Brooke and Jeffrey: Second Date Update - #6 Second Date Update of 2025: Lonely Cannoli

Episode Date: December 22, 2025

A quick trip to move his car ended up being a HUGE mistake for our listener, and it sent his date WILDLY OFF TRACK. Hear how it went down in a Second Date Update!See omnystudio.com/listener for privacy information.

I'm Stefan Curry, and this is Gentleman's Cut. I think what makes Gentleman's Cut different is me being a part of developing the profile of this beautiful finished product. With every sip, you get a little something different. Visit gentlemen's cut bourbon.com or your nearest Total Wines or Bevmo. This message is intended for audiences 21 and older. Gentleman's Cut Bourbon, Boone County, Kentucky. For more on Gentleman's Cut Bourbon, please visit gentlemen's cut bourbon.com. Please enjoy responsibly.

I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas and destructive companies in the history of business. First episode, How Southwest Airlines Use Cheap Seats and Free Whiskey to fight its way into the airline is. The most Texas story ever. Listen to Business History on the IHeart Radio app, Apple Podcasts, or wherever you get. Your podcasts. I knew it was a bomb the second that it exploded.

I felt it ripped through me. In season two of RipCurrent, we asked who tried to kill Judy Berry and why. They were climbing trees and they were sabotaging logging equipment in the woods. She received death threats before the bombing. She received more threats after the bombing. I think that this is a deliberate attempt to sabotage our movement.

Episodes of RipCurrent Season 2 are available now. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Whether it is getting swatted or just hateful messages online. There is a lot of harm and even just reading the comments. That's cybersecurity expert Camille Stewart Gloucester on the Therapy for Black Girls podcast. Every season is a chance to grow.

And the Therapy for Black Girls podcast is here to walk with you. I'm Dr. Joy Harden Bradford. And each week we dive into real conversations that help you move with more clarity and confidence. This episode, we're breaking down what really happens to your information on live and how to protect yourself with intention. Listen to therapy for black girls on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. Dr. Laurie Santos from the Happiness Lab here. It's the season of giving, and this year my podcast, The Happiness Lab, is partnering with Give Directly, a nonprofit that provides people in extreme poverty

with the cash they need as part of the Pods Fight Poverty campaign. Our goal goal this year is to raise one million dollars, which will bring over 700 families out of extreme poverty. Your donation will put cash directly in the hands of these families in need, and they'll get to decide how to use it, whether that's school transportation, purchasing livestock, or starting a business. Plus, if you're a first-time donor, your gift will be matched by giving multiplier, which means more money for those in need. Visit give-directly.org slash happiness Lab to learn more and to donate. That's give directly.org

slash happiness lab. All right, before we get to your number six, oh my gosh, number six second date of 2025, that's crazy we're here already. I just want to say thank you for all the wonderful comments you all are leaving. You know, some people are like, ah, this one should have been number one.

Yeah. So we'll see how you feel about number six today. Yeah, we appreciate you fighting in the comments. I also appreciate the not wonderful comments too. Those are fun to read. Plenty of those. But for a second date today, there is a famous saying from Thomas the Tank Engine. I think you all know what I'm talking about.

Is this the philosopher that you call? I think I can one? No, one wrong switch and the whole trains off the track. Wow. Never saw that episode. That's a wise train. Yeah, I didn't read that book. Meaning all it takes is one tiny hiccup to completely ruin your plans for the day.

And that's exactly what happened to one of our listeners during a great date where one minute he's running outside of a girl's apartment to move his car. next minute he's on a city bus miles away headed in the wrong direction you'll hear how it went so wildly off track in your number six second date update of the year right now second date update on this show we talk about us being foodies quite a bit yeah we love our food

I'm eating right now he's not lying literally because everyone here is hungry constantly but if there's two single foodies out there where's the best place for them to meet up? Like, to meet for the first time or to go on the first date? Like, how about at a local food fair? Yeah.

Just, like, a market? Yeah, two tongues dancing together over one fried gator kebab. I don't know what I'd put that in the description when you send them your date idea. Sounds like love to me. You're trying to go into end on this gator stick? I bring up food fairs because that's where one of our listeners met a fellow foodie recently. His name is Paul. So, Paul, welcome to the show.

