Brooke and Jeffrey: Second Date Update - Second Date Update: Stroll Club Hero

Episode Date: June 17, 2026

Josh tried to be funny to impress Lisa on their date and that plan BACKFIRED so badly, he found himself apologizing to a random 9 year old and his family. Hear how his humor got him in trouble in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Joy is essential and it's also elusive, but now there's a new and exciting way to start your journey toward a more joyful existence, Joy 101. It's a new podcast hosted by me, Hoda Kotby. If you're craving inspiration to maximize your joy, tune into these candid, uplifting, and moving on-air chats. Open your free IHeart Radio app. Search Joy 101 and listen now. Joy 101 with Hoda Kotby is presented by CVS. There was no anything inside those eyes. They turned black. It scared the hell out of me.

Evil, wake up. I'm the one that saw the murder take place by Creveit and DePippo. Anthony DePippo showed no signs of remorse, appearing unfazed after being sentenced to the maximum. I said I'm not guilty. I'll take it to the grief. Listen to the devil's quarry in the Bone Valley Feed on the iHeart Radio app. podcasts or wherever you get your podcasts.

All right, listen up. The Jonas Brothers here. Our podcast is called Hey Jonas. We're here, since everyone has a podcast, we want it to as well. And we've had some incredible guests so far. And now our good friend, Nile Horn, is joining the show. How's it going, boys? Hey, Niall.

It's the same thing with Slow Hands. Slow Hands is not about anything else, really, is it? You know, or taste so good can be about food. You do the same, Nick, with some of the stuff that you've done. You too, Joe. Drop what you're doing and listen to Hey Jonas. on the IHeartRadio app, Apple Podcasts, or wherever you listen to your podcasts.

Every family has its secrets. But what happens when you discover that your dad has been living a double life? That is not the look of an innocent man. Is everyone lying to me about who they are? I felt such desperation. I felt it was what I had to do. Listen to deep cover the family man.

On the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. June is Black Music Month, and on the Drink Chams podcast, we're speaking with the hottest names in the culture, like Sway Lee. Do you realize how legendary you are? I appreciate that.

I'd be seeing it, but I'm like, man, I still got, like, so much more to do. Like, Prince, he dropped, like, 30 albums. We dropped, like, five right now. That's the rate we got to be going. Yep, that's a good attitude. No matter the era, Drink Chams brings you the biggest names

and the most unfiltered conversations. Listen to Drink Chams from the Black effect podcast network on the Iheart radio app, Apple Podcasts, or wherever you get your podcast. Hey, it's Brooke and Jeffrey in the morning, and you've got a brand new episode for your second date podcast. Thanks so much for being here.

Hope you're loving the live videos that go along with these. We've got another one that was posted yesterday on our YouTube page. So if you aren't following at Brick and Jeffrey on YouTube, you should be. Yes. Was it a second date that we posted yesterday? Yes, it was. Okay. So go back, watch that,

you know, watch us. That's how it goes. That's not creepy, right? Yeah, yeah, yeah. And don't watch just like live, live. What do you mean? Like in my apartment as I'm, like, sleeping. Or do if it helps with our YouTube subscriber numbers. Whatever works.

All right, and then we're going to get to a brand new episode in just a second, but first comments, Alexis. Oh, Belinda Mondi is on our YouTube and said, first person to watch from Kenya, 22 seconds after upload. Wow. On it. Dude, on it is right. Yeah.

Thank you. Thank you. Okay. See if you can beat her time next week. Okay. Those live videos go up every Tuesday. Your brand new episode, though, starts right now. Brooke and Jeffrey in the morning.

Second date update. We've talked about how run clubs have become kind of a huge thing lately. Yeah. Even people who aren't actual runners at all can just show up at the start of this race. They all run together or just Uber straight to the finish line to enjoy the drinks and try to hook up with randos there. And apparently one of our listeners met someone. through a similar type of club. Okay.

But it doesn't involve running whatsoever. Ooh, if it involves eating, I'm kind of into it. Ooh, eating club. Or maybe it's just an Uber club and they all Uber together. Let's find out. Josh, welcome to the show. Hey, thank you guys. Okay.

