Brooke and Jeffrey: Second Date Update - Second Date Update: Make up, Make Out

Episode Date: September 5, 2022

One of our listeners chose a unique activity for her date... It sounds like it was straight out of Sex and the City.... but did it help... or hurt her? We're about to find out!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. Now, Mini Questions is returning for another season. We've asked an entirely new set of guests our seven questions, including Jane Lynch, Delaney Rowe, and Cord Jefferson. Listen to Mini Questions on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Seven questions, limitless answers.

$1.4 billion in NFL quarterback contracts. The untold stories behind the biggest deals in football history. I'm AJ Stevens, Vice President of Client Strategy at Athletes First. Introducing the Athletes First Family Podcast, the Quarterback Series. My co-host Brian Murphy, Athletes First

CEO, and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tua Tugnavailoa, and Jordan Love. Listen to Athletes First Family Podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I gotta say, I'm really excited about today's second date update. You look excited. You got a big smile on your face there, buddy. I am. I can't help it because the girl we have on the phone says she went

on an incredible date with Leo. Oh my god. Wait, like me, Leo? I cannot wait to find out what a date with Leonardo DiCaprio is like. So, Jessica, come on, girl. Dish. Spill that tea. Oh, boy.

I wish. Oh, boy. I wish. Oh, my God. Oh, I wish. Come on. What's he like? I think she's going to crush your fantasies, Jeffrey. So I did meet a guy named Leo on a dating app. See, Jeff.

And it must be Leonardo DiCaprio because he's obviously on all sorts of dating apps. He's very attractive. He's got, like like cute sandy brown hair. Okay, wait, what? Sounds like Leo to me. So did he take you to the Mediterranean or did he take you to the Caribbean? Like how much did he spend? Oh, I wish I knew.

Wait, is that really what this Leo looks like? He didn't look exactly like Leonardo DiCaprio, but his hair definitely did. And he just had like a very trustworthy look about him oh man those are the ones that you should trust least i'm telling you so what did you and leo do for your date so we met at a bar and he showed up like very confident and he was like are we gonna do this or what what did wait can i ask though what did he mean by do this like do the date do the deed get drunk where is he at i think, what did he mean by do this? Like, do the date, do the deed, get drunk. Where is he at?

I think he said, like, are we going to do this? Like, are we going to do it? Oh. I think it was a joke. You think? Let's hope. Did it work on you? Not at that time, no.

So wait, so the bar was fun, you're saying? The bar was fun. We hung out for a while and talked about a lot of different things. There was one time where he asked me who my favorite president was. Okay. What? What kind of first date question is that? I think it's an interesting one.

What was your answer? Of course, I said Grover Cleveland. Duh! Of course, yeah. He's a sexy one. Did you have a reason? Yeah, I mean, Grover, like, you know, from Sesame Street. So obviously that's the one I choose.

Oh, my God. You know what? United States history classes have done us so good. So we talked a lot. We got into, like, a conversation about, like, the YouTube shows that we watch. Okay. I told him I was really into makeup tutorials, and he didn't really get it. So I was trying to explain it to him, and he still wasn't understanding.

So I decided to show him what it was all about, and I actually gave him a little mini makeup tutorial at the bar. Wait, he let you put makeup on him? He did. He was a good sport, and I taught him a thing or two. I put some highlight on him and showed him the before and after to show that it made his cheekbones pop. Wow.

He obviously really likes you. He's letting you put makeup on. Yeah. Or he really likes high cheekbones, Jose, okay? He was a believer after that. Okay. Oh, so he looked pretty good after you were done making him up. Yeah, he looked great. His cheekbones popped, as I expected. This sounds like such a fun date.

Like, you talked about interesting things. You did silly stuff. Like, why do you think he's not calling you? Well, I don't know. Like, we even made out at the end. With your makeup on together? Like, did your eyelashes brush against each other while you guys had a passionate embrace? No, but my lipstick got on him.

