Brooke and Jeffrey: Second Date Update - Second Date Update: Dating Is Such A Chore

Episode Date: October 5, 2026

Mike and Chrissy’s first date sounded like the start of a horror movie… Why was a mysterious stranger watching them silently the whole time?? We needed more details in the Second Date Update podcast!See omnystudio.com/listener for privacy information.

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Must be 19 years of age or older to play. Ontario only. Please play responsibly. Concerned about your gambling or that of someone close to you, visit connectsonterio. I'm Melissa Jeltson, host of the What Happened to Her podcast. We're kicking off the season with the Sandra Birchmore story, a case the police rode off as a suicide in a snowstorm. Her family never bought it, and the man they suspected wore a badge. You never know who that devil is because he's wearing in disguise. Sometimes it's a police uniform. And you can get access to all episodes

100% ad-free with an I-heart True Crime Plus subscription exclusively on Apple Podcasts. available only to IHeart True Crime Plus subscribers. So don't wait. Head to Apple Podcasts, search for IHeart True Crime Plus, and subscribe today. Lisa? Tell them about our new show. We have a new podcast. It's called Don't Lie to Me.

I'm Lexi Youanu. We're two best friends, 22 years apart, but so close at heart. And I'm Lisa Di Giulio, the old one, which means we have wildly different references, occasionally different opinions, and at this point in my 50s, I've lived it all. Now in my 30s, being the founder of new shoes, good taste is my business. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Lacey Mosley, author, actor, stand-up comedian, creator, and host of Scam Goddess Podcast. The True Crime Comedy Podcasts all about robbery, fraud, and those who practice it.

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We're doing it again. Another new episode. It's Brick and Jeffrey. And thank you for finding the second date podcast. Yeah. Yeah. We're going to get to the new one here in just a second. I've seen a lot of people commenting on second dates that are over a decade old.

Yeah, which is wild to me. And they're like, this is a repeat. And I'm like, yo. You listen to 2014, my friends. Yeah, you're like, that's not even the right show. Yeah. Scooch up to the present. We got new episodes for you.

What do you got in the comments, Alexis? Yeah, Brody Thompson said, I always tried playing these in the car with my friends, but they all think it's weird. So I go home or drive home and listen to it myself because I love you guys that are my favorite podcast. That's right. A little secret. Yeah, that's right. You could be ashamed of us. Yeah. You're not the only people in our lives that are ashamed of us.

Yeah. So let's get to your brand new episode right now. Brooke and Jeffrey in the morning. Second date update. When it comes to dating, at least for guys, a big part of impressing them is demonstrating your value. What do you mean? Well, some guys can do it just by dressing. nicely for the date or treating

the server really well. Other guys do it by accidentally dropping their bank receipt right on the dinner table. Like, oh, whoops. Is that my checking account balance? Why are there so many commas and extra digits in there? That's weird. I know that looks

like a bank error, but it's not. Alexis is smiling really big, by the way, as I'm saying that. It's what all real real people do, I'm sure. Definitely. But our listener, Mike, said he demonstrated his value, a few different ways, including using humor with a funny opening line. See, that's what I'm talking about. Charming, funny, there's value.

I can't wait to hear this. So, Mike, welcome to the show, man. Hey, how's it going? I thought you were going to give more of a better opening here. Oh, you want to joke? You're not charming the pants off Brooke quite enough. Try again, Mike. Welcome to the show, buddy. Hey, hey, glad to be here. Hey, I think God doesn't want to hang out with him.

That guy sounds loaded. Okay. Now we're off and running. So Mike, tell us about this pickup line that you used on this girl. Yeah. So her name was Chrissy and we matched on the apps and whatever. And listen, she's like very good looking. And I was like, she might be out of my league, but like, let's just go for it.

So we ended up matching. Yeah. And so my opening line was, hey, I saw your future boyfriend. And she was like, oh, yeah? And I was like, yeah. I said, I tried to hug him. but I almost knocked my mirror off the wall. Okay.

