Brooke and Jeffrey: Second Date Update - Second Date Update: An Ex Walks Into A Bar

Episode Date: March 27, 2026

You’re gonna be shocked when you hear how BRIEF the conversation was that brought our listeners date to a COMPLETE and INSTANT STOP. Avoid this sentence if you can, once you hear it, in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

How can 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. End of 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 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 inheriting 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 their 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. Find out how it ends. Listen to the OK Storytime. podcast on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Lori Siegel, and on my new podcast, Mostly Human, I'll take you to some wild corners of the tech world. I'm about to go on a date with an AI companion at a real world cafe right here New York City. There's no playbook for what to do when an AI model hallucinates a story about you. Mostly Human is your playbook for how tech can work for you. Anyone can now be an entrepreneur. Anyone can build an app. And it's very empowering. Listen to mostly human on the IHeart

radio app, Apple Podcasts, or wherever you listen to your favorite shows. In 2023, Bachelor star Clayton Eckerd was accused of fathering twins. But the pregnancy appeared to be a hoax. You doctored this particular test twice, Ms. Ellen's, correct? I doctored the test ones. It took an army of internet detectives to uncover a disturbing pattern. Two more men who'd been through the same thing. Greg Gillespie and Michael Mancini. My mind was blown. I'm Stephanie Young. This is Love Trapped.

Laura, Scottsdale Police. As the season continues, Laura Owens finally faces consequences. Listen to a love trapped podcast on the I-Heart Radio app, Apple Podcasts, or wherever you get your podcasts. 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 pocket. of F1, including the story of the woman who last participated in a Formula One race weekend, the recent uptick in F1 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. Got a little something juicy, a little dramatic, something to make you feel better about your own dating life. Here we are. Yeah. A brand new second date to start your Friday. And before we get to it, Always comments. Yes, and Salima said, Hey, Brooke, Jeff, Jose, Alexis, and everyone else. I just wanted to say that you guys are my primary source of entertainment

when I'm playing on my PS4. Oh, that's a lot from Egypt. Wow. That's awesome. You think she can see the pyramids from her house? Probably not. That's funny a dumb question. You mean it's just a bad, Brooke?

Come on. Not traveled enough. I want to be, though. So we'll come visit soon, all right? Yes. There it is. Do you think her cat is a sphinx? Yeah.

Okay, that was bad. All right, here we go. Let's get this show started. Brooke and Jeffrey in the morning. Second date update. If you're a guy and you're out on a first date having dinner, what are some possible distractions that could derail you that you got to stay away from? Oh, that's a good question.

Like one, a rat runs across the floor in front of you. I think alert everyone, Jeff. Pretend you never saw it. It's probably the owner's pet. It helps him cook the food. like in Rattitoui. All is good. Okay.

Let's go somewhere else. Or distraction too. Let's say the waitress is a little B&L. B&L. Busty and lonely. What? Do not look at her. But she's a B&L.

Don't call her that to her face. You don't, exactly. How do you know she's lonely by looking at it? Oh, you can tell, Brooke. They have that lonely look in their eye. You just keep your eyes on the ground when you put in your order. Okay. And our listener, Eric, had a different type.

of distraction that he had to deal with. Let me guess, a busty rat. Is it maybe that, or could it even be worse than the ones I mentioned? Possibly. Eric, welcome to the show, man. Hey, thanks for taking a call. Absolutely. We'll get to the distraction on your date in a second.

First, tell us about the girl that you met. My name's Vanessa. She works in the beauty industry. Like she's an esthetician, you mean, like that? Yeah, and she is. gorgeous. In fact, I was kind of surprised that she said yes to the date. Oh. That's cute.

And so I thought, you know, I got to turn on the charm. So I took her out. Okay. And I want to take her to this bar and grill. Applebee's. I love that place. No, it's not Applebee's. It's not Applebee. It's got really good vibe. All right. And how was Vanessa when she showed up?

