Brooke and Jeffrey: Second Date Update - Second Date Update: Never Ask About The Ex

Episode Date: December 5, 2025

The guy on the phone today has HUGE regrets about asking his date about Ex...Yet he still wants our help getting in touch with her for a Second Date Update!See omnystudio.com/listener for privacy information.

I know he has a reputation, but it's going to catch up to him. Gabe Ortiz is a cop. His brother Larry, a mystery Gabe didn't want to solve until it was too late. He was the head of this gang. You're going to push that line for the cause. Took us under his wing and showed us the game, as they call it. When Larry's killed, Gabe must untangle the dangerous past, one that could destroy everything he thought he knew.

Listen to the brothers Ortiz on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I knew it was a bomb the second that it exploded. I felt it ripped through me. In season two of RipCurrent, we asked who tried to kill Judy Berry and why. They were climbing trees and they were sabotaging logging equipment in the woods. She received death threats before the bombing. She received more threats after the bombing.

I think that this is a deliberate attempt to sabotage our movement. Episodes of RipCurrent Season 2 are available now. Listen on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts. Cats are masters at using up their nine lives, like chasing laser pointers into walls, or jumping onto high shelves. But the one thing cats never do, text while driving.

So be like a cat and protect your one and only life. Don't text and drive. Don't drive distracted. A message brought to you by the National Highway Traffic Safety Administration, Project Yellow Light, and the Ad Council. And she said, Johnny, the kids didn't come home last night. Along the Central Texas Plains, teens are dying, suicides that don't make sense, strange accidents, and brutal murders.

In what seems to be, a plot ripped straight out of Breaking Bad. Drugs, alcohol, trafficking of people. There are people out there that absolutely know what happened. Listen to Paper Ghosts, the Texas Teen Murders, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas, and destructive companies in the history of business. First episode, How Southwest Airlines used.

cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever. Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Okay, before we get started, I do have to say one week from today, the countdown begins for the top second dates of the year. Yes. Yes, we're going to count down the top ten of this year starting next Friday. You know how we narrow that down. They're all amazing.

Well, it's off of listens. Yeah. Oh, you guys do it for us. Yeah, so there's a number, don't worry. Yeah, there's a number. There's some analytics behind it. Nice. That's always the fun part.

Yeah. I love analytics. No, but today we got a brand new second date update. And I'll just say that there was a lot of talking about exes on this couple's first date. Yeah, there is. And the guy was very into it. So, uh... Yeah, he was.

Which is strange. You don't hear that often. No, you'll hear why coming up in just a second. But comments we love to highlight. What do you see, Alexis? This comment said, hey, I'm the first comment. Love your show. I usually don't.

comment, but mainly I want to hear you to try to pronounce my name. Okay? So I'll give everyone to try. I'm going Mayan, but I feel like that's too obvious. Mayan. Okay. It's M-A-A-Y-A-N. Oh, it could be Mayan. Oh, I love that. Oh, my-en. Because that's

at the end. I can't pronounce the emoji after which is chocolate bar. Good job, Brooke. No, you could do that one. Is it a snack? Yeah, that's right. Your brand new second date starts right now. A lot of people say if you want to date successfully, you've got to be willing to play the game. Oh, well. But others will say, I'm not here to play games.

But then play games anyway. And those people are single and lonely. Okay. But our listener, David, thinks that he's been playing the game too much, too hard for too long. Oh, he's a long-time player. Especially with one lady in particular. and now he fears he might be at the back of the line because this girl is good-looking.

That's according to his email. He has many other suitors, so he's worried he may have screwed it up for himself. David, buddy, welcome to the show. What's going on, man? It's not good, guys. It's not good. We don't know that yet, David.

Usually Jeffrey sets you up and things sound way more dire than they actually are, but not today. Yeah. Well, let's get the story. Tell us this girl's name and why you feel like maybe you mess things up. Yeah, her name's Ava, and we met on an app. Okay. Okay.

I took her to, like, this outdoor mall place, like a tropical drink kind of spot. And, like, Polynesian theme, I think. Cool. Oh, is the Rainforest Cafe? Because that's not really Polynesian. I think it's more Brazilian. Better than that, but yeah. Oh, okay.

That's cool. Tropical cocktails and a fun vibe. Yeah, exactly. She actually really liked it. It's a good thing that she really appreciated that I planned this and I looked into it beforehand because apparently her ex never did that. Oh, is that what she said? Yeah.

