Brooke and Jeffrey: Second Date Update - Second Date Update: Gammy's Bar Crawl

Episode Date: September 2, 2026

Not all surprises are good surprises, and one of our listeners found that out the hard way! Hear what kind of trouble Ava and Dean found themselves in, in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

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We appreciate you. It's Brooke and Jeffrey, and you found the official second date podcast. Before we get into our brand new episode, we do always love to highlight your comments. Yes, and this one said, I saw Jeff in my dream. Oh, I swear it wasn't what you think. He was so quiet, and I told my friend, and I said, he's known as the awkward one in the show. As if I know him my whole life. Well, just a dream.

Dude, somebody once told me, what do they call him? They were like, yeah, the show with Brooke and who's the quiet one? I think it was the quiet one. I'm like, he's the lead. That's Jeffrey, the quiet one. If your comments come in, we got a brand new episode starting right now. Brooke and Jeffrey in the morning. Second date update.

We've heard that guys, even attractive-looking ones, Sometimes on the dating sites can go weeks and end up with zero matches. Yeah. But what about the flip side of that? What happens when an attractive woman is getting matches, but the dudes that she's linking up with always flake on her. Those are probably the same dudes that are complaining about not having matches. That's probably right.

At that point, she needs to change up her game plan. Spice things up a little. Do something new to find herself a different type of guy. Okay. And that's what one of our listeners, Ava did, she changed up her dating profile and thinks she may have finally met the right kind of man, but he's not calling her back now. Oh, wait. So, oh, it's the same.

Wait, wait. Well, I mean, the difference here is that they actually went out. The other guys never even showed up. But now, then she messed it up. Then something went wrong. In person. Different problem. Eva, welcome to the show. Hi, thank you for having me. I'm so curious, what kind of guy were you hoping to match with? I just thought like somebody's fun kind of down for whatever. I mean, in the past, there's just been so many flakes.

I feel like you book a day. It doesn't happen. Okay. The bar is so low, it's just someone who shows up. Yeah. Even that. That's expecting a lot of it. I guess it sounds bad that way.

Okay. Okay. So tell us about what you did. You said you changed your dating profile when you wrote your email. What did you do? Yes. I thought I had to juice up my profile and make myself sound a little more fun. So I said, who's up for a bar crawl?

I'm up for making questionable decisions. Oh, goodness. Oh, wow. Okay. I love that vibe. I used to do that all the time. Jose and I both swiped right on that profile. Yeah. I mean, 10 years ago, yeah.

But you're getting the guys then that aren't looking for a second date. Right. They're showing up, Brooke. Right. I mean, I got a lot of responses. Okay. Yeah. Yeah.

Were any of them quality responses? Yeah. Well, there was this one guy named Dean. Dean. And I thought he was really cute, and he told me that he'd never had a bar crawl since college. Okay. Oh, right. Yeah, it's typically like when you do it.

Eventually the hangover sucks. Did you call him a loser and unblock? Okay. Yeah, he agreed to do one. I mean, it was fun. I mean, we were planning it for a while, actually. And there were a lot of quirky bars near where I live, so I thought maybe I can show them around to a few of them. That's fine.

So what was on the, can I ask, what was on the bar crawl itinerary? Like, what was the plan? Yeah, the first one. It was a teaky bar. So, you know, it was like, it felt like we were, yeah, tropical. There was a DJ and there were little umbrellas on the, on the drinks. I can already tell you're mixing a lot of sugary drinks. Those drinks are never as good as they look.

Yeah, I don't know if you should, like, trust a cocktail that's bright blue. Yeah. And like smokey. Okay. And that was fun. That was a good one. Okay. Fives were good at the teaky place.

What was next? The next place was a speakeasy. That's always fun. Yeah. I mean, even though it's not illegal anymore, it's still fun to find. Where's the handle? How do you get in? What's the secret pass code?

