Brooke and Jeffrey: Second Date Update - Second Date Update: Hoping For A Bad Date

Episode Date: October 23, 2024

A beautiful woman asked one of our listeners to take her out on a date… to a place she HATES! Why would she want that? We’ll get her to come clean in your new Second Date 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. Some guys feel this way. I know I do. But as a man, if a person on a dating site ever approaches me and is very forward and direct in their pursuit, that sends up alarms.

It's funny because I kind of agree, bro. It's like, boy, this person must be really messed up if they actually want me. Oh, well, actually, now that you pinpoint it to just you and not me and the red flag, I actually can see that. Did they lose a bet or something? Am I being lured into a trap of some sort? Seriously. What is going on with them?

Do you know know i do for work but for our listener damon he looked right past those blaring alarms and went forward with a different type of date a date he says he's never been on before in his life and he's gone on a lot so damon welcome to the show what type of date was it so i was on a dating app with this girl marissa yeah and she called it a contradictory date contradictory date never heard of that what what is that like you do opposite things you eat dessert and then you work out it was it was it was weird i had no idea what i was getting into And she told me it's kind of like the person And the type of date

That you would normally not go on So it's counter To what you're used to So is she telling you A little offensive to you Yeah because basically she's saying you're not my type So that's the thing It was kind of like a backhanded compliment

She was like nothing about your profile really speaks to me. But I'll try it. I mean, I can see where you've been doing the same thing for so long, and you're like, it's not working on these apps, so let me do the opposite. Because your type's not always good. Yeah, my type's awful. So maybe what she's saying isn't that you're bad, it's that I have bad taste.

So I need to switch it up. Which also feels icky. Yeah. Yeah, well, she did say that I was cute. So I took that as a good sign. You have to have something for her to, like, go on a date with you. Usually I go with hot, muscular, but you're cute. You're sick.

Yeah. So it's like going for a person you're not normally going for and what was the other part of a contradictory date well it was like going for a person but also going for experiences and her friends apparently told her about this type of date and she was like screw it i'll try it and apparently she was like would i be up for this and i was like sure that sounds interesting experimental why not well i like that she laid it all out there. Yeah, true.

So, like, did she explain what was contradicting? Like you said, the date itself was even a... The activity. Yeah, the activity is supposed to be different. Exactly. So I guess, I mean, like from her profile and from her photos and everything, it looked like she was like a really outdoorsy type of person. And don't get me wrong.

I like going out. But when I'm going out out i like to do more like urban exploration stuff and go to like bars yeah exactly well you want to have five bars on your phone signal wherever you're going so that makes sense to me so what did you guys end up doing yeah we went out to a bar we went out to a pool hall i know and okay okay so it's something you like okay yeah so it's something new for really yeah yeah because she was like i want to do stuff that i don't normally do okay well maybe she's not calling you back because she hated it no no no she seemed to enjoy it and it's weird too because

she was like do something you would normally do and i would normally go and play pool at this pool hall with my friends and so she was like you should also invite your friends so i can like get to know them and everything i was like are you sure for a first day it was weird i mean don't get me wrong like that's not how i play it but at the same time like she was gung-ho about it so i was like all right oh my god what were your friends reactions when you told them what they were meeting you up and meeting up with you for i mean before the date they were like oh my gosh she's gonna be a catfish or whatever and then when we got there and when she got there and we're all playing pool and we're all getting along they kind of pulled me aside they're like dude she's actually really hot hey so that was nice get the

friends sign of approval yeah exactly and so at this first point i was like you know speaking of contradictory date and everything i was i was kind of, usually on one of my dates at this point, I would have gotten a second base by now. So you should contradict yourself. If you want to do stuff that you normally don't do. You should start kissing. That's funny. Did she laugh? I think you said it in a weird way.

She did. She did laugh. Okay. But she didn't kiss you right then? No, no, no, not at all. Okay. So was that the whole date? You guys just did beer and pool with your buddies?

Well, no. So she was actually asking me, like, what do you normally do from here? And the game was on, so we went to a sports bar and were drinking and watching college football. Okay. I'm sure she doesn't like it. I like how she asked what you normally do with your friends, not what you normally do on a date. Like, you're just imitating a bros night, not a date. It does sound like a bro night, yeah.

I mean, she was trying to, like, kind of get out of her comfort zone. Got it. So she was like, how do you normally hang? How do you normally chill? And we can turn that into a date. Okay. All right. So maybe it's like Alexis said.

It's a fun night with the bros, but nothing necessarily romantic. Unless, I don't know know how did it end so i told her i mean you know at that point i was like i i tell you what this isn't over you owe me at this point how about i get a contradictory date and i will do all the things that are outside of my comfort zone and more within your realm. I love that, bro. I mean, that's cute. That's a good one. Try to leave it open, yeah. And I've been texting her only like once or twice. I'm not trying to be like super pushy about it.

