Brooke and Jeffrey: Second Date Update - Second Date Update: Fearsome Foursome

Episode Date: June 24, 2022

What happens when you’re on a date and two mysterious strangers appear and sit down at your table? It happened to one of our listeners and he’ll explain what he did in the podcast!See omnystudio.com/listener for privacy information.

Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews and more. Now this is a second term we can all get behind. Listen to The Daily Show Ears Edition on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Second Date Update. I think most of us, when we go out on a date, like to keep it pretty traditional. I do. One place, two people, twelve margaritas apiece.

Whoa, I like that. You know. That's how our parents' night. Classic. But there are some daring thrill-seekers out there who like to mix it up and entertain multiple people all at once. Dude, if everybody's into it, good on you, man.

I couldn't handle that. It's all about communication. We have one of those talented multitaskers on the line right now for a second date. His name is Anthony. So, Anthony, how many people you juggled that night? More or less than 16? Whoa.

How talented are you? The square of that, I'm only at about four. Okay. Okay. One for each appendage. That's admirable still. I was going to say, I like to be able to drink, like, you know, no, continue. Okay.

It blew her mind. But it's just too much for me. i'm thinking about margaritas and then people and yeah that's more exciting for the drinking yeah so four people which one of them are we calling or are we going to teleconference this thing make it a party well i'm trying to hook back up with someone named mallory okay back up will you dog you are you in a relationship with the other two people you were out with then? It's all casual. All very casual.

Okay. So Mallory's the one we're calling. Tell us more about her. I met Mallory as I do most of them on an app. Most of them? Yeah. She sounded weird.

Is this like a group dating app or what is it? She didn't sit right. We went to a really nice restaurant. Oh, cool. So you want to do impress her. Yeah. We're in Italian.

I'm talking like tablecloths. The whole deal. What were you expecting to get out of this date? Like, were you looking to start something more than just a casual thing? I mean, that's kind of the hope is that it's going to go that way for sure. And it was going that way to start. It was going super well. We had a couple drinks. The conversation was

flowing. And all of a sudden, I guess it's her neighbor shows up. This woman sits down. Well, she didn't sit down right away. Mallory insisted she join our table. So she's the one that invited the other people onto your date. That seems a little awkward.

How did you feel about that? Well, I didn't like it. It was kind of cramping my style. Everything was going so well. It is weird that you're at a fancy Italian restaurant and suddenly there's a third person at your table. It's not like you're at a bar. Yeah.

What happened? That's what I thought. Well, the neighbor sits down It's not like you're at a bar. Yeah. What happened? That's what I thought. Well, the neighbor sits down. She finds out we're on a date. Immediately, she starts talking about all her worst dates. Oh, thank you for setting the tone, neighbor. What are you doing? Well, maybe that's a good thing.

Maybe she's like, oh, I've been on some bad dates before, so this is actually nice. Maybe she's framing it that way. Well, it was until I showed up. That's what she should have said. Well, then I had to hear a bunch of stories from Mallory's past dates, but it was okay. There was, I mean, there was a couple stories that were actually pretty entertaining. Okay. Were you participating in this conversation or was it just Mallory and her neighbor now? That's what I'm imagining. You know, I was being polite. I was being conversational as possible,

but the worst part of it was you asked if the neighbor was attractive. She was an older lady, but her son showed up as well to join her. And he sat down, and he was a super good-looking guy. Oh, no. So now it's you, your date, her neighbor, and her super attractive son. Oh, my gosh. And they all know each other, and you don't. My third cousin walks around the corner. He's a super attractive son. Oh my gosh. All at this dinner table. And they all know each other and you don't.

Yikes. And then my third cousin walks around the corner and he's the supermodel. Do we ever get alone time with just you and Mallory, the person you meant to go out with? Or does it ever go back

down to one? Do you ever? By yourself. Well, we did, but only because the neighbor lady is a nurse and she was on call.

So she got a call and she had to take off immediately to go to the hospital oh you've never been so thankful for a sick person in your life so sounds like not the best first date so far i mean how did it end no yeah it was definitely not what i expected well the worst part of it actually was the bill because... Oh, no. Oh, I didn't think about that. The lady was there. Her son was there.

They were ordering pizza. They were ordering alcohol. And I was left with about $120 bill. Shut up! Dude, they didn't throw down on their own stuff? No, they didn't because they both left in kind of a hurry. And Mallory, she offered to pay but i was trying to be a gentleman and so she wasn't a jerk about it okay it just i mean just the way it worked

out it's not the kid thought the mom was going to probably pay for him then she had an emergency yeah oh man yeah so that that date ends and we kept in touch and then the talk of a second date came up and immediately mallory suggested we go on a double date with her girlfriend and her boyfriend. More people. Wait, not the neighbor this time, like just a friend of Mallory's? Yeah, just one of her best girlfriends. Maybe she's someone that has, like, you know,

sometimes it can be uncomfy to have to, like, have a full conversation with somebody for hours on end. Maybe she just isn't good at it yeah but i mean that's kind of the uh test right if you could have that conversation you see that person multiple times it turns into a thing i mean her her best girlfriend and her neighbor is not going to be sitting in the living room with us if it works out down the road so did you go on the second date no Well, unfortunately, I insisted on not doing a double date. And I told her I had two tickets for a concert.

