Brooke and Jeffrey: Second Date Update - Second Date Update: Way Too Natural

Episode Date: September 30, 2025

One of our listeners got turned down in one of the FUNNIEST ways we’ve heard in a long time… You’ll hear a brand new way to reject a kiss in the Second Date Update podcast!See omnystudio.com/listener for privacy information.

The murder of an 18-year-old girl in Graves County, Kentucky, went unsolved for years until a local housewife, a journalist, and a handful of girls came forward with a story. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County on the Irish. Heart Radio app, Apple Podcasts, or wherever you get your podcast. And to binge the entire season, ad free, subscribe to Lava for Good Plus on Apple Podcasts. Hi there, this is Josh Clark from the Stuff You Should Know podcast. If you've been thinking,

man alive, I could go for some good true crime podcast episodes, then have we got good news for you? Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout in broad daylight. People using axes in really, terrible ways, disappearances, legendary heists, the whole nine yards. So check out the stuff you should know true crime playlist on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I just normally do straight stand-up, but this is a bit different. What do you get when a true crime producer walks into a comedy club?

Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story. Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life. This is Wisecrack. Available now. Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. In early 1988, federal agents raced to track down the gang they suspect of importing millions of dollars worth of heroin into New York from Asia. I had 30 agents ready to go with shotguns and rifles and you name it.

Five, six white people. Push me in the car, I'm going to what about that? Basically, your stay-at-home moms were picking up these large amounts of heroin. All you got to do is receive the package. Don't have to open it, just accept it. She was very upset, crying. Once I saw the gun, I tried to take his hand,

and I saw the flash of light. Listen to the Chinatown Stang on the IHeart Radio app, Apple Podcasts, or anywhere you get your podcasts. Let's start with a quick puzzle. The answer is, Ken Jennings' appearance on The Puzzle with A.J. Jacobs.

The question is, what is the most entertaining listening experience in podcast land? Jeopardy-truthers believe in... I guess they would be conspiracy theorists. That's right. They gave you the answers, and you still blew it. The puzzler. Listen on the IHeart radio app, Apple Podcasts, or wherever you get your podcasts. Brand new second date to start your Monday.

Okay. Welcome to it. It's Brooke and John. for you in the morning and we're glad happy, ecstatic that you are here. Tired. Oh, I thought we were talking about our own. No, no, no, no, no, no, no. We're a good group, yeah.

I will say, we are a little tired when people call in for our help of them not telling us the whole story. Yeah. This guy left out the biggest, most important detail because he thought it was just normal. Like, yeah. I don't understand people's normal sometimes.

Seriously. But you'll hear it in just a second. Wait, not everyone shows a butt naked to I didn't know. And comments, Alexis, what you see? Am said, my question is, what does Jeffrey do while Brooke does the intro? Where is Jeff right now? He's in the Ox Booth of our other producer.

Jeffrey, you know, started as the assistant producer, and he just really hasn't given up on that role. No. He's always working away. Yeah. Yeah. He didn't do a very good job at negotiating his contract. I'll tell you that.

He could have easily gotten out of that job. Ben, you're talking with us, but nope, look at them in there. There he is. Hard at work. He likes to talk. He really loves the work. Yeah. All right, let's get this started. We'll stop talking and we'll get your brand new second date on right now. Second date update.

Every great romantic story usually starts with some kind of awkward, funny, meat, cute. Yeah, that's true. She accidentally trips on her yoga mat and falls right underneath his downward dog. Oh, hello. Hey. Or she accidentally sneezed into her flaming shot of Everclear and caught his pants on fire. Oh, okay. Better than his eyebrows. Yeah.

And one of our listeners apparently met someone in a funny, awkward kind of way. His name is Nick. And I can't wait to hear his story. So, Nick, can't wait to hear who was injured during this meet cute. Yeah, let's find out. Nick, welcome to the show. Hey, thank you so much for taking my call. He's like, I've been a full body cast.

It was so adorable. Thank you for calling me. We'll learn about that. You are going to be kind of like our Ryan Gosling for this, but even more charming, I'm sure. So tell us the name of the woman that you met and how you two came to be. The woman, her name is Sidney, and we met on a pickleball court, actually. Fun. I went by a pickleball court the other night, and it was packed.

