Brooke and Jeffrey: Second Date Update - Second Date Update: There's A Chili In The Air

Episode Date: October 1, 2025

One of our listeners said probably the #1 thing you should NEVER EVER say on a first date… No wonder he needs our help, but we’re ready in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

In early 1988, federal agents raced to track down the gang they suspect of importing millions of dollars worth of heroin into New York from Asia. Had 30 agents ready to go with shotguns and rifles and you name it. Five, six white people. Pushed me in the car. I'm going, what about that? Basically, your stay-at-home moms were picking up these large amounts of heroin. All you got to do is receive the package. Don't have to open it, just accept it. She was very upset, crying. Once I saw the gun, I tried to take his hand. and I saw the flash of light.

Listen to the Chinatown Stang on the IHeart Radio app, Apple Podcasts, or anywhere you get your podcasts. It may look different, but native culture is alive. My name is Nicole Garcia, and on Burn Sage, Burn Bridges, we aim to explore that culture. Somewhere along the way,

it turned into this full-fledged award-winning comic shop. That's Dr. Lee Francis IV, who opened the first Native comic bookshop. Explore his story along with many other native stories on the show, Burn Sage Burn Bridges. Listen to Burn Sage Burn Bridges on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The internet is something we make, not just something that happens to us. I'm Bridget Todd, host of the Tech and Culture Podcasts or No Girls on the Internet. In our new season, I'm talking to people like Anil Dash, an OG entrepreneur and writer who refuses to be cynical about the Internet.

I love tech. You know, I've been a nerd my whole life, but it does have to be for some. something like it's not just for its own sake it's an inspiring story that focuses on people as the core building blocks of the internet listen to there are no girls on the internet on the iheart radio app apple podcast or wherever you get your podcast hey guys it's stepney beatrice and melissa fumaro and this is more better we are jumping right in and ready to hear from you your thoughts your questions your feelings about socks with sandals and we're ready to share some possibly questionable advice and hot takes god that sucks so hard though i'm so sorry can you out petty them Can you match their pettiness for funsies?

Yeah. All the things. Because aren't we all trying to get a little more better? Listen to more better on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. December 29th, 1975, LaGuardia Airport. The holiday rush. Parents hauling luggage. Kids gripping their new Christmas toys.

Then everything changed. There's been a bombing at the TWA terminal. a chaotic, chaotic scene. In its wake, a new kind of enemy emerged, terrorism. Listen to the new season of Law and Order Criminal Justice System on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Have we told you lately how much we love you being here? Hey, yeah, we do, we do, it's true.

Welcome to your brand new second date. This is the podcast. It's Brooke and Jeffrey in the morning. And we do have a brand new second date coming up. But first, we've got to reflect on yesterday's Awkward Tuesday phone call. Yeah. The proposal fails.

And then non-atholic. Yeah. She didn't want to get married to him, supposedly, because he wouldn't give her athletic genetics. Yeah. Yeah. So what are people saying? Yeah, we got one person said,

I want to put my head in the oven after hearing her excuses. Okay. Someone else said knowing a proposal is coming soon. And as a fellow listener with my partner, I'm totally stealing the non-athletic children as a joke for the future. Oh, God. Oh, it's a joke. Watch your timing on that

Okay, make sure it's not actually While they're down on a knee Yeah, you know Yeah, and then a lot of I would break up with her He should have dumped her Why is he such a sim Hey, Brooke is 99% right here

Oh, look that Why are people shocked? I don't know I don't either All right, fine We'll see how right I am today Let's go to it though Let's get your brand new

Second Date update going It starts right now Second Date update You can't spell Desperation Without Brooke and Jeffrey in the morning I can't spell well but I think that's right That's absolutely correct

Pretty much Desperation is what made our listener email us for help today Not saying he's desperate But you know what it feels like When you've tried every other option You've exhausted every good idea You've reached out to every other reputable company And are getting nothing back

Eventually you say fine I'll talk to Brooke and Jeffrey You know It doesn't feel as good to be the last resort When you explain it that way The fact that we are a resort should feel good. That's a good point. We are on the list, even if it's at the very bottom.

And that's what made our listener... Absolutely. That's what made our listener, Dorman, email the show for help today. Dorman, it's an absolute pleasure to have you. Welcome to the show. Fun name. Is that your real name, Dorman? Yeah.

Thank you guys for happening. Yeah, well, desperate times. We are excited to have you on the show. Tell us about the woman that you are trying to get a hold of. What's her name? Her name is Yolanda. Yolanda. Okay.