Once or twice an hour is what he meant. I still feel like at least you gave her the out. Like even if she had a bad date, she can drag you on a bad date next. Like now it's her turn. If you have one bad date, who doesn't want another one? Honestly, I would love a bad date with like now it's her turn if you have one bad date who doesn't want another one yeah honestly i would love a bad date with her okay that's kind of cute let's talk to her get her on the phone and try to convince her to take you on the absolute worst date of your entire life when we come back for a second date update right after this second date update if you're just joining us we've been talking to

damon about his contradictory date with marissa which is a new thing that we just learned about where you go out with someone you normally wouldn't go for and do activities you normally wouldn't do oh man that's a lot of wouldn'ts in there like you know like maybe we just do the one not both well like if we were do the one, not both. Well, like if we were to do that on our show, Jose would run a 5K. Oh, my God. That sounds awful. Well, he'd walk it.

Not even, bro. He'd pay an Uber Eats guy to do it for him. There it is. And Alexis would go out with an American man to a comedy pun-off. Oh, I can't even think about it. Oh, my God, a pun-off. Sorry, I was focused on the American. I know, he speaks English. Oh, I can't even think about it. Oh, my God, I'm hung up. Sorry, I was focused on the American. I know, he speaks English.

Oh, no. But our listener, Damon, was challenged to do that, go on a contradictory date with Marissa, and that consisted of her drinking beers, playing pool, and watching football because she normally doesn't do any of that. Yeah. Do you regret, Damon, if, like, because I know now you want her to take you out doing stuff you don't normally do.

Like, maybe you should have started with that. You know what I'm saying? Like, the first date should have been all about things she likes that you have never done. Well, it's too late now, Brooke. Try to read through the pity of what she just said. Do you feel like maybe you could have done a better job? I mean, don't get me wrong. Like, that is a smart idea.

I would have gone with that. But at the same time, she was the one that kind of came at me with this notion. That's true. As egged on by her friends. So. I like that. That's true. If she didn't like any part of the date when we call her, we just like, hey, that's your fault.

It's your fault. You wanted this. You brought it upon yourself. Blame your friends. Yes. I wouldn't throw it in her face like that. Well, I will. You don't have to.

Let me be that guy. I'm going to call her right now, and we're going to make her feel bad if she didn't have a good time. Oh, my God. That is not what we're going to do. All right. Well, we'll convince her to take you on the worst date ever. That was what you wanted. Yes.

Worst date ever. Let's go. Okay. Let's make you hate this we're gonna do it here we go hello hey is this marissa i think it is hey marissa i think that i think you said yes yeah she did okay she said it. Her phone's not great. But Marissa, you're on the radio right now with a show called Brooke and Jeffrey in the morning. Hey, Marissa.

Hey, good morning. Hi. What's happening right now? What's happening is a segment that we do on the show called the Second Date Update. Hey, you're on the show. Congratulations. Okay. Someone likes you. I don't know. Just try to be positive, Jeff. Yeah, it's on the show. Congratulations. Okay. Someone likes you.

I don't know. Just try to be positive, Jeff. Yeah, it's not coming through. It sounds very sarcastic. It wasn't. I was actually excited. Good for you. But no, we are.

This is why I'm not going to try anymore, Jeffrey. That's the spirit, bro. Now we're talking. Now we're getting it. Anyway, Marissa, we actually are excited to talk to you because we've spoke earlier to a guy that you went on a date with named Damon. Oh, man. Oh, man. Were you hoping we'd say somebody else's name?

Got excited at first. I don't know what I was hoping. You guys have caught me so off guard. Okay. That's okay. I mean, maybe you're just kind of You guys have caught me so off guard. Okay. That's okay. I mean, maybe you're just kind of taking it all in right now. Processing. Yeah.

Well, we're contacting you for a good reason because Damon said he had a really nice time with you. He actually told us about the whole idea, which we thought was really interesting. You wanted to do a contradictory date? Yeah. It is kind of silly. We heard about it it was interesting i mean i gotta say good for you for proposing this and telling him you're not someone i would normally go for yeah and then having him still agree to a date us dudes are so thirsty i felt so bad saying it but you know i

wanted to be up front with him right yeah that's good you're not trying to hide he wasn't insulted at all he was actually really excited about you know how different you were yeah we're just trying to get a vibe of like what did you think about your contradictory date did you have a good time um i actually did have a good time i mean this was not my idea right it was my friends who suggested it i thought they were insane but clearly what i was doing wasn't working for me anyway. So I was like, okay, we'll just try something. And, um, it was probably the most relaxed date I've ever been on. That's great news. It was hanging out. It was watching sports. It was, you know, going to bars and like, you know, Oh little stress, right? Oh my gosh. Wait, were your friends right? Was this like something to get you out of your comfort zone

and find somebody you actually like? Yeah. I mean, I didn't want it to be right. Oh my God. Wait, but was it? But you did have a good time. I'm like embarrassed to say that I did have a good time. Why are you embarrassed?

