Brooke and Jeffrey: Second Date Update - Second Date Update: Persistence Pays Off

Episode Date: March 11, 2024

One of our listeners waited MONTHS to finally get another date with a super-successful guy, which is why she wanted our expertise in search of a brand new Second Date! 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, or wherever you get your podcasts.

Second Date Update. If you go out with somebody that you really, really like. Aw, that's nice. How long are you willing to wait and pursue them, hoping to get that second date? Oh, God. What's your max limit? Is it two weeks before you tap out? Four weeks?

Wait, what? You're going to wait that long to get a second date? That's what I'm saying. How long are you willing to wait for it? I was going to say two minutes. Well, one of our listeners, Jacqueline, sent us an email saying she met a guy so amazing, she's been trying to lock down date number two for the last four months. God, just even when you said it, the music crescendoed and it felt so right, Jeff.

And then it's been four months. But that's a long time. She's willing to do whatever it takes. In fact, she's calling in the big guns to get it done today, and that's us. So, Jacqueline, thank you for calling AT&T welcome to the show thank you four months my gosh have you been dating other people in that time or are you just holding out for this guy I mean I've like met up with some other people but I feel like most of my brain space is taken up by like thinking about Tom yeah he's guy number one in your heart right now so tom is

his name how did you meet him uh we'll move it out online like most people did you know as soon as you met him that there was something really special about him i did i got that like feeling um he's uh a lawyer and he is say no more more. You have won us all over. Thank you so much. I feel like I'm not getting overdraft fees anymore. They're always busy. That's why. I was going to say and drunk. I mean, lawyers like to throw back.

But again, they're rich. That's a lot of positives that you all just said right there. That's like a dream guy, a drunken rich guy. Who's never around? Perfect. It is nice he won't be home. Okay. I i mean maybe he's honestly been that busy yeah like when my best friend was working at one of her firms she was billing i think like 90 hours a week oh my god that's possible so how do things get started between you and tom jacklyn well we have like this really good banter on the app and we have a lot in common of like things we like to do

and he is ridiculously good looking like he's so good looking at first i was like sort of scared okay so now it feels like it puts it into a little bit different perspective yeah like he probably has a waiting list of girls yeah what did you guys do did Did he ask you out? Yeah, he asked me out. And we went out for dinner. And he offered to pick me up, which I thought was, like, so sweet. But, you know, I just have to look out for my safety. So what? Drove yourself?

So I, like, took a car service there. Oh, gosh. That's smart. Before you meet somebody for the first time. So, yeah, we went to this Mediterranean place that I'd never been to. It was outside. It was really pretty. They had all those, like, little fairy lights.

Oh, I love that. So romantic. And what else he did that I loved was, like, one, he was actually dressed properly. Like, I've gone out on so many app dates, and guys are just, like, they just came from the gym or something. And he was, like, waiting outside the restaurant for me, which I also thought was really classy. That's great. That is classy. Playing dress-up is fun.

Okay. And so what about the actual date itself when you sat down to have dinner with him? How was that? It was great. We had so much in common. Like, we were laughing. We had so much to talk about. Like, we had to keep asking the waiter to

come back in five minutes we hadn't even looked at the menu oh that's a great sign yeah i thought so he never took out his phone you remember a lot from a date that happened four months ago every single detail she found a lawyer that doesn't take out their phone i think that that doesn't even exist, you know? Yeah, like, you would remember that. Yeah, you said a lot of good things. Did anything bad happen on the date? Because it has been a long time since you guys hung out.

Lisa, do you remember? I don't think anything bad, like, because I've been running it over and over in my mind. The only thing I can think is, like, I wish i could show you a picture but like his jaw is so chiseled i was like i kept saying like are you sure you don't mew and you you don't mew the exercise to make your chin better yes and he didn't know what i was talking about so like i explained it to him can you explain it to some of the listeners who don't know what that is? Yeah, so you make like the mew sound. You're like, mew, mew, and it like

kind of defines your jaw. Oh, stretches those muscles. And wait, were you doing that to show him during the date? Yeah. Did he laugh? Yeah, totally. I think that might be a funny moment, you know? Like you were trying to be funny. Yeah, I mean, he sort of cuckold,

but, I mean, he did look at me like, what are you doing? But, like, it wasn't like, I didn't stand up on the table and do it for everybody. I mean, yeah, I'm sure lawyers love to be on a date with cats, basically. Oh, come on, Jeff. She's just being playful, you know?

Like a cat? Like, you don't want to date somebody that's super serious and can't... No, maybe she, like, pawed, like, a ball of string around on the table too. Very playful. She's like, you know, hold on, I'm going to get this hairball. So was there any like romantic stuff that happened on the day?

Was there a kiss maybe? There wasn't, unfortunately. He did say he wanted to see me again and gave me a really long, tight, tight hug. Oh, okay. One of those hugs. A tight hug. She's still living in that embrace right now. She can smell him.

