Brooke and Jeffrey: Second Date Update - Second Date Update: Driving Miss Laurie

Episode Date: November 13, 2023

One of our listeners said he changed ONE THING on his dating profile that instantly changed the game for him. He wishes he’d done this years ago and you can hear what it is in 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.

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. $1.4 billion in NFL quarterback contracts.

The untold stories behind the biggest deals in football history. I'm A.J. 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. Second Date Update. Dating older women.

It's like adult braces. Because you're going to get to a point in your life where it's like, gosh, I probably need it. I know it's good for me, but it's also going to be weird. Because everyone around me is going to see me. They're going to be judging probably need it. I know it's good for me, but it's also going to be weird because everyone around me is going to see me. They're going to be judging me for it. I'm going to try and keep it a secret, you know, keep my mouth shut, literally.

That is a younger man's perspective on dating up above his age. Because you're not there yet, but one day. One day I might get to the point where I need adult braces and I need an older woman. But one of our listeners says he's brave enough to admit it right here on our show and even braver to admit that she's not calling him back after their date. Okay. So let's talk to him.

Nate, welcome to the show. Hi, thanks for having me. Nate, you're very brave. Why is this brave? Like, why is, like, that is such a weird. It's brave of her to take on a young guy and have to deal with him. Such a weird thing to say. Like, how much older is this brave? Like, why is, like, that is such a weird. It's brave of her to take on a young guy and have to deal with him. Such a weird thing to say. Like, how much older is this woman?

I mean, I guess if she's 30 years older, then that's a, that's a thing to tackle. Which retirement home did you meet this gal at? I didn't meet her at a retirement home. Oh. I met her on a dating app. Okay. Okay. And what's your guys' age gap?

Do you know? Well, I'm 32. Uh-huh. And she's 49. Okay. And what's your guys' age gap? Do you know? Well, I'm 32, and she's 49. Okay. It's not like you're a 22-year-old. That would be weird. Yeah, yeah. Only because, like, what do you want to do with a 20? I don't know.

22-year-olds are kind of... Which did the math. It's 17 years difference between the two of them. Okay. Is that right? Yeah, that sounds about right. Okay. That's a big gap, but, you know, it's not undoable.

It's definitely noticeable. What's her name, by the way? Her name is Lori. Okay. Okay. And how did you find Lori online? Well, I decided after a long time of just using dating apps, like with people around my own age, that I needed to branch out.

Okay. Because I was getting kind of bored. So what do you think, like, an older woman has to offer you instead of a woman in her 30s? Well, obviously experience, wisdom, but frankly, I just wanted something new. Okay. Okay. And there's probably not much pressure for like babies and marriage because that's, you know.

I could be her daughter. That's done. Yeah. Actually, Nate might be going out with your mom. Oh, God. That's true. I mean. Is your going out with your mom here, Alexis. Oh, my God. That's true. Your mom, Lori?

No, my mom is not Lori. Thank God. Yeah. Maybe online she is, though. Yeah, I thought. Okay. So you went out with Lori. Where did you guys go?

You know, we went out to eat. We had a nice time. Oh, really? Like, what did you guys connect over? We just sort of talked. She actually invited me out and picked the place. She's much more successful than I am. She was like, I'm going to treat you.

Yeah. Older people tend to be, for some reason, they come to the territory. They just have more money. You didn't feel emasculated at all? No, I mean, I'm a pretty progressive guy. I don't need to be, quote unquote, the man all the time. Yeah, for sure.

When you say that she was successful, what do you mean by that? Like you talking about her job sort of deal? Yeah, her job. She's a business woman. She's like, is one of like a higher up, some company. Like she's like a boss. Dude, that's awesome. I like that.

What do you do? Do you mind us asking? I am a valet. Okay. She's a boss, you's awesome all right i like that what do you do do you mind us asking i am a valet okay she's a boss you're an employee did you notice like at any point in your guys's conversation like oh god we do come from two different generations you know i initially i was worried about that but it ended up working okay we talked about video games a lot like we talked about rocket league which is crazy like i can't believe that she even knows knows rocket league at all was there anything like sexy about that yeah she plays video games brooke that is sexy to a man you know but i mean to her it probably feels like she's talking to a teenage boy i don't know she brought it up did she though or did he

bring it up she just knew what it was. Yeah, we were just talking about what we were into, and I said, lately I've been playing a lot of Rocket League. And he was like, I know Rocket League. She didn't just say, oh, it's a game with the Rockets. It's actually a car game. Or like I buy it for my sons. Well, Nate, tell us, was there any weird stuff

that happened during the date? I mean, the waiter thought it was weird like the waiter was kept looking at me like really man okay that's kind of rude i'm imagining nate just like drawing with crayons what are you doing so how did the night end well I invited her back to my place, which she declined, which is in her right to do. Of course. Wow. How mature. And then she gave me a kiss on the forehead.

Oh. Oh. Oh, I told you. She thinks of him as like a kid. That's like a cute, funny thing. I mean, back in the day, you used to take things a lot slower romantically. So you started with a forehead kiss, and then you slowly. There was way more bases back in the day, you used to take things a lot slower romantically. So you started with a forehead kiss, and then you slowly. There was way more bases back in the day.

