Second Date Update: Crying Executive Officer

but could you just like beat that out or something? What? Okay, that's fine, you don't want to know. We can call you a different name if you'd prefer to go by an alias, you know what, all right, Cinderella? Can we do Cindy for short? It's an interesting choice. She's like the third hottest Disney princess. But that's okay. I mean behind Bell and Jasmine for sure. But you know, if you want to be Cinderella's cool with me. Okay, So Cinderella, tell us about the guy that you went out with.

So I have a new boss. So he's been at the company I work at for a couple of months, okay, and I can't tell you the name of the company I work for. I can tell you it's a big company. Yeah, Pumpkin Incorporated, Cinderella, thank you, that's right, exactly. Okay. And let's say he's one of the rulers of the pumpkins. Okay, he's a big, big pumpkin. He's a very rich, powerful pumpkins. He's the king. He's the king. Okay. And he is, let's say, the ugliest pumpkin in the patch. Oh, poor buddy,

that's all right, that's why he's successful. He had to work a little bit harder than all those pretty pumpkins. I mean, sure, I guess. And he he has moded abundantly clear that he likes me. Oh my god, your boss made it clear that he likes you. Yes, he did. And I oversee a small department. I'm not powerful or influential in any way. Maybe someday today, but anyways, but I have to have a lot of meetings with him and other staff members, and he always sort of like

lingers behind. And it's blatantly obvious to me that he's always trying to talk to me more than everybody else. Shouldn't you just be calling hr right now? This seems like or you can call your fairy godmother have her fix this up for you. I guess we're like your fairy godmother in this situation. I mean, at this point, you are anyway. After a certain amount of time, he asked if I was single, and I was so caught off guard and I didn't want to lie, so I said yes, uh huh. And he then asked me if

I would like to join him for dinner over the weekend. Oh, I get it already. You feel like you have to go because wait, boss, but you don't want to go to him. I mean not the first time he invited me. I really tried to put it off. I tried to give him a lot of great reasonable excuses, like I had family or I had you know, previous appointments. But he did not let up, and he kept asking. So I did. I finally I went out with him. Oh my god, what was it like? I mean, rich guys

know how to plan a take. When you say that, okay, he pulled out all the stop, like he closed down a restaurant. What there was one water, there was a violent player. Dude. I couldn't even do that at Denny's. I mean that I guess is awesome, but you don't like this guy, so it's like a ton of pressure for a boss that you don't like, you learn to like him exactly. It was really it was hard to like, really enjoy that filet. I did though I'd be into play.

It's really good. But the plant is is that I still didn't give him any signals that I was romantically interested. You know, we had a nice, fun conversation, but at the end of the knell, he asked if we could go back to his place. Oh, and that's when I finally put my point and I said, I don't think that's okay. Yeah, that's good. You establish a boundary with your rich boss. Okay. How did he react to that rejection? He started crying, Oh my god, it is so unexpected.

How did you handle that? Really crying? I mean, what do you do when you grow rich man surrounded by a violin player? Cried your videotape it and put it up on Instagram. No, no, I felt so bad, and like I put my arm around him and I just said, I just I don't know that this is right. And then after I did that and tried to comfort him, he kissed me. Oh, dude, do you think it was all a ploy. Do you think those were fake tears? I mean, who knows, Like at this point, it's so

hard to read what any of this is. Is it a ploy? Is it real? I don't know. What did you say I might talk to him? I mean I just sort of made an excuse, like I like, that was a great time and I really have to get home, and so I left. Okay, So I don't understand. Then why are you emailing us for a second date? Update? Yeah, because he's again he's relentless, because he continues to call me and text me and at the office, it's a little weird, like he feels like, you know, I had

so much fun, such a great time. We have to do it again. You had such a great time, you ended the date by crying and then like got some pity kiss. Who is this freak? Was still a kiss? But here's the thing again, Like I know this is weird, And this is why I'm calling you guys, because I would go out with him again as friends. We get along, Like he's not like a terrible person. I just need him to understand, like the romantic thing, it's not in