Hey, thank you so much for helping me. Okay, the best part about being someone who loves food is it's so easy to have conversation, right? Yeah. You always have something to talk about. Good or bad. Yeah. Even if you don't like something. No, absolutely.

No, in fact, I met Taylor at a street fair. Oh. Okay. Okay. So her name is Taylor. And how did you, too, like, strike up a conversation, paint the picture for us? All right. Well, we were in line for the Korean corn dogs and just started chatting.

The cheesy ones with the corn on the outside? Or they looks like the corn, but it's cheese? It's beyond description, and the taste was insane. Oh, my God. Now this is my new summer goal to seek out. Write that down, listeners. Korean corn dogs are where real love happens. Dude.

Okay. And so you and Taylor are in line together. Is that how you struck up a conversation? Yeah, because she was behind me. So we just started chatting about that. And then other things we had, and then we kind of hit it off. And then we walked the whole fair. What? That's awesome.

So you guys were both there by yourselves? Yeah, I was just there for me, but Taylor was there with her sister and her sister's kids. Oh, you. So it's easy to split off. She was thankful. Yeah. That's so cute. You're walking the fair together eating your Korean corn dogs.

I mean, this sounds like a great day. Why? Sounds like a Korean soap opera. Yeah. Like, what did you guys connect over? She let me choose the next place, and I happened to pick the exact one that she wanted to go. And we kept doing that back in for us, where we were almost like completing each other's menus as we walked along. Where it's like no way I was going to, I wanted to go there.

How much did you eat? Maybe she's in a food coma still, and that's why she's not calling you back. I did have the sweats, but I tried my best to tamp it down. But that's the goal is to get the sweat slightly at the food fair. I'm sure she had it too. Yeah, that's true. That's true. Okay, okay.

Okay, so was this your date, like just hanging out at the Food Fair Try and stuff together? No, what I did is we kind of parted ways, but I said that I wanted to bring her food from my favorite restaurant. Oh. That is smart. Same day, please tell me a different day. After all this food, you know what you want is more food. It's not same day, please. No, it's not.

It was the next day. That is a thoughtful thing to do. I think anybody who likes to cook or just feed anybody else, that's just, like, such a good gesture, right? And it's his love language. Yeah. Like, how did that go? Yeah. Well, I mean, the food I knew was going to be a home run because I had some kind of lease.

Oh, okay. And you hand delivered them? Hand delivered. It was handmade by an old Italian guy handed it to me. I handed it to her. And, like, handed it directly into her mouth, yes? I wish. She's like, mm, I can taste the Italian.

Yeah. So did you, like, stay for a date, or you just dropped it off and drove off? That's a good question. No, I wanted to stay longer, but the place where I had parked had, like, weird signs, and I think I was, like, in a tow zone, and I really had kind of a short window. And there wasn't any way you could just move your car? Yeah, actually, I tried to move the car because I told her I'd be back. Oh.

Oh, just to go move it somewhere else and then come back and finish your canolies? Didn't you come back? No, I got towed. What? Wait, what? Wait, you got code? Yeah. I had to deal with all that, and so I was just hoping to bounce out,

bounce back, but here I am. I'm trying to get the car off the record, and the guy's not even listening to me. No, they'll never take it off. They act like it's some law, and they call BS. I'm sorry. I have argued with too many tow truck drivers. Texted of your tow truck drivers. As soon as the wheels are uplifted off the ground, we can't do anything, man.

I bet you gave him like a hundred bucks. I have tried. Oh, really? They are really stubborn, but excellently soft lips. So, Jeff always gets his on the time. Right. So you weren't. able to get your car off the toe?

No, I wasn't. Dude. What did you do? Hundreds of dollars? Then they impound it. Then you have to go to the impound place. Then you have to have cash. It all sucks.

Well, no. What did you do about Taylor? Oh, sorry. I'm done with the car. Brick is not like getting towed. So I'm texting her telling you that I'm going to come back. And then now the next thing you know, I'm on a bus to go kit. Wait.

