Brooke and Jeffrey: Second Date Update - Second Date Update UPDATE: Winery Date With Mom

Episode Date: March 17, 2024

We're adding a little extra content to help you get over the Sunday Scaries! Months ago, one of our listeners came to us after his MOM showed up on his winery date... But the woman he was interested in agreed to give things a second chance. What’s been going on ever since? They’re back to tell us!See omnystudio.com/listener for privacy information.

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, the biggest moments of your life. Yeah. Like when you took your very first steps. Yeah.

Or when you scored your first goal in soccer. Oh. In my case, when I scored with Paula Rachitowski in 10th grade. Hey, hey, attaboy. Got to second base, and mom was right there holding my hand. What? Now, this is how you undo the bra. Second base?

I know you're wondering which hand, and don't be gross, okay? Yeah, bro, come on. It was the other hand. I don't know that that makes it better. It makes it worse in my head. Oh, God. It's a memory that I'll never forget. I'm not going to forget it either now.

Yeah, you shouldn't. I'm glad to be able to share it with all of you. Oh, no. One of our listeners, Lucas, says he may have met the one. What? And his mom was there to see it. Oh, no. Not in the same way, though, right?

Lucas, you get to third? No. I don't know about that. You can hang up right now if you want. We will not blame you. Thank God. I'm glad to hear somebody else is close with their mom. But tell us. He's like, no, it was my dad, actually. I'm glad to hear somebody else is close with their mom. But tell us.

He's like, no, it was my dad, actually. Oh, I got you. Okay, you guys, get on to who this one is. I want to know why this sounds important. Tell us about the woman that you met. What's her name? Tracy. Tracy.

Knockout. Knockout. Okay. Where did you meet Tracy? We met at a winery. It was my mom's birthday, and she loves wine, and she loves when I take her out for her birthday. That's cute. That's a good mom date.

Yeah, so that's what you mean by your mom was there for it. Gotcha. Yeah, yeah, she was totally there for it. And Tracy's like your age, not your mom's friend that came along for the birthday celebration, right? She was the hostess. She worked there. She was so friendly. I took it.

Maybe was this flirting? Maybe was this sort of like feeling it out, you know? And halfway through the meal, she comes over and she asked how everything was going. And I said, if you're wondering, we're not dating. This is my mom. That's pretty funny. Good joke, dude. I don't think it landed because it was like her face turned red.

It was awkward. My mom looked at me and almost spit out her wine. Oh, no. Even mom didn't think you were funny. That's never a good sign. You should have just kissed her passionately and been like, don't worry. That's my mom. That would have killed it.

I mean, in your defense, man, it's hard to come off looking suave and smooth while your mom is sitting right next to you. Yes, dude. 100%. No one is smooth in front of their mommy. And it's also hard to know when staff likes you or if they're just trying to get a good tip. That's the thing. I'm like, wait. I think you're right.

I mean, she laughed afterwards, and then I think I just realized she was just being a professional hostess. But like, I was totally trying to impress her. I was talking about wines with her. And that's where sort of I found that opening. I think that was a connection. Bro, it's just effort. You're trying. Even if you're not funny.

Right. You're trying to make her laugh. You're playful. You're playful. You're giving out positive vibes. I think that's what's most important to people. Plus, it's a good look like that you're taking

your mom out for her birthday. Oh, I didn't think of that. You know, like, that's a good look. That's true. So how were you able to, like, establish a connection with Tracy?

Okay, so later on in the dinner, we're winding up and I go over to Tracy and I ask her, could you put the candles on the birthday cake that I brought?

And she said, you are so sweet. And that's when I knew that was my opening. Oh, yeah. Oh, that is cute. So I said, love to hang out. She agreed. She gave me her number. And then her boss all of a sudden needed her to go away.

And I said, bye. And we will communicate later. Oh, I hope you didn't say that, bro. Because girls are like, I'll hit you up and we will communicate later. Oh, I hope you didn't say that, bro, because girls are... They'll hit you up. We will communicate. We will establish correspondence. My people will call your people.