His lipstick got on me. It was like a little weird, but it was really cute. Everybody else in that bar must have just been feeling like, what the heck is going on over there? But then it's like, hey, don't judge. Don't judge. It does sound like a PDA train wreck is what it sounds like. But you were both into it, so it's fine. Yeah.

But at the end, we ended up getting in separate Ubers, and then I haven't heard anything since then. And how long ago was that? That's a week. Oh, man. He hasn't called you back at all? Yep. Typical Leo.

One date, and then you're probably too old for him. But I guess we'll find out for sure. We're going to play a song and when we come back, we'll call Leo for you and get your second date update. All right, Jessica? Thank you, guys. Okay, hold on. Second date update. If you're just tuning in for today's second date update, Jessica is trying to get a hold of a guy named Leo.

And her date sounds like an episode straight out of Sex and the City. They went out on the town. they sip some Mai Tais, they gave each other makeovers, and then they dished about which U.S. president they think are the most bangable. All right, Samantha. We got Jessica. Jessica, would you say that's an accurate description of your date? I would say that's pretty close. Oh my God.

I feel like I'm one of the girls right now. She did put some makeup on her date while they were at the bar together and they ended up making out. But afterwards, Leo has been MIA. So we're going to give him a call right now and find out why Leo has been blowing you off. We didn't get to hear. What's your theory? I don't even have a theory. I just know that I really like this guy and he's not the same as every other guy here.

And so I just really, you know, want to have a chance with him. Yeah. Plus, what other guy would let me put makeup on him for like two hours at a bar? Yeah, that could be the problem that we're actually dealing with here. Maybe not into you. We'll find out though, okay? We're going to give him a call right now

and figure out why Leo isn't talking to you, okay? You got it. All right, here we go. Hello? Can I talk to Leo, please? Speaking. This is Young Jeffrey from the radio show Brooke and Jeffrey in the Morning.

How are you doing? Okay. Is this the Leo, perhaps? Who are you looking for? It's him. No, it's not Leo. We're looking for Leo who went on a date recently. Not Leonardo DiCaprio, right? Well, I'm saying we're looking for Leonardo Di went on a date recently. Not Leonardo DiCaprio, right?

Well, I'd say we're looking for Leonardo DiCaprio if it's him. Is it? I'm not Leonardo DiCaprio. Okay. I don't even want to do this now. He has some disappointment, but we still want to talk to you, Leo. Leo. Oh, my God.

Don't sound so dejected. I'm sorry okay leo the reason why we're calling is because you recently went on a date with a girl named jessica and she's trying to get a hold of you okay this is like what this is weird well obviously you're not calling her back and she wants to know why she says she really liked you. Oh. Uh, she's a nice girl. I just, um, didn't think there was anything worth exploring there.

Are you serious? She described the date to us, and it honestly sounded like you guys had so much chemistry from her perspective. Well, it was fun. She's a fun person. Um, yeah, she told you about the makeup stuff. Yes. Yeah yeah and she said you looked supes cute hey and to applaud you for being comfortable with your own masculinity i say

kudos okay no yeah no that's not that was fun she's a fun person but you know we talked for a long time and you know on a date you're asking yourself can i realistically see myself with this person she said some stuff that made me think no probably not i don't think she realized that she said anything that would change your mind about her at all she she didn't know that john lennon died what john lennon yeah like from the beatles okay yeah okay so she's not up on beatles history i just feel like that's a bit like do i want to spend the whole length of a relationship filling in cultural gaps like that are you kidding me my husband doesn't even know who john lennon is that's a that's a like, old cultural reference. You're gonna hold that against her?

I'm, like, a pop culture guy. It's, like, my favorite thing to talk about, and if someone's that checked out on it, I just don't think that, like, it's sustainable. What's the real reason? What's the real reason that you're not calling her back? This is some BS. She doesn't know some dead pop star

from 40 years ago? This can't be right. This is dead pop, like, the most famous musician of all time. Well, that's arguable. Yeah. I mean, you could say the Beatles are really super famous, but I wouldn't say John Lennon's the most famous musician of all time. He's the most famous Beatle, so yeah, I think I can. Really? Paul McCartney would probably argue against you right there.