Yeah, and it was hidden. It was like totally hidden. So I thought that this would be a little bit more mysterious, kind of like a level up from the teaky bar. Yeah, and you don't want to do that at bar six because you'll never be able to find how to enter. Right. Yeah. We'd never get home, yeah. But we also planned one.

The one after that, I have to tell you about this one, it was a robot arms that make drinks and serve them to you. So I thought we had like a really fun night plan. Good. Wow. That's an amazing array of bars. Can I ask, are you a sloppy drunk? Do you know that ahead of time? She's looking to hang out with you, depending on your answer.

I can just imagine how I would be with a guy at this point, but I'm curious how you would be. I don't want to be, but sometimes if I'm drinking the wrong things, I think I get a little sloppy. Okay. So did you go to all three bars? No, we didn't. Well, speaking of being, yeah, we didn't make it. Oh. You didn't make it to the robot?

It's not because of what you think. It's not because I was sloppy, I promise. Robots cut you off. What was it because of? Well, no, what happened is that at the speak easy, he told me that he lived an hour away. Oh, that's going to be an expensive Uber ride. Yeah.

But it gets worse because he told me, well, that's why I got a hotel room. Oh. Oh, is that a strat? Is that why he got a hotel room, or was it because of what your profile said? Yeah. That's what I'm saying.

Is that a strategy? But it made me think about that I thought, why would he do that straight away? but then I thought about my profile, and maybe he thought the questionable decisions, it was kind of lock and key. Yeah. Yeah.

And was that exciting to you, or how did you feel about that? I wasn't sure what to do, honestly, for a second. But it was later at this point, too. The hotel was brought up. I didn't know what wouldn't make sense if we just kept drinking. So, I mean, look, we did go back to his hotel. Oh.

But we just talked. We, like, talked all night. We talked for a few hours. You only talked. What? I know, I know, I know. It's about the art on the wall. I'm sure.

Just like... Yeah. Hold on. You didn't even make out? He kissed me on the cheek. Whoa. Yeah. Why, whoa?

Why is the way? Why? Whoa. I mean, if you're drinking with a guy, you're at a bar crawl and he's like, come back to my hotel room. No one is thinking that just a kiss on the cheek is going to happen. Maybe the guy was nervous. A guy who gets a hotel room on a first date is not nervous, Jeff.

If it's his first hotel room, he doesn't know how to proceed. He doesn't know how to proceed. I don't want to fool around too hard. They lose the deposit. When did you leave? Like, the next morning or that night? It was that night, but it was very late in the morning. But I didn't want to stay over.

Yeah, because I didn't want to have that part happen. You know, I think I had to kind of draw the line somewhere. Also, they charge you extra if you have a guest in the room. So they had to leave by midnight. You got a kiss on the cheek and you're fully clothed. I don't think you need to be worried about anything at that point. So what's happened since then? Well, I texted him the next day and I said, hey, look, I had a great time.

last night, would you want to like see again, me again? But he's now, he hasn't replied to me at all. Ooh. So maybe. Yeah, I don't know if maybe he just wanted me to come to his hotel room the whole time. Yeah, that's weird. But you're saying that you didn't try anything. No, he just kissed me on the cheek.

Yeah. That is, yeah. It's kind of lame. I know. What's wrong with this guy? We're going to ask him that exact question when we come back and get you your second date update right after this. Hold on.

Brooke and Jeffrey in the morning. Second date update. If you're just joining us, this one's a little bit of a head scratcher. Because our listener, Ava, attracted a guy to her dating profile by saying, who's up for a bar crawl and making questionable decisions? Yeah, A-A-A-B. Which honestly, A-plus, no notes on that, Ava. Well done.

It's how she attracted a guy named Dean. They did at least a portion of that bar crawl together. I mean, nobody ever finishes a bar crawl, Jeff. Have you been on one? Such a good point. You don't get to the end. If you've finished, you've done it wrong. But that's when Dean revealed that he already had a hotel room because he lives an hour away.

