Brooke and Jeffrey: Second Date Update

Second Date Update: 15 Minutes Of Lame

18 min
Apr 3, 2026about 2 months ago
Listen to Episode
Summary

Jason, a returning caller, goes on a 15-minute date with Riley that ends abruptly when she decides to leave the car. Through a live phone conversation, the hosts discover Riley ended the date because Jason didn't make a restaurant reservation and refused to pivot to an alternative plan, revealing fundamental differences in dating expectations and planning.

Insights
  • Poor planning and lack of adaptability on dates can be interpreted as not valuing a partner's time, even if unintentional
  • Communication breakdowns occur when one person assumes rejection is about appearance rather than addressing actual concerns
  • Self-deprecating humor and low self-esteem can undermine romantic chemistry and come across as off-putting rather than endearing
  • Different expectations around spontaneity versus structure in dating can be a core compatibility issue worth discussing early
  • Defensive responses to criticism (like Jason's 'vibes' approach) can escalate conflict rather than resolve it
Trends
Dating expectations increasingly emphasize effort and planning as signals of genuine interestAppearance-focused anxiety remains a default assumption for rejection, masking deeper compatibility issuesYounger daters struggle with balancing spontaneity and structure in relationship buildingCommunication avoidance on dates (not pivoting, not explaining) leads to rapid relationship terminationSelf-awareness about attractiveness levels doesn't correlate with self-awareness about relationship dynamics
Companies
iHeart Radio
Platform where the Brooke and Jeffrey podcast and Pooja Bhatt Show are distributed and available
Apple Podcasts
Podcast distribution platform where listeners can access Brooke and Jeffrey and Pooja Bhatt Show
People
Jason
Returning caller on second date update segment who went on a 15-minute date with Riley
Riley
Jason's date who ended the date after 15 minutes due to lack of restaurant reservation and planning
Brooke
Co-host of the second date update segment
Jeffrey
Co-host of the second date update segment
Pooja Bhatt
Host of The Pooja Bhatt Show, featured in podcast advertisement segments
Quotes
"Indecision is one of the most unsexy traits."
BrookeEarly in episode
"I don't want my time wasted. I don't know why you think like I can just stand outside for 45 minutes. It's a Friday night."
RileyMid-episode
"The plan was just called vibes. You know what I mean? Just be together. You're a cool guy. We're adults."
JasonLate in episode
"You're not going to waste my Friday night with just vibes."
RileyLate in episode
"I feel like I'm about a six and I feel like you're probably around the same area."
JasonEnd of episode
Full Transcript
No gloss, no filter, just stories, spoken without fear. A person who is not generous cannot be an artist. The world will be at peace only when it is ruled by poets and philosophers. Listen to my weekly podcast, the puja bhajjo on the iHeart radio app, Apple Podcast or wherever you get your podcasts. Come for the honesty, stay for the fire. Hey, this may be a world record. Welcome to the brand new second date podcast today with Brooke and Jeffrey. Yeah, for the shortest date we've heard. Oh, yeah, that kind of record. Yeah. 10 minutes in, she's like, take me home. Yeah. We're going to find out why, because the guy doesn't know either coming up here in a second. But first, let's start with comments. Well, kind of the opposite of a short date. John said, I once got lost on a hike on a date. We were lost for like three hours. Almost got ran over by a horse and then went to Waffle House. And now we've been married for five years. Oh, look at that. All right. After the helicopter came and save you. Where does the horse come in? I don't know. Or the Waffle House. Yeah, Waffle House on this mountain. I have so many. I'm starting to think he was just in a field, a suburb somewhere. Yeah. All right. Hey, thank you for sharing your story. I love it. Oh, we got your brand new second date episode starting right now. Brooke and Jeffrey in the morning, second date update. Today we have a quote unquote returning listener. Uh-oh. His name is Jason. Why quote unquote? Well, he says he's been on the show before for this very segment. And you don't believe him? Well, I got to be honest. I looked back into the archives and I can't find his call anywhere. Huh. So was he really on the show? No. Is he making it up just to sound cool? Because that's totally what I would do. But I guess we might be forced to believe him. I mean, Jason, can you at least jog our memory and tell us what happened the last time that you supposedly were on with us? You guys had me on twice. Oh, wait, you were on more than once? We did an update update. Did we just never air it because it wasn't very funny? Yeah. Are you a boring guy? Well, I'll start from the beginning then. Yeah. I was dating this girl, Emily, and she said that she didn't want to go back out on a date with me because I had a hard time saying no. She wanted a guy that could push back more, stand up for his thoughts and opinions, and that's what you guys were helping me out with. So you went out with a woman who wanted her boyfriend to say no to her. Does that sound realistic, Brooke? He's just a pushover. Dude, I love a man who can make a choice. Indecision is one of the most unsexy traits. Yeah, so you said you were on for