Okay. So I said, since you brought it up, is that why you left him because he wasn't really a planner? Oh, okay. We're just going to dive into the conversation about the exes. I mean, are you okay with talking about this at this point or like how are you feeling about where the conversation is going? Yeah, I don't know. Like, looking back at it, I probably shouldn't have brought up.

up, but it was just kind of flowing in the conversation. It was a natural conversation, so I just kind of went with it, you know? Yeah, you're just working with what she's giving you, I guess. It's a real question. All right? Yeah. So you asked, is that why you left him because he didn't plan? What'd she say? Yeah, I mean, she's like, no, no, that's not it, but I'll tell you the story. And it turns out,

she discovered he was cheating on her. Yeah, see, sometimes it doesly do a good story. I was going to say, like, and you want to hear about that. And cheating does take a lot of planning. So maybe he wasn't that bad. Shears aren't at a level. That's his planning energy was going. Okay.

It's kind of weird because when she discovered that he was cheating on her, he came home that night. She actually made him his favorite meal, had a whole candle-like dinner for him, and then gave him the quote-unquote, best sex of his life. Whoa. Whoa. Whoa. Wow. This came up during your conversation.

Is this punishment for cheating? I've never cheated. I kind of want you. I know. What the hell? Why is she telling you? And why will she do that? I know I have had this happen to a friend, too.

Oh, really? I've reacted that way? Yeah. Oh, my God. I need to talk to your friend as well. Alexis is using code because she did it for herself. We know that. It's her quote-unquote friend. All casual, yeah, my friends do this.

This is some weird revenge. Wow. Yeah, I mean, there's more to it. I mean, apparently, after it was over, she asked him, so how was that? And he said, that was the best I've ever had. And she responds, good, because it's the last time you'll ever get it. I know you've been cheating on me, and I'm leaving you. Oh.

Oh, okay. Okay, that's the revenge. But still, it feels like such a good way to get broken up with. Yeah, that is not hitting the way you want it to. Alexis, did your quote-unquote friend do that too? No, I didn't quite end that way for them. I'm guessing they stayed together on and off for the next four or five months. They might be married.

I mean, it's like, where do you go in the date from that point? Do you like the appetizers? So what happened next, David? Well, I mean, that was kind of the end of the date. I mean, we did kiss at the end, but... You kissed after that? Oh, okay. Was it the best kiss of your life?

Because that's a bad thing. That story's just been kind of stuck in my head, because now I'm purposely trying to make her mad at me so she'll want to get back at me. Wait, wait, what are you doing to make her mad at you? Like, we'll go to dinner, and I'll feel fries off her plate just kind of annoyingly. Oh, so you guys have, you guys are kind of dating right now. That's that what you're saying?

We've had two dates. Two days. On the second date, I kind of just started to be kind of a jerk to her. They kind of see what I can get for being misbehaving. Right. Because you want her to be upset with you so that she'll cook you a nice meal and give you the best night. This is not. This is what I can forget the very end where she leaves them.

You're holding onto the wrong part of the story for her. Yeah. Yeah. I mean, I'm just doing the little bare minimum things to annoy her. I'm not cheating on her or anything, you know. I just want to get to the point where she'll want to do those things to me, but she won't dump me. Okay. Okay.

She'll give you a lesser record. I'm going on two dates and you were like one way the first date and then completely different the next day. Maybe she's like, I don't know who he really is. I don't think she wants revenge on you. Yeah. Not yet. She's not invested in you yet. Well, you must be coming to us now because clearly communication is broken down or something like that.

Yeah. What's what's going on? Yeah, I mean, I'm definitely in my head about it because she hasn't spoken to me in a bit. So, wait, I was a jerk to her, and now she's not talking to me. Weird how it plays out. He did say it was bad at the beginning of this. Yeah, it is bad. Yeah, so now I understand why you're probably feeling a little bit remorseful.

I mean, it just sucks, guys, because like you mentioned before, she's been a very attractive woman, and, you know, a lot of guys have been asking her out, but she told me I was, you know, the first guy she's gone out since the breakup happened. Oh. Oh, you didn't. You could have been rebound. Why would you not add that detail? That is so important.

