Brooke and Jeffrey: Second Date Update - Second Date Update: Return Of Roofer

Episode Date: April 1, 2024

One of our SHOW MVPS is back today and his newest love story all started in the back of a city bus. It gets more romantic from there but you can help us welcome him back with a new Second Date podcast!See omnystudio.com/listener for privacy information.

Ugh, we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and find them on Bumble.

Catch Jon Stewart back in action on The Daily Show and in your ears with The Daily Show Ears Edition podcast. From his hilarious satirical takes on today's politics and entertainment to the unique voices of correspondents and contributors, it's your perfect companion to stay on top of what's happening now. Plus, you'll get special content just for podcast listeners, like in-depth interviews and a roundup of the week's top headlines. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Second Date Update I have been waiting for this moment for an entire week. Second Date Update. I have been waiting for this moment for an entire week. I am so excited. I know, you're actually smiling. Ladies and gentlemen. What's happening? Making his glorious return.

What? Please welcome back to the show a fan favorite. Oh! Can I get a drumroll, please? For the one, the only, Roofer. Oh, Roofer. Roofer, welcome back, dude. Yeah, thanks for having me back, dude. Wow, Roofer.

You're getting more requests than song requests. Oh, my God. We have people constantly remembering you, bro. Will you remind me, Roofer, what you were on? Like, we did a second date last time, but I can't remember if it was successful. It's been over a year since he was last on with us. Rufus has actually been on the show three different times. The most memorable one for me was the coffee date that you had with a girl,

which you forgot about because that morning you were, let's call it, medically enhanced. Sure, we'll go with that. You may or may not have been staring at the clock, or you stared at it for too long and zoned out. I remember now. So we're just going to say that you forgot. Yeah. That didn't work. Yeah, that sounds good.

That sounds good. Sounds like me. Anyway, we don't need to go into any more detail about that. The bottom line is, Rufa, you're a friend of the show. We love hearing from you. So let's talk about this new woman that you just met. Okay. What's her name?

Yeah, her name is Cheryl Okay, where'd you meet her? And we met on the bus Oh, was she passed out too? Why am I not surprised, Rupert? I expect nothing less from you First of all, she was awake I want to really emphasize that

Good for you, dude Do not edit that part out. We know Jeffrey's humor. You're good, man. Yeah. Well, I didn't have a bus pass, so she offered to cover my bus pass. Oh. Wow.

Look at you, not even digging in the trash for a transfer. Yeah, I was going to say. You didn't have to. Okay. So how did you and Cheryl get to talking to each other or interacting with each other? I mean, like I said, she bought me the bus pass, and then she decided to sit with me. Okay. So how did you and Cheryl get to talking to each other or interacting with each other? I mean, like I said, she bought me the bus pass and then she decided to sit with me. So I started talking on the bus ride. Oh.

She liked what she saw. That's a risky move on her part. Yeah. Meeting a man at a bus stop and sitting next to him. Yeah. So how did that conversation with her go? Well, she said she was going to the botanical gardens. Oh, cool.

Oh, beautiful. I was like, oh, man, I got nothing else to do. Wait, you invited yourself or did she invite you? It was a little of both. I was kind of like, can I tag along? I like botanicals. I like greens. Oh, you're going to a funeral?

Yeah, sure. You know, I got time. Oh, my God. I say good for you. Okay. Was she open to that? Yeah, that's the question. Yeah, I God. I say good for you. Okay. Was she open to that? Yeah, that's the question. Yeah, no.

She was like, cool. Okay. Okay. So you guys went to the botanical gardens together. Hey, how was that? Disappointing. Oh. Oh.

Wait, why? I guess I didn't know what a botanical garden was, but I was picturing it like an underwater thing. No, it's not an aquarium. Just plants. It was just a regular garden. Did you voice how much you thought it sucked?