an update update. That means you two were together. What happened? Well, I started being able to stand up for myself from time to time, and we actually did end up dating for a little bit there. All right. So why did it end? Okay, she broke up with me because she got a dog and she wanted to name it Spinner. And taking your guys' advice, I was like, no, that's a dumb name. No, no one told you to talk to people like that. Brooke, why would you tell him that a man should stand up to a woman? That's horrible. It's not your dog. Yeah. Geeze. B, that is kind of mean. It's all aggressive. I mean... No, I said you need to name an acute human name like Kevin because that's funny. Yeah, we love that. Get your own dog and name it Kevin. There we go, okay. That's kind of what she said. I didn't back down. So I was like, no, you're not naming the dog Spinner, and she ended up breaking up with me. Wow. I met her and Spinner. Really happy though, for real. After you gave her exactly what she wanted, a guy that says no, and then she didn't like that. And known her own life decisions. Yeah, it's... Hard to decipher what women really want. It's not. So did you do that again to another girl now? Is that... No, but good guess because I am now dating a different girl. Her name is Riley. All right. Is that a stupid name? No, it's a human name, so he's okay with it. Okay, we like her name. Humans with human names are okay. Okay, that's a bold stance to take, but good for you. Okay, so here's the problem. The date only lasted about 15 minutes. Whoa, that's not good. Do we even consider it a date at that point? Is it just a run-in at that point? Did you plan on it being a quick date? I planned a whole day. So I picked her up at her place and it just started like a normal thing. You know, how's your day? Where are we going? Like what's going on? Nice to meet you, Anastas. And then all of a sudden, we're barely 10 minutes down the road and she just says, I think it's best if we don't go out, actually. Oh my gosh. Before you even get to the destination where you're driving to? That's drastic. Yeah, yeah, yeah, yeah. Like the AC barely got the car cool. Okay. Did she see like duct tape and a shovel in the back seat and that's why she wanted to turn around? Yeah, she had to. No, I kind of thought, I mean, I never tried to catfish everybody. All my pictures are current online, but I'm like thinking, okay, she probably got in the car, thought I was ugly, want to go back home. Oh, is that fair, Alexis? Does that happen a lot? I mean, bull. Brooke, why are you laughing? Why are you giggling about him thinking that he's ugly? Why would that be your first thought, man? Put that aside. I mean, if she didn't think you were ugly, what else? Like, was anything else happen? How much Brooke shovels, duct tape? No, I mean, I said that's where I said, like, what do you mean? Like you want to go back right now? The only thing she gave me was that it just wasn't what she expected. Oh. Like, I mean, I don't know exactly what she meant by that, but she obviously, I want to talk about it. Okay. Did you use your, the lessons that you learned from before and say, no, you're staying in this car and we are going on this day? That's a great idea, Jeff. I think that's a romantic move. I think it's kidnapping, but... Yeah, didn't quite go there. Good, good, good. But I dropped her off and that was kind of it. So maybe this isn't the best question to ask, but I need to know, was there a kiss? Oh, come on. It would be funny if they made out passionately and then they left. He's like, oh, she spent the night. Oh, no. No, no. I brought her, I bought her flowers and she just like, she just threw them in the backseat of the car, got out and left them. I texted her afterwards, no response. I guess I'm not shocked, but like, I just want clarity. It sounds like even if she did say ugly, you could take it. I mean, yeah, I saw him six. There we go. All right. Okay. That's not bad. We can work with a six. Yeah, you're more attractive than anybody in this room. Look how high Brooke's voice is going. Yeah, six isn't bad. That's actually really effective. That's right. I believe you. Yeah, point six. Let's see what Riley has to say if we can get her on the phone. We'll try and get you your second, second date update on this show. Oh, yeah. Memorable guy. Super memorable Jason. We have to remember him this time. Right after this. Hold on, man. Brooke and Jeffrey in the morning, second date update. If you're just joining us, we've got a return caller, Jason on the phone, who describes himself as a solid six. But is he in New York six or in Idaho six? We didn't ask that. Because there is a difference. Come on. There's somebody for everybody, even an Idaho four out there. All right. Totally. But he only brought up his own looks because after just 10 minutes of driving together, Jason's date suddenly changed her mind and said, actually, this isn't what I was expecting. And she has to be taken home. So his thought was, well, maybe she just didn't think I was attractive enough in person. Like she finally looked left 10 minutes into the drive and was like, oh my gosh. What if it's not about him? What if she wasn't wearing the right outfit? You know, like he explained what they were going to do for the date and she's like, I don't have tennis shoes. No. She would have just said, hold on, let me run inside real quick. I'll be right back. He's trying to make it not about sad, ugly. It's