I bet she kissed the server on the forehead, too. She wasn't born in the 1950s or 40s or something. Have you seen what Alexis' mom is wearing out? She's not doing forehead kisses. Alexis' mom don't wear much. Let's be real. You left the date. She went home.

What's happened since then? Well, I've been trying to get a second date, but she's like really busy. I mean, she's got this crazy job and everything, but she did try to see if I was free this coming Tuesday at 2 p.m. It's a weird time. Did you say yes or no to Tuesday at 2? I said no because I'm at work. I mean, I'd love to meet her at 2pm on a Tuesday but I'm parking

cars, man. Makes sense. And then she's just been elusive when you've asked her out. This is definitely a new one for us. You don't think it's just that she's not interested because he's a younger guy that spent the day talking about video games? And he doesn't have an equal job

to her? I don't see a single wrong thing with what you said there so she wouldn't meet me at all though the thing i think if she didn't like me yeah she pursued him on the app like she swiped right on him just the same way she swiped right on her whatever sometimes you have ideas and then they turn out to be not as great as you thought i don't know okay i don't appreciate that attitude coming into the second part we're gonna call this lovely mature woman who is totally into you 100 we're not gonna as great as you thought. I don't know. Okay, I don't appreciate that attitude coming into the second part. We're going to call this lovely, mature woman who is totally into you 100%. We are not going to call her that

when we talk to her, okay? Whatever the right thing to call her is, we're going to figure that out and then we'll try and get you a second date update right after this. Second date update.

We have a guy on the line named Nate who just revealed to us he went on a date with a woman 17 years his senior. Yeah, that's a big gap. It's pretty decent size. They're not connecting afterwards.

And I know the girls in the room think it's because he was too immature. And she's not going to want to talk to him about video games and Rocket League. And that was a turnoff. I mean, that happens with no age gap so. Excuse me let me remind you the man to my left Jose Bolaños plays video games all the time and he's the most mature person I know.

Hit him up at HilariousJose on Twitch and find out what a catch he truly is. And I will say for the record I am the most single person I know. That's by choice. Maybe that's not correlated. No woman can hold him down.

That's why. That's what it is. Yeah, that's it. But I also think our listener, Nate, brought up a good point, too. The ladies think she regrets going out with a younger guy after the date, but she's the one who is asking him to hang out again. Not a younger guy, just him. And asking him a time no one's ever free.

Yeah. The Tuesday at 2. Just the point that she's reaching out, still engaging him, asking to see him again. I mean, that must mean something. Right. Right, Nate? Yeah, she must like me to some degree,

but she hasn't answered my last four texts. She's busy. Okay, she's busy. She's a career texts. She's busy. She's busy. She's a career woman. Let's just give it a shot. We're speculating forever. We need to call and find out. I've never called someone this old before, so I wonder if she'll pick up a landline. Do not do that when we're on the phone

with her. I can't wait. She is going to hang up on us. Okay, I won't say it. Jeffrey, I swear. I promise. I'm not crossing any body parts. I won't say it. Okay, here we go. Hello? Hi. Is this Lori?

Speaking. Who's calling? Hi, Lori. Yeah. Sorry. You're on the radio right now. Your voice kind of took me by surprise. Why?

I don't know. I know why. You have some weird preconceived notions. No, I'm sorry. Who is this? Sorry. We're a show called Broken Jeffrey in the morning. Yeah.

Why are you calling? It's a great question, Lori. Yeah, we do a segment called the Second Date Update, and that's where we help our listeners who've gone out with somebody hook up with them one more time. Go out with them one more time. Sorry, this is not a good session. I think you might have the wrong number. I'm so sorry.

No, it's not the wrong number. Well, it may be the wrong number. Are you the Lori that went out with a guy recently named Nate to dinner? Oh, God. Oh. A little younger than you? What? How do you know this?

I'm sorry. How do you know this? You are having a reaction right now to that name. Sorry. We're not trying to, like, make this awkward for you, but Nate reached out to our show and told us that you guys went out and he's been trying to see you again. Oh, God. He really liked you. Oh, no. Okay. Oh, no. to our show and told us that you guys went out and he's been trying to see you again but oh god

he really liked you oh no okay okay that's not good why i'm well i just i don't i think something got uh like some um wires have been crossed here what do you mean we're we're a little bit confused because he told us that you even mentioned a specific time and a date, like 2 o'clock on a Tuesday, where you wanted to meet up with him and you couldn't make it. Yeah. Well, I feel bad because, to be honest, I haven't been 100% up front with him about my, I guess, my intentions for wanting to meet up with him. You met him on the dating app, right? Like, I mean, if you meet anybody on a dating app, it feels like the intention is to date.

Romantic. Oh, so you're just looking for a fling? No, I'm not. I'm married. Wait, what? Wait, what? Oh, wow. What do you mean you're married?