He just said it. He just gave us the detail. I know, but at the beginning. That changes everything. You told your story poorly, so we're going to hold it against you. There's so many more things wrong now. Clearly, you may have dug your own grave here, but we're going to try and turn this around for you. Get you the revenge that you've been seeking.

Is that what you're looking for, or do you think that you actually want to date this girl? I mean, can I ask for both? I kind of want to be in a relationship and hook up with her. That makes sense. Not a lot of relationships go that way, but we'll try to work our magic. Jeff, don't be too rude to her. She may take a liking to you. Be friendly here.

It's going to be a really weird ending when we come back. And we're going to call Ava for you, try to get you your second date update, revenge style. Yeah. Right after this, hold on. Second date update. Never in the history of this show have I heard a tragic breakup story and said, gosh, I wish that would have been me. Oh, my God.

That's so true. But it happened today because our listener David was on a date with a woman named Ava. They were talking about exes and she said, quote, once I found out he was cheating on me, I made him his favorite dinner and gave him the best s s shth you'll ever have in his life. Wow. And then she left him. Wow.

That will show him. Obviously the men in the room learn their lesson too. They're not all begging to cheat now. For some reason, that got into David's head, so he's been purposely trying to annoy Ava so that he can be the beneficiary of her revenge tactics. That didn't really work, though. No, it's been kind of backfiring. And remember, the X was an X. They dated for a while.

True. It wasn't just two days. Totally different situation. That's what's brought him here. Oh, David. Oh, yeah. Where is your head at? A lot of people texting in, oh, David.

Yeah, I told you guys, I screwed up. That's true. So he knows, that's true. I have a question, though, like, are you wanting to own up to your behavior of being a jerk on the dates? Or are you honest about it? Or are you wanting her not to know that was on purpose? Yeah, I mean, I'm willing to if it just kind of comes up organically, but I don't want to kind of put my business out there right away. That makes sense.

Like, if she says, well, I'm not calling him back because he's a jerk. Then we could say, well. Yeah. There might be. He was doing it on purpose. He had the wrong idea of what you liked. Yeah. Yeah.

And, you know, we're about to call her here. But my advice for you, David, is if we do get her on the phone and you do get a chance to talk to her, try and be playful with her. Because it's kind of a funny thing that's happened, this whole way that this was played out. Oh, just Jeffrey advice all of a sudden away. Yeah. It's very rare. I don't usually give advice to our listeners here, but, you know, it's kind of a typical guy thing to think the way that you thought. So hopefully, if you lay it out playfully, she'll see the humor in it.

I can be playful. Okay. Thank goodness for chat GPT, because that, was not my idea. I was wondering. All right, but I felt like you needed it. Anyway, I'm going to dial her number, and let's see if she picks up. Hello.

Hi, is this Ava? Yes, this is. Who's speaking? Hey, this is Jeff. I'm on a radio show called Brooke and Jeffrey in the morning. Yeah, the whole show is here, Ava. Hi. Good morning.

Hi, guys. I had to get my number Great question Yeah We got it from a guy Who listens to our show We've been very eager To talk to you about this guy

Because we know you two went out On a date recently Two dates in fact Yeah, double Yeah Who is it It's a guy named David And so

Oh God Oh What do you mean? Oh God So you're not calling him back on purpose Obviously No response is a response guys. Yeah, definitely.

Okay. That's interesting. Why would you have such hesitation to see him again? I can't believe you guys are calling me about this. It's so weird. He asked us to call you because he's a little bit uncertain about what's happening between you two right

now. Well, I'm not new to the dating scene and I'm like dating around and I want to keep my options open, so why do I have to be locked in on one person that I wasn't that big of a fan of? Oh, but does that mean you liked him a lot? So you were scared you were going to like him too much and you don't want to date anyone?

She just said that she's not a big fan of. Yeah, okay. It's good attempt, Jose. And it's totally fair for you to feel that way, Ava. We don't judge you on that at all. But if I told you that David has been dating for a little bit longer than you, and he feels like he messed up. Oh, you're just going to, okay.

You could probably agree with me that everybody deserves a second chance. What? What? She says what? Everybody's a bold statement. Jeff's really on a advice kick today. We don't know what's exactly going on. We don't even know why she's not a fan of him.

Aren't you curious about that? I 100% agree with you, Brooke. And the perfect person to tell you that is actually David himself. Would she be the perfect person to tell me how she feels? Brooke doesn't know, Jeff. Brooke, you don't understand how dating works. You've been married for too long. Yeah.