She looked really cute and really friendly and approachable and the thing happened. Okay. The distraction. Yeah, and it wasn't a rat or any of that. Like 20 minutes after we sat down, someone walks in to the restaurant. Who is it? He was my ex-girlfriend.

Oh, my God. I thought you said there wasn't a rat. What are the odds? So do you just, I mean, dang, is it a big restaurant? Can you ignore her? It's not a big place. She was with her guy. She was with her new guy.

It was pretty awesome. When's the last time you saw her? Like, has it been years or it's, like, recent? It was about six months. Okay. Okay. And then I look over, like, a few minutes later, and, you know, I'm trying not to look over, but I see that she's, like, sucking down margaritas, and, like, and she's

laughing, and she's having a great time. Oh, God. I know Brooke is a grade. She's having fun. Well, you know how it is, like, when they come in and they're doing the extra loud laugh just to, like, get your attention. She's, like, hamming it up. I mean, it sucks for you because it ruins your.

your whole date. Even if you don't say anything, you're distracted, you're no longer fully present for... And then if you mentioned your ex, then it sounds like you give a lot of drama. Yes. But did that come up? Did your date, Vanessa, know that your ex was in the restaurant, too? I told her. I said, look,

I was super awkward, but my ex-girlfriend just came in. What was her reaction? She was, I don't know, intrigued. And I was like, don't look, don't look, but she looked anyway, of course. Oh, I want to see. And she's like, oh, wow, she's really pretty.

And I'm like, okay, anyway, let's talk about you. Why didn't you say let's go find another spot? Oh, I offered that. But Vanessa, she was like, no, no, no, it's right. It's right. Like, we were here first, and she had a point. Yeah. If your date wanted to stay through it, then that's on her.

Were you able to get things back on track? Well, that's the thing. I felt like the vibe of the date kind of changed from there. And, like, it didn't never go back. Okay. Oh, no. Are you over? your ex?

I mean, we're not together. That's not the question. I mean, I think that makes it even trickier, right? Because like, maybe Vanessa picked up on that. Well, that's the thing. At the end, I mean, there was this thing that happened. Another thing? At the end of the day, it's like we're walking out.

And I guess I just wanted to show Vanessa that I was sort of like above it all. And so I approached my ex-girlfriend's table and I said hey I hope you have a great night it was good to see you and I said your hair looks great. I know I was like why would I say that yeah but she changed her hair she changed her hair and I thought it looked good and it just came out okay well that's the part you probably should admit omit from there the conversation did Vanessa hear you compliment your ex-girlfriend's hair yeah where was she standing even I don't know she might have like she was really close to me. She definitely heard that.

And you didn't introduce Vanessa? I mean, that's the baller move. Yeah, that's like, hey Vanessa. This is my upgrade. I should have done that. Yeah. I just panicked. And I was like, I just conversating with like three or four seconds and then I left. I was out of there. And I'm sure you're all flustered

now walking Vanessa to her car. Yeah. Your hair also looks nice, by the way. What happened when you leave? We hugged in the parking lot and that was it. Yeah, this is awkward. But from the way that he's talking about it, you can tell that he regrets how he handled the situation. Yeah, totally.

For sure. I mean, it's totally unfortunate. Do you think the date would have gone flawlessly if your ex hadn't walked into that restaurant? Yeah, it just, it sucks as that happened, but it feels like it's out of my control right now. Yeah. That wasn't your fault. It's a universe. And as long as you didn't, like, go home and post a long TikTok or Instagram post about seeing your ex and how great she looked, but you're past it now.

Or message for that. pathetic to two women, not just one. Exactly. As long as you didn't do that, then we might have a chance to save this for you. Please tell us you didn't do that. I didn't do that exactly. Exactly. Oh, oh, no.

You posted on MySpace. It's going to be one of those where we find out something. Whatever damage you did to yourself, we're going to undo it when we come back and get you your second date update right after this. Hold on. Brooke and Jeffrey in the morning. Second date update.

