Brooke and Jeffrey: Second Date Update - Second Date Update: Numbers Don't Lie But You Should

Episode Date: October 17, 2025

In today’s Second Date Update we had a listener caught in the most awkward position you could hope to be in on a first date. Find out what it was in the podcast!See omnystudio.com/listener for privacy information.

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Welcome to your brand new second date podcast. And we got one for you today. Yeah. We love that you're here. Thank you so much for subscribing and sticking along with us. In fact, we love your comments so much. We always like to start the show by reading one. We do.

And Terry Fowler from Reno, Nevada, said, I've been listening for two years now, daily listener. I just wanted to say my dog Leah just had nine puppies this morning. I'm so grateful. Name one after one of the members of the show. Oh, my gosh. You could do everybody on the show. You could.

Yeah, but you don't want to waste, like, all those names. Oh, you just choose one. You just want Jose I one, Jose two, Jose three, Jose four. I just mean literally no one wants the name for all show. It's eight of us. That gives him one. Hey, congratulations on being a new, Would that be a doggy grandma?

Is that how that works? Oh, yeah. You know what I mean? Your baby had a baby. Uh-huh. Yeah. Well, we love it. Yeah, I guess.

Yeah. And, hey, hope all the little puppies enjoy this episode of your second date podcast. Yeah. Yeah, it starts right now. Second date update. When your date plans change at the very last second, not by your choice, but because of like an unforeseen obstacle with the venue. Okay. Like the baseball game got rained.

out. Oh, yeah, you can't control that. The KFC ran out of chicken. That doesn't happen. What's your mood? Like, how do you respond? You could instantly give up right there and say, no, I'm not doing this. I'll facetime you from my bubble bath, but I don't pivot on the fly.

Makes it super datable. Yeah, be flexible, Jeff. Come on. Be spontaneous. That is the other option. Shake it up, do something new. And apparently that's what one of our listeners, Sierra, had to do recently on her date. And I'm curious what that looked like.

So, Sierra, welcome to the show. Hi. Hey. You sound like a go-with-the-flow type of person. That's right. You sound like a baseball-in-the-rain kind of lady. Yeah. That's good.

Sorry to hear that your date plans crash, but tell us what happened. So I met this guy, Ashwin, on a dating app. Oh, he sounds fancy and rich. His name is Ashwin. It's so fancy. I don't even know how to spell that. Yeah. Not going to lie, the name intrigued me.

but what I really like the most was he was funny which is so important but he was also playful like he was kind of saucy but not disrespectful you know what I'm like rosy a little bit but like totally joking it's like talking to your grandpa but 60 years ago no Jeff not at all

everyone erase that everybody has a grumpy grandpa who likes to poke fun at them right grumpy yes he's not an old man this is playful flirty his name is Ashwin he sounds like a grandpa already Okay, you got us there, Jeff, but the rest of us lost us on. Okay.

Well, we all have different images of what Ashwin is, but what was the plan for the date? Well, you know, I'm happy to say that wasn't my first impression. That's good. I liked him enough to say yes to a date with him. And I think that he was kind of trying to impress me, which obviously is fine with me. Yeah, totally. He had made rooftop bar reservations at this, like, trendy place. Rooftop bars are always good

You've never been to a rooftop bar That's like not cool It's true I don't know why Like you put him in a basement Not awesome Yeah that's a dive bar Yeah but on a roof

It means something Yeah Okay So you sound like you're excited To get some rooftop drinks Oh I was so excited I love this kind of thing And he seemed exactly like his profile

He was super cute Super nice funny Everything that I was hoping We go up the elevator and the guy at the door said he was so sorry, but the whole place was closed for like some kind of a cryptocurrency

event. Oh, God. I'm sorry, Brooke. Brooke isn't mad their clothes. It's the crypto thing. I know. I was so mad. People who could afford to rent out an entire rooftop. I just picture a bunch of dudes with receding hairlines. Yeah, telling each other the same things.

In puffer vests. Yeah. Careful, you're turning a Lexus on too much with your description. Even I draw the line in crypto. Oh, no, but what a bummer. Your whole plan for the night just got totally ruined. Yeah, I mean, it was really disappointing.

And I could see that Ashwin looked so disappointed. Like, you know. Totally. That shows you he was excited for the day, too. So what did you do? So I just said, screw it, let's take a walk. I'm not wearing the greatest shoes for it, but I just really wanted to spend time with him at that point.

So we walked down the street, and we walked and talked for a while, And we just kind of ended up at this old, like, it was just like a diner, like a normal, you know. Oh, okay. It wasn't like a cute, like, oh, we're trying to be retro diner. It looked like it had just been there for like 70 years. You went from like no mood to the waffle house. Yeah, the grease trap hasn't been cleaned in at least two years. But that's where the food tastes are good.