Where'd you guys meet? We met online. And what made her stand out to me was like, obviously I thought she was very attractive and cute, but like just her prompts and stuff, she seemed really intentional and playful at the same time. Sorry, what do you mean by intentional? What does that mean to you? To me, that means like somebody who's actually like being honest and transparent.

She took the time to fill out her actual profile. It wasn't just like one or two word answers, you know? Can I ask what your favorite thing that she wrote was? Yeah, I forget, like, the exact wording of it, but it was, like, a joke about, like, Harry Potter and, like, she had a tattoo of it. And people just thought, like, it's the little lightning strike, but people just thought it was about the Flash, the superhero.

Oh. Okay. She's got weird tattoos. Not weird. Cool tattoos. They're cool tattoos. And old people are the only ones that would associate it with the Flash, right? Yeah.

What does that mean? I mean, there's a new Flash TV show. show. That's airing right now. Pretty big. I didn't want to call her out. Oh, I didn't know that. I didn't know that either. Oh, okay. You're just going to insult the Flash for absolutely no reason. I just thought that was like a 70s superhero or something.

I think all the superheroes are coming back. Does someone hot play the Flash? Yeah. No, Alexis, they picked the first ugly guy ever to be the star. Then I don't care anymore about it. Okay, good. So, bottom line is you appreciated her and her profile. So tell us about how you

interacted with her. What was your date? So I was thrilled that she wanted to go out. I picked this spot. It's, like, really known for their chili. It's supposed to be, like, world famous. Oh, that's kind of cool. Oh, chili's a great first date food. It's kind of fun.

I don't know, but, like, people love chili. I mean, my point was that you don't think of chili as a really romantic food that you want to eat and then make out afterwards. Also that. Yeah, you can be a little gassy. But I guess going on an adventure to taste the best chili in town, that could be a bonding experience, right? So how did that go? So it was good. I'm going to be really transparent with you guys

because I'm asking you for help so like at the restaurant I did catch myself rambling and when I reflect on that I was like okay that's nervousness and maybe a hint of insecurity like I was just like this girl is so cool

and I haven't had a girlfriend in a while and she would be an awesome girlfriend she's smart she's funny she was like super self-aware of everything it's a good feeling when you can see yourself with somebody. Yeah, and it sounds like you have a lot of self-awareness. I mean, you maybe have babbled a little bit, but... It gets worse

a little bit, maybe. I don't know. Oh, there's more rambling. There's more to that. Okay. How does it get worse? Well, I just told her I'm close to my mom, and like, I talk to her daily. Yeah. And there's a tradition from years ago where, like, every Friday, before I go to work, I go to my mom's place to see

her, and she always, like, packs my lunch for me. Oh. She packs your lunch? Yeah, just kind of like how she used to when I was a kid, you know? Okay. Well, at least you know, again, self-aware, right, Brooke? This could be it.

Yeah. What was her reaction? I mean, in the moment, she was super nice. She was just listening. I kept rambling and then I changed the subject to something else. But I just don't know how it landed. Okay. Yeah.

That's a lot. You wouldn't take that guy home immediately, Brooke, after he came out with that information? Honestly, I think if you just said every Friday, I go see my mom, awesome. Perfect. Awesome. Yeah. It was the details. It was the lunch and the childhood.

But what if the mom would pack her lunch, too? Then I might be into it, you know? Now we get two first. I like that. Okay. Look, make all of us lunch. I'm not your mother. If it doesn't work out with Yolanda here,

Alexis is ready to jump on board with you and your mom. I would need to see the menu. Oh, okay. Are you kidding me? Just see him, just the menu. All you need is an uncrustable every Friday. It would be good. All right.

So your mom might be on the hook here soon, but how did the date with you and Yolanda? end? Overall, it was good, but I will say it wasn't the longest date because I didn't think the chilly thing through. I was like, I got to hit the restroom. Oh, no. Oh, it did backfire. So you're the one that ended things early and you had to rush home to use the restroom. And I'm the one that drove her there. So I was like, you know, I have to keep this all together to still drive her back home before I get home to myself. Okay. Okay. Sometimes that could be a vibe too. If someone ends the date and you're not expecting it. Totally. Or,

speeding at 80 miles per hour home. It might be another hint that something's wrong. And profusely sweating with a generous face. With a bumper sticker on the back of your car that said, we just had the best chilly in town. Look out. So happy I bought this bumper sticker.