No, that you're listening. No, it's not about healthy communication. It's about David explaining what's going on because I need to. I need to tell you, Eva, he's on the other line right now listening to this. Oh, great. Listening to what? I'm not sure because she hasn't said anything.

To us. I don't know if we want her to share anymore. I do. David, are you there? Hey, you? Oh. Hey, David. Alex.

Sorry. What is happening right now? Like, why are you doing this? Well, I'm doing it to get under your skin. Aren't you mad at me? What? That's why you're doing it. Yeah, I kind of am, but also.

like why oh gosh i bet you want to get back with me huh what i hate it you should probably have me over for dinner tonight oh no because i don't want to have anything to do with you i didn't even like hanging out with you you were rude and disrespectful uh well you're right i am that guy and you need to teach me a lesson wow now it's funny they're what is happening what is happening are he doesn't up any signs at all. I mean, David, are you trying to be funny right now? Yeah, that could be in it. Book, he's just being playful, like, what ChatGPT said to do. It's icky.

That's a good word. The girls got the ink. Blame it on ChatGPT. David, you're doing great. Keep going. David, be yourself. Yeah, there you go. I fear this is him. That would be the word. The act was the first day. Okay, David, clearly she feels like

something weird is going on. Okay. You know that story you told me about your ex-cheating? You know, on our first hangout, you said you caught your ex-cheating. So, you know, to get back at him, you made him the best dinner ever. And then you, you know, you hooked up with him. And it was the greatest ever. Oh, my God.

Oh, my God. Are you serious right now? Wait, you thought that was going to happen to you? I mean, would it make you mad if I said yes? He's still trying. He's doing it again. All right. off, I dated that guy for a year, and I would never do that again.

Oh, like, if you know someone cheating, you'd never do it again? You're saying that you regret that revenge move that wasn't really... Of course. Oh, why? Don't say that. It didn't. We're trying to help the guys out there in the world. Probably the meaning, you know, it's like, yeah.

He didn't deserve that. Yeah, we were all like, dude, you gave him a treat on the way out. Yeah, the guy's in the room, definitely. Yeah. The text boards kind of lit up to it. David, are you hearing her? Yeah, and I didn't know that. Well, now you do.

Okay. All right. And so... Yeah, David, you need to follow that up with something, like an apology or... An idea moving forward. I'm not really that person. Okay, then I probably should tell you, like, after you told me that story, I was doing things to bug you on purpose because, you know, I thought it would work. Are you, like, the biggest idiot ever?

I mean, I kind of feel like an idiot now. Oh, my God. So hold on, is that why you kept stealing my fries, even though you had a plate of your own? What? You had your own fries? David. I don't take a big handful of his and put him back on my plate. Fryfinding now.

David, is there anything that you want to say to Ava here? Listen, I'm just telling you, I am a nice guy. No, you're not. You stole my fries, and then you were just rude to me all night. I mean, actions kind of speak louder than words right now. You'd have to, like... But that wasn't the real him, though. I mean, you'd have to have Ava give you another chance to prove who you really are.

Oh, you mean, like, if she wanted to, you know, make me dinner one night? Oh, that's a nice action. Yeah, that's not happening. Good. Do you learn nothing? It's just when you told me that story, it kind of got in my head and it screwed me up. Like, it's kind of your fault for describing it the way you did. Oh, wow.

It's my fault that I was telling you a mistake that I made before, and then you were just trying to make me make the same mistake? Not happening. It was just a story. and I will be honest with you, Ava. Before we had you two together, he sounded very regretful. So why isn't he sounding regretful right now? He has the chance. You have the chance right now, David.

No, he's an idiot. Well, yes. He admits that. He admits that he's an idiot and he feels that way. And that's why I think that you should be willing to give him maybe one more chance. And we'll even offer to pay for the next day. It'll be on us if you say yes. Oh.

Nah, I'll pass. Yeah. You just hear this entire conversation. It's like I lost brain cells. You know how many people say that after coming on our show? That's a good point. But she didn't lose enough brain cells to say yes to another date. So I'm sorry.