What up? Are you going to tell us about this club? It's a stroll club. We all, like, get together and you just kind of like walk wherever you want to walk. Oh. Oh, okay. All right. And did you join this stroll club to meet?

other singles because sometimes that's people's motivation or you're just really passionate about strolling you know i have a small group of friends who like we went together we actually have gone since a couple of times where like the goal is not like to date somebody but it is to sort of like branch out our friend group and like meet new people just chat while we walk right and you're not out of breath like the running club right right so it's easier to have a conversation well it depends on how out of shape you are sometimes a stroll could be exhausting that is absolutely true so i start chatting with this girl name Lisa and we decide that we're going to go on a date. That's so sweet.

What a great way to ask her out. Yeah. Yeah, yeah. We were both sort of making jokes about how we both like doing anti-sports, like the girl club, like not run club. We're just sort of like here to walk. So I thought it'd be funny to take her to not golf, but mini golf.

Hey, there it is. Way better anyways. I don't appreciate you diminishing the value of mini golf as not being a real sport, but that's okay. The plan is to sort of like do mini golf have a drink. There are places where you can do that now where you can like have a drink at mini golf. Yeah, they've added alcohol

to literally every activity. Yeah. And you can always sneak alcohol into mini golf even if they don't sell it there. So this isn't anything new. Okay, but that is actually what happened though. I didn't really realize that we ended up going to like more of a kid's mini golf than like an adult's mini

golf course. Oh. It's like clowns and windmills. Yeah, you didn't pick the trendy one. You picked the Family Fun Center one. Yeah. My, my, my, Knowledge on mini golf is not as great as it should be, clear. Okay. When it's just you two, is it the same good energy that you had when you were in the stroll club? Or was there awkward moments?

No, I didn't feel like there was any of that sort of like dead air space between us talking. Do you know what I mean? Like where it was sort of like, oh, God. It flowed. Yeah, for sure it flowed. When you say that it flowed, do you mean like your personalities were matching or was it just the alcohol was working? And flowing. No.

What do you mean? No. I mean both. Both. All right. So, yes. The words were flowing. The opposite of note.

That's great, though. It's good vibes. Okay. Was it flirty? Oh, yeah. It was definitely flirty. Nice. What do you mean?

Oh, yeah. Like, how flirty are we talking? That's true, yeah. We were making jokes with the golf club. We were sort of like pretending to smack each other in the butt or whatever. And like, it was cute. Okay. She was doing that to you, right?

As well? No, I was doing that to myself. No, of course. She was doing that. Okay. Okay. You're swinging golf clubs at each other flirtatiously. She figured he's like hitting her in the leg with the club.

She's like, leave me alone. It is a good question to ask people on our show. Why do I feel like you guys were such a distraction at the family golf ball and mini golf plays? You're in your own world? We for sure were. Okay. Did you make it all the way to the final hole or did you get kicked out by employees before then? So we did make it to the final hole and there's a little bit of a story there.

Oh. What happened in a hole 18? So there's a little sign that says no trick shots because obviously every. Everybody's trying to do something silly on hold number 18. Me included. Oh, no. And I try to be silly and, like, bank a shot off of the side. And this is going to sound, like, actually absurd.

But the ball goes off the course and goes smack into this probably, like, nine-year-old's birthday cake. Oh, into the cake. Oh, a birthday party. Why is that better than a face, though? I thought for sure it was going to be hitting a child's head. Yeah, yeah. It now just seems like part of the day.

decoration for the mini golf cake. Yeah. Maybe it was mini golf theme. Was the family so mad at you? Did they, what happened? They were not super happy. But we, like, I did apologize. I was like, I'm so sorry. Is it a situation where you have to play it as it lies?

Just hit it out of the cake? Yeah, so I just ripped my putter through the cake. Oh, man. Oh, good. That's a mood killer. Yeah. How was your date reacting to all this happening? a lot for her to witness too. Yeah. We were both so like, oh my God,

oh my God, what just happened? And then after the fact, we were making jokes about it, like, immediately. Okay. Okay. So it didn't end in a weird mood. Yeah, she found the humor in it too. It definitely helped that we've been drinking for like 45 minutes straight up until then.

Okay. Okay, good. So as you're apologizing, you reek of alcohol as well to the family. That is a cute look. Yeah. So, fine, these balls are slippery. You know what I was trying to be funny. So after you gave a nine-year-old a birthday that they'll never forget, how did you two leave it?