I tried to kind of keep it to myself, but then after about 20 minutes of just looking at flowers and stuff, I got bored. Seen one flower, you've seen them all. Did you try to talk to your kind of you know i got bored ah yeah seed one flower you seen them all pretty much did you try to talk to your kind of date the girl at all did you ask her any questions when you got bored oh yeah i just kept talking like basic small talk what do you do for work and all that

kind of stuff but i also brought this thermos and uh she shared some of my pre-mixed stuff pre-mix what does that mean i'm afraid to ask what was your pre-mixed stuff. Oh, no, no. Pre-mixed? What does that mean? I'm afraid to ask. What was your pre-mixed in your thermos? I call it a morning trucker. It's just like whiskey and OJ. It's kind of like whiskey and... What? There you go.

Sounds delicious, dude. Did you tell her what was in this before she took a big sip? Like I just said, it's whiskey and OJ. Okay, you told her. She was game. Did that change the date around, make things go a little bit better? I mean, you know, took the edge off a little bit, but it's still a boring garden.

But it is a boring garden still. Well, maybe you need to change the scenery at that point. Well, I tried. So after an hour, I was like, you ought to go to like a bar or something. Oh. What time in the morning is this? Yeah, we're after pre-fun. You already have, yeah, your mixed thermos of whiskey and OJ.

Oh, which sounds awesome. Oh, yeah, that's what she kind of said, too. Are you already drinking? Oh, okay. Well, it's kind of, I want to mix it up, get other drinks. You can't day drink unless you start in the morning. So you offered to change scenery, go to a bar and drink. What did she say?

She did not want to do that. Yeah. Doesn't sound very fun. Makes sense, dude. I mean, she took a bus with the sole purpose of spending time in this garden. She was really excited about it. Honestly, Rufa, I'm surprised you'd even want to call a woman like this back. What?

Killed your buzz. She was still over, it was the garden that sucked. Oh, see? It wasn't her. You felt the vibe, you just think it was the setting that messed it up for you? Yeah, totally. Did she share her phone number with you, Roofer? Yeah,

I did get her number, and I mean, it could be my fault that she, like, why she's not calling back. I kind of let the old Cricket wireless account expire there. Oh, so your cell phone's off? Where are you calling us from right now, bro? I was going to say maybe she's not single. No, it works now.

Oh, it was shut off temporarily. I always wonder who had Cricket. A lot of people. That's Roofer. Okay. Now your cell phone's back up and running, and you still haven't heard anything back from her? No texts, no calls, nothing?

Yeah, I mean, again, it was down for like a week. No, it's not too long. I did text her when it got back up, and yeah, nothing. So, I mean, was there anything romantic about this? Because maybe she went in it thinking more of a friend. Brooke, did you not hear him say morning trucker out of a furnace? Yeah. That should have won you over, like, by miles.

I mean, are you proposing at this point? Yes. Yeah, I mean, I don't think, like, the first hangout needs to be romantic or anything, but, like, we totally vibed. Good. Let's look for something awkward. Yeah, we just need a good starting point to jump off from, so that's what we're going to do. We're all going to have some morning truckers and come back. Okay. We're doing it for roofer coming back and calling Cheryl, try to get your

second date update right after this second date update. Quick recap for our good buddy roofer, who's back on the show. We're getting a lot of texts at 7592, by the way, people very excited saying roofers back. Love me some roof. Raise the roof. A lot of roof puns. Yeah, I feel like we should just be chanting Roofer, Roofer.

We should. Tons of fans of Roofer. So, Roofer, is there anything you want to say to your radio posse who's listening right now? The roof heads?

Oh, man. I mean, you guys already hit it, but like, thank you? Yeah. But Roofer has come to us again today, this time because he met a woman on the bus.

Public transportation is where all the hidden hotties lie. That's right. And this one is named Cheryl. Roofer invited himself to the Botanical Gardens with her, where she was already going. And they shared his thermos full of trucker moonshine whatever it was and after about an hour of that they decided to call it a day hey roofer don't let him talk about you like that what is it called again it's a it's morning trucker yeah it does sound better when you when it goes by a name yeah like a screwdriver it doesn't sound that bad true but i don't like that when

he doesn't like vodka he has I thought he just cussed. No, he said vodka. Okay. Rufus got some class, but he did feel something when he hung out with Cheryl. And it's not just the headache that he woke up with after regaining consciousness in the bushes. He really liked her. And Rufus knows when you like someone and they're not reaching out back to you, you come to us. That's right.

