Brooke and Jeffrey: Second Date Update - Second Date Update: Crying Executive Officer

Episode Date: November 2, 2021

Today we're taking friend zoning to a whole new level... By doing it over the radio!! Honestly, it's one of the most uncomfortable calls we've ever done!See omnystudio.com/listener for privacy information.

John Stewart is back at The Daily Show, and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition podcast. Dive into John's unique take on the biggest topics in politics, entertainment, sports, and more. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Second Date Update A woman emailed us for a second date update today. Apparently, she went out with a guy and does want a second date. Okay. Just not a real date. Second date. What?

Uh, what? Date. Did I say date enough? I mean, you said it a lot and I still don't understand. Date. What's your favorite fruit? Yeah. Date.

Yeah. What keeps you regular? I don't know. Her email's kind of vague is the point, but she's on the phone. Her name is Tessa. Hey, Tessa. Hey, I know you just said my name, but could you just like beep 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? Call me Cinderella. Oh, right. Cinderella. Can we do Cindy for short? That's an interesting choice. She's like the third hottest. Oh, right. Cinderella. Can we do Cindy for short?

That's an interesting choice. She's like the third hottest Disney princess, but that's okay. I love that Jess ranked them all. I mean, behind Belle and Jasmine for sure. But, you know, if you want to be Cinderella, it's cool with me. Okay. All right, so Cinderella, tell us about the guy that you went out with. Now I'm thinking about Disney princesses.

So I have a new boss. So he's been at the company I work at for a couple of months. 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. Duh, Cinderella. Thank you. That's right.

Exactly. And let's say he's one of the rulers of the pumpkin. Uh-huh. Okay. He's a big, big pumpkin. He's a very rich, powerful pumpkin. Okay. He's the king.

He's the king. Okay. And he is, let's say, the ugliest pumpkin in the patch. Oh, poor buddy. Okay. All right. 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 has made it abundantly clear that he likes me. Oh, my God. Your boss made it clear that he likes you? Yes, he did. And, you know, I oversee a small department. I'm not powerful or influential in any way. Maybe someday. but that day is not 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...

Wait, he's the VP, Brock! Or you can call your fairy godmother. Have her fix this up for you. I guess 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. Anyways, 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. And he then asked me if I would like to join him for dinner over the weekend.

Okay. So now I get it already. You feel like you have to go because it's your boss, but you don't want to go. You're not attracted 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 went out did not let up, and he kept asking. So I did. I finally went out with him. Oh, my God. You gave in. What was it like? I mean, rich guys know how to plan a date. What do you say to that?

Okay. He pulled out all the stops. Uh-uh. He closed down a restaurant. What? There was one waiter. There was a violin player. Whoa!

Damn. Dude, I couldn't even do that at Denny's, like, let alone a great place. 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'll learn to like him. Exactly. It was really, it was hard to like really enjoy that filet. I did though.

I'd be into filet, but it's really good. But the point 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 meal, he asked if we could go back to his place. Oh. And that's when I finally put my foot down and I said, I don't think that's okay. Yeah, that's good. You established a boundary with your his place. Oh. And that's when I finally put my butt down and I said, I don't think that's okay. Yeah, that's good. You established a boundary

with your rich boss that's in love with you. How did he react to that rejection? He started crying. Shut up. Did he pull out a hundred bills and wipe his tears?

Oh my God. That's awful. That is so unexpected. How did you handle that? He really cried? I mean, what do you do when a grown rich man surrounded by a violin player cries?

You videotape it and put it up on Instagram. No, you don't. 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 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 talked 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? Oh, yeah. Because he's, again, he's relentless. 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 got some pity kiss. Who is this freak? It was still a kiss.

But here's the thing. Again, 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. He's not a terrible person. I just need him to understand that the romantic thing, it's not in the cards. 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. Cinderella, Cinderella. What are we going to do with you? All right, we're going to 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 it works all right hold on 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 yeah because she asked us to censor it and use a different one she chose the name cinderella

okay the third hottest disney princess again to you, by the way. 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 it and the night did end with a pity kiss after he cried remember right 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 not at all. I mean, I think it'll be totally normal. Will he know who we're talking about if we say Cinderella?

Probably not. But once you mention, like, a violin playing date, then, yeah, I think that's probably a tip-off. I don't know. It could be a lot of dates that he goes on like that. Can you imagine? He's like, oh, yeah, the chill date. Yeah, yeah.