You know, there's a little bit of regret. Yeah, and, you know, I was just in my defense trying to avoid any awkward situations in the car. Totally. Totally. I mean, it could happen to anybody. So how long has it been since that date happened? It's been about eight days.

I mean, eight days, it could have taken her that long to recover from the chili dinner. So maybe she just needed a little extra time. Oh, man, must have been hot chili. I'm really hoping we were done with talking about this part. Well, we'll have to see when we call Yolanda and try and get you a second date update, a successful one coming up. Right after this. Hold on. Second date update. If you're just joining us, let's recap the highlights from Dorman's first date.

A couple big bowls of chili. There were a few stories of Dorman's mom making his lunch, still to this day. Just like she did in child. Only on Fridays. Only on Fridays, and he's only 34 years old. Followed by a rocket ship car ride back to Yolanda's house because the chili was starting to kick in. It sounds like you put a quarter in one of those machines outside of like a grocery store.

That's what it felt like to his insides, I'm sure. You know what we didn't ask is if he even came to a full stop before she was. got out of the car. Dorman, did you make her tuck and roll out the vehicle before you sped home? No, but she's the first girl in a long time that has girlfriend potential, you know? Yeah. Well, listen, if she can see past all of this, then she may be the right person for you. She would be wife material.

Yeah. Yeah. We're going to do our very best to go to bat for you and make sure you lock down a second date with Yolanda. Are you ready to do this, man? Yeah, let's do it. All right. Is your mom ready to do this?

She's not behind you, is she? If she was back on the speaker phone, I swear. Just me this time. All right. We'll work with what we've got. Here we go. Hello. Hey, is this Yolanda?

Yeah. Who's this? This is a radio show called Brooke and Jeffrey in the morning. Hey, Yolanda. Hi, good morning, Yolanda. Why are you at home? Great question. Right to the point.

I've heard better questions, but you know what? I'll answer this one. This, it's a segment that we do. It's called a second date update. Okay. And I still don't know where you guys are calling me. Okay. So the second date update is where we have a listener who isn't sure why they're not getting a call back for another meetup after they went out with a lovely person.

I'm so sorry, guys. I really feel like you might have the wrong person. Well, okay. Wait, you don't have been on any dates lately? No, I mean it's just confusing. Yeah, we got your number from a guy you went out with recently named Dorman. There's probably more than one. It's pretty common names.

I've never heard that name. I have so many Dormons in my life. Does that ring a bell, Dorman? Yeah, I know who that is. Why did he give you my number? That part I don't get. Well, because he felt like the two of you had a really nice time going out to the chili restaurant. I mean, he honestly had some really lovely compliments he gave about you when we talked to him.

So that's why you're calling me? me? No, he just really liked you. And he's confused why there hasn't been another meetup. Are you upset with him? Because you sound kind of. I'm just shocked. Oh, my gosh.

This is so weird. What the heck? Is it just weird? It's weird because there's like, I don't even know how many people are on the phone. And you're asking me about details from a date. Like, this is weird. I understand that this is definitely a lot. It can be really overwhelming.

So maybe we can just cut to the chase. We just want to know, is there one main reason, one big red flag for why you're not wanting to see Dorman again? We're not trying to tack you or anything. Not yet. Shut up, Jeff. So I'll just say this. We were at dinner and he brought up a really uncomfortable conversation that, like, didn't sit well with me. Oh, man.

Yeah, we kind of might know what that is. He did say something to us. Something involving his mother, maybe. No, no, had nothing to do with his mom. Oh. He loved the fact that he hadn't been with a woman romantically in three years. Oh. He told you that.

Wait. He said that. Like physically he hasn't. Okay. How did that come up? It didn't. It didn't come up. He just said it to me.

And he then he followed it up with like looking me dead in the eye. And he's like, I hope that can change soon. Oh, brother. No. Okay. It was so awkward. What did you say? What the heck is this?

I didn't know. I didn't say anything. He did say that he was rambling a lot during the date and was just saying every thought that came to his mind. Maybe that was one of them. He was really nervous. I guess you're nervous, but like, why make me nervous too? Well, I think he was excited. You check a lot of boxes for him.

And it's probably more common than you would think. Like, Alexis, that's happened to you multiple times, right? Yeah, I would totally date those people. Yeah. So see? I would totally give them another chance. She would be a guy on a two-week drive. Okay.