To go get your car. Did you not tell her that your car got towed? No, I thought I could just get the car and come back like nothing had happened. rookie mistake yeah that's just like murphy's law right oh man so wait did you ever make it back there at all no i didn't i just told her that i'd hit her up no wonder she's not yeah she feels like you like ditched her in the middle of the day did you ever explain yeah i told her i'd explain it on our next date but it didn't sound like she was interested i mean i totally get your circumstances and why you wouldn't want to say anything but to her it's probably a red flag yeah yeah

That you're that unreliable. Red flags also a sign you shouldn't park in that area. If you see a bunch of red flags. Pretty big, Jack. Usually it's blocked off. So how long has it been since your mishap with Taylor and the canollies? It's been like a week. Oh, no.

We have to get you a second date so that that $600 or whatever it was to get your car out of an impound was actually worth it. Also, did she eat the canolies? How good were they? This is the best restaurant you've ever been to. You know, I really like how Brooke is super focused on the money. Jose is really focused on the food. Alexis, I'm not sure if she's paying attention.

I'm focused on TikTok. TikTok. Okay, at least you're focused on something. We're going to do something. We're going to get some answers for everybody when we come back and do your second date update right after this. Hold on. Second date update. One of the most tragic stories we have ever heard on this segment about a lonely canoli.

Yes. Sitting on a plate, crying. Yes, Jeff. Waiting for a warm mouth to bite into it, swallow it, and help fulfill its culinary destiny. That's right. I feel like this is a children's movie, an animated canoli. We don't think she'd just ate two. It's possible.

I would have. We don't know because our listener, Paul, never returned to eat his canoli and finish his date with Taylor. Because his car got towed. So wild. And we all feel bad for Paul, but that canoli, oh my God. What a tragedy. It is so crazy. sit down at a person's house to share a meal with them, go to move your car, and then never

return. Yeah. And keep telling him, I'll be back. I'll be back in a second. Yeah. Never show. But at least, like Jose said, he was texting her, trying to keep her informed on what was going on. Vaguely trying. He was going to tell her the whole story on their next date that just never happened. Yeah. So we're going to try to make that happen for him. Yes. Hopefully get redemption for Paul, but more importantly, for that canole. Yeah. Paul, you ready for this? I'm absolutely ready.

Everybody, hashtag team canoli, if you're posting on socials right now. I bet she cried into those canoles. Aw, crinoli. Yeah, but it's a crinoli. Only one way to find out is by dialing her number right now. We'll see if she picks up. Here we go. Hello.

Hey, we're looking to talk to Taylor. This is she. May I ask you calling? Okay. Yes, you may. We're a radio show called Brooke and Jeffrey in the morning. Hi, Taylor. Hi. Hi.

All shows here for you. Yeah. We're all wanting to talk to you about actually a date that you went on recently with one of our listeners, a guy named Paul. Oh. Wait. Okay. I think I know what this is. I think I've seen you guys on social media.

Oh, that's awesome. Hey, thanks. Did you like and follow? smash that subscribe button she just undid it now she's like uninstalled TikTok forever after you're listening to it but yeah this is a second date update and we know that you and Paul met at a food fair recently and you had a brief hangout with him the week after

that didn't go quite according to plan I think it was the next night yeah yeah it was weird it was gross gross gross gross Oh, I was gross. Not the food, not the food, just the, oh, the situation. Wait, him? Well, it makes sense why you'd be upset for sure.

Yeah, because we're aware that things were left on kind of a weird note because he said he was leaving to go move his car. It was supposed to be real quick and he'd come back, but he never, he never did. He told me that he had to grab something out of his car. Okay. Well, I think he's going to go both. He's going to grab something and then move it. The truth is he had to move it. Yeah.

Yeah. And he didn't do a very good job of explaining what happened next. No, he didn't because he never told me that. Yeah. Which we don't apply, but, you know. I think he was hoping to explain in person because he was pretty embarrassed. Yeah. So there's a lot of, sorry, go ahead.

I don't know. I appreciated him bringing me dinner, but yeah, he was definitely in a different state of mind. Like, the whole situation was pretty weird. What do you mean the whole situation? Of him leaving was pretty weird? Was there something weird before? Yeah, I mean, he was definitely different than he was the day before. Like, he sat down.