So, I mean, I will say that the date ended with a kiss. And then the next morning, I texted her, she texted back, said like too much fun yesterday. That's actually really good. Have you actually asked her out in those texts or no? Yeah, I bet one that was like, hey, let's sneak alcohol into a library. Maybe that would be fun too. Oh, yeah. What other childhood places could we ruin with our fun times together?

I would like to say a library is a very adult place, Jeff, that I enjoy. Okay, so he doesn't need alcohol. Then why are you drinking there? Well, because it's fun. Yeah, okay. I'm kidding. I'm kidding. I think we're on the same page except for with Lisa here, so we're going to reach out to her when we come back

and try to get you a mulligan on a date. Hey, I like that. That's golf reference. This is good as we're going to do with your second date update right after this. Hold on. Brooke and Jeffrey in the morning. Second date update. It's funny how your dating life can just snowball so quickly.

That was the case for our listener, Josh, who recently met a woman named Lisa at Stroll Club, which rolled into golf clubs at a mini golf place and ended with them in Kiss Club, which I was the president and sole member of my high school kiss club. How do you be the sole member? So I know just how enjoyable that can be. Lisa even messaged him the next day saying how much. fun it was. So it is weird that she suddenly stopped responding

to him. And Josh, you definitely sounded pretty disappointed in part one and not sure what could have caused her to suddenly ghost, right? Yeah, no, I felt like we had a great time. I wonder if just the issue here is that then you asked her to go drink at a library.

Like, maybe you took the joke too far. Yeah. You know what I mean? Like, sneaking alcohol places when, like, your adults could go to a bar. Yeah. Yeah. Yeah. Actually, I want a real date. I mean, first of all, it just a little thing over text. But second of all, like, we were flowing in terms of our sense of humor. Like, she was getting my jokes.

I think that that joke would have landed with her. You know what I mean? Oh, okay. So you're surprised she didn't laugh back. Like, it should have been obvious that you weren't being serious. Yeah, for sure. Yeah. After drinking for 45 minutes, you should be laughing at pretty much everything together,

even if it's not funny. I just want to say, you guys, though, like, I met her in the real world and not on a dating app. Like, it feels like crazy to do that these days. And so, like, it does feel like something kind of special. and I really don't want to let it go. So whatever we can do to make it work. Okay.

That's really nice, man. Well, just like we used to say in my high school kiss club, let's just close our eyes and go for it. So here we go. We didn't say it because you were the only person in the club, Jeff. Yeah, there's two of us, Brooke, in the mirror. Like, hello. Well, you ought to diminish me in my high school self.

I was thriving. Jeff, I got your back here. Thank you. I'm just going to try to tear you down this whole thing. Somebody had to. All right, here we go. I'm going to dial, so we'll see if she answers. Let's do it.

Hey, is this. Lisa? Yes, is this? Hey, Lisa, we're a radio show called Brooke and Jeffrey in the morning. Hi, Lisa, good morning. The whole show's here, Lisa. What? Why was that funny?

What are you laughing at? Nothing. Is this like one of those jokes when you had a joke club and you were all alone? We did. We cracked each other up in comedy club. Sorry, Lisa. Sorry, are you there, Lisa? Yeah, I have no idea what's going on.

We don't either. Yeah, that's the case a lot of the times here. But this is a segment called a second date update. Okay. I don't know if you're familiar with it, but basically we're trying to help out a listener that went on a date with you. And afterwards, there hasn't been a lot of momentum building towards a second one. So he's trying to figure out if there's a reason for that.

And it's a guy named Josh. Yeah, I find it a little strange that he's relying on a radio station to intervene here. but yeah, I remember him. That makes sense why you would think this is strange. It is an odd way, but he was really excited about you and about your guys' time together. I mean, yeah, it was fun. We had a really good time. It was a lot of fun.

Oh, good. He even mentioned that you texted after the date saying what an awesome time it was, so that's why he's so confused that there hasn't been a second meetup. Maybe there doesn't need to be a second date. I don't know. I don't know if you've ever been out with someone and it goes really well and you feel like they're a good person. But you just don't know how much romantic connection you may have with them. Were you not attracted to him?

Wait, he said that you guys shared a kiss at the end of the date. Wasn't it good? Like, it feels like that's as flirty as you can get. Okay, well, I didn't realize he was one to literally kiss and tell. But, yeah, we did. Well, we pulled it out of it. him, yeah. Like, how did the day-in- He didn't offer that up? Yeah.