Like, I didn't believe it. You just to rotate and play with the older people. But, yeah. Okay. So were you at Brooke, seeing yourself? citizen pickleball tournament. Is that where you met him? No, I was doing league night with my friends. Okay.

And how'd you meet, what was her name again? I'm sorry. Sidney. Okay. We were playing mixed doubles, and while we were playing, there was a rally, and I hit the ball and struck her right in the chest. Oh, like that's a pickleball. They're made to be not people. Yeah, but still sucks.

Like, you hit someone in the neck with a tennis ball. But did you celebrate because you got the point? Yeah. No. I'm going to mock her a little bit. Bro, you better say no. No, no. And so after the game, we usually go out and have a drink.

And so we invite to them, and I pick up the first round because I felt bad about hitting this woman I've never met before. Yeah. But you're playing mixed doubles, so she's with a guy, right? Well, she was with a guy, but it was not so much she was seeing. Oh, okay, cool. Yeah, yeah. That's a good call, that, bro. Yeah, I mean, I just assume always.

that they're together. Yeah, that should be actually a rule in pick a ball, that if you have a partner, you have to kiss. But we'll work on the pickleball rules later. So you took Sydney, and it sounds like a bunch of people went out to get drinks afterwards. Yeah, I think there was like six of us. But Sydney and I talked for a while and realized that we have more in common than just pickleball. Oh, that's cool.

It was really nice, actually, because I wasn't going there to meet anyone. Oh, that's great. At what point of the night did it dawn in you? like oh my god this could be something um i feel like the fact that she never went away to talk somebody else i was like oh she's staying here talking to me oh that's cute that's a good point man it's going to pick that up are you saying is this the date that you were on with her or was there another meet up after oh i'm sorry i'm being slow here this leads to another date okay oh this is tough to me okay so we better get to that other date we only have so much time in a segment

yeah yeah tell us about that so i was like Like, I'm going to the farmer's markets far morning. Do you want to come? Oh, my God. Dude, hold on. Hold on. I got to stop you as a guy. Were you really going to the farmer's market or did you know this is perfect?

Well, I do know that there is a farmer's market. Okay. It was a move. But it's cute. That's a great idea. It's a cute date. Okay. So we went to this huge farmer's market.

I've actually never been before. That's great. What is this? Okay. And we walked all around and it was really fun. And then after that, we walked to a park and walked all around this huge park also. And we were together for like three hours. Oh, my goodness.

Walking, talking. Getting your steps in. Yeah, you know, and stuff. Like, I can't believe you said getting your steps in in a sexy way. Yeah. You guys clock and miles. Three hours of straight walking is a lot. That is true.

No, for real. You felt like you were connecting, obviously. Yeah, and then I walked her back to her car. And I was feeling the vibe. and I leaned in for a kiss and she did this, like, old-timey comedian thing where she, like, went straight down like it was an elevator.

Oh, like, she bent down, like, physically? Like, she literally ducked. Yeah, ducked. Was that a joke? No, I don't think so. I ended up kissing, like, the top of her hair. That's so. How did you recover from that?

What did you say? I was just like, huh, all right, see ya, I'll see us. Oh, no. You didn't push the up button to get the elevator back up to the top floor where you're at? Come on. Or just push her down to the ground at that point in front. That's so awkward.

That's kind of brutal, man. Yes, I feel that. And so then, you know, I haven't, she hasn't texted me back since then. How long ago was the farmer's market meetup? It was about a week ago. Do you think it's just the ending, the kiss? I don't know. I feel like

I feel like I did something something happened but since I don't know what it is it's kind of driving me crazy okay well why would she stick around that long like if she wasn't feeling it I mean you don't get me wrong

some people just like to kiss right away especially like on the fourth date we'll kiss I mean your broad daylight broad daylight kissing in a pocket is different than end of the night

type of like had a couple of drinks yeah that's not really the vibe yeah it's pretty embarrassing but I just didn't know it was that that And if it is that, I think that's something you can come back from. I would think that, but since you didn't respond, I thought maybe there's something else. All right, well, we're going to come back.

We're going to try and call Sydney and get some answers for you and reunite you with your pickleball queen. Aw, pickle queen. I love what you might not call her that? Pickle ball. It's really, really important that you say that. We'll do it with your second date update right after this. Hold on. Second date update.