And the concert was actually sold out. And that's actually true. But after I was insisting on that one one-on-one date, I did not hear back from her. No to a concert? I don't know what's going on. Maybe she just doesn't feel comfortable being alone around you or something. That's not a good sign. Yeah, you may just literally be friend-zoned.

Yeah. She's like, yeah, you're fun to be around, but not on hold. In fact, I'm feeling a little bit uncomfortable with you on the phone right now, so I'm going to put you on hold for at least three minutes while we play a song. Yeah, still, we need more people in here. I don't feel safe. Okay. So we're going to come back.

We will call Mallory for you and try and figure out what's going on with your second date update. Do you want to invite the janitor? Yeah, let's get anybody else in here. Anthony is creeping me out. All right, we're going to do it next. Second date update. All right, let's get out our calculators to figure out what happened to our listener, Anthony. Oh, our calculators to figure out what happened to our listener, Anthony. Oh, our calculators?

We start with two people. Okay, got it. Add in one neighbor plus her attractive younger son. Okay, plus another. Add one pizza, times it by three, multiply the awkwardness by ten. I can't go that fast. Then subtract the cute son minus the neighbor, and now we're down to one. Okay, I didn't have a TI- 89 to do that okay it's just Anthony

he's all alone and out over a hundred and twenty bucks just trying to get a hold of Mallory for one more shot strangest part of this whole thing is afterwards they were trying to arrange a second date and Anthony was like hey I'd really like to take you to a concert just you and me yeah her reply how about a double date instead so they were at an impasse and another hangout never happened that's why he's turned to us for help Brooke is there anything that I missed from Anthony's disaster date no I don't think anything was I mean it was all out of his control it was all out of her control honestly for the most, she was probably just trying to be nice. Yeah, totally. So, I don't know.

I think that you guys deserve another shot. Yeah. You know? Clean slate. Hey, Mallory. What? That was not Mallory. That was Brooke.

Are you drunk? Were you drunk on the date? And maybe that's what you're leaving out. I think there was just so many voices happening on the date And maybe that's what you're leaving out I think there was just so many voices happening on the date He doesn't know which voice is Mallory's at this point Yeah I was just practicing Getting ready to talk to her Okay

How about you let us talk to her first We're gonna make the call You keep practicing what you want to say Just make sure you're practicing in your head Not out loud Got it I'm gonna dial Mallory's number right now here we go hello hey is this mallory yeah who's this hi hi sorry i'm waving my hands in real life i'm waving back at jeffrey this is jeff from the morning show broken jeffrey in the morning the whole show is here to talk to

you hi hi mallory that's super weird what's up yeah we're doing a segment right now called the second date update because we're trying to help out one of our listeners named Anthony. Oh, yeah. Yeah. Anthony says he went out with you the other night. That is correct. Okay. And it turned into a big party at the restaurant. From what it sounded like.

That's a nice way to put it. It sounded like a good time, honestly. I mean, it wasn't quite a party, but yeah. I mean, my neighbor showed up and yeah. I mean, it wasn't just me and him. Can I ask, when your neighbor showed up, yeah i mean it wasn't just me and him can i ask when your neighbor showed up were you excited about that dreading that like inside what was your emotion so um i knew she was gonna show up oh alexa dude you planned it well okay so uh yes but, like, that's not unusual.

It's kind of like my test on these dates. Oh, sneaky. So, wait, are you trying to get her opinion on who you're going out with, or are you trying to have an out to get out yourself? I mean, it's, like, all of the above. So, like, if I'm having a bad time, I can leave with her, you know, and it's less awkward than just, like like going to the bathroom and never coming back. OK.

I don't think any of us can blame you for wanting to have a safety net there on your date. But do you feel a little bit bad that Anthony got stuck with a giant bill paying for you and all of your neighbors and friends? Yeah. No, not really. I mean, I offered and he was a good guy and was like, no, I'll take care of it. So he passed your test then. So what's the problem? I mean, he did, but he was kind of weird about it and like wasn't really social with like my neighbor and her son and stuff. And I don't know, I feel like it shouldn't have even been a question that like, of course, he's going to cover it.