I mean, I don't even know if I can say this, but I kind of just have second thoughts on how he would be in bed. Whoa. Oh. Based on the kiss or just based on the full experience of hanging out with him? That's actually a good question. The kiss was fine, you know, but I don't know. I just, I don't know if I had that spark

that makes you want to jump a guy's bones. What his golf swing? I mean. I like to say something Whoa Hey I wanted to hear about the spark more Yeah

That's way too early No the not spark more Well I mean What he's missing I just want to say like Hold on hold on Hold on Josh Because I mean at this point

It's kind of blown Lisa we need to let you know Josh has been waiting On the other line Listening into the conversation Waiting to not very patiently You're supposed to wait I'm sorry

Yeah we're gonna get more information But yeah Josh is here Surprise Well I shouldn't be surprised even though this whole thing's been kind of a surprise. Look, we were at a mini golf course. Like, it's okay that there wasn't like the craziest romantic spark. I would love to take you out to like a very nice dinner, have oysters and then see if there's a spark.

What? Why? Acidesiac. Yeah. Yeah. You're saying that the environment of all the children and families at the mini golf place wasn't conducive to being romantic with Lisa. Is that what you're saying? I just wanted to have a good time together on that date. I wanted it to end with a kiss.

I wasn't trying to make it end with more than that. You know what I mean? I mean, Lisa, do you see what he's saying? Does the setting of where it's happening matter in terms of creating romance? I got to be honest. I don't think so because I've definitely done stuff at a mini golf place before. Okay, done stuff. Oh.

Okay. I don't think we need the details on that. And a baby shower, a graduation ceremony, you know, just. I don't think it's really the setting. I think it's the vibe. You hooked up in a baby shower? Nothing gets you going like... Fertility, right?

Really? It's evolution. It's evolution. It's not me. Are you just saying you didn't have that chemistry with Josh? Like, that's the issue for you. Correct. Is there any way he could fix it?

I mean, look, I'm happy to dress sex here when we're not going to mini golf. Oh. What does that even mean? Show a little clean on button a little bit. I just mean I'm happy to dress up nice and like, I don't know what Lisa is into. Maybe it's that. Maybe it's tearaway pants. I'm willing to adjust whatever she's into.

Oh, my gosh. Look at a man who will do anything to make you happy, Lisa. That sounds pretty good. Yeah, I got to be honest. I wasn't expecting this sort of persistence. Yeah. Does that help his situation? Is it turning you on a little bit?

I think those tear away pants help the situation. Okay, let's relax with that. What if we brought a baby in here with a bunch of gifts? Would that do something for you then? You got to play the dirty diaper game to get me going. Oh, wow. Could we have at least done the clothespig games? Yeah, I didn't play any other game.

Looking out of a diaper, okay. Is the objective here to get another date, Josh? Is that? Yeah, it's called a second date update. She puts it so sexily, too. It is very much that, yes. Wow. So romantic.

I think he's kind of cute. He's funny. You're funny. I think that if you gave it another shot, you may find something there. And before I ask Lisa, I just want to ask the girls, just in general, is this something that has happened to you before where you're hanging out with a guy? Even if you have like a really nice time with him, you don't feel that romantic spark right away, that like desire to jump his bones. And it happens later? Is that what you mean?

Or maybe you never do. It just never comes where the romantic connection happens. And oh, that's the friend zone. That's never happened to the brook. Yeah. It's very common area. I'm trying to help Josh here, Jeff. I don't think that our answer is going to help him.

No, I'm trying to just make it like a normal thing. Like, there is hope down the line that there could be romance. That the attraction could jump in. And Brooke, I'm sorry that I even brought it up to you because I know you hook up with pretty much everybody. Yeah. Well, I think that that's the first step. And then the friends come later. That's how you find out if there's a spark fast.

Ah, yes. Short cut. Okay. So you hear that? Lisa. you're talking to the loosest morning show in the entire country, and we all think you should go for it.

Yeah. You might not know that the attraction's there until you actually try something with Josh, so... I don't know that Jeff's helping here, but I do think that you should give him another go. Yeah. Add a Chucky Cheese, maybe. That's better. That's better.

Well, I don't know. The baby shower got her back. All right, relax. I should have never said a thing about the babies. Oh, okay. But if you agree to this, Lisa, we're just putting it out there. We would pay for the date. You know, I, I, have to just be honest and say that I've never had a man call a radio station to get my attention before and it's quite a romantic task.

