Brooke and Jeffrey: Second Date Update - #4 Second Date Update of 2025: After Date Double Date

Episode Date: December 26, 2025

One person almost ended up in tears just 9 holes into a mini-golf date..and our listener says it’s all his fault! We’ll have him explain coming in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

I'm Stefan Curry, and this is Gentleman's Cut. I think what makes Gentleman's Cut different is me being a part of developing the profile of this beautiful finished product. With every sip, you get a little something different. Visit Gentleman'scutburbon.com or your nearest Total Wines or Bevmo. This message is intended for audiences 21 and older. Gentleman's Cut Bourbon, Boone County, Kentucky. For more on Gentleman's Cut Bourbon, please visit gentlemen's cut bourbon.com. Please enjoy responsibly.

I'm investigative journalist Melissa Jeltson. My new podcast, What Happened in Nashville, tells the story of an IVF clinic's catastrophic collapse and the patients who banded together in the chaos that followed. It doesn't matter how much I fight, doesn't matter how much I cry over all of this, it doesn't matter how much justice we get. None of it's going to get me pregnant. Listen to what happened in Nashville on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Have you ever listened to those true crime shows and found yourself with more questions than answers? Who catfishes a city? Is it even safe to snort human remains? Is that the plot of footloos? I'm comedian Rory Scoville, and I'm here to tell you, Josh Dean and I have a new podcast that celebrates the amazing creativity of the world's dumbest criminals.

It's called Crimeless, a true crime comedy podcast. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Who would you call if the unthinkable happened? My sister shot 22 times. A police officer, right? But what do you do when the monster is the man in blue? This dude is the devil. He'll hurt you. This is the story of a detective who thought he was above the law until we came together to take him down.

I said, you're going to see my face till the day that you die. Listen to the girlfriends, untouchable, on the ice. Heart Radio app, Apple Podcasts, or wherever you get your podcast. From NBA champion Stefan Curry comes shot ready, a powerful never-before-seen look at the mindset that changed the game. I fell in love with the grind. You have to find joy in the work you do when no one else is around. Success is not an accident. I'm passing the ball to you. Let's go. Steph Curry redefined basketball. Now he He's rewriting what it means to succeed.

Order your copy of the New York Times bestseller Shot Ready. Today at Stefan Currybook.com. All right, here we are. We're at the number four second date episode of the entire year. Oh, my gosh. Thank you for being with us.

If you're planning a fun activity for a first date, is there anything better than minigolf? That's a good one. Dude, minigolf is fun. And they have those little pencils. Oh, especially the ones where you can drink at it. That's good, yeah. Yeah, they have a lot of those.

Because you get a little friendly competition going, a little playful flirting, and of course, the windmill sets the mood for hot Dutch-style romance on the 18th hole. At least you got a little fan. Yeah, you know what happens. But don't. How in the world did one person almost end up in tears on hole number nine? Uh-oh. No one got hit by a flying golf ball, but the dude says it is all his fault.

So we're going to find out what happened in your number four. Second date update of the year right now. Second date update. You guys know the term double date, where you go out on a date along with, like, maybe a friend of yours who also has a date with then. Wow, Jeff. It's two dates at the same time, Jeff. I think everybody knows what a double date is. So explanatory.

Yeah. I'm glad that everybody's on the same page because one of our listeners, Justin, went on a different kind of double date where he saw the same girl twice in one night. Oh. What? You mean he went on two dates in one night. I don't know. Yeah, a double date. Exactly.

Okay. Then it would be second date update, and then we'd be too close to that. So, okay, we'll go with yours. Yeah, it's a different twist on the term. And I'm just curious. It's like an after date. There you go. Justin, what did she say when you snuck up behind her as she was trying to get into her car? Oh, gosh. That's not what happened. I think he's joking. What I think? It didn't really work out that way. Oh, good. Good. Okay, you double date differently than I do. Oh, nice. I guess start from the beginning of your first part of the day. What's this girl's name? Her name is Tracy. Tracy.

Okay, and how did you arrange the first hangout? We actually met on Hinge and we had been chatting for a while and then we decided to go out play minigolf, something that we both were into. And, you know, it's kind of interactive, it's easy. I apologize for my female host. She's not really a fan of fun. No, it's just often people don't describe themselves as into mini golf. You know what I mean? Like you do it, but you're not into it.