I mean, that humor will definitely work on some people. How did Chrissy respond? I got the LOL, you know, LMA, FO, you know, whatever. So she was like, let's get together. She didn't really care what we did. But, like, she was really adamant that I go pick her up. And I drive and I was like, that's fine, like, no problem. That's so strange to me because I feel like in the dating world and the dating

I mean, I haven't done it, but like... That's like the opposite of what you want. Yeah. Like, I would recommend to all my girlfriends, like, meet them in a public place. Don't give them your address. Yeah. Yeah. I mean, I think that's a positive.

She obviously trusts you. Definitely. So how did it go? I mean, I thought it went okay, but I get to the place. I park, I text her here. Okay. No response. Oh.

I'm like, okay, I'm just going to go up to the door. Well, yeah, I think that probably should have been the move to begin with. Yeah. You just pull up and honk like, get out. I'm here. That's what the text here. is exactly right. It's like the modern day home. So you knock on the door and what happens?

Well, I actually don't get to knock on the door because right before I was going to, she comes around from the side of the house. Oh, it's a house here. Okay. Hey, you're here. I wasn't expected, you know, this is like the lost track of time. I'm just doing some yard work. Oh, right. Oh, shoot. So she probably just didn't even have her phone on her. Maybe, yeah. And I mean, being me, I'm like, okay, totally cool. I mean, like, do you need help?

And she said, yeah, come on back. Okay. Wow. All right. Now you're demonstrating your gardening skills, more value. You're the most valuable man we've ever had on the show. That's an issue. I imagine you in your best sneakers and cute outfit.

Like, you're ready for a date. You don't want to get dirty in what you're wearing. That's a good point. Yeah. What do you do? Well, I would say we did yard work, but to be honest, I did most of the yard work. Wait, what? Really?

Yeah. And I'm talking like, I was hauling brand. benches. I was cutting stuff down. Oh my gosh. Are you feeling used at any point? I know. It does feel kind of like intentional. Yes. But we were talking so I was like down for it. But I will say

something that was strange was apparently she like lives with her brother. And he didn't want to help her. But he watched us through the window. So I saw him. What? Wait, he never came out and even said hi? No. Not a wave. Not a high. She was like, oh, that's my brother. Yeah, he doesn't

really want to help. Huh. Weird. You think he would help his sister. This wasn't a red flag for you in any way? I told you she was out of my league and I was just happy to be there. Okay. All right.

At any point does the yard work portion of the day end and like the romantic date begin? Here's the thing. I finished my chores, so to speak, right? And she was like, you know, I'm too gross. And let's just reschedule. It's reschedule. What? She owes you at least a cocktail.

She totally used you. Yeah, at least order a pizza. And use your shower. inside. Oh, there you go. To put what clothes on after? Like the sweaty ones back on? His brothers, her brother's clothes, maybe. Oh, that's a weird. Oh, yeah. She won't go to date with a guy wearing her brother's clothes,

Jeff. Yeah, it's a good idea. Oh, okay. How do I always end up at the weird one in these scenarios? Okay, so she says no, she doesn't want to grab drinks, and what? So we have been texting back and forth, like, for a while and I've been asking her about, can you go out on this day? Can you go on this day? I've asked

like three times to, like, go out for these drinks. and she's always too busy, but then continues to text with me. Okay. So that's why I need your help. So maybe she's just waiting until her shrubs grow back so that you have to cut them again? You did too good. Now you're like her better brother, which is awful. You got family zone.

Yeah. You know what I mean? It's like a productive brother to rely on. What level is that? That's worse than friends. That's weird. Okay. So you're looking for us to help you actually lock down like a date.

Romantic. Get it on the calendar. under once and for all. Yeah, I need your help to, like, get a date going, or even just, like, get to the bottom of what is actually going on. I was going to say, figure out if she was just using you for the yard work. I mean, that seems like an important piece of this, right? Yeah, that thought has, like, crossed my mind, but she's initiating a lot of our conversations.

And when I ask her to all these days, she's like, I mean, I want to, but I've got to do this, this and this. So there seems to be some interest. Yeah, she just wasn't responding. It'd be easier. Yeah. Something's up. That's strange.