Have you had zero contact with him since? Some? Where yet? What's happened in the last four months? Well, at first I texted him a little bit more. Yeah, of course. He said he wanted to see me again and everything. Yeah.

And then his birthday was two weeks ago, so I texted for that why do you know that um i just know it okay just came into her brain naturally okay yes so now it's been four months since that dinner date with this lawyer guy and you've come to us hoping that we can get him to agree to a second date. Yeah. Jeff, you have to be on your A game because this is a lawyer. You will get a suit somehow. Maybe we just say this is a belated birthday present. Oh, yeah.

That won't creep him out at all. Let's do that when we come back and get your second date update right after this. Hold on. Second date update right after this. Hold on. Second date update. Four months. Most people don't wait that long to reach out to us trying to score another date. But our listener, Jacqueline, is a unique individual. Hey, and she met a unique man.

She did. Yeah, she did. She figured out that man's birthday happened recently and won't tell us how she knew that but that really doesn't matter the bottom line is this her date Tom was very attractive he's a lawyer so duh she wants to see him again no they had a real connection Jeffrey it wasn't just that she really enjoyed him but her first two points to us were he's beautiful and a lawyer. And his jawline.

Yeah, the jawline. I'm trying to help her. He doesn't even have to mew for that jawline. That's all natural, baby. But the big problem is he's not reaching back out to her in the last four months. So we're going to try and change that for you today, Jacqueline. How are you doing? I'm good.

How are you guys? I don't know that I was totally clear. Did he ever hit you back at all? No. Okay. Just zero communication. I mean, honestly, I don't want you to be, like, hurt if he doesn't remember who you are. Yeah, as of one date four months ago. Totally.

But at the same time, I haven't reached back to my mother in the last, like, four to five years. So that doesn't necessarily mean that it's completely dead no she is looking for you actively though yeah and do you know her first name i you know what come back to me at the end of the segment and i'll remember it for you exactly but let's give this guy tom a call tom the lawyer we'll see if he answers are we calling his cell phone yeah um i gave you his cell phone and he he's definitely going to remember me. Okay. That's positive. I like that thinking. Maybe.

I'm not sure if I like the way that you said that, but okay. We're going to dial it. Here we go. Hello, this is Tom. Hi. Oh, you're so formal when you answer your phone. Professional. Yeah. Hey, Tom. Nice to when you answer your phone. Professional, Jeff. Hey, Tom.

Nice to meet you. We're a radio show called Brooke and Jeffrey in the Morning. Do you have a second? Hello, Thomas. Okay. Did he hang up? A little too much. Hello?

Tom, are you there? I'm here. I'm sorry. Who is this? My name is Jeff from an award-winning radio show called Brooke and Jeffrey in the Morning. Don't laugh. That's actually true. I know.

It happened a long time ago, but it happened. It's like when the books say they win prizes, but it's like, you know, everyone has one. You're on the radio right now. May I ask what the call is regarding? Yeah. That's a great question. Actually regarding you and your dating life with a woman that you went out with about four months ago named Jacqueline. Jacqueline. Yeah. Okay. Do you named Jacqueline. Jacqueline.

Yeah. Okay. Do you remember Jacqueline? She definitely remembers you. You guys met online and went out to like a restaurant? Oh, it was Mediterranean. Mediterranean food? Yeah.

She loved your jaw? Yes, I do remember who you were talking about. Okay. Okay. Got a little laugh out of you? Yeah. Were you thinking about calling her back? No, if I'm being completely honest with you folks.

Okay. Oh, okay. That's okay. We hear that sometimes. Is there a reason why? I'm not going to be calling Jacqueline back. I'm going to be staying away from her. Oh.

It was strange. What was strange? was strange what was strange the date well the date no the date was fine um we had a lovely time okay we're out that's good the problem was that she was overly forward after the date what do you mean what happened after jacqueline was leaving voicemails at my place of work oh she knew i was an attorney and um apparently found out where i worked she said that you weren't answering her and so she was trying to reach you any way possible because she was really really excited about the potential for you guys's relationship yeah did that feel like a boundary that was crossed there for you? 100%. Okay. Did you tell her, though? Because, you know, people who maybe don't work in your line of field don't feel the same.

Well, after about the fourth or fifth voicemail, I remember she did get in contact with my secretary. Oh. And my secretary... Oh, no. What'd she say to her? My secretary had her on the line, and I had to, you know, fib and say, I'm extremely busy busy with a case, which truth be told, I was busy with a case. But the other issue with all of this is that I never gave Jacqueline the information of what law firm I work at. How did she find you? LinkedIn?

You know, I do not know off the top of my head. I did not inquire about her further into this, I guess, to say it lightly. Okay. I just wrote that off. I found that it was a little bit of a really intrusive move, if I'm being honest with you. That's going to be good for her to hear. Definitely a little odd. Yeah.