Let's recap Eric's first date for those of you just joining. Eric met a woman named Vanessa for dinner recently. She's in the beauty industry. And for the first 20 minutes, everything was great. It was perfect. The conversation was flowing. The connection was easy. It was all gravy until Eric's ex-girlfriend walked in and sat down with an eye shot.

Dude, what are the odds? Yes. So vibes changed after that. And he had to admit that his ex was there. He did. He was so weird. He told Vanessa, not sure if that was a bad idea or a horrible idea, but he did it. I mean, he had no other choice. It was necessary.

The worst idea is what happened after. It was on his mind, and that's why right before he left, he stopped by his ex's table and told her she has nice hair. And that's the bad part. So great date if it was just Eric and his ex, but Vanessa was present too and isn't calling him back. I wonder why that could be. Yeah. And as a joke earlier, I said, Eric, you didn't post a TikTok about how good your ex looked that night. And your answer was not exactly.

Yeah, what did you post? What does that mean? Well, I didn't post anything. I just, I did text my ex one time. What did you text her? I'm so sorry for the awkward encounter, and I didn't know what to say. Okay. Okay, that's actually not bad.

It could have gone way worse. Did your ex respond? She gave me a thumbs up. Oh, yeah. Okay. The sexiest of all the things you could write back. She's over it. Yeah, she doesn't like you.

Unless they were both into thumb play. You don't know, Brooke? Ooh, it's their thing. I don't. I'm not even going down. You're not advanced enough to get to that stage of romance. Nobody play thumb wars with Jeff. Yeah.

Definitely don't like any of my post that I sent to you because I'll read it in a different way. But let's find out what Vanessa thinks. I'm going to dial her number and we'll see what she has to say. ready, Eric? I'm ready. All right, thumbs up to that. Here we go. Hello? Hey, is this Vanessa? Yes.

Hey, Vanessa, thank you for answering. Yes, you sound busy, sorry. Yeah, but who's this? We don't want to take up a lot of your time. We're a radio show. We're called Brooke and Jeffrey in the morning. Okay. Good morning. And just to cut right to it, we're doing a segment called the Second Date Update,

trying to help out one of our listeners that you went out with recently. Yeah, who? It's a guy named Eric. Okay. Very sweet sounding guy. Oh, so you like talk to him or whatever so you know what happened. Oh, you're right to the point. And I like that about Vanessa.

There's no sugarcoat and anything here. All that we know that happened is Eric's ex showed up in the middle of the date. Oh, yeah. I actually honestly think he handled that really. well. Oh, really? Oh, that's good. He was worried that he was like awkward about it and yeah. No, he was 100% honest and upfront with me about it. Like, he was really classy. He even said goodbye to her to prove that he's above all the drama. So you were, you like, yeah, you liked that. I thought it was really mature. I was not expecting that. We thought for sure you were

going to say that he didn't seem like he was over his ex or something like that. Oh, no. He told me some stories and oh my god that woman is a piece of work. Whoa. Oh, so he even shared some crazy X stories, huh? Mm-hmm. So is that what upset you? I'm not upset. Where do you keep asking that?

I meant like why you're not calling it back. Yeah, we're trying to figure out what's happened with you since the date with Eric. Yeah. I mean, so we said goodbye in the parking lot, but I stayed. because I wanted to follow his ex home. Oh. What? What?

I'm just saying? Casual way you mentioned this. What do you mean? Does she make sure she got home safe? Well, no. I wanted to make sure that what happened to Eric didn't happen to the guy

that she was on a date with. Wait, what happened to Eric? What was his story? Well, it's his story, so I don't really want to share it, but it sounds like she traumatized him. Oh, no. So what happened when you got,

back to where she was going. Well, he dropped her off and she kissed him, but he did not go inside. And so I went up to talk to the guy when he bent to back to his car. Wait, wait, wait. Whoa. Okay.