the cards. So yeah, so you want us to call your boss and tell him that you do want to accept his date offer, but just as friends, right, like, let's be friendly. I have no problem with him like that way. Cinderelly, Cinderelli, what are we going to be? All Right, We're gonna play a song, we'll come back, and then we'll call your boss and let him down. Easy for you, Okay, thank you. I hope it works. If you're just tuning in for the second date update,

we've been talking to a lady on the phone. Now we're gonna have to go back and bleep her name out because she asked us to censor it and use a different one. She chose the name Cinderella. Okay, the third hottest Disney princess. These are the ratings. I've decided she's the third hottest, and that's how it's going to go. But Cinderella works at a big corporation where one of her big time bosses has taken a very keen interest in her. Oh my god, and they have meetings, weekly

meetings together. Yeah. The problem is she doesn't find this particular boss very attractive, and he's been trying to make something happen between them for a while. Eventually, she did give in and agreed to go out to dinner with him one night, where he went all out, rented the entire restaurant, got a personal violin player. It was kind of awkward for her. Yeah, and the night did end with a pity kiss after he cried. Remember right, literally, But now she wants to tell him that there is

not going to be a romantic connection going forward. They can hang out again, but just as friends, and she needs our help to deliver that news to her boss. Yeah, I mean, is that too much to ask? Nope, Nope, not at all. I mean I think it'll be totally normal. Well, he know who we're talking about. If we say Cinderella, probably not. But once you mentioned like a violin play date, and yeah, that's probably a tip off. I don't know. It could be a lot of dates that he goes

on like that. So yeah, oh my god, she is so uncomfortable. He better get the message. I mean, if he honestly, if he's a good person, and if he's a good boss, he will say, oh my god, I had no idea I was overstepping my bands. And of course we can just be friends, I hope. So yeah, it's probably best, Cinderella, if you tell him the message directly, Like, we can help get him on the phone and get him ready to hear some bad news, but ultimately it

should probably come from you. I mean, I know you're right. I don't like that you're right, but you can do this. You can do this. I mean, honestly, you have all the power right now. Okay, enjoy that. Okay, yeah, go on a power trip when you're you know, I ask for some money right away. That's not what I'm saying. I'm saying that he has to listen to what you have to say, and he has to respect it. Yes, channel your inner ugly step sister, really really let him

have it, all right, I'm tuning into her. Okay, I didn't even ask what his name is. We just know him as the king. What's his name? His name is Max? All Right, remember your fairy godmothers, all three of us are here for you. Okay, can we just maybe layoff the whole Cinderella references. I think you should have really thought that before you chose that you did this. Okay, you're right, you're right. So we're gonna call Max for you,

and we're gonna give him his happily never after. Okay, see, we can't stop, all right, let's sto the phone number. Here we go. Hello, Hi is Max there? Um, May I ask who's calling? My Name's young Jeffrey from Brooke and Jeffrey in the Morning and we're doing from the radio show. Yeah yeah, oh my god, are you guys second date updating me? Well? You got to that real quick, Max, quick? Yeah. Oh my god. I love you guys, to listen to you guys all the time. Oh my god, this is

so much fun. Okay, that's one perspective. Okay, so you you know how the second date updates work, then I do. And fortunately for me, I've been on a date recently, so I think I know where this is going. Okay, so I think she most likely wants to go out on another date. I mean there were spark well okay, there was a lot. Yeah, let's tamper that a little bit. We just need to talk to you about this a little bit. Don't worry about how all this works and

everything special. I mean I totally know how it all worked. I mean I listened to it. I mean yeah, okay, yeah, we're so just hold on, Max, we're going to get tall that in just a second. Okay, But the woman that we're talking about this is the girl that you took to a restaurant and rented it out had a private violin player. Oh it was great, I mean it really was. It was like the food was fantastic. First off.

I mean, it was genuinely romantic. Can I just ask you, Max, did you ever think that maybe that was a little bit too much for a first date? You know, I didn't see it as pressure. I saw it as just sort of like, you know, I have the means to do something special for someone who I think is special, and I have no regrets. I think that's a nice sentiment.

