Brooke and Jeffrey: Second Date Update - Second Date Update: Small Town Stranded

Episode Date: August 9, 2023

One of our listeners took his date to a quaint, little remote town....and they almost didn’t come back! Find out why in your Second Date podcast!See omnystudio.com/listener for privacy information.

John Stewart is back at The Daily Show, and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition podcast. Dive into John's unique take on the biggest topics in politics, entertainment, sports, and more. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Second Date Update. How many times has Brooke come to one of us saying,

Oh my God, I have the cutest date night idea ever. There's this adorable little shop. It's just a two and a half hour drive away. And a blind woman there teaches you how to cut off your own hair and turn it into a shower loofah. Isn't that fun? I just forced my husband to do it with me and it was so romantic. Oh my God.

And he has such thick hair. You wouldn't believe the loofah that man is able to make. I mean, it's just a head of gorgeous hair. Sometimes good friends

give terrible dating advice. And apparently that's what happened to one of our listeners recently named Will. Will, were you tricked into making loofahs out of your own hair? No, not a loofah.

Okay, good. And I was going to say, don't call it a hairball because it's not one. All right. I was going to call it that. Okay. Tell us about the date that you went on. What's her name? Her name's Heather.

Heather. Okay. What did you and Heather do for your date? Yeah, well, I was trying to think of a date idea because I wanted it to be cute. You know, I thought you seemed really nice. So I talked to a friend of mine and she was like, go try out this little downtown area. It's on like the end of this little peninsula. I had never heard of it before, but apparently it's really cool.

But it's kind of far away and i don't have a car she doesn't have a car so we took a bus oh okay wait took a bus to like some isolated peninsula far far away i thought it was kind of weird but i like trust this person who told me that it was cool so i was like like, okay, whatever. And wait, I mean, is the destination like a cafe? Like what's the whole point of this? She said there was bars and restaurants. Oh, it's like a little town.

Okay. Yeah. Yeah. Like little beach area and things like that. Like a touristy thing. Yeah. Yeah. Yeah. So you bust over there with Heather.

Yeah. Heather and I bust over there and i didn't realize that this place like how small it was gonna be but it literally took us 20 minutes to see everything ah oh no it's that small it was very small but they still had like a restaurant so we went and ate i bet it was busy restaurant if it's the only one in the whole town. I mean, what was Heather's reaction? I mean, because I'm guessing the bus ride took a long time. The bus ride took kind of a long time, but I don't know. I was trying to read the vibe, and she was still having a good time. And we went and ate dinner, and that was a good time.

But then there was kind of like nothing else to do after that. They don't have a hair loofah class that you could take over there? He didn't plan correctly. Sadly, no. I didn't see any ads for those. They're usually in basements, so it's hard to find the flyer. Should have gone and checked in around people's seats. Makes sense.

Okay. I try actively not to check basements for hair loofahs. That sucks. You guys do a little walk or something? What do you do? Yeah, well, we walked around for a second, and we were like, all right, let's just go back to the restaurant. They had a little bar.

Get hammered. That's always a good idea. True. I like that you've been there an hour and you're already a regular. We're back. Was it fun? Yeah, it was fun. So we're getting drinks and then we decide we want to leave and we missed the last bus out of that place this is like when spongebob missed the last bus out of the city remember that episode

i'm gonna take your word for it though everybody understands i mean that means you just got a pony up for a super expensive uber right yeah that was plan, but there were no Ubers in the area. Because it's a tiny town. Yeah. No Ubers, no Lyfts, no nothing. A bike? Nope, they moved there. He's actually living there now.

Pay one of the locals to drive you home. They're like, you're the mayor now. Yeah, I'm calling from the peninsula. It's been a comfortable life. We have to get a tiny hotel room. What? Oh, God. Which is also attached to the restaurant.

Oh, man. It's just one building. It was pretty close to the restaurant. Okay. Wait, what was her reaction? I mean, like this could go two ways. Either she's really excited and she's like, oh, don't worry about two. We'll split one.

Oh, yeah. We know which one Brooke would do. So I didn't want to assume anything and she didn like, oh, don't worry about two. We'll split one. We know which one Brooke would do. So I didn't want to assume anything and she didn't tell me otherwise. So I just got a room with two beds in it. That's pretty assuming. That's safe. What are two beds assuming you're not going to sleep together?

I think you would have to get two different hotel rooms. Like a first night. I don't know. If you're not going to assume anything. You're going to make a guy pay for two rooms? That's so much more money. I mean, they could call someone to pick him up. Dude, it's him. And it's his bad planning.

So what happened? So long story short, nothing happened. Like we fell asleep watching Pirates of the Caribbean. Nice. And we woke up in the morning, no breakfast, caught the first bus back. It was just kind of awkward, like having to be like forced to. Caught the first bus back. It was just kind of awkward, like, having to be, like, forced to stay together, like, the first night.

Not only that, you don't have a toothbrush. You don't have all of your, like, face stuff. Like, you're waking up feeling blech. And you didn't, like, hook up at all? It was not great. No, nothing happened. In separate beds? Weird.