You parked, got out of your car, approached his car in the dark. Yeah, because I had to warn him. And I was like, what are you doing right now? Do you want to grab a drink with me? Wait, what? What's the goal by asking you this guy out? Because I wanted to warn him.

Because like Eric told me all these stories and I needed time. If they weren't stories, I could just tell them on the street. You just met Eric. You don't know what's true. What's not true. It's a one-sided story. Like Eric's still alive. It's not like you're saving someone's life.

So what happened when you went out and talked to the other guy? I told him all the things about why they broke up and how she's a big time manipulator. And he was kind of like, maybe I can kind of. to see those signs or whatever. This was like, I think, their second date, and I was like, okay. I mean, she's a bad person, I guess. But you don't.

I mean, I've been talking to Eric for like a week or so before our date, and he seemed like a trustworthy guy, and I absolutely believed him. And so you've got to trust some people out there. Sure. For some reason, Brooke doesn't trust our own listener, who just happens to be on the line right now.

quietly listening in on this phone call. I bet he is speechless right now. Because, yeah, he is there, actually, Vanessa, on the phone right now. Who is? Eric is. Yeah, I'm sorry, I didn't sneak up on you, Vanessa, but, like, what, why, why did you, why would you follow? What? I mean, you know the stories you told me.

I had to save this guy from going through what you went through. Wow. Wow. I didn't ask you to do that. No, you didn't. But I feel like I needed to give him the heads up. Well, I was trying to be honest with you. And now I feel like this could blow back on me.

How? Yes. How, Eric? We mean how, Jeff. Of course the ex-girlfriend's going to find out about this. No, he will not hear from her. I made him promise not to tell her anything. I don't know why he stopped.

going on dates with her. We trust everyone, but the woman we've never spoken. What did your ex do that was so awful? We're on the radio. I'm not going to say that. But you telling me this stuff on our date is pretty much giving me permission to go and tell this guy. Oh, no. Is it?

No, it would be permission if you told me we're going to do that. And then I say, yes, that would be permission. That's what permission is. You had already left, though. Yeah. Superman doesn't ask for permission to save somebody's life when they're in danger. He just swoops in and saves them. Okay, but Eric, honestly, was this guy in any danger because of your ex?

I don't think he was in danger. That's exactly what you said when you started to date her, bro. Wouldn't it have been nice if at the start of your last bad relationship, Vanessa had come up to you on date number two and been like, look, this girl is bad news for you. She is going to hurt you, and she would have been right. I mean, maybe, yeah, it was a pretty bad ending, and I guess that could have been good. See? Clearly, she has a heart of gold and wants to save men from terrible women, but I think we're missing the point here. If I'm just summarizing what I think I'm hearing.

It's not like a glaring red flag that she's following strangers over the night with her car. And interfering in relationships, she knows nothing about. Okay, tomato, Brooke. I pretty much said the exact same thing. We're avoiding the main question here, and that's Vanessa. So why aren't you talking to Eric since that night? Well, I was focusing on making sure that this guy was okay. The other guy.

Have you got him more than one hangout with this guy? Yeah, of course. He didn't believe me at the start. So, like, I went to go talk to him again during the day time. Wait a second. So you are seeing my ex-girlfriend's new boyfriend. Eric, they went on two dates. That's not a boyfriend.

Yeah, don't be crazy. Eric, she ended it for him. Right. She's not seeing him. She's warning him. In fact, I'm seeing him again tonight, and I'm going to warn him for a third time. Wow. Oh, wait a minute. Sounds like he's enjoying the warning. This doesn't sound right. There's something off here.