It sucks getting rejected. her a kiss the normal way. But it sucks even worse when you lean in and they bust out a comedic elevator going down move so that your lips meet the top of her hairline. Dude, please don't tell me she like push the button first.

But I mean, it sounds like a joke, but that's actually how Nick's date ended with a woman that Brooke remembers her name. Sydney. Sydney, that's right. I think Jeff was just checking because he forgot.

Yeah, I actually kind of forgot too. Well, now we remember it's Sydney and they spent three hours together so a really strange way to end the date. She might have just not been ready for the kiss. That's no bad on her. Sure, but now that a full week has passed

it's pretty clear to Nick, something is up. Yeah. And he just wants to know exactly what that might be. Before we call her, Brooke has generously offered to give you a good luck kiss on the cheek though. So Nick, how much tongue do you want with it? Are you talking to me?

Yeah. Yeah. I can say all tongue. too. No lips. I always use tongue on cheek kisses. We didn't give you a choice there. You just got it. So now that we have luck on our side, let's dial Sidney. We'll see if she picks up the phone and hopefully has some answers for us, but here we go.

Thank you so much you guys for doing this. Don't thank us until you hear what happens after you. He was thinking he for a kiss. I don't know what you're talking about. Jeff. He's not about you. Well, I'll kiss you when we're done no matter what. So here we go. Wait, what? Hello? Hey, is this Sydney? Yeah, it is.

Sydney, thank you so much for answering. This is a radio show. We're called Brooke and Jeffrey in the morning. What's up, Sydney? Hi, good morning. Hi, is this the radio, you said? Yes, and you're talking to the star of the show, Jeffrey Dubot. Oh, yeah.

It's totally how it's called. You can Google it. Your name pops up every once in a while if you go down really far. Pitch 200. Yeah. I'm on there anyway. So what's going on exactly? Sorry, Sydney.

We're doing a segment from our show. It's called, I'm not sure if you're familiar with something called the second date update. Not really now. Okay, that one will pop up on Google, unlike Jeff's name. Okay. So wait, it's about a date? Yeah. It's about a date that you went on recently with one of our listeners named Nick.

Oh, yeah. Yeah. Yeah. And apparently you're not calling Nick back like a week later. So he's reached out to us to try and help him figure out why. Right. Sounds like you two had a lot in common. You met at pickleball. He talked forever, it sounds like, when you did the farmer's market. Yeah, we talked for a while. Which must mean you had some sort of connection going on.

Maybe more like I couldn't quite find a way to get myself out of there. Oh, really? Oh, no. At what point did you want to leave? I mean, like an hour in, I was kind of ready to go. Oh. That's interesting because we definitely did not get that vibe from Nick. His read was that it got better and better and better.

I want to know why you wanted to leave. Yeah. I mean, the conversation and stuff, like, he seems like a nice guy, but there was just some stuff that. was it just wasn't my vibe I don't know Okay something you guys didn't match on Could you be a little bit more specific

About what stuff you weren't vibing with You guys had different favorite colors Okay so He wanted to go to the farmer's market right As soon as we got to the farmer's market He took his shoes off And then asked like one of the people at like a stall To like watch them for him

He left his shoes at one of the booths? Yeah And then, like, proceeded to walk the whole farmer's market without shoes on, which, like, ow. Is it all on grass? No, not on grass. What the heck? He went barefoot over a pavement in a farmer's market? Yeah, we were downtown in, like, the city farmer's market.

Oh, no wonder the walk took so long. You can't move very fast. It's like, yeah. I mean, I don't blame you. I mean, you're just fast-forwarding in the relationship. You're like, dude, I don't want those feet in my bed. No, that's what I was thinking, too. Why didn't he do that, though?

That's really interesting. He just kept being like, oh, I can really feel the earth right now. Like, I'm like, bro, you're walking on cement. I mean, I've met people that are like that, but the people are like on airplanes that'll immediately take off their shoes. I had a college teammate that refused to wear running shoes. It was a problem. Oh, what? But that's usually like a hippie vibe, you know?

And he didn't seem very crunchy to me. I don't know. So that feeling of ick about his bare feet carried over for the next. next three hours? Yeah, and it, like, got worse, too. I was, like, really doing my best to just kind of, like, pretend. Like, he wasn't doing that. And then he's like, okay, you want to go to the park?