You throw the idea out and people go, oh, that sounds fun. But no one's like, oh, my God, I did. nine rounds last week. I'm so ready for our day. Justin, would you like to apologize for the way that you worded that to us? I guess when I brought up the idea, she was into it. I was into it. Yeah, we get it.

We get it. I just tease me a little bit. Yeah, we're just going to make this as difficult as possible. So keep going. We'll keep roasting you. Perfect. So we had a good time, honestly. We like played for a while. At one point, I decided to play a joke on her. So when she turned around to putt, I hid behind one of those big mountains that they have.

And I was back there for a bit and she was calling my name. You hid for her? I heard her say, did I seriously just get ditched again on a date? Oh. Oh. Again, that's what I heard. Like this has happened to her before? You can't jump out and yell surprise after she says that out loud.

Yeah, now you actually have to leave. Yeah, you hear him leave, like run away. So what did you do? Oh, no. I felt really bad, but I was still having fun, so I just kind of came out and surprised her. She definitely was a bit put off at first, I think. Yeah. But she started laughing.

Regardless, I think it was a funny moment. She was angry and embarrassed, but it was funny. Yeah. Well, she must have been really relieved to find out that she wasn't actually getting ditch, so the only place for this date to go is up from here. Also, in your defense, bro, you didn't know that she had been left on dates before and you weren't trying to trigger anything. You were just having fun.

Is it funny regardless? Yeah. It was a good attempt. So. Yeah, like it wasn't really like that butt out. It kind of was in the moment type of thing. Yeah, obviously. She did finally laugh about it.

Yeah, after she stopped crying, she laughed about it. What? Wait, she was crying? No, I'm just kidding. I'm just kidding. Oh, your sense of humor is, it's even darker than mine. Yeah, he's a prankster. All right. So was that like the middle of the night, or did you have a lot of hangout time

after that? So after that, we ended up going back to her apartment and we hung out. We had some drinks. And towards the end, she was a bit tired. She had a long day. So we just kind of wrap things up and we planned to see each other again. So I went outside. I get to my car and I realized someone slashed my tire. Oh, no. Oh, God. Maybe that she was pranking you back. Oh, that is not a prank. Slashed your tire? Do you have like a crazy X or something out there? I'm glad you said. No, not that I know of. Oh, so this was random? I guess so.

I didn't know who it was. I mean, she could have a crazy X, too. Oh, who sees a car in the driveway and... But hopefully not. What was it like going back to her door and telling her what happened? Yeah. First off, she doesn't really live in the greatest neighborhood, so at that point, it was kind of like, I need to kind of get out of here. And I didn't want to wait on the sidewalk for AAA or whatever.

So I went back there. I mean, she was shocked that it happened, but, like, she invited me back in. Yeah, I bet she felt so bad. Yeah, I mean, even though it's not her fault, right? Like, whenever somebody comes over to my house and something bad happens in my neighborhood, I'm like, oh, my God. Save her someone in my apartment parking garage or car gets hit. I'm like, I'm so embarrassed. Okay, so does that mean that you ended up staying the night at her place?

Yeah. Oh, silver lining. But I stayed on this house. I didn't like stand as good or anything. Okay, okay. Was everything okay the next morning between you two? Yeah, actually. So the next morning, AAA came while we were waiting for them to change my tire or whatnot.

We had orange juice, split a bagel. It was nice, actually. Is this the second date? Yeah, I think him going back into her apartment in the same night. That would be the double version of the date. It just clicked for me. Sorry. I mean, guys, I even got a quick kiss before I left.

Oh, you did. I definitely think it ended on a high. Dude, Ann, you didn't have a toothbrush with you. So that says a lot that she would give you a little kid. She better have done that. I mean, at least. And orange juice bread. Okay.

We weren't going full throttle, but I got a kiss. Okay. It was a mouth kiss then. Yeah. Well, it could be like a, oh, I feel bad for you forehead sort of kiss. Oh. Where were you guys thinking? I don't know.

You guys are sick. I need to go, like, wash my brain out of whatever thoughts you were having. It's us. That's the problem there. Yeah, you're poisoning me. And once we're all fresh and clean will come back. and do a very clean version of a second date update. I mean, I can't promise that, but fingers crossed, I'm hoping.