Yeah, but that's what makes the prize taste so good. Yeah. We're putting a lot of emphasis on like the location of the day, but what about the bond, the connection between you and Ashwin? Did that change? once you ended up at the crappy diner? No, I mean, it was, honestly, it was kind of perfect. Like, we were sitting there eating cheese fries and drinking milkshakes and in our formal clothes and just talking, you know, and probably because the plans had changed and we

were thrown in this situation, we ended up having just the greatest, most real conversation. That's awesome. That's such a good sign for anyone. If you can be anywhere with someone and still have a good time, that means that you actually have a real connection. Yes, and after our plans fell through, you know, like, it just felt so good. It felt so comfortable talking to him. We've talked for hours.

Oh, my gosh. How could he not be calling you? Yeah, I mean, how did this night end? Well, okay, so one thing led to another. He kissed me good night and I did, of course, end up at his place. Really? Post-chilly cheese fries, you guys went back to his place. Hey, I'm telling you, I felt very.

comfortable with him and I didn't leave till the next morning in fact which is unusual for me but what did he say was he there when you woke up yeah no he was just his sweet playful selfie gave me a little kiss on the nose which I thought was adorable and okay so it wasn't even awkward the next morning yeah no not at all it makes me wonder if it was like one of those typical guy things where it wasn't enough of a challenge and it became too easy so the guy gets bored he doesn't sound like a guy that is like that, though, Jeff. This sounds like they made it. They never do, Brooke. Yeah. They're always the prince charming until they goes to me. But it sounds like they were just vibing on a deeper level than that. If he just wanted to get in her pants and that's all he wanted

or he was disappointed in that, they could have gone anywhere and just gone and drank and then gone back to her place. That sounds exactly like what they did. No, they went to a diner. They talked for hours. They walked the city. Like, that is a totally different thing. Maybe he knew that crypto event was happening and this was all set up as like a little ruse to be like look at me look how spontaneous i could be let's go back to my place you are so cynical against men right now brook i'm just telling you this i've heard guys do stuff like this and sometimes even worse i know i still want to think for the best jeff i'm sorry all right well you can be naive if you want but let's call ashwin and we'll see what he has to say thank you guys your second date update right after this hold on

second date update wow another first first date blown up by a pod of crypto bros. You have like this happens all the time. Every single week we deal with this, because our listener, Sierra was supposed to meet a guy named Ashwin at a rooftop bar, but of course when they arrived, the entire venue had been rented out by a bunch of crypto nerds. Geekin out over yield farms and stabilizing their coin pools or whatever they like to talk about. Bro, look at these candlesticks popping. Sorry, I've done a little training. Don't even know what that means, but it disgusts me.

No wonder I don't enjoy any of it. Here's the thing. Sierra and Ashwin didn't let that kill their night. They actually swung it into a really fun evening at a local diner, which eventually led into a sleepover. Aw. Really good. It sounds so sweet.

It did until Ashwin is suddenly not calling her back. Dude, he kissed her on the nose for goodness sake. Like, that is... Is that a romantic move? It is a absolutely romantic. Yeah. Like, that's a I really like you move. Is there another way to read that?

See? Yeah, come on. It's so sweet. And you've reached out to him or you haven't. You're just waiting to hear from him. This was what was so weird. We texted a little bit after that. Oh, you did.

I got the vibes that he was not interested. Oh, even through texts. Yeah. Yeah. You can feel that energy shit for sure. I hope it's one of those where he's just scared of real love. You know? Yeah.

No, really? No, that's stupid. But sometimes, like, you had said, oh, there's a little challenge. Like, if it's too easy and everything is great, sometimes people don't like to be in that space. I don't know. We'll see which category Ashwin falls into if we're able to get him on the phone here. I'm going to dial his number right now. Let's hope it's the too perfect category.

Yes, yes. We're praying for a Disney ending. Here we go. Getting her another nose kiss, Jeff. Through the phone. That's right. What a promise. Okay.

Here we go. Hello? Hey, is this Ashwin? Yes. Hey, man. Thanks for answering. You're on a radio show right now. It's called Brooke and Jeffrey in the morning.

Hey, hi. Good morning. Welcome to the show, Ashwin. Hi. Sounds like you might be busy or something right now. Yeah, I hope you have a second to talk to us because we're doing a segment called a second date update. Uh, sure. Um, this is weird.

Okay. Yeah. He's nice. Give him a lot of credit. Uh, so the reason that we're calling is because you went out on a date recently with a listener to our show, a woman named Sierra. Oh. Oh. Yeah.

He lost the niceness. Yeah. So here's the thing. Sierra, we talked to her and she told us about your hang the other night. The diner. It sounded so cute. It sounded pretty good. Despite all the obstacles that came up, you two were able to have a really good thing.