I will send a messenger, Doug. Sorry, that's my science background. No worries, man. We're just joking around with you. So you were able to get her number? Yeah, we texted for like a couple days and we set a date for an actual meetup. All good days.

And like at the last minute the day before, she said, oh, I'm sorry, I have to cancel. And then a couple days later, nothing. And I have no idea why I'm getting ghosted, but I am and I'd love for you guys to maybe help and figure this out. That is how it is nowadays. Jose and I were just talking about this

because he was talking about how he always gets canceled on. I think like the last three dates I've had. It just seems like it's part of like dating right now. Yeah, I think it is part of the culture maybe like taking less personal. But it sucks. I mean for me I'm sure it is my fault but for you I'm sure it's just dating in general bro. Is there anything that you could think of

from the date that you would think might be a red flag to her? I don't think so, because she wouldn't have given me her number. And I couldn't imagine there's anything I did or said or came across as being rude or anything like that. No. I mean, like I said, she's a knockout. It's beautiful. So maybe she has a bunch of guys in her dating queue. And, you know, why would she why would she spend time with me?

I don't know. She definitely does have a bunch of dudes, bro. That is how the Internet works. dating cue and you know why would she why would she spend time with me i don't know buddy she definitely does have a bunch of dudes bro that is how the internet works but that doesn't mean that you don't deserve a shot you know talk to the hot girls you sound awesome you could be the best of the bunch of dudes so let's we'll play a song we'll come back and we're going to establish correspondence with tracy we will communicate with her and figure out why she's not calling you back, why she canceled on you at the last second. That's not cool.

We'll do it right after this when we do your second date update. Hold on then. Second date update. You're in the middle of a second date update update, and we're going to find out how the couple is doing right after you hear part two. They say one of the keys to impressing a woman is to do something excellent in her presence. And I feel like just listening to Lucas's story today, you know, he may not sound like the most suave guy in the world, but the fact that he walked up to the hostess that day and said,

Hey, baby girl, I brought some special candles for my mama's birthday. Oh, can you grab these from me and put them on top of her moist birthday cake? Oh, I had to get the bedding. I think he had her at moist. I don't know. I mean, if it was maybe somebody else's cake. No, don't listen to her, Lucas. That was a pro move.

No, you don't use mom and Moist in the same thing. Yeah, you do. You're no amateur, Lucas. You are a suave man. I am. Yes, I am. That's right. That's the confidence I'm talking about.

Anyway, him and Tracy never really ended up having a date date. Right. But he did get her phone number, and they did set up a time when they're supposed to meet. She canceled, though, right before it was supposed to happen. So we're going to try and help him figure out why. You ready, Lucas? You going to turn the charm up to 11 for us? Charm up to 11, but I can't say that I'm not nervous.

Okay. Yeah. I mean, you're super likable. You seem awesome. I think we can do this. Thank you. Are you ready, man? We're going to call Tracy here. I'm ready. I'm ready. All right. You seem awesome. I think we can do this. Thank you. Are you ready, man? We're going to call Tracy here.

I'm ready. I'm ready. All right, here we go. Hello? Hey, is this Tracy? Yes. Hey, Tracy, my name's Jeff from the radio show Brooke and Jeffrey in the Morning. How you doing? I'm okay. You Jeff from the radio show Brooke and Jeffrey in the Morning.

How you doing? I'm okay. You're from a radio show? A morning radio show. Hey, Tracy. Hi. Hey. And we do a segment on our show called A Second Date Update.

That's where we help our listeners reconnect with people after they've gone out on a date. Now, you didn't go out with this guy on an official date yet, but you were supposed to. His name's Lucas. Oh. He reached out to you? Yeah. Yeah, he was really excited about you. Yeah. Oh my god. This is really embarrassing.

