Brooke and Jeffrey: Second Date Update - Second Date Update: Motel 7

Episode Date: August 30, 2023

The guy in today’s Second Date had ONE SHOT and ONE NIGHT with a woman while she was in town… and he admits… some weird stuff happened.See omnystudio.com/listener for privacy information.

Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews and more. Now this is a second term we can all get behind. Listen to The Daily Show Ears Edition on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Second date update. You ever been out with someone and thought, what am I doing? They are way out of my league. I don't think so.

I'm going to say no. Maybe. We've got some liars in the room because everybody's felt that. I think maybe one time. Have you ever had your own mother tell you, sorry, honey, that girl is way out of your league? You should give up and save yourself the embarrassment. My mom thinks I'm the most handsome man in the world.

There's no way. Again, another good liar there. That's what happened to one of our listeners, Alex. His own mom doesn't believe that he's got game. I mean, you relate to this so heavily, don't you, Jeffrey? I do, but Alex proved her wrong by hanging out with a solid seven, according to him, and getting a cheap hotel room with her. Alex, am I right?

Or was some of what I said exaggerated for entertainment? Well, technically, it wasn't my hotel room. It was hers, but yeah. Okay. Make her pay for it. That's right. She got the hotel room? Yeah, she was out of town,

so it was a business hotel room. Oh, okay. Jeffrey, you painted it. Yes, that was exaggerated for entertainment purposes. Oh, okay. I was hoping that it was perfectly accurate, but why don't you start from the beginning? Tell us about this girl you met.

Well, you said solid seven. I agree, but I thought she was really beautiful. Wait, does she have a name? Yeah, her name is Tiffany. Oh, okay. How'd you meet her? So we met on a dating app. We were just swiping,

and I guess she was looking for something because she came from out of town. If you're coming in from out of town and you're getting on Tinder, are you just bored? Probably. Are you looking for a one night, like? Let's not sell our man short that, like, she just matched with him because she was bored, looking to kill time. I think she saw something that she liked on that dating profile.

I mean, yeah, that's what I'm going for. You know, I post a lot of, like, shirtless pics and stuff. So if anyone comes out from out of town, then they know what they're getting into. Wow. I think that she definitely was only looking for one thing. If she swiped right on a shirtless dude and she's in town for one night, like, it kind of goes together.

How did the date go? It was going great. We were having a good time at first. Where did you guys meet? Just like at a hotel, like at the bar or something? Yeah, just kind of like at a bar across the street kind of thing. Okay. I thought it was going well because she did,

eventually she took me to her hotel room. Oh. Yeah, not much to do there. What? I think he's being sarcastic. Oh, no, I'm not being sarcastic. There's not a lot of stuff to do in a hotel room. That's why you go to do the last thing.

Okay. You should be focusing on the TV. There's stuff to do in there. You can watch TV and peruse the mini bar. I wouldn't be doing any of these things. Wait, why did you go to the hotel room then? Please don't tell me to iron. No, I mean, I thought things were picking up.

I thought things were getting about just about to heat up. Good. And I was curious to see what the decor in her hotel room looked like. Oh. Oh. I cannot tell what a sarcasm is and what it's not with you. I don't think any of it is. No, he's being serious.

What kind of paintings you got in there? But yeah, I mean, I thought it was going well, and then she, I think she tried to ditch me, though. Wait. She tried to ditch you? In the room't try to ditch you in the room or where are you at she pushed you out of the elevator and then shut the door oh we made it to the room i checked out the decor and then she left me for four hours yeah it's kind of odd i think she wanted me to go with her. She was going to go see a friend, but she made it seem like it was going to be real quick, like just to say hi.

So I was like, oh, I'll just stay. So she left you in her hotel room to go meet up with a friend real quick and then said she was going to be back? Exactly. She asked me to come with her a couple times, but I was like, no, I'll just chill here. You say hi, and I'll be ready when you're back.

Oh, no. Oh, yeah. So you said no. You stayed for four hours. You say hi, and I'll be ready when you're back. Oh, no. Oh, yeah. So you stayed for four hours? You're committed. I mean, she texted me a couple times. I was like, hey, what's going on? And she said, no, I'm sorry. I'll be back soon.

She was texting me. Okay. And she never once asked you to leave? No, she didn't ask me to leave. She did say, like, if you want to leave you can so you didn't take that as like a hint that maybe you should go yeah no i mean i don't know why i would leave i was i made it to the hotel room i'm gonna stay i'm gonna wait it out just wait for her to come back i can't tell if she's trying to get rid of you or not. She is. Because the fact that she won't know, but listen, the fact that she invited him, like, hey, come with me.

