update? Either a mistake has happened or some kind of miracle. But for some reason, Chad and Samantha are both back on the phone right now for an update update. Wow. Is Samantha, are you still seeking revenge on Chad?

Yeah. I mean, because last time, Samantha, you made it pretty clear that you wanted nothing to do with him. So what is this? Yeah, I know. I think I said I'd rather scratch my eyes out or something. Yeah, I think it was a little darker, but what's going on with you, too? Well, after we were on, it was like a couple weeks, and I did not feel bad about it at all. I thought he got what he deserved.

Okay. Obviously, he sent me an apology text. Wow. Chad, you actually apologize after taking that verbal beating? Hey. Well, he said, like, you know, again, I'm really sorry. Like, I didn't mean to, like, hurt your friend or whatever. But I really did have a better time with you.

Oh. Like, oh, my God. He's so pathetic. He's still trying. Okay. That wasn't changing your mind. That same day, I had had a pretty big falling out with her, my friend. Oh.

And we had not been seeing eye to eye for a long time. So I thought in my head, well, let me use this Chad to get back at her. Oh, my gosh. Is Chad on the phone right now, too? Is he hearing this? Yeah, yeah, I'm not going to lie. I definitely thought it was a trick. Chad, you're being used twice.

Yeah, bro. Yeah, I mean, I sent her that text and that was sincere. But when she said she wanted to go out with me, I was like, I have to see this. Oh, yeah. Okay. So you went in knowing. Or not knowing. Yeah.

And so what happened? I mean, we went on a date and one date turned two and then it just another and another and we've honestly been hanging out ever since. Oh, my God. Yeah. Like I didn't mean for that to happen, but there was chemistry. It's undeniable. Wow.

Why do I feel like she's still in this for the long game? It's not. You swear you're not like tagging. your old best friend on Instagram and posts of you and Chad. No, no. I'm going to lure him into a marriage and then we're going to get a divorce and I'll be like, ha, that's why.

I like her fights. I like it. Sleep with one eye open. Yeah. It's a beautiful story. Ready for a different take on Formula One? Look no further than no grip. A new podcast tackling the culture of motor racing's most coveted series. Join me,

Lily Herman, as we dive into the under-explored pockets of F-1, including the story of the woman who last participated in a Formula One race weekend, the recent uptick in F-1 romance novels, and plenty of mishap scandals and sagas that have made Formula One a delightful, decadent dumpster fire for more than 75 years. Listen to No Grip on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Bailey Taylor, and this is It Girl. This podcast is all about going deeper with the women's shaping culture right now. Yes, we will talk about the style and the success, but we are also talking about. talking about the pressure, the expectations, and the real work behind it all. As a woman in the industry, you're always underestimated. So you have to work extra hard in a way that doesn't compromise who you are in your integrity. You know, I like to say I was kind of like a silent ninja. Listen to It Girl with Bailey Taylor on the IHeart Radio app, Apple Podcasts, or wherever you get your

podcasts. Marsh Madness is here. And if you're trying to keep up with everything happening on and off the court, we've got you covered on the podcast, flagrant and funny. You want to start with the first measure for the Big Ten coach of the year? Oh, whatever. Would you like to? Yeah, she don't know.

So you're a Spartan, is that what I'm getting? Exactly. On Flakron and Funny, we're giving our unfiltered takes on the biggest moments the conversations everyone's having. So whether your bracket is busted or you just want the latest on the tournament, we got you. Listen to Flakron and Funny with Kerry Champion and Jamel Hill on the Iheart Radio app, Apple Podcast or wherever you get your podcast.

Presented by Capital One, founding partner of IHeart Women's Sports. 10, 10 shots, five. City Hall building. How could this have happened in City Hall? Somebody tell me that. A shocking public murder. This was one of the most dramatic events that really ever happened

in New York City politics. I scream, get down, get down. Those are shots. A tragedy that's now forgotten. End of mystery. That may or may not have been political. It may have been about sex. Listen to Roershack,

murder at City Hall, on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcasts. I became a millionaire overnight and lost everything that actually mattered. Hold on, Sophia. Did you just say they lost everything after becoming a millionaire? That's right. And it gets worse. It's narrating too much drama week on the OK Storytime podcast, so we'll find out soon. This person writes, I just inherited a fortune after losing my mom. And now my girlfriend's entire family is coming out of nowhere with her hands out.

And my girlfriend is already giving my money away. So the girl he wants to marry is already sending money out the door. To find out how it ends, listen to the OK Storytime. podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.