We've always gotten them on the line, at least. Yes. Not a date. I don't think we've ever gotten them on the line at least. Not a date. I don't think we've ever gotten a successful second date for you yet. This might be the one though, Roofer. I feel I feel. You feel. Worst case, you made more fans. That means that you haven't had enough

morning truckers. If you still feel. You're right. Let me tap myself off real quick. We're joking. I don't know if that's a good idea. Don're right. Let me tap myself off real quick. No. I'm joking. I don't know if that's a good idea. No. Don't refill. It sounds like you've got to untap.

Yeah, bro. Look what you've done, Brooke. All right. She's in the fridge. Here we go. We're going to call Cheryl. You hold on to that drink. We're going to talk to her for a bit.

Here we go. Hello? Hi. We're looking to speak with Cheryl. Yes, this is she. Oh, man, is this going to be a surprising phone call, Cheryl? Cheryl, you're on a radio show right now, and everybody in this room thinks that you're a very, very lucky woman. Hi.

Brave woman. Hi, Cheryl. Hi. Hi. Hi. You're confused. So we're a show called Brooke and Jeffrey in the Morning, and we do this segment called The Second Date Update

where we try to help out our listeners with their dating life if they want to see somebody again after going out on one date. Okay. And there is a guy that wants to see you one more time. I mean, I guess you weren't really a date date, but... His name is Roofer, is how we know him. I don't know if he introduces himself a different way. Oh, my God.

Roofer. Okay, you know him? That was like six months ago. What? Wait, what? Six months? You did the... Are you sure you're talking about the same guy,

the guy that you met on the bus? You guys went to the garden? Yeah, yeah. Oh. We, okay. You know what? We never asked how long ago the date was. We all assumed it would be like a week ago because that's normally what people do on this.

It was a totally different season that you were in the botanical garden. Okay. Well, I'm sorry about that. We're going to have to ask you to go way back into your memory bank, though, and see if you can recall what that hangout with him was like. I mean, it was memorable. It's a little hard to forget. Yeah.

Memorable's good. It could be, yeah, positive. Yeah, I mean, I didn't say that. Well, we've heard a little bit about the date or the hangout from Roofer, but sometimes with these calls, the guys will remember things differently than the girls do. So can we ask, how did you feel when you met Roofer on that public bus and he invited himself to the Botanical Gardens with you?

I mean, he seemed really interested in the Botanical Gardens, which is not many men that I know are cool with, like, going to smell the flowers or whatever. Yeah. He thought it was underwater. To be fair, he didn't know exactly what the botanical gardens were, so it was more of a discovery mission than anything. I feel like she's getting to that when he was. Yeah.

That makes a lot of sense, actually. Okay. Why do you say that? Why? What was he like in the gardens? I mean, so, like, we got there, and we were, like, wandering around for a little while. We ended up in the main building, and, like, he starts talking to one of the employees, and he tells them, like, that he doesn't feel well, and is there anywhere for him to, like, lay down?

Oh, no. Oh, God. What is going on? Is he okay? Is this after you guys shared the whiskey and orange juice out of his thermos? Oh, that was later. That was after this. Oh.

Was it good, by the way? I don't like orange juice that much. Sorry to sidetrack you. You're in this building and he's talking to the staff about laying down. The staff finds a room for him to go into to lie down.

But as soon as he gets in there, he pulls out his phone charger and starts charging it. No. Wait, was it an excuse for a phone charger? Is that what you're implying? I think so. I had no idea what was going on. He's got so many phone problems.

Yeah, he's resourceful. That's true. It didn't take anything from that. Did you stay in the room with him? I wandered around and looked at some of the stuff in the main building. And like 10 minutes later, he walked out and was like, let's keep going, I guess. So we walked outside. We were in the garden for a while.

Okay. And like, I turn around, and suddenly he's just gone. Nowhere to be found. Okay. So I go and I look around this, like, one of those, you know, boxwood hedges that really, like, thick bushes. Yeah. He's behind the bush peeing into another display.