And she did tell I mean, she told us all about the evening, and she said that she had a really good time and she respects you a lot, and you know, she told us about all the extraordinary lengths that you went through that night for her clothes in the restaurant and the violin. And here's the deal, though, how do I say it? You know? I mean, I think I know what you're gonna say. No, don't. I don't know if you know what I'm gonna say. I honestly, I think I know why you guys are calling And

I think it makes a lot of sense. So wait, I don't understand. Why do you think we're calling you? I mean, I think it's I think it's pretty obvious. Is that, you know, love can spark and really bizarre places, and the fact that we're both working in the same company, and I think that's probably an obstacle. And I really think this is the real deal. I mean, I would

be willing to step down, step down. Well, let's hold on here, Okay, so before you voluntarily give up your job, that maybe we should talk to the girl that you went out with. Definitely she's gone right now. Yeah, I mean she hasn't told us everything, and she'd probably be the best person to help us finish up what we're trying to say to you. Cinderella. You there, I am here. Hello, Hey, why are they calling you Cinderella? I don't understand. Um, you know, I just wanted to try and keep this

little profile with my real name. So yeah, so can they call me Prince Charming? No, I'm down to call your Prince charming. Max. Thank you, you're Prince Charming for me? Oh my god, Max, you sound really nice, really kind, but I think you need to like step back into reality for a second. So go ahead, Cinderella, tell Prince Charming what you wanted to tell them. Oh um, Max, Like, okay, so you heard what they said, so very nice. Sleep.

And I've really been thinking about this, and it's not a good idea for us to see each other in this way. You know, I completely agree, I really do. This is why I'm saying. I think it's important if I step down. I mean, I'm really I'm oh god, I really sorry about That's not even no, you are really good at what you do and this company needs dudes like you, and I just look, you and I are not the best fit. Okay, Um, so what are you saying. I'm saying, Max, it's not going to happen.

There's not a romantic spark here, and that's just that's just it. I'm sorry, all right, Well, I mean I hear what you're saying. Um, great, Yeah, I really thought there was a spark there. Oh buddy, No, I mean I think that's totally cool, and I think that maybe maybe that's a good idea. Gains of anything that where to happen, I hope we will just be bread, which is really great anyway, like having a friend. Calm down. Take a breath, Cinderella, you just made Prince Charming cry.

Take a deep breath. Okay, you are you are really talented at your job. You are someone that that Cinderella really cherishes as a person, and she does want a relationship with you, just not like where you make out and take your clothes off. Just one. That's a friendship, and that can be beautiful too, just in a different way, gonna be beautiful. I already see it, all right, Okay, I didn't really well what I call Max or Prince Charming?

All right, okay, okay, all right, Max, Now that you know how Cinderella feels, buddy, I mean, she wants to be friends with you. Still, we would like to send you out on a friend date. Ye, and we'll pay for it. I don't need any gift cards or anything. I mean I listen to the show very regularly. I can take us out again. Well, we know you can, but just let us treat you, Max, I mean, that's the least we can do for putting you through all

of this. Okay. And I'm sure that there are so many listeners that are like single and would love to go on a date with you. You sound lovely. Gold diggers on the Yes, what was that last thing? A lot of gold diggers. A lot of people know that you make money. I'm saying, it's just so hard. No, Max, you know how a lot of relationships start like you start off his friends. You have no idea how many people we've talked to where it's like, oh, I didn't

really like him that way at first. He was kind of weird to me, but like, the more I got to know him, the more I got to like him. This is exactly what I mean. I think we really have a shot. Were doing we were there, Jeffrey, I'm sorry, Prince Charman's crying? What do you What do you think? Max? Can you at least give the friendship a shot? Oh my god? Yeah? Okay, it's just friends, Max, It's just friends, right right, Cinderella, just friends? Yes, yes, Cinderella. Are you

cool with this? I'm ready? Friends all the way? All right, Well, this has been a successful second date update. I think kind of I feel like Max, you still have your hopes up. I want you to not have those. Yeah, okay, you don't want me to have hope? No? No, why would you say something like that. Yeah, don't listen to Brook. Okay, I'm trying to be a Realisay, Yeah, just be a realist and remember when you wish upon a star, it makes no difference who you are. That's exactly what I

could kill. That's what I'm saying, my god, Froak and Jeffrey in the morning.