Because if you really want to, you make time. Yeah. Totally. Well, hopefully figure out what's going on when we come back. Call Chrissy and get your second date update. Hopefully her brother's not snooping in on the conversation. Listening. Well, if he's listening to you, he's got to figure out who borrowed his clothes, Jeff.

So I wouldn't blame him. And hopefully the boyfriend isn't still in the mirror peeking at us either. We'll do it. Oh, you really like that joke. It's called the callback. Let's edit that out. Now, pat myself, excellent humor. Second date update continues.

Peak comedy right. after this. Brooke and Jeffrey in the morning. Second date update. Man, how much fun does a yard work date sound? Sounds fun for her. Yeah, I mean, it might be fun if you had actually planned on doing it, but our listener, Mike, didn't know until he showed up to his date,

Chrissy's house and learned that she'd lost track of time, was in the middle of doing yard work, and he offered, like a gentleman, to go and help her out with it. but after a few hours of cutting branches and mulching leaves and whatever they were doing, Chrissy said, now I'm feeling too gross and tired to go grab drinks. Let's reschedule this for another time. And to her credit, she has stayed in contact,

but just can't seem to find an open slot in the calendar for that second date. And both Brooke and Alexis were saying red flag. Why, Brooke? It's hard not to speculate that she planned it all, right? I don't know, maybe in the story we missed where she was like super apologetic and incredibly grateful and wanted to pay you back in some way. Did that happen? I mean, yes and no, right? Like she was thanking me and was like, inside I did a good job or whatever.

But like, no, she hasn't like attempted to pay me back for it or anything. Let me just like buy you dinner, right? Like it feels like. Or have her come to your house and do your yard work. Oh, that'd be sweet. Let's hope you don't live in an apartment building. Yeah. Yeah, I mean, listen, I don't know what's up with this girl.

I just need the closure. Like, what's going on? Is it yes or no? You know what I mean? Okay. Let's try to get you some of that right now. We'll call Chrissy and hopefully get you some closure. And if not that, at least book you for another yard work session.

Because it sounds like he did a great job. So let's lock it in. I'm going to dial it right now. Here we go. Hello. Hey, is this Chrissy? Yes, it's Chrissy. Hey, I'm not sure if you know us, but we are a radio show.

called Brooke and Jeffrey in the morning. Hey, Chrissy. Welcome to the show. Hey, good morning. I think I recognize those voices. I've heard you guys. We go viral sometimes online. Yeah.

That's actually kind of like my friends. I was just with some girlfriends. They're like, hey, a friend of mine sent me one of your clips. She has no idea that I know you. Yeah. I'm like, wow. This is kind of cool because now you get to be on that famous segment. Hey.

Me? You. Okay, what's this about? This is about a guy that. that you were scheduled to go on a date with, and you did kind of hang out, according to him. His name's Mike. Oh, Mike. Okay.

Nice guy. He's real nice. Yeah, good looking, too. Oh, he's going to be excited to hear that. I mean, I guess this is kind of different, too, because you guys are still talking. We're texting, yeah. We've been trying to see each other.

Yeah, he mentioned that to us, but according to Mike, there's been a struggle to lock down a specific date. and he feels like it's more in your court, like you're shutting it down. He doesn't know why. Well, just I've been kind of busy with different things here and there, and I'm trying to sort out a few things. That always sounds like maybe you're in a relationship right now.

Is that what it is? No, no, I'm no longer married. Married. Well, that would be a relationship. Yeah. No longer. No longer married. All right.

So has it just? not been enough time since the divorce. Is that what it feels like? Yeah. It's just super messy right now, but I do want to see Mike. Ooh. We love, we love messy. I would love to hear more.

I know we're kind of strangers to you, but would you mind opening up a little bit about like what's holding you back from seeing Mike again? Yeah. Or even like just going into more details about your date. Like he mentioned the yard work situation. We thought that was pretty noble of him, like step in and help. Yeah. He was great with that.

He really helped me with all the branches and the trees. And I've been trying to get that done for some time. And he's really awesome. Okay. Why didn't your brother help with that? Can I ask? Brother. I don't have a brother.

Your brother was inside watching the yard work. Did you say you don't have a brother? I don't have a brother now. A brother in law? But, no. now what you said is actually making sense now. What's making sense?