He was checking his phone. He seemed like rushed and nervous. Maybe anxious. Maybe a little hungry wanting to eat that canoly. He was really looking forward to sharing it with you. He made that very clear to us. Do you think maybe nerves played into it at all? So I think I know what the real story is,

and that's why I'm actually not responding to him. Oh, that's interesting. Real story. Yeah, what do you think the real story is? Well, I mean, I was cleaning up after he left And I found the receipt still on the bag that he brought And it was a name and a dress To like a completely different street

Like a delivery going somewhere Oh my gosh And he accidentally takes someone to go Like I've almost done that The canoly order wasn't for him Maybe not Yeah, I mean, I don't know He must have stole the meal from like an Uber Eats driver

Oh, he stole the Ketlai They're kind of stully. Stop, stop. That is such an accusation. Seriously. How do you explain the receipt with all the different information? And then he's like, I'll be back in 10 minutes. I'll be back in 20.

Yeah, well, we should find out right now because Paul, are you there? Yeah, I'm here. Taylor, he's actually been on the other line listening wanting to talk to you. Oh, God. Oh, God. Paul? Taylor, Taylor, I promise you, I did not steal that from an Uber-Eats driver. Where did the receipt come from?

There's probably a mix-up. I am an Uber-Each driver. What? Oh, what? Wait, still doesn't explain it. I don't get it. Why didn't you tell me that? I just didn't.

It was going to come up eventually, but I just didn't really know how to say it, and I was just more interested in the food and your reaction to the food. Wait, but why was the receipt to somebody else, Paul? Did you not order the food? It doesn't matter if you're an Uber-Eats driver or not. The order was for somebody else, and they had canceled. and so I had the food and so I did they really cancel then cancels no one

I ate someone else's canoley you would cancel if your Uber's taking a long time because you stopped to someone's house you would get a point yeah it's true wait so wait I thought your car got towed I thought that was the whole thing are your car got toed no look I wait I didn't for the show I just thought it would sound better if my car got towed Oh, you lied to us, bro. You left because you had to finish a shift. It's on your own time, though.

It's Uber. Yeah, but if you have food in the car that you have to drop off at somebody's house, Alexis. He stole the food, dropped it up in her house, and he's like back to the order. Oh, you had to finish another order? I didn't think it was going to be that busy that night, but my phone just kept blowing up, and I just kept getting delivery after delivery. Oh, my gosh, he's been lied on so many different levels. because look I'm not on apps

and I don't really date a whole lot and I don't really meet people that really set me off like the way you did when we met at the food fair I was like on another world and so just to have an opportunity even if it was just short to spend any time with you

for me was worth anything including just a small lie that sounds really sweet but like I can't see someone who has lied to me so many times like upon meeting. Taylor, are you forgetting the gift of the delicious canoli that was 100% free?

Someone else is canoly. And those things aren't cheap. All right. Those are expensive treats. Taylor, you have to admit that a canole was amazing. Can you deny that? It was amazing. But the rest of it is just too weird for me.

Just to help my boy out. Paul needs to apologize. He lied from the moment the food got there. He lied to us. He lied to her about why he left. I support him lying to us. But the other stuff, that's not okay. If I could just apologize, and I'm sorry for putting anyone through this,

but I really just want a second chance. And if I could take you out and really, really show you who I am, I really believe this can be a thing. Did you hear that, Taylor? He's inviting you on to his next Uber Each shift. Which is actually super helpful because if one person runs the orders out and the other stays in the car. So you don't have to find parking.

I see. All the free food samples. She doesn't want to eat together, too. Yeah, that does not sound very enticing to me. Well, I'm going to ask an unpopular question here. Taylor, do you have a problem dating an Uber Eats driver? Oh. Well, no, of course not.

But an Uber Eats driver who has lied to me in bed very, like, mysterious, fishy strains. Like, yeah. Yeah. Look, then, fine. I'm going to be 100% honest with you. I stole someone's food and I gave it to you and you ate it. Well, that has to be refreshing to get that kind of honesty, Matt Taylor. Wow, that is refreshing.