Why is it embarrassing? I got such a fun day. Why aren't you calling Damon back if you guys had a blast together? What's embarrassing about it? Well, he is normally not my type. That's not something that I've ever done before. I feel like we just

left to the third date where you just get to hang out. It was so chill and it was so comfortable and I don't know what to do with that. That's like not what I'm used to. You know, it freaks you out that you are so comfortable with him. Is that what you're getting to?

Yeah, I guess. Does that sound crazy? That does sound crazy. So now you want to go back to your normal type. The ones that make her really uncomfortable on edge. And you're never going to call back. And you're not having fun or ever feeling like you don't feel like yourself well well when you put it that way it doesn't sound so good does it that sounds like what you're saying you want

isn't that what dating should be no well not like yes for a little bit i don't think so i think that when you meet somebody that you feel more yourself with than anyone else, then that's a sign that that could be it. Like, that could be the person you're supposed to be with. I don't know about forever, but at least for right now. Okay, you saying that actually scares me a lot. What? What are you doing?

I don't think it'll freak you out. Why are you scaring the women on the phone by talking about them feeling good? Just because you like him doesn't mean you have to rush into anything. Oh, yeah. I've talked to people for like two years and we're still not dating. Trust me. Trust me. Yeah, listen to Alexis.

If you want to feel like uncomfortable and like you don't know what's going on, then let me do this to you and surprise you by telling you Damon's been secretly listening to this conversation wanting to talk to you. Doesn't that freak you out? Oh, no. Hi. Hi. Oh, shut up. Oh, no. Hi. Hi. Oh, that was cute.

So it sounds like you were shocked that you had such a good time with me, huh? Well, yeah, I didn't expect to, but I did. I mean, like, nothing in my body says, like, I should have had a good time, but I did. Your body's rejecting him? Is that what you're saying? I mean, I've kind of been thinking about you, which is weird. Damon, you're making her feel too comfortable. I mean, I'm kind of blushing on my end.

I mean, I'm glad I've made you feel good. I'm sorry that apparently other dates haven't made you feel good. Or that she doesn't like to feel good. She doesn't want to enjoy your time. She's scared of good. Oh, boy. Oh, boy. You are so cute.

Are you opening to feel more good in the future? Because like I said at the end of our date, I'm down to have a contradictory date the other way. Yeah, you show him around. You can have a bad date like you wanted. You just tell him to treat you poorly all night long.

That would definitely make me feel more comfortable if you could. One of my friends has a shirt that says, don't be mean, it turns me on. Damon, are you capable of that? Can you be the opposite of what you normally are? I mean, that would be way outside my own comfort

zone, and that's not exactly what I had in mind for a contradictory date, but if that's what you've been to. He's a sweet guy. It's different, huh? It's the same as he normally did. That's awesome. It is possible, like Brooke said, that maybe there's a chance you two are just made for each other. Opposites attract.

They do say that. So this contradicting thing may be on to something. Makes me sick to say it, but yeah, you guys sound cute. Oh, Jeff. And that's contradictory to everything that I believe in, so. He hates you. Yeah. I mean, this is disgusting.

Did you just go bleh? I am. I want to get off the phone with these two. I'm wondering if Marissa's been out with you before. Yeah, this is her type. Mr. Grumpy over here. I mean, she's not my type, so yeah, probably. Yeah, watch.

She likes him now. Anyway, look, we want to send you guys out on another date. That's the whole reason that we called you, Marissa. Oh, you better go, Marissa. They do have to. We will pay for it if you say yes. If you don't say yes, I'm going to call all your girlfriends. Uh-oh.

I'm going to let them know. Are we able to threaten listeners? I don't know. We just did. Oh, my God. All my girlfriends are going to start dating this way. This is going to be crazy. Sweet.

I think they would kill me if i if i said no so damon i would like to go on another date with you this is so cute puke it's disgustingly beautiful oh my god congratulations i'm so excited to go on the worst date of my life. I will do whatever I can to make it terrible. This is the rom-com we needed. Brooke and Jeffrey in the morning. Was that the most sweetest, touching second date update we've done all year? I think so. And my soul needed that.

It was so good. Look, there's hope for love out there, people. Don't give up. Try something new. Try something different. You can do it. Wow. Okay.

Tell me you don't want to hear a part three from these two. Absolutely. Get an update, update. I don't know if I could stomach it. Unless they go on the second date and it's terrible. Yeah, that's what I want to know. I want to know, is she going to have just as much fun as he has? This is just making all of our single listeners

feel bad, listening to stuff like this. You should give them hope. Nobody wants hope. Yes, Jeff, that's what we all want. Just tell me it's over so I can move on. Well, if you do have any hope left, yikes, but you can always email the show. We'll call

that person who's not calling you back. Go check out all of our second dates wherever you get your podcasts at Brooke and Jeffrey. Brooke and Jeffrey 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 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.