Nothing is making sense right now. Hold on. Mike was under the impression that you lived with your brother. That's what he said you told him. I might have told him that. Yeah. So who was the dude in the house?

Yeah. What's going on? Don't hate me. But it was my ex-husband. We're still living together. But we are divorced. Wait. What?

And he's watching and not helping? No, what are you divorced? Yeah, honestly. Tell him to get his ass out there and do the yard work himself. That doesn't make it better than being married and he's not doing the yard work. I mean, I don't want him to be out there. I wanted to make him jealous. Oh.

Oh. Yeah. Wait, so you were using Mike. The whole thing was planned. I thought I was speculating that you just wanted him to come over to do the yard work. A little of both. Yes and no. I mean, he's a good looking guy.

Why were you wanting to make your... Ex jealous. We were married to him. You already had him. Yes. It does feel good, though, to get back at your ex a little bit. It was the only thing I could do to think of getting him to feel jealous, and he got to watch all of it, and I'm sure he was burning up a bit from watching it.

Oh, my God. Cubs out offers ice tea. You're probably right that your ex was burning up watching that happen, but I feel like Mike might be burning up, too, as he's listening to this conversation, because he is on the other line, right? No. Yeah. and he's been waiting to talk to you.

You've got a lot of men watching you from afar. Yeah. Mike? Uh-oh. Yeah. Yeah. I'm sorry. I just got to go through this again.

All right. So you wanted me to pick you up so that you could show me off in front of your ex-husband that you told me was your brother just to make him jealous. You're really, well, you're really handsome guy. Yeah. I mean, that is flattering. And I do like you, though. I do.

So, so, I mean, like, was there ever a moment where, like, you actually want to go on a date with me? Like, I'm confused. Did you just bring me over there to make him feel jealous? Because that's what it sounds like, right? That was the main reason. But in the two hours when I'm watching you cut and mow and do all those manly things, I was like, wow. So once you saw my manual labor, you were like, well, maybe. I was definite

Not a maybe Definite You're still living with the ex-husband You're not over What's definite about it? I have to find an apartment And I'll be probably out of it In another month

I'm looking around It's not so easy to move Do you know what I'm hearing She needs help with moving in a month That's what I was going to say Well only if he wants to It's nice to give him a choice in the matter That is kind of sweet

So Mike, sorry, I know you asked a lot of questions to her, but we don't really know how you feel about Chrissy after hearing all this information. Are you still interested in meeting up again? Because if you were, we'd pay for it. Come on, Mike. I think you're amazing. I think we would have fun together. I just need a little time to find an apartment and then I'll be good. Plus, if you drive by, you can make him cellist a second time.

Oh. Everybody wins. Yeah. In all seriousness here, everything you're saying, I could totally accept in a text message, in a communication that is not right here and right now. We've been talking for so long. What, you'd accept it as in you'd be okay with it? Yeah, Mike, are you saying that you're offended that she lied to you about this whole secretive plan for a while? Like if she had been clean from the get-go, you'd be gay?

And what would you mean? Exactly. That's exactly it. I am offended that it's taken this long to get that information. I've asked you out three times and you've been, quote, busy. You could have told me I would have totally been okay with that, but now I can't be what someone's going to withhold that with me. Yeah. If you're going to try to manipulate your ex-husband, at least let Mike in on the plane.

And then have her manipulate Mike. Yeah. You're cool with that. I'm sorry. I didn't hear anything. I was on my phone. What did you guys say? She's hunting for apartments.

We got to give her a break there. Whatever. She's stalking her ex's Instagram, Jeff. Well, whatever it is. Mike, it sounds like this isn't going to happen, so no second date for the two of you. But Chrissy, I mean, what do we say to her? Wish her good luck on her apartment hunt? Just get remarried to the guy.

I thought we just start with get off the dating apps. I'm single. You can't tell me how to run my life. Why do I feel? You sound like her ex-husband. We're going to have three weeks from now a similar call with a guy with a different name. Yeah. He's like, this girl made me go to her house and wash all of her rugs.