Keep it clean right after this. Second date update. If you're just joining us, our listener Justin had his first date end with his car tire randomly getting slashed. So we know he lives in Alexis's neighborhood. She's not arguing against that. No, no, no, our cars get stolen. Yeah, yeah, yeah.

All four tires got. But this specific incident happened outside of his date's apartment. So he kind of turned it into, hey, it's kind of late for me to get a tow right now. So it was it cool if I stayed the night? Yeah. And he did. Even got a kiss the next morning. But ever since then, his date, Tracy, seems to be avoiding him.

Yeah, which is strange. I mean... Was the quick peck that bad? I'm just kidding. Like I said, he didn't have a toothbrush, so maybe it was. Oh, come on. It can't be morning breath. Justin, we don't know.

Is there anything that's going through your mind for why Tracy's avoiding you? I mean, I can't really think of it. I liked her. I thought it was a great date. Unless it was like the mini-golf situation, I don't know. Because you tried to prank her at the mini-golf course by hiding behind a mountain for a second? Not for a second. She thought that she got ditched again.

Do you remember that? Just long enough for her to shed tears. Okay. Although it did sound like you guys recovered because you did go back to her place she invited you there. So maybe there's just some simple misunderstanding we're going to fix. It has to me. Yeah, hopefully.

Yeah, I mean, on this show, it's always like a simple reason, an easy misunderstanding. It never gets weird. There's a first time for everything, Jeff, and I am an optimistic person. We're looking at a good start. That's what we're saying. Oh, Alexis, I am. Yeah. Okay, well, let's just dial Tracy and see if she answers.

Okay, here we go. Hello? Hey, is this Tracy? Yeah, this is Tracy. Hey. Well, hello, you're so pleasant sounding. I know she is, isn't she? Good morning.

And who is this? Oh, this is Jose. Sorry, Jeff, you do your job, bro. We were a whole show. Oh, yeah. I interrupted, my bad. I was going to let you guess a few times, but. She likes that game.

Yeah. If you don't want to play the game, I guess we're a radio show. We're called Brooke and Jeffrey in the morning. Yeah. Why are you guys calling me? Well, I'm Jeffrey. We don't need to go through all the interviews. Brooke, do you want to say who you are?

Remember before I'm Jose. Just tell her why we're going to get up. Okay. We're not doing the fun version of this segment today. We're doing the straight down to business version where we ask you, why aren't you calling back our friend Justin after we went on a date with him? Justin? I thought you'd explain the segment first.

You didn't want to have fun with it. You didn't have to tear the Band-Aid off like that. Okay, put the Band-Dade back on. We're doing a segment. It's a fun one called Second Date Update. Ooh. Did she hang up? Tracy, you still there?

Hello? Yes. Yes, sorry. Oh, thank goodness. You know what? We thought Jeff lost another one. I probably shouldn't be asking any more questions. Brooke ask her something.

Yeah. Well, we heard that you went on a date and now I forgot the guy's face. I should not be talking to him anymore. What? I don't know how much you know. But there are some really, really sketchy things that happened that night. What do you mean? Whoa.

To him, right? I mean, we don't condone people hiding behind mountains and acting like they ditched you mid-date, if that's what you're talking about. I don't think that's what she was. He did tell us about the mini-golf incident. That was pretty shady. That's not what I'm talking about. I just, I felt like I was lied to.

Wait. Lied to. Did you catch him in a lie, you're saying? I caught him in a lie. Oh. That's why I've not been calling him. him back. Okay. Does he know about this? He doesn't know that I know. He doesn't know that you know. No. He knows what he did, but he doesn't know that I know what he did. Okay. Don't you want to

call him out? I mean, that's what people tend to want to do when someone lies to them. You want to be like? No. He left the next morning. And a couple hours later, my apartment manager said he wanted to talk to me. And I was really confused because he never wanted to talk to me about anything before. Like, I'm like, am I in trouble? And he told me that there was video surveillance of Justin slashing his own tire. What? What? Wait.

He slashed his own tire so that he could come and stay with me. Shut up. No. Wait. Yeah. Are you sure? Like, I mean, it's dark on those surveillance things. Oh, my God. No, there was a street light right over the car, and you could see very clearly that it was him.

Wow. That's crazy. The reason my apartment manager contacted me about it is because you could see Justin walk up to my door. Oh, my God. That's kind of scary. He slacks his tires and knocks on your door. This is not going to look good right now. We got a much different version, well, not a much different version of that story when we talked to Justin about it.