No. Yeah, she wanted him out of the room. She was trying to get out of the room. She wanted him gone, and then she was gone for four hours just in hopes that he would actually be gone by the time he came back. She saw his hunky, shirtless body and was intimidated and was like i need some more liquid courage in order to deal with this hunk of a man what did she say did she say that when she came back into the hotel room not with those words no she uh yeah you know it was about midnight at that point she got back and yeah at first she was apologizing she's like oh my friend you know we

just catching up we had to talk okay yeah no worries. And then she finally was like, well, I have an early meeting and yeah, I think I finally got the hint at that point. Oh, that's when you got the hint. Yeah. So how did you leave it? I just said, oh yeah, no worries. And kind of left. But I feel like we had a good time before

that. You know, her friend kind of got in the way. Oh, this is hurting me. Yeah. So wait, what do you want? Like, you want to go out with her again? Yeah, I want to go out with her. I made it to the hotel room. That's the only time I've ever been invited to a hotel room.

Because you asked to see the decor. It is kind of a smooth line, though. And not when it's sincere, Jeffrey. She could have said no. I bet she realized that now. Have you texted or called her? Have you talked to Tiffany at all? I texted her.

I said, we should hang out sometime. You're ever back. She just said, sounds like a plan. Oh. Oh. Yeah, that's easy to say when you live out of town. You think that's good? I don't think that's good. At least there's hope.

I don't think it is. She could have said no. Can I confess something to y' that's good? I don't think that's good. At least there's hope. I don't think it is. She could have said no. Can I confess something to y'all? Yeah. I don't know if I want to. I just, there's one thing, you know, people always ask, like, is there anything that could have made it weird? I do sometimes Photoshop my pictures.

Okay. We did. I don't think that's it. I'm going to guess it was the shirtless one. I think the weird part was you being in a hotel room for four hours. The hope is dwindling. Let's come back and try and get you a second date update right after this. Hold on.

Second date update. Look, we have a listener who has come to us with a problem. Yes. He needs our wisdom, our encouragement. And what we don't need, Brooke, is your condescending sighs. And oh, honey. I didn't say honey once. This is cringe slamming his interest in hotel decor.

Listen, he called for honesty. All right. No, he did not. He did not ask for honesty. He asked for help to get another date. You have a responsibility, Brooke, to our listener here. We need to stand up and be an advocate for the Photoshop shirtless men of this world. Oh, man.

Not a lot of guys would have the willpower, the mental fortitude to wait alone in a woman's hotel room for four hours after she excused herself. But Alex did. And we need to show him some respect Gosh darn it Impressed you are Okay, Alex wanted me there But like I think she was missing an opportunity because I think you sound like a nice person. Okay. So you think she might want to go for a second date?

Yeah. Alex, do you feel supported by Brooke's words there? I feel like she's being nice, but I'm glad she's trying anyways. All right. There we go. He knows that you can't do your job or you aren't willing to help him, but he's still going to stick through it, just like he stuck around in that girl's hotel room. All right.

Let's call her and try and get you a second date. You ready, Alex? I'm ready. All right. I believe. Let's do it. Who got this team? Hello?

Hey, we're looking for Tiffany. This is she. What's up, Tiffany? You're on the radio right now with Brooke and Jeffrey in the morning. Yeah, what is this about? This is about something we do on our show called The Second Date Update, where we try and help our listeners reconnect with people that they met up with online or went on a date with yeah and uh you met up with a guy recently named alex uh right alex yes oh man i bet it was a memorable night uh yeah you could you could say that. Okay. Sounded pretty fun from our end of the conversation.

That was our takeaway. I mean, I think the first half hour maybe when they were actually hanging out. There was definitely good moments, we've heard. Yeah, I mean, look, I was just trying to have some fun. You know, it was a work trip. I hopped on the app, thought maybe we could hang out, have dinner. Mission accomplished. Fun achieved.

Okay. So what did you think when you first saw Alex? I could tell pretty quickly that, like, he was a nice guy, but we weren't necessarily a good match. And, you know, even, like, in his pictures, he seemed like a kind of nice, wholesome guy. And when we met up he was really nice and i don't know he seemed really interested in my trip and what hotel i was staying at yeah yeah he he was mentioning that to us and that he wanted to see what the decor in your hotel looked like and we thought it was like just a line but it sounds like he was truly interested in the decor

yeah yeah it wasn't a line. He like walked into the room and was like caressing the curtains. Oh, what? Like the crown molding was mind-blowing. Oh, wow. Hey, that's actually fancy.

Crown molding. I mean, what were you thinking when he's doing all this? I mean, I mostly was so... Too turned on? No, just, you know, when like you're, you take a risk and you say like, I was bringing this guy into my hotel room, a good idea.

And no one really seems to be interested in this, but it wasn't anyway. It wasn't much really. And I was ready for the evening to be over. So I said, Oh, like one of my friends is also in town so i'm gonna meet up with them in the lobby do you want to come with and he just said no okay yeah it's too it's too early to be meeting the friends of the people that you're dating on night one i think i want to get acquainted with this crown molding over here what wait so the friend wasn't made up the friend was real oh no the friend was entirely made up you lied to him that sweet innocent man why would you ask him to go with you then like what i mean at this point i was just trying to figure out a way to get him to leave the room because it didn't

feel like he was going to so you know i thought maybe i'd get in the elevator and i'd jump off or something i don't know what the solution was he was in there he said for hours and you never came back yeah i was trying to figure out what i was going to do to get this like man out of my hotel room and it's wrapped out of your own room. And it's not because you felt threatened by him or anything. It's just. He was never mean. You know, he was persistent. And obviously I made a mistake taking him there, but he, you know, was polite when I came back and he didn't make a pass or anything.