No, I can see where that'd be pretty shocking on a day. That's just a different thing to say. Okay. So now you know, I'm going to go now. Well, hold on. It's really important that we know, but it's actually more important that Dorman knows that. Well, then just tell them. Well, I don't have to because he's on the other line listening to this right now and wanting to talk to you.

Oh, my God. Oh, my God. Oh, my God. I'm sorry. Dorman, are you there? Oh, God. Yeah. Oh, buddy.

Oh, buddy. Dorman, say hi to Yolanda. Say something. Hi, Yolanda. Hi. Okay. Say more. Dormon, apologize.

I'm sorry. We were having chili. I don't know. I just rambled. Chili brings up. I don't know why you would tell your date that you hadn't had sex in three years. It's a lot.

The chili was spicy. We were talking about our love life while eating it. And fun fact, I just haven't done it in a while. It just started rambling. And when I get nervous, I rambled,

whenever you're in front of a bowl of chili, you feel like... It's like a truth serum. That's good. A lot of girls are going to test that on their boyfriend. Yeah. I mean, it's kind of like that interview show, the hot ones.

Oh, you're right. People are spicy. People confess things. They don't realize they were going to say because they're just not in control of what's happening. Yeah, I can't focus. Yeah, I don't know why it came out. I'm sorry that it did, but now it's out publicly,

so I have to depend on this, but it just came out. I'm sorry. It doesn't matter who brought it up. You're the one who's set it on a first date. Like, that's so weird. Yeah. I mean, it's not weird. Making love is natural thing.

That's just not happening currently. Don't do that, Dorming. I wish that it. was and I was just expressing it. You telling women that makes it even less likely to happen. Wait, wait, wait, though. I mean, listen. You don't think I know this.

My mom says the same thing. You tell your mom about your lack of intimacy? Again, I'm not the one that brings it up, okay? She just tells me that, like, her and dad, do it more often. Oh, my God. No. That's okay. Dorman, let's not talk anymore.

I didn't think I could be more turned off at the start of this call, but congratulations. He did it. Now I don't know if I'm going to have sex for three years. Oh, wow. You turn her off to it. I hope you don't. Then you'll know what it feels like. Oh, hashtag relatable.

Wow. Oh, my God. I can't with you. You know more than anything. You want to go back after a date and tell his mom all about it. Okay. This is not going... Darn it.

I mean, maybe it's going a little bit better. Then what? Compared to... Ben his conversation with his mom about his mom's sex life? Well, it's his mom's fault that she's rubbing that into her son's face. I feel like that... You know what, Dorman, shame on your mom for bragging to you about how much action she's getting from your dad. Hey, let's leave the mothers out of it.

Okay, you were the one who brought it up. That was your information. Yeah, you brought it up. Okay. Not on the radio. That was over an intimate bowl of chili. Okay. That was a private bowl of chili.

I cannot believe it was this and not the other things that we had already. Dorman. You need to stop talking because every sentence you say makes it work. Oh, buddy. You know what? At this point, guys, I'm sorry. I'm getting nervous, skin, rambling. I've said everything that I needed to.

I'm just going to keep talking. Like, fun fact, even when I was getting it three years ago, it wasn't that great. And, you know, it wasn't even like the fun stuff. You want to explore it out. We don't want details. Okay, we've heard enough. Yolanda, I just think there's a connection here that we should explore. Stop talking.

Okay, he's going to stop talking, and I'm just going to pick it up and offer to send you two on another day. And we would pay for it. You don't even have to bother. I'm all that. Yolanda, would it change your mind at all if it's not chilly? No. No. Oh, come on.

I can't even ask that. It's possible. I left that Jeff thought that was easy. Well, chewing seems to be the thing that's bringing up all of these deep-seated memories and thoughts. What if we lined up with some cob salads? Guys, I appreciate it. Some people are just too judgmental. You know, that's the issue.

That's well said, Dorman. And we appreciate you coming on the show and being open with us far too open for anybody to be comfortable with. But you know what? I need like a break after this. Just a breather in the other room. We've got your back, Dorman. We all wish you a lot of luck getting over your hill that you're trying to climb here. Yeah.