Was she angry? Was she sitting with her arms? Were you, like, in one bed cuddling, watching it? Or were you in separate beds? No. No, angry? Was she sitting with her arms? Were you like in one bed cuddling watching it or were you in separate beds? No. No, we were in separate beds the whole time. Oh, God. She might have been mad. I don't know.

She was just kind of like not saying anything. Oh. So anyway, I emailed you guys because I have not heard from her. I feel like it's just as much her fault. I would never not Google that stuff. Right. Before I go on a bus with someone somewhere. And if you're with a dude that you don't want to be with, you'd call your girlfriend. You would never not Google that stuff. Like before I go on a bus with someone somewhere. And if you're with a dude

that you don't want to be with, you'd call your girlfriend. You would get picked up. You would get somebody to sacrifice. Yeah, I know. That's what I thought. Okay, well, good idea. Let's call her and shame her in a few seconds. I don't think that's it. I think it is. I think that he did something in the hotel room that made her not happy.

I think she was into it until a certain point. At least she didn't call the Coast Guard to come get her. I need a chopper. The Coast Guard who also runs the restaurant. It's a peninsula. It's a busy guy. Well, he's the mayor now. He has contacts.

I control all the helicopters. Well, we're going to come back. We're going to call Heather for you and see if it was your fault that it ended badly or hers when we do your second date update. It could have just been the circumstances. We'll find out for sure. That's not fun, Jose. for you and see if it was your fault that it ended badly or hers when we do your second date update the circumstances we'll find out for sure it's not fun jose get your second date update next second date update if you missed part one of the second date will and heather ended up stranded in a tiny town on a remote peninsula where the last bus had already left, which gave them no choice but to stay the night in one hotel room with two separate beds. Brooke immediately said before we left in the first part that something happened in that hotel room.

Oh, scary. Like a gruff detective who's been working the hooker beats on the wrong side of town. Something don't smell right over here. All I was trying to say, Jeffrey, is if she agreed to the hotel to begin with, she was feeling something good. Okay, or comfortable enough. Yeah, and then it turned to nothing but Pirates of the Caribbean movie watching. Well, if she hadn't done that, what was her option? To sleep outside?

To get her own hotel room. She's a grown woman with her own credit card. I'm sure she could have covered herself, Jeff. We don't know what her credit card situation is like. Maybe they're all maxed out. That's true. Jeff persons first when she gets on the phone, ask her her credit score. Alright. Well, we're going to see if Brooke's

gumshoe ways are right on or way off. But Will, maybe you should tell us did you blow the ending of the Pirates movie? Because maybe Heather hadn't seen it yet. Oh, that's it. Yeah, I'm not much one for spoilers. Oh, really?

He's like, Johnny Depp gets away. No, come on. You're the worst. Oh, God. So funny. Well, we don't have any spoilers for how the second date's gonna end. So let's get right into it. Hopefully it has a happy ending.

Yeah. You ready to do this, Will? Yep, let's do it. All right, here we go. Hello? Hey, we're looking for Heather. Yeah, this is Heather. Hey, we're looking for Heather. Yeah, this is Heather. Hey, Heather.

I said we because you're on with a whole morning show right now called Brooke and Jeffrey. Hi, Heather. Hey. Do you have a second? Whoa. Yeah. What do you mean? Like a morning, like a radio?

Yeah, we're a radio show. What if we weren't? What if we were just like a morning show that got together every day and just called people? Just like a bunch of randoms. But didn't broadcast? We podcast, too, if that makes it any better. That is true, yeah. We're a legit show, and we're doing something called a second date update. Okay.

Yeah, that's where we try and help some of our listeners who've gone out on dates but are getting ghosted afterwards to try and figure out if anything went wrong or if there's a chance you guys could meet up again. Okay. There's a guy that you went out with recently named will yeah yeah um did he call you yeah we heard from will a little bit about you guys going to this little town on this peninsula missing the last bus out and having to stay the night there. Wow. Okay. He told you everything. I don't think he told us everything because he didn't tell us why you weren't calling.

Yeah. No, I bet he didn't tell you everything. Because we've heard that you haven't been reaching back out to him after your night together. Yeah. So honestly, like I was actually really enjoying the date. Like it was going really well. It was funny, like that we kind of got stuck. And to be totally honest, I knew the bus schedule

because it was a complete flop. I wanted to know my way out. Wait, wait, wait. So you purposely missed the last bus? Is that what you're saying? It wasn't even that. I just kind of checked my watch and realized, okay, if we were to catch the last bus, we would have to sprint right now.

See? And Alexis, I think, mentioned that. Why would you not know the bus you're smart and safe girl i did not expect to hear that from you if i'm being honest so you were into him then oh yeah yeah like it was going very well and so i just kind of wanted to see what he would do like how he would handle that situation because like everyone puts on their first date face and I was like, this could be interesting. This would be like a fun little plot twist. It is brilliant. Wow. Because your first date face is a thing.

If you went on one date with me, you'd think I'm the perfect man. Okay. Second date, it's like, oh my God, how are you even alive? Already by the second date. Yeah. Yeah, I dropped it. We fall quickly. So everything was okay when you got the hotel room?