Are we really arguing right now about who was the most popular beetle of all time is that what this has devolved into i mean ringo right no no this is john lennon and everyone should know he got shot okay okay so that's what you want us to tell her that's why you're not calling her back you can tell her whatever you want to tell her i just think it's crazy that she didn't know that. I mean, she says she was like too young and wasn't around, but I wasn't around when JFK got shot. I know that that happened. Okay. He has a point.

I don't know that they're the exact same thing though, right? It was pretty close. Okay. A president being assassinated and John Lennon being assassinated. I mean. Both American leaders, bro. Both big hits on peace, world peace, but not in the same way. Look, you're all coming after me, but you all know that John Lennon got shot.

Like, doesn't that say something? I mean, you reminded me. Yeah. All right. So you hear that, Jessica? John Lennon getting shot is the reason that Leo has zero interest in dating you. So how does that make you feel? Leo, are you freaking serious?

You're not calling me back because of stupid John Lennon? They didn't tell me you were on the phone. I'm sorry. Oh, yeah, that's right. Oh, my God. I'm crazy, and I don't know what I'm talking about because I forgot how this cultural reference works for this show

we don't tell people that the other person's on the line listening so Jessica's actually been listening to this entire conversation Leo I don't believe it you're being so judgmental like not everyone my age is going to know

facts like that you might not know that the that Notorious B.I.G. died. Yeah, I know Notorious B.I.G. died. I know T-Pock died. I know... Well, wait, wait. First of all, that is not for sure. There's a little controversy behind that. He could still very well be alive.

You guys, I think you're missing the point here. I think you're missing the point here i think you're missing the point you had fun with jessica leo yeah it was fun jessica okay you're perfectly nice you're a catch i just don't think we're compatible all right oh so you need like you're looking for a partner that just has like a whole list of dead celebrities in their brain that's what you want like why didn't you just put that on your profile weird way to put it but yeah i am looking for someone who's like plugged into the culture and the lexicon and like knows important information about who died when yeah

the lexicon i don't even know who that is oh my god hey leo i think you should give her another shot listen my husband knows nothing about pop culture. He couldn't even tell you who is in the Beatles, right? If we're going to go back to Beatles, let alone could he tell you when B.I.G. got shot, you know? Like, and it works. It works for us. We can have different interests and still be in love. That's okay.

Yeah, Leo, you guys have nothing in common. So let's see if you're willing to go out with her on a date. Would you be willing to give Jessica a second chance? We will pay for a second date for you guys. Absolutely not. And Jessica, just FYI, Ringo Starr and Paul McCartney are still alive. So maybe just jot that down. Write it down.

That's fine. I didn't want to go out again with you anyway obviously you're way older than i thought yeah that was a beatles burn sorry jessica no second date but you know who also is still alive leonardo dicaprio and i really wish that leonardo dicaprio had answered this call maybe somebody else will come in with. He would have known. 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 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. What if you asked two different people the same set of questions?

Even if the questions are the same, our experiences can lead us to drastically different answers. I'm Minnie Driver, and I set out to explore this idea in my podcast. And now, Minnie Questions is returning for another season. We've asked an entirely new set of guests our seven questions, including Jane Lynch, Delaney Rowe, and Cord Jefferson. Listen to Minnie Questions on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Seven questions, limitless answers.

$1.4 billion in NFL quarterback contracts. The untold stories behind the biggest deals in football history. I'm AJ Stevens, Vice President of Client Strategy at Athletes First, introducing the Athletes First Family Podcast, the Quarterback Series. My co-host Brian Murphy, Athletes First CEO, and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tua Tugnavailoa, and Jordan Love. Listen to Athletes First Family Podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.