Yeah, I'm sure that's the reason he got it. Maybe, yeah. Definitely seems a little presumptuous. But they did go to his hotel, hung out in his room for an hour. I thought that she was there longer than even an hour. Yeah, it sounds like a few hours. But not. She didn't stay the night.

No, she did it. Is the point. Even Ava sounded a little disappointed when she told us. But ever since, Dean has. been acting even stranger, not really responding, so she's come to us asking what is going on. I think that maybe he just wanted to sleep with me. See, I don't think so. I think that he would have done more.

I've never heard a guy ever just wanting that. But what guy only goes in for a kiss on the cheek, if that's what he wants? Like, he's the worst. Yeah, well, that's what I don't know. I don't know. And if he still wanted to, like, he's already had a night with you. Why not have a second date with you? Yeah, exactly.

Why? Because that's an hour away from his house. and he can't afford all those hotel rooms. You're right. It's like 500 bucks for him every time he wants to hang out. I mean, I wish she would just tell me that. Let's get those answers for you right now. I'm going to dial his number.

We'll see if he picks up and hopefully we can get everything answered. But here we go. Hey, is this Dean? Yes, this is Dean. This is a radio show called Brooke and Jeffrey in the morning. Hi, good morning, Dean. What's the reason for the call? I think we got business Dean on the phone right now.

I like it. Yeah. I'm a fan of business, Dean. So let's just. hung over, that's for sure. We're going to get right down to business, Dean, and tell you that this is called a second date update. It's a segment where you do where we help our listeners.

If they've ever gone out on a date with someone and they're not getting a call back afterwards, we can reach out on their behalf to see if there's a reason why. Okay. That's the most business-like explanation I can give of it. Yeah. This is an organized thing. Yeah. And the reason we're calling you is you went out with one of our listeners named Ava.

Yes. Yes, I did. Hey, bar crawl, Ava. I hear a smile on his face. I do, too. Ava tells us that you have been a little bit more distant since the bar crawl. More distant. He hasn't called her at all. Or text her back. I think that still qualifies as more distant.

So she's confused and doesn't know if she did something wrong or what's going on in your head. That's why we're here. Okay. Well, you know, she didn't do anything wrong. Actually, she's a super fun, really, really nice girl. I actually kind of feel bad. That's good to hear. You do.

When you showed up for the first bar, you were excited. Oh, yeah. Yeah. She told you our date. Yeah. Yeah, we got the highlights of it. Some tiki bar action, speak easy action. And then I want to tell you about a moment that Ava revealed to us that was kind of interesting.

Because this is a girl who's been drinking with you for a few hours. she goes with you to your hotel and there's a moment Why are you laughing? She told you about the okay. I'm sorry, she told you everything. She did and she said there was a moment where you got to maybe go in and kiss her and you went in for a peck on the cheek. And for us, it seemed a little odd.

No, it just seemed anticlimactic. You get a hotel room, you're at a bar crawl. Like most people would assume at least a makeout session was going to have. happen. Yeah. So why just going for a peck on the cheek at that point? Well, okay, so we had a lot of fun. We went back to the hotel and I mean, we just got deep into conversation. It was awesome, really connected. But then something kind of came up and it was just, it was a huge turnoff to me. Oh. Like something in conversation made you not attracted to her. She's got eight kids. Actually, yeah. Well, we were talking about nicknames growing up.

and things like that. And then she said she had a nickname, Gammie. And I'm like, oh, that's funny. Like, where did that come from? And then this is the first time I've ever heard of this. She's like, oh, well, you know, I have two kids. And I'm now a grandma, hence Gammie. Oh, what?

Whoa. She sounds like she's 25. We didn't ask her age, but. No way. Hey, don't judge. Where I come from, that's pretty normal. Well, she said she had kids super young. Yeah.