It was going great. And I was like, okay, I'm excited. And so, yeah, he ended up booking us a hotel room. Okay, wait, was that the right move for you? What were you hoping him to do? Well, I was kind of hoping it would be one hotel room. Oh, okay. I was super into it.

Okay. So what changed? Yeah, so we get up to the room and he's like, let's watch Pirates of the Caribbean. I was super into it. Okay. Okay. All right. So what changed? Yeah. So we get up to the room and he's like, let's watch Pirates of the Caribbean. And I'm like, great. A classic. Let's do it. Yeah.

Plus it's like, it's a movie you've already seen. So I always, that indicates to me like, okay, you don't actually want to pay attention to the movie. You can tune in if you want. Yeah. Yeah. It's really background. Right. Like, I feel like everyone has seen that movie.

Yeah. Okay. So anyway, about like 30 minutes into the movie, he pauses the movie just kind of like randomly. Okay. And like dials a number on his phone. And he like turns it on speakerphone. And I'm like, what is about to happen?

Whoa. What? And this voice comes on and it's a girl. And she's like, is my baby ready for his nightly routine? Wait, does he have a girlfriend? What the heck? Guys, it's his mom. And she starts reading Good Night Moon.

Get out of here. This has got to be a joke. I'm still waiting for the weird part. Jeffrey. Yeah, it has to be some joke that just ended up not funny or something i'm like shook at this point so i'm literally like i didn't say anything because i kind of kept waiting for it to be a joke did he tell his mom that you were there yeah yeah he was like okay yes i'm ready but i've got a friend over so it's got to be quick. What? And the mom still went through with it.

Not unusual. I would have been like, oh, let's do this another time then. Does that mean he's done this in front of other women before too? Whoa, whoa, whoa. Can I stop you right there? Please. No, I want it to keep going. No.

I need an excuse. I need like some logical logic. This story was just getting good. Hang on, hang on. What's happening right now? Is this? Yeah. Will, is that you? Yeah, that's Will. Hang on, hang on. What's happening right now? Is this? Yeah. Will, is that you? Yeah, that's Will.

Hey, Heather. Hi. Hey, what's up? We swear his mom isn't on the phone, too. I promise. That's how this segment works in the second dates is we have the other person listening

so that they can hear what went wrong. How would you not think that's a... What went right? How do you leave that out? I think it's weird that you don't appreciate that I have, like, a good connection with my mom. Oh, me. Well, that's not normal.

You're a grown man. Oh, grown men aren't allowed to love their moms? That's not what I'm saying. I'm saying grown men don't have their mom call them on a date every goodnight moon. Like, do you not see how that's an extreme turnoff? We don't get to mom call them on a date every good night moon like do you not very often so this is like something that we do together and it helps me sleep there is no way there's not been another person telling you that this is weird and creepy before obviously i don't like have people around all the time but you were there and I thought you would be okay with it and would think it was, you know, like, kind of cute. Huh?

Is that how you felt? Feel like maybe there was a little bit of cuteness to it? This was not the worst part, though, you guys. Let me cut to the worst part of this. He gets off the phone, and then he decides that this is the time to come on to me. What? While on the phone?

No, no, he hung up. He hung up the phone, and he was like, okay, now I'm going to try to be cute and like cuddly. And I was like, no. Oh, no. If I'm you in that situation and I see that someone that I'm with has a really close connection with their mom, that's a turn on for me. Yeah.

Good. I don't think most women think that. It shows emotional maturity. I'm just saying. Can you imagine on their wedding night, he's calling his mom for a bedtime story? What's wrong with that? Don't knock it.

She's a great storyteller. Yeah, I could get you right to sleep. I think Brooke is just jealous because she's not as good of a mother as Will's mom is. I never will be, Jeffrey. I never will be. I never will be. She has to get over that. But really, it comes down to Heather.

And if you're willing to give Will another chance for a second date, because if you are, we're willing to pay for it. Man. I just am, like, I can't imagine a future where this is something I have to abide. Like, if this was how it was on my first date, how much worse does it get? Oh, and then you have to, I mean, when you are with someone, you're with their mother, too. I mean, it's like an in-law situation. Yeah.

Heather, I don't get you. Like, it's just a story, you know? It's how we connect. I mean, she can read a different story if you want. Okay. Heather? I think you're missing the point. Maybe you would like to read him the goodnight stories, no i don't think will would let anyone replace his mother that's true

i don't want to impose so is this not happening no i i think that is like so short-sighted i think we had a good time and i think it's dumb that you don't like that i have a good connection with my mom well i don't want you to to go home empty-handed tonight. You know what I'm going to do? Tonight, I'm coming over, and you and I are doing Big Spoon, Little Spoon. We'll have your mom read a goodnight story to both of us. You're going to love it. It's a great story.

Do we have consolation prizes on this show that people never even expected? Or wanted. Everyone's winning it today. Except for Heather. Sorry, Heather. Brooke and Jeffrey in the morning. Jon Stewart is back at The Daily Show, and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition Podcast.

Dive into Jon's unique take on the biggest topics in politics, entertainment, sports, and more. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts

or wherever you get your podcasts.