It is? Don't be embarrassed. But for who? For you or for him? I don't think I should talk about this. Oh, you can't even tell that. Are you in a relationship and he didn't know or something? No, no, no, no. I just, oh, God, I don't know what to say.

I just, like, I don't want to embarrass him. Him? Yeah. Oh. He told us about the terrible jokes he made. Yeah, he knows he wasn't the funniest. He said you laughed, terrible jokes he made. Yeah. He said you laughed, though. I did.

OK. And not only that, he said that you gave him your phone number and you guys actually set up a time to meet. But you canceled at the last second. Well, it's just it's been a lot since we met that day. It's been a lot. What's been a lot since we met that day it's been a lot what's been a lot like he seems like a really sweet and sincere and nice guy i'm sure he is i it's just why are you convincing yourself did he come off like too much of a player because i kind of i kind of got that vibe yeah man, man. Sometimes near his mom. You know. She's even laughing.

It's funny you mention his mom. So in the days afterward, like, I started to get some text messages from her. What? From Lucas's mom? What? Yes. How? Huh?

I really don't, I don't know how she could have gotten my number. Maybe they live together. Why would he give it to her? And what is she texting you about? Yeah. What was she saying to you? She, like, texted me if she could call me. No.

And I felt awkward, so I ended up answering and ended up talking. What? You answered? What about? Yeah. She said, look, if I'm going to be frank, your boobs are too big. What? What? I did not see that comment.

Wait, his mom called to body shame you? Like, what the hell? Oh, my gosh. Yes. And I'm like, she has to be kidding. And she's like, well, I'm serious. And she says, well, Lucas doesn't have much experience with that. And he's used to dating much smaller chested women.

What? No. No. What? Like herself. Like he can't handle that? Like herself? She did not bring herself into that.

She did not say that. Yes, she did. No. No. She's just like, your boobs are going to overwhelm him. No. They're going to overwhelm him. You should have seen him when he was a baby.

He didn't know. Like, we had a real hard time latching. I'm imagining him, like, sneaking out of the room and calling his mom like, mom, I'm really overwhelmed right now. What do I do here? I mean, I don't think there's any way that Lucas could have possibly known that this was going to happen. Yeah, I hope not. I mean, that's the one benefit. Yeah, but maybe he did know. Because we should probably ask him, and that's why I need to tell you, Tracy, Lucas is on the other line right now.

Oh, my God. Oh, my God. He needed to hear this. He really needed to hear this. Lucas, you there? Yeah, I heard everything. And my mother's in the other room. And I'm about to explode.

Wait, why is she in the other room? Well, it doesn't matter why she's in the other room. And I want to go talk to her right now. This is so embarrassing. I'm so mortified. Now's not the time. Hold on, Lucas. Did you know that your mom was texting Tracy?

No, I had no f***ing idea. Sorry. Oh, okay. So you know that your mom was texting Tracy? No, I had no idea Surprise for you Lucas or is this a discussion you've had with your mom before? Complete surprise and it probably comes from that magazine she found when I was 17. No, you did not need to say that. Really, that does not help. I forgot what a magazine even was. That's hilarious. I mean, Lucas, I really think you need to talk to Tracy here because

she sounds pretty freaked out. Yeah, and apologize. I am going to apologize. Mom! I'll get you in a second. Oh my God. Can you focus on Tracy for a second oh my god okay can you focus on tracy for a second okay rip yourself away from your mom for two minutes sorry everybody i'm nervous um tracy i want you to listen to me you made me laugh and you're the most beautiful woman i've ever met in

my life and when i walked in and i saw you gazed at me and you just... Yeah. It's too much time. Okay. Can we check on him? Can we turn the charm to like a two even? I think he just took his inhaler out. He's trying, guys. He is. You're sweet, Lucas. Yeah.

I feel like you're trying, but maybe it's just a different experience. Maybe we're in different areas of our lives. You're really close with your mom in more ways than one. I don't think that's funny, but sure. I'm sorry. I have to laugh. I'm sorry. I mean, Tracy, you can hear he feels terrible.