Oh, that's right. At least there's grass in a park, theoretically. I'm hoping he picks up his shoes at some point. There's some poor booth owner that still has his shoes. No, he, like, grabbed his shoes and he's, like, walking around with him in his hand. Oh. It's like girls in Vegas. So you got to the park, and now he's holding his shoes.

and what happened there? So we sit down on the bench. I'm already, like, really fighting the whole ick thing, but I'm just, like, trying to power through. And then all of a sudden just gets up, walks over to this tree not far away from me at all, like within eyesight, and just goes to the bathroom behind the tree.

What? Wait. Oh, what? I don't even want to ask number one. Just like public urination on a date in the middle of the park. Yeah, in a public park. I mean, I don't know. I get, like, guys do that sometimes,

but like on a date? Yeah, not on a date. Public park should have public bathrooms. Yeah, but he probably did want to go into a bathroom barefoot. Oh, that's it. A little Bernie Spears situation. That actually is great. We can back him on that one.

He has standards. Yeah. So it's the bare feet combined with the going to the bathroom in the park that gave you all of the icks. Yeah, exactly. He's just a little too, one with nature for me, I think. Okay. Well, I can't speak to him being one with nature, but I do know he is one with this telephone call right now, because he's on the other line, listening and wanting to talk to you.

Shoes on or shoes off, though? Who knows what's on? Nick, are you there? I'm here, yep. Hey, hey. Sound a little embarrassed. I mean, it's good to know. Okay.

I can't believe you didn't think of this before. Yeah, maybe you need to address to her what was going on with your attired decisions. I think she's in shock that he's on the phone. Yeah. I haven't heard anything from Sydney. Sydney, are you okay? I don't know. This is just awkward.

Nick, why don't you talk to her? I mean, you have a lot of explaining to do, dude. I didn't know about you, honestly. I really, really do not like wearing shoes when I'm outside. In the city, on the street. Yeah. And, you know, I do wash my feet before I climbing to bed. Just put that out there.

That's actually a relief. That's reassured. Well, you would have had to wash them quite a lot that day because they were black when they got to the park. That is, I mean, I'm not denying that. That is true. We're focusing a lot on the shoes. What about the other big red flag during the date where you went to the bathroom in the park?

Yeah, well, I feel like... Are you with nature? Is that you, like, connecting with nature again? I'm not connecting with nature, no, but I do believe that trees have been around longer than plumbing. What? That's not... I mean, it's true. I'm kind of following the logic, actually.

Now I'm worried how he washes his feet off. Man, you're on a first date. You don't want to pee in front of anybody on a first date. Yes, I understand. But in my defense, the tree was blocking me from sight. Okay, so it wasn't in front of her directly. It's kind of behind her. Oh, Sidney, you didn't see it, so it's fine.

Yeah. I didn't have to see it. I heard it. Oh, nobody wants that. Well, if you can hear it, that must mean it's pretty healthy. Yeah, you got a strong stream. Strong urethrust. So I don't know if that's really a selling point, but that's what we're going with.

Yeah, we were walking for a long time, and I had to go. Yeah, but man, there's like, there's public restrooms for that. It's like you said, he couldn't go in because he didn't have his shoes, Brooke. This was an emergency. Out of all the people defending being shoeless in public, I didn't expect it to be you. Somebody's got to stand up for Mother Nature, and shockingly, it's me. Okay. Me and Nick.

And I'm also going to stand up for love today because I'd like to offer a second date for you, Sydney. if you'll agree to meet up with him one more time, we would pay for it. And he might even agree to wear shoes on the next one. Shoes on. Shoes on. Oh, wow. Look at that. His boundary is a date with you. Yeah, I don't know about that. I just feel like we're different people.

That's not always bad, though, you know? I actually feel pretty okay about all of this. Pretty okay. Well, you know what, Sydney? We appreciate you answering the phone and just being fully honest with us about what really happened. Yeah, of course. I'm sorry, it didn't work out. Just the way it is, man.

Hey, we never complimented her on her way of dodging a kiss. Being so unique. Oh, we told you about that? Yeah, yeah. I did pretty good, right? Yeah, like reflexes. Yeah. Yeah, a little too good.