possible. Jason, have you considered that Riley hates herself a little bit? What? Wait, that's what you got? How she looks. Oh, now I get it. And considering that I might hate myself a little bit now. Okay. Good. This is not going in a positive direction. You've been, he's kidding guys. He never got any specific answer on what was such a let down. So that's what he's hoping to get today at a bare minimum. Yeah. And then maybe we'll see where it goes from there. And this may be the first time, the hope is that she thinks he's ugly. Yeah. Because two people who both don't find themselves attractive could be meant for each other. That's the optimism that she wanted, right, Brooke? No, I was just saying she wasn't prepared for whatever he had planned that day. Not that she was ugly. Not her face. Yeah. Okay. Well, we can all hope for different things. Okay. She's made, he's ugly. Yeah. Could be the perfect match. Let's just call it. Okay, Jason, I'm going to call her here in a second, but real quick, how was she looking that night? Your opinion? Uh, better than a six? Pretty good. Okay. There you go. I won't quote you directly on that, but yeah. Let's dial her number and see what she has to say. Here we go. Hello? Hey, we're looking to speak with Riley. Uh, speaking. All right. Hey, Riley, this is a radio show. We're called Brooke and Jeffrey in the morning. Welcome. Welcome to it, Riley. Hi. Hey, how you doing? I'm sorry. Who is this? Oh, that hurts every time. Yeah, I thought we were getting momentum. Yeah. But now we're radio show. We're called Brooke and Jeffrey in the morning. And this is the radio show. We're a radio show. We're called Brooke and Jeffrey in the morning. And this is a segment that we do called the second date update. Okay. I know you're not a woman who likes her time to be wasted. So I'm going to get right to this. Jeff, you went out with a listener of our show, a guy named Jason. And he told us the date didn't go how he thought it was going to go. It didn't really go at all. Yeah. Is that a fair assessment? We didn't really go out. Yeah. We're sorry about that. That sucks, huh? No, not really. Oh, right. We heard it was your idea to not continue the date, but Jason is a little bit confused on why you felt that way. Yeah. I mean, I don't know how he could be, but really, you think it's something that obvious? Yeah. I mean, we were in the car and he said, we're going to this restaurant. I know the restaurant. I like the restaurant. Okay. And then when I'm in the car, he's like, oh, I didn't make a reservation. Oh, no. And I was like, you know, it's a busy night. Like you probably should have made a reservation. He's like, oh, well, I don't know any other restaurants in the area. Okay, but we have phones. So just Google, but he's like, you know, it's fine. We can just stand outside and do like small talk. Oh, that's an awful backup plan. Like when you do adjust, you know, he should have done better. He should have just planning before you even get to the restaurant though. Brooke, what's going through your mind? I'm curious. It sounds like an argument you have like three years into a relationship. Yeah. So it's a good sign. Oh, you didn't make reservations. Of course you didn't. You never put any effort into these dates. You know what? That's it, Bill. Turn the car around. So Brooke's saying it sounds like you belong together. Oh, God. We absolutely don't. Okay. I don't want my time wasted. I don't know why you think like I can just stand outside for 45 minutes. It's a Friday night. Like I'd rather hang out with my friends. Maybe he just misspoke. You know, maybe he meant like we'd go to a bar or we'll walk down the street and see if there's something else while we wait. I said that and he then clarified. I was like, oh, you mean like get, you know, a drink inside or somewhere next door. And he was like, no, we can just stand outside so we don't miss our name. Oh, for this. He sounds like a type of person that arrives five hours early for a flat. I can understand how that would be a red flag for Riley where he doesn't plan ahead enough and she's feeling like he doesn't value her time. But that's a fix. I mean, why wouldn't you make that clear to him in that point? Like, hey, it doesn't feel like you really care about your time with me. Well, I did say I don't think we're a good fit. You mind just dropping me back off and he said fine. So I thought it was clear. Okay. Well, we value your time very much. And that's why we don't want to waste any more of your time and letting you know that Jason is listening to this phone call right now. He's actually been on it the entire time and wants to talk to you. What? Yeah, Jason, are you there? Hey, Riley. Hey, are you just making all that stuff up because you think I'm ugly and you're not trying to hurt my feelings? Oh, what? Oh, dang. Stick into his first theory. Why would you say that, Jason? That's not what she said at all. I was just, is it illegal to ask? It sounds like it's something that's in your head a lot. Well, this is good to get it out of the way. Do you find Jason attractive or not, Riley? I mean, I wouldn't have gone on a date if I didn't find you attractive. I was interested, but your lack of planning just felt like you didn't care and you just thought you could, you know, it seemed kind of arrogant. Yeah. She's mad about you not having a full plan, it sounds like. No, it's not that I didn't have a plan. The plan was just called vibes. You know