And I don't have any kids. I don't know anything about that. And the fact that she's a grandmother, I mean, it just, I don't know, something in my body. It just froze up. And I kind of really just closed everything off. And I just kissed her on the cheek. And I was like, okay, well, you know. That is what you do to your grandma.

I mean, but if she had a kid at 18 and then her kid had a kid at 18, that's 36 that she could have been a grandma at. You know what I'm saying? Like, I mean. I don't know if it's. It's necessarily like an age question. It's more of like, where is she and her personal life versus where is he and his? Yeah, she's about to retire. Okay, okay.

What do you got against grandmas? I mean, why was that a turnoff for you? Well, I mean, I don't even have any kids. So if we're going to date, like, I'm immediately like a grandpa. I can see that being a lot of information to intake after a night of drinking. Yeah, that's true. And not to overload you with even more sudden. information, but we do have

grandma waiting on hold right now listening in on this conversation. Okay, great. I mean, Gammie. Sorry. Yeah, Gammie's there. Gammy? Yeah, hi. Hi, grandpa, Gene. Oh, my God. I love that she's leaning into it.

You know, I wish you just would have said something. Well, I think he, which is you would have said something earlier. Yeah. Yeah. I didn't know what. to say honestly and I didn't I didn't want to be rude I mean I enjoyed hanging out with you I mean you're super fun I just I wish maybe you would have said something kind of while we were messaging each other before we met her up I mean you know it's it's no it's no big I mean it is a big deal

just because it doesn't know what to say yeah I just feel like we're getting to know each other and you know for me that's a lot of extra pressure and I I just wanted to hang out with you because you just seem fun and spontaneous and... Yeah. I mean, grandmas can be spontaneous, too. Ooh. How was that sexy? Yeah.

What do you mean, Eva? Well, I mean, I didn't bring it up because I didn't want you to view me that way immediately. I would understand that. I probably wouldn't put grandma on my dating profile. No. But if Brooke could be like, Gil. But it's tough when you're about to lean in for the kiss. And she's like, by the way, my dependents have dependence.

I mean, look, I can kind of. see how maybe it affects you because I know that we talked a lot and you mentioned that you never really had a grandma around growing up but maybe I could be that for you. What? Wait, what? What did you just talk about? What? You're offering to be

his grandma? What's happening? What's happening? I think you're just trying to be fun and flirty. I think she's just trying to make it a fun thing. Is that what Yeah, maybe? Like a positive Yeah, I mean, and that's what I mean, that's what is attractive about her. She is very fun. She's very flirty. I mean, there's a lot of responsibilities that come into play and it just kind of made me take a step back.

Can I ask, you keep Sade responsibilities? What do you think you'll be responsible for if you start dating her? I'm really confused at that piece. Well, I mean, you know, she's going to have her kids over, then the baby's going to be over and then like, what do I do with that? No one expects probably you to do anything, Dean. Is it like, yes. Eva, you're not expecting him to be an Insta granddad. Of course not. Of course not. Okay. Yeah. The goal of these segments, Dean, is to just see if you reconnect with her and go out on one more date. Yeah, not meet the kids or anything. Become a grandpa.

You guys raged and got wasted and ended up in a hotel. This is not something like grandma activities, bro. And it sounds like you connected on a really deeper level, according to you. Yeah, we did. We did. And I'm sorry that I didn't message you back, by the way. I do apologize about that. Okay.

Well, that's really nice. So before I ask the question, Ava, why don't you try to sell Dean one more time on why it would be good for him to date a gammy? I mean, Dean, I saw the stains on your shirt when we first sat down. Oh, no. I can help you with that. No, girl. The positive is there's no pressure. You've already done the kid thing.

It doesn't matter what happens. Let her cook. Okay. Grandma sew the holes for you and fix them. Okay. No more stains on your shirt. What else? Yeah.

I mean, I can cook for you, Dean. Yeah. Don't pick me. That doesn't sound too bad. You're already to cook. Right. You said that. So what do you think, Dean?