Yeah. Okay, but we don't want to leave you empty handed or empty foreheaded Nick. So before you leave. Oh. There you go. I think he just dodged last first. Did you duck neck? Damn it.

Brook and Jeffrey in the morning. All I know is what I've been told, and that's a half-truth is a whole lie. For almost a decade, the murder of an 18-year-old girl from a small town in Graves County, Kentucky, went unsolved, until a local homemaker, a journalist, and a handful of girls came forward with a story. I'm telling you, we know Quincy Kilder, we know. A story that law enforcement used to convict six people and that got the citizen investigator on national TV. Through sheer persistence and nerve,

this Kentucky housewife helped give justice to Jessica Curran. My name is Maggie Freeling. I'm a Pulitzer Prize-winning journalist, producer, and I wouldn't be here if the truth were that easy to find. I did not know her and I did not kill her, or rape or burn, or any of that other stuff. They literally made me say that I took a match and struck and threw it on her. They made me say that I poured gas on her.

From Lava for Good, this is Graves County, a show about just how far our legal system will go in order to find someone to blame. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County in the Bone Valley feed on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. And to binge the entire season ad-free, subscribe to Lava for Good Plus on Apple Podcasts. Then have we got good news for you. Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time.

There's a shootout in broad daylight. People using axes in really terrible ways, disappearances, legendary heists, the whole nine yards. So check out the Stuff You Should Know True Crime playlist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. You know, normally if shoes are coming off on a first date, that's a pretty good sign that things are moving in the right. direction. I mean, you know he doesn't leave his socks on during the acts. No. But yeah, in this case, it was not a good sign.

It was a weird sign. Yeah. I didn't expect that of him, honestly. No, we didn't see that coming. Alexis, which was worse for you? Walking around barefoot or the urinating in public? Barefoot. The barefoot?

Why? Being in public, I'm jealous guys can kind of do that anyway. Yeah, honestly. It's fun. But I feel like if he's on a hill and he's barefoot, Downhill I'm just saying I head did not go there

God you really thought that out bro Brooke needs to do a wilderness survival show and this needs to be episode number one Dude gravity is not your friend when peeing in the woods Okay Let's pitch it to Nafrolet

But make sure to add all of those For your first date checklist Show up on time Tip your waiters, keep your shoes on Don't pee on trees Come on Brooke And make sure you're not peeing on a slope If you're going to be barefoot

valid there you go so much you can learn by listening to our second date updates you can find them online wherever you get your podcasts they're at brook and geoffrey the murder of an 18 year old girl in graves county kentucky went unsolved for years until a local housewife a journalist and a handful of girls came forward with a story america y'all better work the hell up bad things happens to good people in small towns. Listen to Graves County on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. And to binge the entire season, ad free, subscribe to Lava for Good Plus on Apple Podcasts.

Hi there, this is Josh Clark from the Stuff You Should Know podcast. If you've been thinking, man alive, I could go for some good true crime podcast episodes. Then have we got good news for You. Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout in broad daylight, people using axes in really terrible ways, disappearances, legendary heists, the whole nine yards. So check out the stuff you should know true crime playlist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I just normally do straight stand-up, but this is a bit different. What do you get when a true crime producer walks into a comedy club?

Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story. Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life. This is Wisecrack. Available now. Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. In early 1988, federal agents raced to track down the gang they suspect of importing millions of dollars worth of heroin, into New York from Asia. I had 30 agents ready to go with shotguns and rifles and you name it. Five, six white people pushed me in the car.

Basically, your stay-at-home moms were picking up these large amounts of heroin. All you got to do is receive the package. Don't have to open it, just accept it. She was very upset, crying. Once I saw the gun, I tried to take his hand, and I saw the flash of light. Listen to the Chinatown Sting on the IHeart Radio app, Apple Podcasts, or anywhere you get your podcasts. Let's start with a quick puzzle. The answer is Ken Jennings' appearance on The Puzzler with A.J. Jacobs.

The question is, what is the most entertaining listening experience in podcast land? Jeopardy-truthers believe in... I guess they would be conspiracy theorists. That's right. They give you the answers and you still blew it. The Puzzler. Listen on the I-Heart Radio Act. Apple Podcasts, or wherever you get your podcasts.