what I mean? Just be together. You're a cool guy. We're adults. That's not a thing. You're not going to waste my Friday night with just vibes. Different personality times for sure here. But why didn't you pivot and say, oh shoot, we have a 45 minute wait, let's pop by next door and discover a new spot. If we got there and there was like a place next door, you know, I wouldn't say that I was opposed to that necessarily. I just thought it'd be better to make sure that our name, we could hear our name because what if we missed it all together? That'd be bad. At least we got to the core and know exactly what the issue was that caused the problem on this date. So why don't Riley, Jason, you two talk to each other. See if there's some natural chemistry when you just are left alone to your own devices. Go ahead. Jason, why don't you start it off? Okay. Now that we got past that little speed bump here, Riley, if I have any reservations this time, are you in to go? Is that, if that was the only thing that was holding you back? Oh, right. Yeah, it's kind of a smart. I don't know. I think you have a lot of self-esteem issues going on. No, there's no self-esteem issues. I know exactly where I sit. I'm a solid six. We know this. We've been over this. No, that was you. But yeah. Just because everything didn't go exactly your way, I think we're already learning how to compromise. I think this is the start of a beautiful partnership. Wow. That's good. I've shown you that I can take criticism and respond in a favorable manner. Who doesn't want growth in their relationship? Oh, I appreciate that. I do appreciate that. The jumping to conclusions that I thought you were ugly kind of makes me nervous. Why? Well, no, let him respond to it. Why? She just went over the self-confidence. I think he's shook a nerve with Jeff. Jason. Well, like I said before, I feel like I'm about a six and I feel like you're probably around the same area. Oh, it seems like a good fit to me. That was like a kind of a jab. Smooth delivery. Are you trying to be funny? It's a good match. You know, we're both not classically attractive. Oh, okay. Classically attractive. Jason. We were there. You did it already. You already turned into real much. So we're both men. Hold on. Hold on. Riley, is your heart beating fast hearing Jason say that to you? I definitely the most romantic thing I've ever heard. Well, I'm going to take that at face value and ask, would you like to go out on another date with Jason because we'd pay for it and we'd put the reservation in for him. Absolutely not. Oh, man. Jason, man, I'm sorry that we couldn't get this to work out between you and Riley. But hey, we look forward to your third attempt at a second date update where we'll definitely remember who you are. We got to make a note or something on him. Yeah, he's Jason the six. Okay, perfect. Broke in Jeffrey in the morning. No gloss. No filter. Just stories. Spoken without fear. Addiction is a disease and it should be looked upon as any other disease. How did you cope with a reckless father like me? Join me, Pooja Bhatt, as I sit down every week with directors, actors, musicians, technicians and beyond. You don't need to work with the biggest people and the biggest sound to have great music. I have gone through the sub-CD hutchaker, reached the pinnacle, stung by the sneaker and I've fallen down again. Yeah, I am not writing actively anymore and when I see my old work it kind of saddens me. I'm only as good as the last shot that I gave. Mom's gone but don't shut the theater. The show must go on. Listen to my weekly podcast, the Pooja Bhatt show on the iHeart Radio app. Apple Podcasts or wherever you get your podcasts. Come for the honesty. Stay for the fire. If you're on the way to a nice date and the person tells you on the way, no I didn't make a reservation and you know you're gonna have to stand out for two hours, I'd be like whoa, whoa, whoa, whoa. I'm here for the food, not for the company. You didn't give him a chance though at all. Brooke, I was like me, don't stand outside for two hours. But I will say at least you didn't cost him any money. Yeah, that's true. And didn't even take the flowers. Yeah, I know. We thought about her throwing the flowers in the backstage. That part, it was all out of control because I agree, he probably should have made a reservation but I do think it was harsh to call everything off just because there was no serious plan in place. Well it wasn't just that, it was that he wouldn't even pivot to go get a drink next door. Yeah, come on. I mean listen, even go to Denny's, like that's something. Whatever it was, it didn't work out for Jason this time around. Yeah. I'm sure he'll be back. Oh yeah. He will be. Will we remember him? We need one of those customer cards where you get a punch every time you come in. But no matter who you are, if you've been on once, twice, a million times, we're always here to help. Yeah. Email the show, we'll call that person who's not calling you back and you go find all of our second dates. Wherever you find them online, get it at your podcast at Brooke and Jeffrey in the morning. No gloss, no filter, just stories, spoken without fear. A person who is not generous cannot be an artist. The world will be at peace only when it is ruled by poets and philosophers. Listen to my weekly podcast, the Pooja Bhat Show on the iHeart radio app, Apple Podcasts, or wherever you get your podcasts. Come for the honesty, stay for the fire.