Why are you on an app? I didn't mean to be on a dating, the dating, I'm on this app and you can, you can look for friendship. I was, you know, I put on my profile. Oh my God. Wait, so you were on the wrong section. Or he was on the wrong section. Did you, did that come up during your date that you're trying to be his friend?

You know, I, I guess I didn't, I wasn't like explicitly saying, you know, I'm just looking for a friend. I think I just, what's happening is I have a stepson and he is, he's 17 and he can't drive. He can't figure out driving. And I was looking at this app, you know, some friends of mine that use it and they said you know take a look because sometimes you can meet people that have different

skills that can actually help you out in the real world i don't get it i came across nate's profile and i thought he's a valet and my son is having trouble with parking oh like why wouldn't you just be out front and ask him like hey and tell him what's going on as soon as you message him on the app well i mean he we were talking about you know what do you what do you like to do in your spare time yeah and so nate brought up that he likes to play this game rocket league League. And I was like, oh, I know Rocket League because I have a kid who plays Rocket League. Oh, that's how you know. Okay.

Well, this is clearing up a lot of things. I don't know. I don't know what to say other than we need to tell you that Nate is on the other line right now and has been listening to this conversation. Oh, great. Okay. Wouldn't that be good?

Because now it's clear. Nate? I mean, actually, I think this is, I mean, I don't, I can't believe he wouldn't just talk to me, but I couldn't. Now's your chance to do it, Nate. You there? Yeah, I'm here. I'm in shock. Nate, did you have any idea she was looking to just hire you to help her son?

No, and I'm regretting calling the radio about it. That's a little embarrassing. Why do you think I bought you dinner? I bought you dinner. It wasn't a date. I didn't want you to think it was a date. It was like sort of an interview, you know? You don't go to dinner for interviews like i've never taken a babysitter out to dinner because i wanted poor babysitters i've never like been like hey is there a young 30 something man that wants to babysit my kids and let me take you out to dinner like that just seems you should give it

a try it works out really well. That's weird. It doesn't because she's here. Well, on the app, we were chatting before the date, and he was saying how he was interested in, you know, in other business and e-commerce. And so I have experience in that. And I thought, you know, I'll scratch his back if he can scratch mine. I think he meant literally.

Some actual skin-to-skin contact huh i can't see that like i can see why there's a miscommunication nate are we clearing things up for you here so just to be clear the 2 p.m thing that's not like a hangout afternoon delight sort of oh yeah you have to hang out with him on a tuesday at two um no i wouldn't my son's off from school at that time so you know i just thought it'd be the perfect time for a driving lesson before the cross or a perfect time before your husband gets home no you can go to my profile right now and it says looking for friendship. Okay.

So does my Tinder back. Hot tip, men don't read the profiles. That just usually means you're not looking for something serious. Yeah, he's right. I mean, maybe include a picture of you and your husband next time. There it is. That could mean something else. Yeah.

Not a bad idea. I guess i'll do that i will do that well hold on we still have nate on the phone with us here maybe there's some sort of deal that we could strike up oh yeah i mean are you still looking for like helping your son out because like i could use some money oh okay so maybe he's interested I'll take money over forehead kisses any day. I'm so sorry about the forehead kiss. I honestly didn't know what to do there. I do that to

all my babysitters and people that help with my kids too. She does it to us even every day when we leave. It's super awkward. I mean, I'm absolutely willing, you know, if the offer stands, I'm willing to help you out with some business acumen and, you know, different tips and everything. If you can help me with my son. That's pretty good.

What do you say, Nate? There's a once-in-a-lifetime opportunity. You know, I've got your number. Let's work something out. Okay. All right. So now we're actually paying for a real business dinner this time. Yeah, I guess so.

Yeah. Well, look at that, Nate. We're trying to hook you up with like a romantic partner, but we may have just gotten you a part-time job instead. There we go. You know what? I'll take it. Hey, make sure to put us on your LinkedIn, okay?

Will do. It'll be a reference for you. Brooke and Jeffrey in the morning. We're getting a lot of texts in 78592 from people saying they meet friends on these dating apps all the time. Dating apps? But you go on the friend part. Like Bumble BFF. You could meet friends on the

dating part too. According to our listeners it's more common than you'd think. Should we set up a friend? Maybe we should set up a friend seeking profile for Brooke on Tinder. You up for that Brooke? That is so sketchy, dude. No, how good is it going to feel to have all these people who want to be your friend and

you can reject them one by one? Yeah. Or just kiss them on the forehead. I'll claim I was just hiring him for my kid. I swear. See, now you get it. Then you'll end up on some other morning show doing another second date. You'll be here on Ryan's Secret.

So sketchy. All of that is so sketchy. Okay, well it's not for everybody, but if you ever do go out on a date, please just let's save it for the dates. Yeah. We're not doing the friend match online for this segment. Yeah, if your friend's not calling you back, we don't care.

I'm sorry, that hurts more. You know, being rejected by a friend is way more painful. No, if you want help hooking up your romantic life, email the show. We'll call that person who isn't calling you back. Brooke and Jeffrey in the morning. 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 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.

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. $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.