Oh, David. Your strategy didn't work. All right, guys. I appreciate it. All right. David, just be yourself next time. I will. And, and, Ava, if you're thinking about this tonight or tomorrow and it gets you really mad,

give me a call. Oh, trust me. I won't be thinking about it. Yeah. Brooke and Jeffrey in the morning. May 24th, 1990, a pipe bomb explodes in the front seat of environmental activist Judy Berry's car. I knew it was a bomb the second that it exploded. I felt it ripped through me with just a force more powerful and terrible than anything that I could describe.

In season two of Rip Current, we ask, who tried to kill Judy Barry and why? She received death threats before the bombing. She received more threats after the bombing. The man and woman who were heard had planned to lead a summer of militant protest against logging practices in Northern California. They were climbing trees and they were sabotaging logging equipment in the woods. The timber industry, I mean, it was the number one industry in the area, but more than it was the culture. It was the way of life. I think that this is a deliberate attempt to sabotage our movement.

Episodes of Rip Current Season 2 are available now. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. For 25 years, I've explored what it means to heal, not just for myself, but alongside others. I'm Mike Delarocha. This is Sacred Lessons, a space for reflection, growth, and collective healing. What do you tell men that are hurting right now? Everything's going to be okay on the other side, you know, just push through it.

And, you know, ironically, the root of the word spirit is breath. Wow. Which is why one of the most revolutionary acts that we can do as peoples just breathe. Next to the wound is their gifts. You can't even find your gifts unless you go through the wound. That's the hard thing. You think, well, I'm going to get my guess. I don't want to go through all that.

You've got to go through the wounds you're laughing. Listening to other people's near-death experiences, and that's all they say. In conclusion, love is the answer. Listen to Sacred Lessons as part of the My Coutura Podcast Network, available on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Is it just a blanket statement that people should never talk about their exes on a first date ever? I don't know about ever. Sometimes people are like, yeah, my ex sucked, my ex sucked, and you bond over.

Oh, I feel like this gives another reason as to why that's not a good idea. Usually nothing good will come out of it, even if the backstory is super juicy. I mean, yes, it's good for us, but not great for the daters. This guy, he just couldn't let it go. No. Let it go, man. It's like, he invented this whole scene in his head, and it's like, it's going to happen. It's like, dude, you're inventing this, imagining this.

It's not you. Yeah. But that's all started with X's. What's a good subject to talk about on a first date, Brooke? Ooh, all of the second date podcast that you totally binge from our... Wow, look at her ready. Spotify. Yeah.

Yeah, send them to more horror dating stories, bro. Or the YouTube videos you watch at Brook and Jeffrey. Oh, yeah. They're up on Apple, Spotify, wherever you get your podcast. You're going to get revenge bangs so hard after that. While listening to maybe a second date update. Whatever you need to do. Let's find them online at Brook and Jeffrey.

I know he has a reputation, but it's going to catch up to him. Gabe Ortiz is a cop. His brother, Larry, a mystery Gabe didn't want to solve until it was too late. He was the head of this gang. You're going to push that line for the cause. Took us under his wing and showed us the game, as they call it. When Larry's killed, Game Must Untangle the Dangerous Past, one that could destroy everything he thought he knew.

Listen to the Brothers Ortiz on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I knew it was a bomb the second that it exploded. I felt it ripped through me. In season two of RipCurrent, we asked, who tried to kill Judy Berry and why? They were climbing trees, and they were savabody. How is she logging equipment in the woods?

She received death threats before the bombing. She received more threats after the bombing. I think that this is a deliberate attempt to sabotage our movement. Episodes of Rip Current Season 2 are available now. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Cats are masters at using up their nine lives, like chasing laser pointers into walls. Or jumping onto high shelves. But the one thing cats never do, text while driving.

So be like a cat and protect your one and only life. Don't text and drive. Don't drive distracted. A message brought to you by the National Highway Traffic Safety Administration, Project Yellow Light, and the Ad Council. And she said, Johnny, the kids didn't come home last night. Along the central Texas planes, teens are dying. Suicides that don't make sense.

strange accidents, and brutal murders. In what seems to be, a plot ripped straight out of Breaking Bad. Drugs, alcohol, trafficking of people. There are people out there that absolutely know what happened. Listen to paper ghosts, the Texas teen murders, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back.

making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas and destructive companies in the history of business. First episode, How Southwest Airlines Use Cheap Seats and Free Whiskey to fight its way into the airline is. The most Texas story ever. Listen to Business History on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.