Brooke and Jeffrey in the morning. All I know is what I've been told, and that's a half-truth is a whole lie. For almost a decade, the murder of an 18-year-old girl from a small town in Graves County, Kentucky, went unsolved, until a local homemaker, a journalist, and a handful of girls came forward with a story. I'm telling you, we know Quincy killed her. We know. A story that law enforcement used to convict six people and that got the citizen investigator on national TV. Through sheer persistence and nerve,

this Kentucky housewife helped give justice to Jessica Curran. My name is Maggie Freeling. I'm a Pulitzer Prize-winning journalist, producer, and I wouldn't be here if the truth were that easy to find. I did not know her and I did not kill her, or rape or burn or any of that other stuff, They literally made me say that I took a match and struck and threw it on her. They made me say that I poured gas on her.

From Lava for Good, this is Graves County, a show about just how far our legal system will go in order to find someone to blame. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County in the Bone Valley feed on the IHeart Radio 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. to give you an NFL perspective a little bit different. Did you see the Colts Pretzel? That was my other big takeaway from that game. What was that?

Oh, my. We think NFL coverage should be informative and entertaining. And twice a week, that is exactly what you're going to get. Listen to NFL Cover Zero with Matt Jones and Drew Franklin on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Toyota, the official automotive partner of the NFL. Visit Toyota.com slash NFL now to learn more. Brooke, you've had a few moments to recover after that fiasco. Are you feeling any better about what we just heard?

Oh, my. I honestly think that he's a good person and that he, like, I don't think he means to be socially awkward. So open? Yeah, too open. Let's close it down a little bit, buddy. Yeah. I don't think we've ever had somebody on the show in the middle of a date. admit I haven't gotten

action from a woman in three years but I'm hoping that's going to change looking at you at least he didn't say never I mean that's still not bad either I just think it's got hope crazy she wasn't like oh I get to be the lucky one I'm a believer in manifestation

in trying to put your wants out there into the world I don't think this is quite the right way to do it no that's into the world not into your date although who knows maybe after this Dorman's going to have 12 women in a single week almost as many sessions as his mom and dad have

keep dreaming Dorman I'm still looking for someone to text in to go out with him I'm literally looking somebody's out there for him and there's somebody out there for everybody if you need some help in your dating life email the show we can call that person who's not calling you back go check out all of our second dates wherever get your podcast they're up online at Brooke and Jeffrey

in early 1988 federal agents race to track down the gang they suspect of importing millions of dollars worth of heroin into New York from Asia. I had 30 agents ready to go with shotguns and rifles and you name it. Five, six white people. Pushed me in the car. Basically, your stay-at-home moms were picking up these large amounts of heroin. All you got to do is receive the package.

Don't have to open it, just accept it. She was very upset, crying. Once I saw the gun, I tried to take his hand, and I saw the flash of light. Listen to the Chinatown Sting on the IHeart Radio Act. Apple Podcasts, or anywhere you get your podcasts. It may look different, but Native Culture is alive. My name is Nicole Garcia, and on Burn Sage, Burn Bridges, we aim to explore that culture. Somewhere along the way, it turned into this full-fledged award-winning comic shop.

That's Dr. Lee Francis IV, who opened the first Native comic bookshop. Explore his story along with many other Native stories on the show, Burn Sage Burn Bridges. Listen to Burn Sage Burn Bridges on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The internet is something we make, not just something that happens to us. I'm Bridget Todd, host of the Tech and Culture Podcasts or No Girls on the Internet. In our new season, I'm talking to people like Aneal Dash, an OG entrepreneur and writer who refuses to be cynical about the Internet. I love tech. You know, I've been a nerd my whole life, but it does have to be for something.

Like, it's not just for its own sake. It's an inspiring story that focuses on people as the core. or building blocks of the internet. Listen to there are no girls on the internet on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast. December 29th, 1975, LaGuardia Airport. The holiday rush, parents hauling luggage,

kids gripping their new Christmas toys. Then everything changed. There's been a bombing at the TWA terminal. Just a chaotic, chaotic scene. In its wake, a new kind of enemy emerged. terrorism. Listen to the new season of law and order criminal justice system on the iHeart radio app, Apple Podcasts, or wherever you get your podcasts. Hey guys, it's Stephanie Beatriz and Melissa Fumero, and this is more better. We are jumping

right in and ready to hear from you. Your thoughts, your questions, your feelings about socks with sandals. And we're ready to share some possibly questionable advice and hot takes. God, that sucks so hard though. I'm so sorry. Can you out petty them? Can you match their pettiness for funsies? Yeah. All the things. Because aren't we all trying to get a little more better? Listen to more better on the IHeart Radio app,

Apple Podcasts, or wherever you get your podcasts.