Would you agree with that? I mean, we did. It was probably one of the most amazing states I've ever been on. What the heck, bro? Why aren't you cold? We're all over here waiting to find, like, the crazy reason. That's so sweet. Sorry to be so emotional about it, but it's just that, you know, Sierra's really confused.

It's just kind of embarrassing. For you or for Sierra? For me. I mean, if it's too much to share. You should do it anyway because we could really use the content. I don't want to pressure anybody, you know? And Sierra really deserves to know, wouldn't she say? Yeah.

Yeah, no, she is. She's really awesome. This is mostly a me, a me thing. Okay. Well, if you're willing to open up to us just even a little bit and we could pass the message to her, I think that would go a long way. we had this amazing, amazing night. And she told me that she doesn't do this a lot where she goes to a guy's place

and that she was curious where she ranks. Oh. Where she what? Ranks? Ranks. Where she ranks, like compared to other people? Yeah, I was very, I was very thrown off by that question. That's a weird question.

Is it a joke? You had to have a joke. Oh, it has a joke. It's a really funny. It was not a joke because I asked her to clarify. I said, what do you mean? And she said, well, I'm sure you've been with X amount of people. Wow.

Well, that's kind of a rude assumption. Yeah. Okay. But you know what? Or it's a testament to your experience that you had. I guess. You could take it as a compliment. What did you say?

I mean, did you actually rank her? God, no. Well, I told her that I'm not sure how to answer that. Yeah, that's good. And eventually I said top three. for sure. Oh. See, that's cute.

That's a good safe answer. I like, what? Only top three. Oh, I take top three. That's great. And you don't want to say number one because then you're too eager. And I don't believe it if you say number one. Yeah.

I've seen myself. I'll find out I'm not that good. Then I told her, since I answered this for you, you have to reciprocate. Why would you do that? You don't want that. She asked it to him. Oh, God. What did she say?

She said you're definitely in my top five. Okay. Okay. Not bad. She liked a little bit lower than what you ranked her, but it gets worse. I asked her out of how many. No. And she said maybe five. Oh, five out of five. So you're in the top hundred percent.

That changed everything for you. I would assume because it just changed everything for me. What did you assume? It just kind of felt it felt a little humiliating. did you tell did you laugh or did you say okay that's rude i didn't really know what to say because i already felt so vulnerable you know we're in my bed naked and we've just been together oh okay it's like getting a participation trophy yeah well hold on let me try again then yeah well you know maybe maybe there was some sort of miscommunication or she didn't say quite

what she meant and i'll give her a chance to explain herself right here because i need to let you know Sierra is on the other line of this call listening, wanting to talk to it. Oh, God. She's the one that should be embarrassed. Ashwin, hi. Oh. Please tell us five is like the number one rank. Like it's the best.

Oh, yeah. You were going backwards. Yeah. I don't know. She's like, I can't lie. You tried to save you. I feel so bad. First of all, Ashwin, I'm so, so sorry.

I can't believe I made you feel that way, and you've been feeling that way this whole time. Oh, that's a great apology. Does that feel good, Ashwin? She acknowledged she did something wrong. Yeah. Yeah, thank you. Thank you.

Hey, guys, we're mending a little. Hey. I mean, you're still top five. Jeff. Is it okay if I explain a little bit? Please. Yes, go into details about why he's going to. No.

Just literally explain yourself. Men that can take constructive criticism is not a bad thing. Once it's one through four have that he doesn't. Just one thing he could do better. Let's work on one step at a time. And for some reason, I didn't do enough foreplay stuff. I'm open to, I'm open to feedback. Do not interrupt that statement, Jeffrey.

Not enough men make it. You should assume you didn't. Okay, well, you know, actually, maybe we shouldn't be asking what he could change maybe it's better to ask you sierra why you said that to him yes when i said oh you're definitely in the top five of five i was trying to be playful i was trying to make a joke i was trying to be kind of talking you're kidding yes i was kidding and i was so sorry why did you lead with that it was a joke dude don't you have a laughter sound button or something we could have hit there he's definitely

top four for sure let's just put it up that's a joke too yeah I think so doesn't matter it's better yeah still climbing the rankings there bud you have to do anything

that was great can we can we please stop talking about what number I'm ranking okay fair all right

yes I'm so sorry I'm just so embarrassed I was trying to make a joke it didn't land you definitely have said your apology yeah you said that a lot And I think Ashwin gets the idea that you didn't mean it.

But we mean this when we say we'd like to send you out on another date, the two of you. Ashwin, if you're willing to give her one more chance, we would pay for it. Yeah, don't let your pride stand in the way of this one, Ashwin. Yeah, no, her explanation definitely makes me feel better and embarrassed that I can't take jokes about bedtime. Bedtime. Yeah, no, I definitely would be interested in another date. Oh, that's cute. All right.