And then help her move to an apartment. We're some creepy guy watching. Brooke and Jeffrey in the morning. The Hard Rock Beck Casino app is now in Ontario. The name you know and trust, which means credibility, impeccable 24-7 customer support, and an easy-to-use app are also here.

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I'm Melissa Jeltson, host of the What Happened to Her Podcast. We're kicking off the season with the Sandra Birchmore story, a case the police rode off as a suicide in a snowstorm. Her family never bought it, and the man they suspected wore a badge. You never know who that devil is because he's wearing in disguise. Sometimes it's a police uniform. And you can get access to all episodes 100% ad-free with an Iheart True Crime Plus subscription exclusively on Apple Podcasts, available only to Iheart True Crime Plus subscribers.

So don't wait. Head to Apple Podcasts, search for IHeart True Crime Plus, and subscribe today. You know what I just thought about? What? The ex who was staring out the window the whole time? Yeah. I think he made the wrong move. He should have hired a hot cleaning service lady to clean the inside of the house while she hired

a hot dude to tidy up the house. outside. It was almost an episode of Fixer Upper with Chip and Joanna Gaines. We were this close. I see. During one of their marital spats. Yes. Yes. Yes. That makes sense. I see. I'm going to watch that show differently now.

Yeah, we were this close to a weird romance, but once again, doesn't work out. No. I still can't believe that guy was like, well, I would have been okay with it had she just told me. I know. Whatever. How hot is this woman? That is a bunch of crazy. Hey, I'm totally not over my ex-husband. He's

going to be here watching us? I want to come over do yard work? I'm in. Say nothing else. And by the way, I still live with him. Yeah. But hey, if you like things a little bit messy, definitely hit up our YouTube page. Listen to all of our messiest second date calls that we've done over the years. They're all there for you. Just search Brooke and Jeffrey. I'm Melissa Jeltson, host of the What Happened to Her podcast. We're kicking off the season with the Sandra Birchmore story, a case the police rode off as a suicide in a snowstorm. Her family never bought it and the man they suspected wore a badge. You never know who that devil is because he's wearing in disguise.

Sometimes it's a police uniform. And you can get access to all episodes 100% ad-free with an I-Heart True Crime Plus subscription exclusively on Apple Podcasts, available only to IHeart True Crime Plus subscribers. So don't wait. Head to Apple Podcasts, search for IHeart True Crime Plus, and subscribe today. Lisa, tell them about our new show. We have a new podcast. It's called Don't Lie to Me.

I'm Lexi Youanu. We're two best friends, 22 years apart, but so close at heart. And I'm Lisa DiGulio, the old one, which means we have wildly different references, occasionally different opinions, and at this point in my 50s,

I've lived it all. Now in my 30s, being the founder of new shoes, good taste is my business. Listen on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hi, this is Kylie Breakman,

Angel Geratana, Jeremy Colhain, Patrick McDonald. And we're the hosts of the Artists on Artists on Artists on Artists Podcast. The Improvised Character Comedy Podcast where each week a new panel of artists discuss their craft. Join us for a panel of Eurovision participants. And we do a little Halloween sometimes. Does the Pope dress up? He winks on Halloween.

He gets right up next to the microphone. I hear you can almost hear the eyelashes hit each other. You never seen Italy so quiet as when the Pope gets up to wink on Halloween. Listen to Artists on Artists on Artists Every Thursday on the IHeart Radio app Apple Podcasts or wherever you get your podcasts I'm Lacey Mosley, author, actor, stand-up comedian, creator, and host of Scam Goddess Podcasts.

The True Crime Comedy Podcasts all about robbery, fraud, and those who practice it. Each week I bring on an amazing guest. Ooh, I scammed them. What? I can talk to you for an hour. You're a generational yapper like me. That's why I had to make yapping a job.

And now you can catch full episodes of my show on YouTube. Start listening to Scam Goddess on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. If anyone wanted to commit a murder, up here would be the greatest place in the world to hide the body. But no one will find it. He acted friendly. He talked friendly. He sounded friendly. They all knew that I did the scary boogie stuff, and I said, maybe she'll find out where this girl is.

I saw him violent. Backhanded her. Listen to The Devil's Quarry Season 2 in the Bone Valley Feed on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.