He had nothing to do with it. And we don't even know if that's true. That's just what his mom said. Lucas, what do you think? Could you handle a bigger pair? Yeah, man. You got this, bro. Yeah, your mom doesn't believe in you, but I sure do.

Yeah, bro, I do, too. You can handle that. That's a pep talk you needed, Lucas. Tell her, bro. Yeah, your mom doesn't believe in you, but I sure do. Yeah, bro, you too. You can handle that. That's a pep talk you needed, Lucas. Tell her, Lucas. Tell Tracy that you could handle her. Tracy, I can tell you this with 100% certainty that your boobs will never overwhelm me. Oh, look, I'm right in the eye. Man, I could just see that in the wedding vows.

Yeah, Tracy, that was really beautiful. It was. And I think this is a good time to ask, Tracy, we would love to send you and Lucas out on another date. Mom will not be there. Yeah, a real one-on-one date, and we will pay for it. Just don't bring a lot of cleavage. We're like a turtle boat.

What do you say, Tracy? I mean, I thought talking to his mom was the weirdest thing. And this has really been strange. We didn't help. I don't know. I don't know. Maybe we can keep texting

for a little bit. See where it goes. That's something. The door is still cracked open. Yeah. Lucas? Tracy, I would love to receive a text from you, and then I will send a text back. Oh.

And then we can start all over and stuff. Oh, that's sweet. If you want to send me a picture, that's totally fine. I'll send you a picture. Okay. All right. That's not perfect. I don't know. Maybe a good idea.

Prep him a little. Terrible timing. That was bad. Maybe we can share a bottle of Pinot Noir. Yeah. Hey! That's the charmer. Brooke and Jeffrey in the morning.

All right. We've all been waiting for this. Tracy and Lucas are back once again to give all of us an update. Is his mom on the phone too? I don't know. Lucas, is your mom there? Well, she's in the bathroom right now. Let's hope that she stays there for this because we don't have a lot of time.

But obviously, we have a lot of questions we want to ask you, too. But let's start with the simple one. Are you two currently together? Are you not together? Like, what's the relationship status? Yes. Well, we are back together. Wait, back together?

What? What does that mean? That's good news. I have to be real. I was kind of hesitant to go out with Lucas again. And there was about a month before we even arranged to do anything. I mean, there's just some exchanges. We had some texts and there were some nice things that he said.

So I did decide to go out with Lucas again. Lucas, how are you doing? It was a rave review right there. Yeah. I'm doing really great. And I just wanted, you know, I have some news for everybody and the listeners and everything. And last week, I actually asked her to be my girlfriend, like exclusively. Cute.

Has she answered? Yeah. Yes, yes, I did. Oh, okay. Okay, good. She did say that together. Okay, you guys guys are official how does your mom feel about that oh she loved it she even paid for my back wax your back wax okay well i'm not sure if we wanted to know about that but the question that we did want to know the answer to tracy was lucas's mom

right was he not up for the challenge of handling a woman of your caliber? You know, I'm happy to say that his mom was 100% wrong. Oh, really? He can handle the big guns. I was totally nervous. Here's what I did. I looked up tutorials on YouTube about techniques. Oh my god, I don't need

to know that. I didn't know what you were nervous for, but now I do. Okay. Okay. Okay. The tutorials paid off, though? Oh, my gosh.

Yeah. I mean, actually, I'm going to start making a blog to help, like, other nervous guys. Okay. Oh. No. Please don't do that.

Okay. Get some diagrams. Well, good. Keep us updated and let you know when your blog goes live so that Jose and I can check it out. I know we could use some pointers still. And congratulations on your back, my friend. That was a joke.

I was just kidding. Oh, I didn't get it. That was a joke. I didn't get it either. I thought he was serious as well, Jose. All right. Brooke and Jeffrey in the morning. 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 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.