And I'm sorry that she, I know you said you're trying to avoid her. Sorry. I'm sorry that she, I know you said you're trying to avoid her, but we made kind of an oops because she's actually on the phone with us right now on the other line listening to this. She heard all that. What? Yeah, that's how this segment works, and she's wanting to talk to you. Yes, hey, guys. Hey, Tom. You're coming in cheery.

Perky. Tom, I'm so happy that, like, I get to hear your voice. It's been such a while. Jacqueline, what are you doing? Oh, I was just trying to get a hold of you because I've been thinking about you and I had such a good time when we went out. You said you wanted to see me again. I did at a certain point, but this is getting borderline stalker behavior.

This is insane. You're using a radio station to contact me. I'm working right now. I thought this was a client. Oh, I'm so sorry. But if you would have gotten back to me, I wouldn't have called them. And I think stalker is way overblown. I've left a couple messages at your work.

To cover us legally, please say that often. It's not technically. Jacqueline, if it's not stalkerish, how did you find out where I work? Yeah, actually, that's a good question. It's going to be hard to win an argument against a lawyer right now, Jacqueline. Okay, in my defense, it was so simple.

Like all your pictures on the app, like I saw that there was one picture of you outside in the courtyard and you could see the courthouse across the street. So all I did was go on Google, find the courthouse, and then I knew you were working in the building across from it. So,

you know, I just called a couple different law firms until I found you. That made it sound worse. You did detective work based on a picture on his profile. Yeah, all ladies do that. Like, you look for contact clues in the pictures. Girl, that's not true.

That can't be true. You don't call me voicemails. Oh, yeah. You don't leave voicemails. You actually, wait, 100%! So you do it, but you just don't know where they work. What's the harm in that? Yeah, yeah.

So tell them. You can't leave the evidence behind that you've been. Okay, I wouldn't have left voicemails if you would have just returned my call and you know he had mentioned that he wasn't really loving his new secretary so i thought maybe oh you didn't love wait did you just say he didn't like his new secretary he mentioned that when we had dinner oh oh so wait are you trying to be the new secretary tom can you see how maybe you've brought some of this upon yourself? Oh, stop it. Not in the slightest. But at a bare minimum, you have to be impressed with how she was able to figure out where you were.

We were all impressed. Or scared, Jeffrey. This is insanity. You said to me, Tom, on the date, what's your best quality? And I said, I'm determined. And so I think I'm proving that I was determined to get a hold of you again. You know, there's a good side and a bad side to every quality. It's very true. And also, Tom, I'm going to have to, like, disagree with you about your secretary because she's totally friendly when I call.

And obviously, she's still there. She is? Oh, she's still there. We can confirm. Yeah, not for long if she keeps giving out Tom's information. I found his information. I figured that all out on my own, so I kind there. We can confirm. Yeah, not for long if she keeps giving out Tom's information. I found his information. I figured that all on my own, so I finally want credit for that. Oh, okay.

He's not impressed. Tom. Maybe he'll be impressed if you wish him happy belated birthday right now. What are you talking about? Oh, he didn't know. You figured out it's your birthday. That's called persistence. I thought she texted you the birthday message.

I blocked her a long time ago. I don't see anything she sent to me. He didn't get the message. You better tell it to him. Better wish him happy birthday right now. Yeah, I didn't know that. Or better yet, you can wish him happy birthday when you meet face-to-face for your second date. A date that we will pay for if tom

agrees to it what do you think tom unblocker absolutely not yeah i think that's a pretty clear message well are you sure you want to say that because i'm pretty sure jacklyn's on the other side of the door from wherever you are right now so you might want to say yes just say yes we'll go right now i i would not be surprised at this point. Yeah. Oh, my God. Jacqueline, you do understand what he's saying, right? Yeah. No, I get it.

I mean, there was a couple times, like, one of my friends wanted to meet for lunch, and she sort of lived over by that courthouse, like, down that way. So we went, and we had lunch, trying to maybe run into Tom, and I didn't. Oh, my gosh. Oh, no. Wait, there's more than one crazy of you? Well, I don't want Jacqueline to leave this phone call empty-handed. That's why, Jacqueline, we're going to offer to send you out to lunch

with Tom's secretary, who you get along with so well. Thank you. Please don't go to lunch with my secretary. Please. Brooke and Jeffrey in the morning. I think this is going to be one of those dates we look back at and say, you know what? Maybe they'll be better off as friends. I was thinking it would be one of those dates where we turn the audio over to authorities.

Yeah. That would be nice. And they can be friends and he can visit her every few months while she's in prison for whatever mischief she gets herself into after this. I don't think there's any friendships ahead. No, it would be nice. They could write each other letters back and forth. I think that it'll just be back and back and back.

He's never going to respond. But remember, you can listen to all of our podcasts with our second dates, our awkward Tuesdays, closure calls, and a whole lot more up at Brooke and Jeffrey, wherever you get your podcasts. 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 top 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.