And then like we were supposed to go on another date, like double date with some of my friends and he didn't want to do that yeah because he wants to date you he doesn't want to date all your friends and your neighbors and i know but like i don't know him yet like doesn't he want me to be like comfortable and also if you're worried about going out and getting stuck with the bill again then i don't know i can be with somebody who can actually afford to do that. I don't think anyone ever said he was worried about getting stuck with the bill again. That's what it seemed like.

Because y'all are asking if I feel guilty about it, and no, I don't. So would it have been better if he interacted more? Is that what you're saying went wrong? Or he would have been more cheerful when he paid the huge bill? Here's my credit card. I have been waiting to do this all night thank you mallory for offering i mean to be fair 120 is definitely not the highest bill that i've stuck a first date with if he's asking me out then it should be my preference and what i want to do

right like he's trying to impress me and i want to see how he is around my friends i want to you know see how that goes and when he said no just okay then you go find somebody else okay chemistry with the friends and you yeah and you immediately you put anthony sitting right for me you put anthony through a test by having people surprise him on the first date. So we're going to put you through a little bit of a test right now and surprise you with Anthony. Who's actually been on the other line listening this entire time. Yeah, Mallory. Oh, wow.

I didn't realize. Maybe if you told me that you brought all your neighbors on all your dates, I could have been prepared for it. And I even understand, like, it's dating guys, it's scary out there, but did you have to invite her hot son as well? Forgot about him. Don't hear the term hot son. He is like an adult, right? Yeah, let oh let's hope so yeah he's like 23 okay and also that shows how secure you are with like your own attractiveness he's also a test that's perfect how many tests does a guy have to go through in order to date you it's like going through college

i know we got an ugly guy a hot guy a, a funny guy, an older woman. A guy who doesn't speak. I can't believe how many people she gets to agree to participate in said test. They get a free meal, Brooke. I guess. Yeah, I mean,

they do get a free meal because the guys I date should be able to pay for it. And if they can't, we'll just move along to the next one. It does sound fun. I would want to be

one of the friends to go in and to meet the date and to get free food. Mallory, it sounds like you want to be a strong woman. Like, why don't you just make your own money? Oh, I do.

No one likes that answer. You don't have to concentrate on how many people you can afford to take out. We don't like strong, independent. We want weak, independent. Woo! Just that is not. Watches only. Why is that not an option for you?

Well, I do make my own money. And once I'm like in a relationship, like I split things. It's just at the beginning. Sure you do. It's the test. I want to see that he's got his crap together, you know? Like, I don't know. No, I mean, it's a lot of like putting people in scenarios, engaging their reaction.

It's so much test. Why don't you let things happen naturally? It sounds exhausting. No, y'all. It's fun. Maybe Anthony. It's fun for you. Why don't you let things happen naturally? It sounds exhausting. No, y'all, it's fun. Maybe Anthony sees some red flags here. Am I right? Do you, Anthony, or are you enjoying this?

I mean, no, I wouldn't say enjoying. I didn't enjoy the seeing operation of neighbors at the first date. I mean, I also, I do understand. And I also, I'm sure I would try a double date. It would be cool if everybody could go Dutch besides, you know, I'll cover Mallory. But I don't know about all her friends, you know, I think. Yeah, I mean, I think it's kind of weird that you're, like, making it clear that you would need to, like, go Dutch. I think that if you were just cool with it, you would just do it.

And, you know, my friends would like you a lot more. I think Anthony was joking when he said that. Isn't that right, Anthony? That was totally a joke. You want to pay for it. I'm willing to pay. I am willing to pay for it. She's very hot. She's literally saying we won't like you

unless you have a lot of money. She's looking for a sugar daddy. I have one more test for you, Anthony, because we will offer to send you guys out on the date and we are not gonna pay for it anthony is gonna cover the entire bill we've never done that isn't that right anthony when i signed up for this i don't remember you guys saying you were gonna change yeah the rules are the rules are fluid on this show and i do think Mallory would appreciate if you would step up like that. So Anthony, but it would go a long way with her.

It's Anthony's fault. If he still wants to go out with her. I mean, that's your dude, Anthony. I think she's worth all the pizza in the world. Wow. That might be the most romantic sentence ever uttered on this show

so congratulations mallory next to the hot sun well mallory i think i already know what you're gonna say now that we've basically strong-armed him into paying for you and all your friends on your next date but officially i need to hear what you have to say you know i'm actually thinking that maybe you are you have a little more potential than I thought. So maybe let's do this. What a coincidence. I think your intuitions are right, Mallory. Okay. Okay.

If you want another opinion, I'm free. Okay. So better bring a second credit card on this one, Anthony. You can come. Yay. Okay. Wait a second. Wait, wait, wait, wait.

Why am I going on another date and paying for everything? I don't understand. Because you're a chivalrous man. Or you're a pushover. I don't know which. That's the same thing. Yeah. We'll be back in the morning.

Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews, and more. Now this is a second term we can all get behind. Listen to The Daily Show, Ears Edition on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.