Wow. So we are running out of time. It sounds like it's a yes from Lisa, correct? It is a yes. All right. A-rah! A-rah! Nothing turns the woman on like that phrase.

Don't always say that again on the day. Brooke and Jeffrey in the morning. Happy Pride Months, Toronto. Pride is an opportunity for you to create your own space, to celebrate your existence. IHeart Radio is proud to be an official sponsor of Pride Toronto Festival, and we won't stop. Celebrate Pride.

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In the moment, it felt like it was going on forever. I didn't think I was going to live. I was terrified. There was no anything inside those eyes. They turned black. It scared the hell out of me. That was your first murder case? Yes, sir.

Fair to say this was the biggest case of your career? Yes, sir. Rape and murder for a child of a 12-year-old child. As bad as it gets. I would think so. Evil, wake up. I'm the one that saw the murder take place by Creveit and DePippo. Anthony DePippo showed no signs of remorse,

appearing unfazed after being sentenced to the maximum. I said, I'm not guilty. I'll take it to the grief. Listen to the devil's quarry on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. And to hear the devil's quarry ad free with exclusive content, And subscribe to Lava for Good Plus on Apple Podcasts. I'm always pleasantly surprised whenever we meet people who have kind of lost their filter.

Oh, like her? Yeah. Like we knew that lady for maybe two minutes before she's sharing how she got it on in a baby shower, a graduation ceremony, her dad's root canal. Pretty much anywhere, any place you can imagine she's done it. But for Josh, it just wasn't happening. It just didn't click for her. No. I mean, man, it didn't feel like she had a lot of hard parameters either.

I know. Which is not a good look for Josh. It doesn't bode way. Hey, maybe the next time they hang out, because they are going to go out again. Maybe it'll spark. It is interesting. What turned her is that she found an intriguing he went through us in our show. I still think it was the tearaway pants he mentioned.

Maybe. I don't know what turns people on anymore. Hopefully it's listening to our podcast at Brooke and Jeffrey. That's quite the date night. Go find us wherever you get yours. Just look, Brooke and Jeffrey in the morning. Joy is essential and it's also elusive. But now, there's a new and exciting way to start your journey toward a more joyful existence.

Joy 101. It's a new podcast hosted by me, Hoda Kotby. If you're craving inspiration to maximize your joy, tune into these candid, uplifting, and moving on-air chats. Open your free IHeart Radio app. Search Joy 101 and listen now. Joy 101 with Hoda Kotby is presented. by CVS. There was no

anything inside those eyes. They turned black. It scared the hell out of me. Evil, wake up. I'm the one that saw the murder take place by Crevette and DePippo. Anthony DePippo showed no signs of remorse, appearing unfazed after being sentenced to the maximum.

I said I'm not guilty. I'll take it to the grief. Listen to the devil's quarry in the Bone Valley Feed on the IHeart Radio app. Apple Podcasts, wherever you get your podcasts. All right, listen up. The Jonas Brothers here.

Our podcast is called, Hey Jonas. We've here, since everyone has a podcast, we want it to as well. And we've had some incredible guests so far. And now our good friend, Nile Horn, is joining the show.

How's it going, boys? Hey, Niall. It was the same thing with Slow Hands. Slow Hands is not about anything else, really, is it? You know, our taste so good can be about food. You do the same, Nick, with some of the stuff that you've done. You too, Joe.

Drop what you're doing and listen to Hey Jonas on the Iheart radio app, Apple Podcasts, or wherever you listen to your podcasts. June is Black Music Month, and on the Drink Chams podcast, we're speaking with the hottest names in the culture, like Sway Lee. Do you realize how legendary you are? I appreciate that. I'd be seeing it, but I'm like, man, I still got like so much more to do. Like Prince, he dropped like 30 albums. We dropped like five right now. That's the rate we got to be going.

Yep, that's a good attitude. No matter the era, Drink Chams brings you the biggest. names and the most unfiltered conversations. Listen to Drink Chams from the Black Effect Podcast Network on the Iheart Radio app, Apple podcasts, or wherever you get your podcast. Every family has its secrets. But what happens when you discover that your dad has been living a double life? That is not the look of an innocent man.

Is everyone lying to me about who they are? I felt such desperation. I felt it was what I had to do. Listen to Deep Cover the Family Man on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.