The laid-back one. Oh, my gosh. This 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 bounds. And of course, we can just be friends. And you said he's a nice guy. 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. OK, enjoy that. OK. Yeah. Go on a power trip when you're doing this phone call. You know, I asked for some money right now. Okay? Enjoy that. Okay. Yeah. Go on a power trip when you're doing this phone call. Ask for some money right away.

Like, hey. No, that's not what I'm saying. I gotta tell you something. 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 stepsister. Really, really let him have it. Alright. I'm tuning in to her. Okay. Alright. I didn't even ask tuning in to her. Okay. All right.

I didn't even ask what his name is. We just know him as the king. Oh, yeah. What's his name? His name is Max. All right. Remember, you're fairy godmothers. All three of us are here for you.

Okay? Can we just maybe lay off with the whole Cinderella references? I think we get it. Oh, I got excited. You should have really thought that out before you chose that name. You did this. Okay. You got excited. You should have really thought that out before you chose that name. You did this. Okay, you're right. You're right.

So we're going to call Max for you, and we're going to give him his happily never after, okay? Oh, no. See, we can't stop. Okay. All right, let's dial the phone number. Here we go. Hello? Hi, is max there um may i ask who's calling my name is 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 wow you got to that real quick max quick yeah you got a fan what's up oh my god i love you guys

i listen to you guys all the time oh sweet oh my god this is so much fun hey okay yeah that's one perspective okay so you uh 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 was spark well okay there was a lot going on 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 works i mean i listened to you to it. I mean, yeah, okay. Yeah, so we're... Just hold on, Max.

We're going to get to all that in just a second, okay? But the woman that we're talking about, this is the girl that you took to a restaurant, 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 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?

I mean, I think I know what you're going to say. I don't know if you know what I'm going to say. I honestly, I think I know what you're going to say. I don't know if you know what I'm going to say. I honestly, I think I know why you guys are calling. And I think it makes a lot of sense. Wait, I don't understand. Why do you think we're calling you? I mean, I think it's pretty obvious is that, you know, love can spark in really bizarre places. And the fact that we're both working in the same company, 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 from my role. Step down, bro. Aren't you like the boss? Well, let's hold on here, okay? So before you voluntarily give up your job. No, don't do that. Maybe we should talk to the girl that you went out with.

Definitely. She's on 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 uh i am here hello hey why are they calling you c? I don't understand. 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 you Prince Charming, Max. 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 him.

Max, like, okay, so you heard what they said so very nicely, 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, Oh God, I have, don't worry about the money. Like 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? 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 it. I'm sorry. All right. Well, I mean, I hear what you're saying.

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's totally cool and I think that maybe I think that maybe that's a good idea Max

because then in case of anything that were to happen I hope we would just be friends which is really great anyway because who doesn't like having a friend? No, Max, calm down, dude. Take a breath.

Cinderella, you just made Prince Charming cry. No, Max. Take a deep breath, okay? You are really talented at your job. You are someone 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. It's going to be beautiful. I can already see it. It's going to be really nice. All right. Oh, God. I didn't realize he was going to cry.

What do I call him, Max or Prince Charming? Just go with Max, please. Just call me Max. Okay. All right, Max. Now that you know how Cinderella feels, I mean, she wants to be friends with you still. We would like to send you out on a friend date, 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 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 yeah a lot of gold diggers on the test what lovely. Yeah, a lot of gold diggers on the text board. What was that last thing? A lot of gold diggers. A lot of people know that you make money on our text board. This is what I'm saying. It's just so hard.

No, I didn't know that was sensitive. Max, you know how a lot of relationships start. Like, you start off as 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.

No! What are you doing? We were there, Jeffrey! I'm sorry, Prince Charming's crying. What am I supposed to do? 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, 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? Yeah, just friends. Wink, wink. Cinderella, are you cool with this? I'm ready. Friends all the way. Alright, 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 hopes? No, not at all. Why would you say something like that? I'm not trying to be mean.

Yeah, don't listen to Brooke, okay? I'm trying to be a realist, okay? 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 think, too. That's what I'm saying, bro. Oh my god. show ears edition podcast dive into john's unique take on the biggest topics in politics entertainment sports and more joined by the sharp voices of the show's correspondents and

contributors and with extended interviews and exclusive weekly headline roundups this podcast gives you content you won't find anywhere else ready to laugh and stay informed listen on the iheart radio app apple podcasts or wherever you get your podcasts.