You know what? Go with your gut, Eric. You're right. The thing that's off is that I haven't offered to send you two out on another date. Thank you for reminding me, Eric, because we would love to put up however much money it takes to get YouTube back together. for one more meetup. I guess I should ask Vanessa, what do you think? Listen, Eric, my focus right now is in this other guy, and once you 100% believe me not to go out with your ex, then I will focus on you. I don't know, Vanessa. Well, we're out of time, and it's sounding like it's a no for Eric.

So instead, the gift cards are going to Vanessa and the dude that she followed home to say from dating your ex-girlfriend. I don't think I've ever said those words in my entire life, but I'm glad that I get to today. No. Because at least it gives Jose hope that someday a woman might follow him home without asking. Oh, yeah, that has to be how it goes down. Oh, so romantic.

Brooke and Jeffrey in the morning. The newest tracks. Let's go. New music. And the next big thing. Always on the new music first. Your first place to hear at home. Because you're going to like it, love her want to play it twice.

Playing now. I heart new music. Your digital station for brand new drops, fresh vines, and tomorrow's bangers. I think we need something new. Discover I heart new music. Always fresh, always first. Stream now on the free Iheart radio. In 2023, former bachelor star Clayton Eckerd found himself at the center of a paternity scandal.

The family court hearings that followed revealed glaring inconsistencies in her story. began a years-long court battle to prove the truth. You doctored this particular test twice in so-ins, correct? I doctored the test once. It took an army of internet detectives to crack the case. I wanted people to be able to see what their tax dollars were being used for. Sunlight's the greatest disinfectant. They would uncover a disturbing pattern.

Two more men who'd been through the same thing. Grega lesbian, Michael Marantini. My mind was blown. I'm Stephanie Young. This is Love Trap. Laura, Scottsdale Police. As the season continues, Laura Owens finally faces consequences. Ladies and gentlemen, breaking news at Americopa County as Laura Owens has been indicted on fraud charges.

This isn't over until justice is served in Arizona. Listen to Love Trapped podcast on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. I would not be surprised if Vanessa hangs around that woman's apartment all next week. She might even move into the building with her Just to warn any future dudes that she stops by with Don't date her She's crazy Trust me, I would know

We never asked she did sound busy when we first called her Like she could have just actually been in her car Outside of her apartment Yeah Just scoping out the place Ready to save any dudes from their own demise It could get worse like if the other girl sees her Then she's gonna start following her

Eventually they're gonna stock each other Yeah You know I feel like he needs to call his accent and warn her. Yeah. It's always good when a crazy girl says, you know, that other girl is crazier than me. Look out.

But there's a whole podcast full of crazy people going on even crazier dates. It's ours. Yeah. So go find it. We're the ones hosting that. You'll feel a little bit less crazy when you find us on Spotify, Apple, wherever you get yours. Brooke and Jeffrey's second date update. Like and subscribe.

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 Rorschach, murder at City Hall, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Lori Siegel.

And on my new podcast, Mostly Human, I'll take you to some wild corners of the tech world. I'm about to go on a date with an AI companion at a real world cafe right here in New York City. There's no playbook for what to do when an AI model hallucinates a story about you. Mostly Human is your playbook for how tech can work for you. Anyone can now be an entrepreneur. Anyone can build an app. And it's very empowering. Listen to Mostly Human on the IHeart Radio app, Apple Podcasts, or wherever you

you listen to your favorite shows. 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 inheriting 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 their 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.

Find out how it ends. Listen to the OK Storytime podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. In 2023, Bachelor star Clayton Eckerd was accused of fathering twins. But the pregnancy appeared to be a hoax. You doctored this particular test twice in so much. I doctored the test ones. It took an army of internet detectives to uncover a disturbing pattern. Two more men who'd been through the same thing. Greg, a lesbian. Michael Mancini. My mind was blown.

I'm Stephanie Young. This is Love Trapped. Laura, Scottsdale Police. As the season continues, Laura Owens finally faces consequences. Listen to Love Trapped podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. 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 F1, including the story of the woman who last participated,

in a Formula One race weekend, the recent uptick in F1 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.