It was just kind of a. Well, overall. Gotta go to work in the morning. I mean, he's not good at picking up the hints but overall he sounds like a nice guy yeah i thought that until the next day when i checked out of the hotel why what um oh yeah so apparently he ordered a movie to the room while i was gone and i was like well i didn't watch anything you know i saw the bill and he they said well it was I ordered a movie to the room while I was gone. Yeah. You did? And I was like, well, I didn't watch anything.

You know, I saw the bill, and they said, well, it was rented at this time to your room. And I looked at it, and it was, I don't even know how to describe this movie other than it's titled Flutter Island. Flutter Island? What? Hey, I have to say something here now. Is that like a Planet Earth butterfly special thing? No, no, no. Hold on. Tiffany, that's Alex.

He's been on the other line listening this whole time wanting to talk to you. But what was the name of the movie? Flutter Island. Oh. Oh. Like Shutter Island, but more fun. That is so uncomfortable. That is not a documentary.

Why would you do that, Alex? First of all, I went down and I paid the guy with cash and I told him to take it off the bill. So that should have never happened. No. That is like unforgivable. I swear I would have never made you pay for that. That's on the hotel.

No. Gross, dude. You were in her room. She's on the hotel. No. Gross, dude. You were in her room. She had to sleep in that bed. That is disgusting. Don't go to details, Brooke. He didn't do anything in there. He just watched a movie.

No, he didn't. We don't know what he did. I don't want to know what he did. Nothing happened. Nothing happened. And it wouldn't have happened if she hadn't lied to me. Oh, true. Dude, no.

He was up there for four hours. What else is he going to do? Leave! We were taking such a long time, and I thought, you know, I thought it maybe helped me get in the mood and, you know, in case something did happen, and it didn't.

Nothing happened, which is fine. Oh. And that wasn't even supposed to be on your bill. I'm sorry. It's not it being on my bill that is the problem here you get that right well what did you want me to do they said it leave leave it's not your space why would you think it's okay to rent a movie in the first place well he thinks something's gonna happen though it doesn't matter you may know that but no one said leave it's her room it's not his room it's her room her space you

invaded it I was invited but yes I as a point and I think he's still interested in seeing you one more time Tiffany if you're up for seeing him again we would pay for a date to go out wherever you live. I'll cover the flight. I just, you know, Tiffany, I think we did have a good time. And that part of it was weird. But I think, you know, communication wise, we'll get better at that. And we should try again.

How can you be that clueless, Alex? Yeah. It's called persistence, Brooke. No, it's not. It's called idioticy. That's not even a word. What is it? Idiot?

I don't know. Dumbness. I don't know. Hey, she wasn't even supposed to know about that. It was, I asked a guy to pay, I paid him with cash. Where did that go? You have to, we should make a complaint to the hotel, actually. It's a rinky-dink hotel's fault.

Some guy made 20 bucks in the front desk and is just laughing. Yeah, he did. Tiffany. Yeah, he did. You are not going to ask this question. Give Alex one more chance. Don't let that hotel's mistake ruin a shot at love between the two. Just think, this time you could invite him into your apartment and he could just end up

living there. Plus, I just Googled it. There's a Slutter Island 2. You guys have to watch that together. We'll pay for it. Tiffany? You know, I think I'd rather sit in a hotel lobby for three nights straight. Nice. Hey, I don't know that that's

clear to Alex. You may just need to say no. Brooke and Jeffrey in the morning. Here's a question for my co-host. I want to know, did renting the movie sink his ship or was it the movie choice? The movie choice. It was fully 100% the movie choice. If he was watching Minions by himself, it would have been fine.

That would have been okay. How do you not know this? Why are you even asking this? How is this not obvious? Have you seen Slaughter Island, Brooke? No, Jeffrey. How can you say that it's a bad movie if you've never even seen it? Because I won't allow myself to even say that title out loud.

Wow. That was Martin Horsese's best directing film. I bet it was almost nominated for an Oscar. Yeah. And here we are shaming him for it, just off the title alone. I'm sure. Starring Matt Damon, right? Bruce Bader Ginsburg documentary.

If he had watched that, he would have been a freaking hero. Dude, slept. Starring Matt Damon. Yeah. Oh, with the Ruth Bader Ginsberg documentary. If he had watched that, he would have been a frickin' hero. Dude, slept with him the same night. That would have been hot. Another ship sunk by Slutter Island. It's Brooke and Jeffrey in the morning. Brooke and Jeffrey in the morning. Jon Stewart is back in the host chair

at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late night legend Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show, ears edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews, and more. Now this is a second term we can all get behind. Listen to The Daily Show, ears edition on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.