Peeing? Yeah. Peeing into a display of flowers or something? Those are like expensive, super well kept flowers. There are so many bathrooms at a botanical garden. What did you do?

I pretended I didn't see him and was... Okay. I can see how that would be a jolting experience for you. I will say we didn't hear that version of the story from Roofer. Well, it's because he doesn't know that she saw it. Or because it was

six months ago and he has a hard time remembering it. Oh, come on. I think the only way to clear everything up is to just connect you with roofer right now who's actually on the other line at the moment oh yeah roofer you there yeah what's what's going on sounds a little looser than when we started the call i mean the phone thing makes sense my phone's always running out of juice. Makes sense.

You don't remember that? You remember going and charging your phone? I don't, but I probably... But it checks out. It sounds like you. Yeah, that's something I would do. I'm sorry. The bushes, I mean, that's usually what bushes are for, right? No, bro. That's if you're in the wilderness.

Yeah, especially in a botanical garden. Yeah, there were a lot of bathrooms around, Rupert. You could have definitely gone in one of those. Hey, when you got to go, right? No, not right. That's not right. I mean, the worst thing is it was like a raised box. A raised box?

It was in its own display? I probably thought it was a urinal. There it is. It's like the visual confused him after all the morning truckers. I think I probably put my coffee in it too and coffee just goes right through me. Coffee with the orange juice and whiskey?

Called a morning trucker. What else do you drink in the morning? I think that's called a four loco. Oh my God. Wow, okay. Just for the record, I don't remember any coffee in that thermos. I think it was mostly whiskey and a quiet whisper of orange juice. Okay.

Well, the good news is that the memory... She couldn't even taste the coffee. The memory has stuck with you so long. Yikes. Possibly because of such a strong connection that you and Rufo have. Oh, nice, Jeff. Otherwise, you would have forgotten this months ago. Certainly. It was certainly a colorful experience.

One that you would like to have again? That's a great idea, Brooke, and we would love to offer to fund that second date in a brand new location. Totally on us, paid for by the radio station. What do you think, Cheryl? Oh, um...

Listen, I'll leave the thermos at home, alright? We'll get drinks in a regular... Oh, you're still gonna drink. I promise not to piss on any endangered species. You're on the radio. And I'll buy your bus pass

this time. What a gentleman. Don't let a gentle poet like this slip away from you. Oh, my goodness. Give him one more chance. As chivalrous as this offer is, I think I'm going to have to pass. Oh, darn it.

We almost did it, Roofer. Yeah, buddy. I mean, bummer, but, you know. Yeah. What? What? Roofer, I feel like. Back to the public transportation system for me. This guy gets more dates than I do still.

Leave the thermos at home, my man. Why would you leave the thermos at home? That's the whole point of a thermos. Yeah, Brooke, you have a thermos in front of you right now. I think Brooke thinks you should put it in a camelback. That way you can wear it. It gets way more liquid in there. That is not it.

That's a good idea. That is not it. Don't listen to him, Rupert. You're like, is gets way more liquid in there. That is not it. That's a good idea. That's not it. Don't listen to him, Rupert. You're like, is he drinking brown water? Gross. Brooke and Jeffrey in the morning. I don't know if we've ever had a listener go 0 for 4 on second date updates before. Or get four chances.

I mean, it's amazing that there's no embarrassment from him, though. I give him props for that. That's the thing about Ruffer. Even still, after all that public rejection, he is such a chill, happy dude. How could you not love him? I mean, I can see why you wouldn't want to date him. But yeah, lovable. He may need to make some lifestyle choice changes.

I don't think so. Some health changes. I heard Alexis is going to put a shirtless picture of Ruffer up in her cubicle next to Michael B. Jordan and Harry Styles. I don't even know what he looks like. I feel like pictures of Ruffer are more pantsless than shirtless. Can't we just hop on a bus and find him ourselves? Yeah, probably. You can probably smell him out.

That's true. But Ruffer's always going to be a friend of the show. You could be a friend of the show, too. All you have to do is trust us. How hard is that? Email the show. We'll call that person who isn't calling you back. And go check out all of our second-day podcasts, wherever you get yours, at Brooke and Jeffrey.

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.