She has proof. Yeah. That's crazy. Although you can, like, Photoshop and video edit a lot of weird stuff. Yeah, I'm sure that's what the manager was doing. Some apartment managers are sketchy. And we should probably at least hear what Justin has to say about it because

he is on the other line right now waiting to talk to you. That is so uncomfortable. He's on the other line. So he's been, he's heard what I said. Oh, I'm sorry. Yes, we had no idea. He did not. I don't want to talk to him. Well, we need to at least hear what he has to say about this if he's still there. Justin,

are you there? Are you there? Yeah, I'm here. Justin, I'm going to step away and give you the floor here so you can explain yourself. I'm sure there's probably a very good reason for why you did that. A very noble reason. Always noble to slash one's own tires.

Justin, go ahead. I didn't see any cameras out there, so honestly, that's on me, I guess. So you did do this? That's your, oh my God. Listen, it was probably one of the best dates I had in a really long time, and that's why I did it. I wanted to spend more time together. We got

paying out the next week. No, no, no. No. That is... I had a great time. Hey, you had a great time. It's so disgusting. I can't believe that somebody would actually stoop to that level and slash their own tires. Well, I mean, if it's any consolation, it wasn't cheap. It still cost me $250.

I had to replace my damn tire. Oh, wow. That's your move? Your move is slashing your own tire. Like, you don't have confidence enough in your game. I just didn't know. I thought it would make a great story down the line to family reunions or a wedding. Whatever.

No one in the history of the world has ever thought slashing tires is cute. It's like a story for the police maybe I felt really bad about it because this happened in my neighborhood I felt like it was my fault and now listening to this and his excuses I don't care how much money it cost

that was really really kind of creepy It was just so manipulative Justin Honestly not really I mean guys do crazy things all the time so they can spend time with girls like It's not that crazy Wow Have you done this more than once?

Oh that's a good question Listen I am not a serial tire flasher, all right? I didn't say cereal. I said more than once, yeah. I did this one other time, and that was only when we were six months together. So it's not like I've done this a million times. One other time.

So the last time it worked to get a long-term relationship is what you're saying. Actually, she was trying to break up with me last time, so it was sort of a different situation. Oh, okay. You only pull this move out when you're really, really desperate. It's an emergency. Right before the restraining order takes effect. I mean, that's the type of move. This is Justin.

Why don't you feel bad? Why haven't you apologized? Oh, I mean, I'm sorry. Like, it was my tire. Okay, it was my tire. Tracy, you've heard his explanation, which was he felt like it was the best state of his life and he just didn't want it to end. Is there any part of you that feels compassion for him? No.

Yeah. Clearly, they need to mark the area better that says this area is under surveillance. If you're psycho and pleading to slash your own. That'd be a nice warning. You know, it's really, really weird, and I just think that you should have spent $250 maybe taking me on the date the next time because I would have said yes. I'm just taking lobster time right there. Yeah, like buying flowers, doing normal things, not psychotic things.

You guys are acting like I committed murder or something. I mean, I literally flashed my own tire. Get over it, guys. Oh, my God. Well, that's fair. Let's give him credit for not murdering on the first day, okay? He deserves credit for that. I can't believe we're looking at murder red flags right now.

Yeah. But I'm pretty sure this is one of them. And in the bar. Tracy, he's not a murderer. So maybe that's enough to give him another chance. The guy who obviously keeps a knife on him for his tire slashing. I'm sure it's in his card. It was a screwdriver.

Oh, see. Whatever it was. Unfortunately, I think that this one's definitely a no-go. You could build an IKEA furniture for you. Come on now. You're missing out. Listen, I'm pretty crafty. I'm romantic.

all of it. Yeah. Hey, I stole you these flowers. That's why your ex-girlfriend stuck around after the last time. I mean, she stayed around a couple more months after I flashed my tie the last time. That's sweet. It's manipulated her into it. Okay. Justin, man, look, I'm sorry.

I'm not. Well, Tracy doesn't want to go out with you. Clearly, this isn't going to work. Ever. It won't ever work if you do this. I mean, you're probably 50% right. Okay. That's optimistic.

