Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Demented or Determined

Episode Date: October 26, 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 Second Date!See omnystudio.com/listener for privacy information.

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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? 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 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 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 jacklyn thank you for calling at&t welcome to the show thank you four months 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. Thinking about Tom. Yeah, he's guy number one in your heart right now. So Tom is his name.

How did you meet him? We were on the internet 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 feeling. He's a lawyer and he is... Say no 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. And time for you. 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 mean, maybe he's honestly been that busy. 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 did things get started between you and Tom, Jacqueline? 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 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 he ask you out yeah he asked me out um and he 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. So what drove herself? So I like took a car service there.

And that's smart. Before you meet somebody for the first time. So, yeah, we went to this Mediterranean place that I've never been to. It was outside. It was really pretty. They had all those like little fairy lights. Oh, I love that so romantic what else he did that i loved was like one he was actually dressed properly like i've gone out on so many um ab 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's 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. Oh, really? We hadn't even looked at the menu. Oh, that's a great sign. Yeah, I thought so. He never took out his phone.

Do you remember a lot from a date that happened four months ago? Dude. I mean, that's 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 i know um i don't think anything bad like i 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, are you sure you don't mew?

You don't mew? The exercise to make your chin better? Yes, and he didn't know what I was talking about, so 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 the mew sound, you're like, mew, mew, and it

kind of defines your jaw oh stretches those muscles anyway were you doing that to show him during the date yeah 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.

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, but he did say he wanted to see me again and gave me a really long, tight, tight hug. Oh, okay. A tight hug. She's still living in that embrace right now. You can smell him.

Have you had zero contact with him since? Some? Where yet? What's happened 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 him for that. You remember his birthday? You know his birthday? Why do you know that? I just know it. Oh, wow. Now we're getting some hints into it. It just came into her brain naturally.

Okay. 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. Yes. All right. 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. 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. Yes, she did. 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 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't want you to be like hurt if he doesn't remember who you are as a 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 exactly but let's give this guy No, she is looking for you actively, though. And do you know her first name? You know what? Come back to me at the end of the segment, and I'll remember it for you. Yep, 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, I gave you his cell phone, and 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. You answer your phone. Professional.

Yeah. 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's just... 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 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. 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? The date? Well, the date, no, the date was fine. We had a lovely time while we were 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 apparently found out where I worked. Well, 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' 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 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 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 jacklyn the information of what law firm i work at how did she find you linkedin uh 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 that off. I found that it was a little bit of a really intrusive move, if I'm being honest with you. Yeah. That's going to be good for her to hear. Definitely a little odd. Yeah.

I'm sorry that 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. Yeah, she heard all that what yeah that's that's how this segment works and she's wanting to talk to you yes hey guys hey tom i'm so happy that like i get to hear your voice it's been such a while oh my god jacqueline what are you doing, 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, and 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, like, I wouldn't have called them.

And I think stalker is, like, 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, if it's not stalkerish, how did you find out where I work? 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 context clues in the pictures. Girl, that's not true.

You don't call me voicemails. Oh, yeah. Girl, that's not true. That can't be true. You don't call me voicemails. Oh, yeah. You don't leave a voicemail. Wait, 100%! So you do it, but you just don't... You can't know where they work. What's the harm in that? You just don't 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... Wait, did you just say he didn't like his new secretary? He mentioned that when we had dinner. 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 worked. We were all impressed. Or scared, Jeffrey. This is insanity. 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 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 on my own, so I kind of 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.

She 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. Oh, that's why. He didn't get the message. You better tell it to him.

Better wish him happy birthday right now. Okay. 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 Jacqueline'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 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 lives 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 no 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 gonna 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.

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