So congratulations. That means Sierra, you got what you came for. Another date with Ashwin. Thank you so, so, so much. Oh, my God. I feel like we just had two listeners who own their own mistakes, which was just wild on this show. Yeah. That never happens.

It's a little bit too mature for my life. This means tomorrow's going to be really bad on the show. Brooke and Jeffrey in the morning. We often think we know our type in dating. Tall, funny, a certain job. But the research shows were used. usually not the best predictors of who will actually make us the happiest. As we often say on the Happiness Lab, our minds lie to us about all kinds of stuff,

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confidence. When you treat dating as exploration, instead of sticking to a rigid type, you open yourself up to happier, more meaningful connections. So maybe your type isn't tall, dark, and mysterious. Maybe it's loves podcast as much as you do. Stay open, stay curious, and let yourself be surprised. Download Bumble today. Hey, it's Ed Helms and welcome back to Snafu, my podcast about history's greatest screw-ups. On our new season, we're bringing you a new snafu every single episode. 32 lost nuclear weapons? Wait, stop? What? Yeah. Ernie Shackleton sounds like a solid 70s basketball player.

Who still wore knee pads? Yes. It's going to be a whole lot of history, a whole lot of funny, and a whole lot of guests. The great Paul Shear made me feel good. I'm like, oh, wow. Angela and Jenna, I am so psyched. You're here. What was that like for you to soft launch into the show? Sorry, Jenna, I'll be asking the questions today. I forgot whose podcast we were doing. Nick Kroll. I hope this story is good enough to get you to toss that sandwich.

So let's see how it goes. Listen to season four of Snap-Foo with Ed Helms on the I-Hart Radio app, Apple Podcasts or wherever you get your podcasts. Can we all agree where do I rank is a question that should not come up until at least date number three? No, Jeff, never. You just let them tell you. You just don't ever, ever.

You've never had that conversation with your husband. God, no. With your husband. Why would you have that conversation? You just let someone tell you that was the best, that was great, or you just don't bring it up. That is a terrible conversation to have. If she was joking, it's a funny joke. Yeah, that's a good joke.

She was kidding. That was actually really good. I don't know if she really was joking. But it was the right thing to say in that moment in order to say it. Well, finally, finally the right thing to say in that moment. Exactly. And I fully expect to hear from both of them when we do an update. I love it.

I think they're so cute. Yeah, we're hopefully by then he's climbed the rankings into her top three. But she hasn't added like 10 more. Well, you know what? I'm rooting for him. system. We don't know what type of relationship they're going to be in.

Right. That's also true. I can't say we are open to our listeners ranking us on our podcast. I hope we're in the top five. Don't compare us to your others, okay? Or top 10. We'll take top 30 even.

As long as we're ahead of JLD, then we are a big win in our books. Dude, just lie and say we don't even have a list. We're good to all this. We've never done this before. Go and find us wherever you get your podcast. We're up at Broken Jeffrey. Johnny Knoxville here.

Check out Crimeless. Hillbilly Heist, my new true crime podcast from Smartless Media, Campside Media, and Big Money Players. It's the true story of the almost perfect crime and the Nimrods who almost pulled it off. It was kind of like the perfect storm in a sewer. That was dumb. Do not follow my example. Listen to Crimless, Hillbilly Heist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Hey, it's Ed Helms host of Snafoo, my podcast about history's greatest screw-ups.

On our new season, we're bringing you a new snafu every single episode. 32 lost nuclear weapons. Wait, stop? What? Yeah. It's going to be a whole lot of history, a whole lot of funny, and a whole lot of fabulous guests. Paul Shearer, Angela and Jenna, Nick Kroll, Jordan, Klepper. Listen to season four of Snafoo with Ed Helms on the IHeart Radio app, Apple Podcast.

or wherever you get your podcasts. Two rich young Americans move to the Costa Rican jungle to start over, but one of them will end up dead and the other tried for murder three times. It starts with a dream, a nature reserve and a spectacular new home. But little by little, they lose it. They actually lose it. They sort of went nuts. Until one night, everything spins out of control. Listen to head.

Tell in Heaven on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. People called them murderers. Ten years later, they were gods. Today, no one knows their names. A group of maverick surgeons who took on the medical establishment who risked everything to invent open-heart surgery. Welcome to the Wild West of American Medicine. I'm Chris Pine, and this is cardiac cowboys. If you like medical dramas, if you like heart-pounding thrillers, you will love cardiac cowboys.

Listen on the IHeart Radio app or wherever you listen to podcasts. Sponsored by Jasper, AI Build for Marketers. The murder of an 18-year-old girl in Graves County, Kentucky went unsolved for years. Until a local housewife, a journalist, and a handful of girls came forward with a story. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And to binge the entire season, ad free, subscribe to Lava for Good Plus on Apple Podcasts.