With all that being said, we'd like to offer to send you on another date with Ava. And if you say yes, we'll pay for it. Now we'd go out on another date. But here's the deal, though. Here's the deal. I mean, I'm not changing diapers anytime soon. Are you talking about hers or the grandkids?

You guys. No, I would, though. I would. That's great. I mean, look, maybe next time we go out, you can give me a kiss on the mouth and use a little tongue this time. Hey. Okay.

Okay. Grab me and a little tongue too, Alexis. Put that on your dating profile next time. Brooke and Jeffrey in the morning. Behind every night spent making the kids' lunches, there's a lot of suspense. Will they finally eat the veggies? Will the pasto survive the first bite? Will the lunchbox come home empty, half full, or come home at all?

And will you finish episode 8 before you're done slicing the cucumbers? Get Bell Pure Fiber Internet with Craved Netflix and Disney Plus from $94 a month. Price guaranteed for two years on internet with a two-year term and auto pay credit. Visit bell.ca for details and to check availability. Bell, connection is everything. If your bookshelf and your for-you page are equally important to your personality, welcome home. This is Prose Society, the weekly podcast that's part book club, part group chat for thought daughters, pop culture obsesives, and anyone who thinks pride and prejudice and Love Island deserve the same level of discourse.

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I rarely brag that we just hooked a guy up with a grandma, but today we can say that with confidence. Somebody just scored a gilf and it's all thanks to us. Good work team. Hot grandma's for the win, honestly. Get it, ladies. But I do understand, like Brooks said, like late 30s, early 40s, grandma, you're not broadcasting that on your dating profile. Nor should you.

No. Like, maybe I wouldn't even tell him until six months into the relationship. Oh, wow. If ever. See if he notices. But I'm glad it worked out for these two. And if it worked out for them, it definitely can work out for you. Whatever situation you're in.

Email the show. We'll call that person who's not calling you. back and go check out all of our second date updates. They're up online wherever you find your podcast at Brooke and Jeffrey in the morning. On the new podcast Solita, we share the messy reality of traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering me a ride on his motorcycle. I chose option B. I'm Julie Pinero and I travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word Solita, trading the pity for possibility.

Listen to Solita on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Mangishatigler, and I'm back with a new season of my podcast, Skyline Drive. This time I talked to scientists, biopunks, curmudgens, blues owners, super seniors, and Goa's top cryotherapy lab to try to understand this obsession with living forever and what it means for all of us. And I get into a bit of trouble along the way. I'd say probably start bone smashing. That doesn't work.

Make it look more defined. They say it works. I don't know. Listen to Skyline Drive, How to Live Forever, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast.

College football will hijack your weekend, ruin your sleep, and break your heart. And that's why we make the Solid Verbal College Football Show. I'm Ty Hildenbrand. He's Dan Rubinstein. Every week, we preview the games

that matter and the storylines that are going to ignite your group chat. And you can join us in the app as we react to what happened, why it matters, and how the sport went completely bonkers yet again. Listen to the Solid Verbal College Football Show on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey there, everybody. Amy Robach and T.J. Holmes here from the Amy and T.J. podcast. We're going to cover everything you need to know during this heated political season. Yes, we just saw Lindsey Graham, the death of a long time, Senator. Also, we've got a couple of missing members of Congress.

Congress. Also, we got a lot of members of Congress behaving badly. We got accusations, allegations flying all day long on Capitol Hill. Listen to Amy and TJ on the IHeart Radio app, Apple Podcasts, or wherever you listen to your podcasts. On August 4th, 1962, Marilyn Monroe died. Then the rumors started, and she died again. And now, we're going to set the record straight and learn about the way Marilyn Monroe actually died, the third way. I'm Jake. Brennan. And on my podcast, Hollywoodland, I revisit some of the biggest stories from Hollywood history, separating the myths people want to believe from the reality underneath them. Hollywoodland is part of the Exactly Right Network. Listen to new episodes every Monday on the

IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.