Yeah, probably maybe. And if you aren't happy with our services to you today, just remember, Brooke's car is the EV Subaru that's parked underneath our building. Okay, so go to that one. Brooke and Jeffrey in the morning. I'm investigative journalist Melissa Jeltson. My new podcast, What Happened in Nashville, tells the story of an IVF clinic's catastrophic collapse

and the patients who banded together in the chaos that followed. We have some breaking news to tell you about. Tennessee's attorney general is suing a Nashville doctor. In April 2024, a fertility clinic in Nashville shut down overnight and trapped behind locked doors were more than a thousand frozen embryos. I was terrified. Out of all of our journey, that was the worst moment ever. At that point, it didn't occur to me what fight was going to come to follow.

But this story isn't just about a few families' futures. It's about whether the promise of modern fertility care can be trusted at all. It doesn't matter how much I fight, doesn't matter how much I cry over all of this. It doesn't matter how much justice we get. None of it's going to get me pregnant. Listen to what happened in Nashville on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Stefan Curry, and this is Gentleman's Cut. I think what makes Gentleman's Cut different is me being a part of developing the profile of this beautiful finished product.

With every sip, you get a little something different. Visit gentlemen's cut bourbon.com or your nearest total wines or bevmo. This message is intended for audiences 21 and older. Gentleman's Cut Bourbon, Boone County, Kentucky. For more on Gentleman's Cut Bourbon, please visit gentlemen's cuthuburn.com. Please enjoy responsibly. Man, we got to write a book on unique ways to woo a woman. No, Jeff.

Chapter 5, gaining sympathy by slashing your own car tires and blaming her crappy neighborhood for it. See, I feel. like we should also write a book, but the title should be like, how to spot a psycho. Yeah. Psychos for dummies. That could be good. We'll do the sequel. That's the sequel to this one. We can also do dummies for psychos.

Yeah. You can switch it. Yeah, you know. A lot of options here. Oh, my God. We're going to have so many bestsellers when we're done writing all this stuff up. But yeah, it didn't work out today. The good news is we do have hundreds of successful phone calls that we have done for other couples. Yeah. I feel we can get anyone together. There's like a tire repeat. hair woman out there who loves this guy. Yeah.

She just didn't hear the break yet. Okay. So, I think there's a tire shop that loves his idiotity. Absolutely. And you can find all of our second date updates wherever you get your podcast on Spotify, Apple, wherever.

Type in Brooke and Jeffrey's second date update. Brooke and Jeffrey in the morning. I'm Stefan Curry and this is gentlemen's cut. I think what makes gentlemen's cut different is me being a part of developing the profile of this beautiful finished

product, with every sip, you get a little something different. Visit gentlemen's cut bourbon.com or your nearest total wines or Bevmo. This message is intended for audiences 21 and older. Gentleman's Cut Bourbon, Boone County, Kentucky. For more on Gentleman's Cut Bourbon, please visit gentlemen's cuthuburn.com. Please enjoy responsibly. I'm investigative journalist Melissa Jeltson. My new podcast, What Happened in Nashville, tells the story of an IVF clinic's

catastrophic collapse. and the patients who banded together in the chaos that followed. It doesn't matter how much I fight. It doesn't matter how much I cry over all of this. It doesn't matter how much justice we get. None of it's going to get me pregnant. Listen to what happened in Nashville on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Have you ever listened to those true crime shows and found yourself with more questions than answers? Who catfish is a city? Is it even safe to snort human remains? Is that the plot of Footloos? I'm comedian Rory Scoval, and I'm here to tell you, Josh Dean and I have a new podcast that celebrates the amazing creativity

of the world's dumbest criminals. It's called Crimeless, a true crime comedy podcast. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Who would you call if the unthinkable happened? My sister was y'all 22 times. A police officer, right?

But what do you do when the monster is the man in blue? This dude is the devil. He'll hurt you. This is the story of a detective who thought he was above the law until we came together to take him down. I said, you're going to see my face till the day that you die. Listen to the girlfriends, untouchable, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Welcome to Decoding Women's Health. I'm Dr. Elizabeth Pointer, chair of women's health and gynecology at the Atria Health Institute in New York City. I'll be talking to top researchers and clinicians and bringing vital information about midlife women's health directly to you.

A hundred percent of women go through menopause. Even if it's natural, why should we suffer through it? Listen to Decoding Women's Health with Dr. Elizabeth Pointer on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.