Oh, good. Yeah, I'm going to have to go. Well, before you go, I just need to ask you if you'd like to meet up with Paul one more time, maybe on that Uber Eats route. I'm assuming it's a yes. I don't know how else to say it, but that's a giant no. Did the little Italian place get a new customer? I'm never eating at canoli ever again

You can't spell no without canoli There we go You can't spell cano You can't spell canoley without no Yeah you can sell can't though I'm gonna start smelling no as canola Darn it Well sorry Paul

That's a canoli from her It's a no noi Brooke and Jeffrey in the morning I'm Stefan Curry And this is gentleman's cut. I think what makes Gentleman's Cut different is me being a part of developing the profile

of this beautiful finished product with every sip you get a little something different. Visit gentlemen's cut bourbon.com or your nearest total wines or Bevmo. This message is intended for audiences 21 and older. Gentleman's Cut Bourbon, Boone County, Kentucky. For more on Gentleman's Cut Bourbon,

please visit gentlemen's cuthuburn.com. Please enjoy responsibly. Sometimes it's hard to remember, but Going through something like that is a traumatic experience, but it's also not the end of their life. That was my dad, reminding me and so many others who need to hear it, that our trauma is not our shame to carry, and that we have big, bold, and beautiful lives to live after what happened to us. I'm your host and co-president of this organization, Dr. Leitra Tate. On my new podcast, The Unwanted Sorority, we weighed through transformation to peel back healing and reveal what it actually looks like, and sounds like, in real time. Each week I sit down with people who live through harm, carried silence, and are now reshaping the systems that failed us.

We're going to talk about the adultification of black girls, mothering as resistance, and the tools we use for healing. The unwanted sorority is a safe space, not a quiet space. So let's walk in. We're moving towards liberation together. Listen to the unwanted sorority, new episodes every Thursday on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Is honesty always the best policy? Oh my God. Honestly, any honesty would be a good policy.

Just even an ounce of it, Jeff. Well, Paul was honest at the end there and admitted that he stole the canoli from somebody else and even that wasn't enough to win her. Don't get credit for being honest after you lied, lie, lied, and then got caught. 15 minutes of lies later. That is true. He did lie to us multiple times before that. And you should know we don't like to be lied to.

No. We like to be lied on, am I right, bro? Wait a minute. Okay. You know what the mess up? I actually still really liked Paul. I hope Paul fixes his line issue, because I think that he sounded like a good guy. You're just sweet talking him for free canoles.

And I don't blame you. It's not a bad plan, Jeff. If you want free stuff, we do this show for free. Yeah. You're welcome. Go check it out wherever you get your podcast at Brooke and Jeffrey. And if you want our assistants, email the show. We can call that person who's not calling you back.

Brooke and Jeffrey in the morning. I'm Stefan Curry, and this is Gentleman's Cut. I think what makes Gentleman's Cut different is me being a part of developing the profile of this beautiful finished product. With every sip, you get a little something different. Visit Gentleman's Cut Bourbon.com or your nearest Total Wines or Bevmo. This message is intended for audiences 21 and older. Gentleman's Cut Bourbon, Boone County, Kentucky. For more on Gentleman's Cut Bourbon, please visit Gentleman's Cut Bourbon.

Bourbon.com. Please enjoy responsibly. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas, and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever. Listen to Business History on the I Heart Radio. Apple Podcasts, or wherever you get your podcasts.

I knew it was a bomb the second that it exploded. I felt it ripped through me. In season two of RipCurrent, we ask, who tried to kill Judy Berry and why? They were climbing trees and they were sabotaging logging equipment in the woods. She received death threats before the bombing. She received more threats after the bombing. I think that this is a deliberate attempt to sabotage our movement.

Episodes of RipCurrent Season 2 are available now. Listen on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Whether it is getting swatted or just hateful messages online, there is a lot of harm and even just reading the comments. That's cybersecurity expert Camille Stewart Gloucester on the Therapy for Black Girls podcast. Every season is a chance to grow. And the Therapy for Black Girls podcast is here to walk with you. I'm Dr. Joy Harden Bradford, and each week we dive into real conversations that help you move with more clarity and confidence. This episode, we're breaking down what really happens

to your information online and how to protect yourself with intention. Listen to therapy for black girls on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. What are the cycles fathers pass down that sons are left to heal? What if being a man wasn't about holding it all together but learning how to let go? This is a space where men speak truth and find the power to heal and transform. I'm Mike Delo Rocha. Welcome to Sacred Lessons. Listen to Sacred Lessons on the IHartRadio app, Apple Podcasts, or wherever you get your podcast.