Brooke and Jeffrey: Second Date Update - Second Date Update: Gucci First, Questions Later

Episode Date: August 8, 2025

One of our listeners is worried he gave off a bad vibe and waiting three days before sending his first post-date text… He swears he has a good reason…See omnystudio.com/listener for privacy information.

The Stuff You Should Know guys have made their own summer playlist of their must listen podcasts on movies. It's me, Josh, and I'd like to welcome you to the Stuff You Should Know Summer movie playlist. What Screams Summer? More than a nice, darkened, air-conditioned theater, and a great movie playing right in front of you. Episodes on James Bond, special effects, stunt men and women, disaster films, even movies that change filmmaking, and many more. Listen to the Stuff You Should Know Summer Movie playlist on the IHeart Radio app, Apple Podcasts, or wherever you listen to podcasts. Hey guys, it's AZ Fud. You may know me as a gold medalist.

You may know me as an NCAA national champion. You may even know me as the People's Princess. Every week on my new podcast, Fud Around and Find Out, I'll be talking to some special guests about pop culture, basketball, and what it's like to be a professional athlete on and off the court. Listen to Fud Around and Find Out, a production of IHart Women's Sports and partnership with unanimous media on the IHart Radio app, Apple Podcast,

or wherever you get your podcasts. Have you ever looked at a piece of abstract art or music or poetry and thought, that's just a bunch of pretentious nonsense? That's exactly what two bored Australian soldiers set out to prove during World War II when they tricked the literary world with their intentionally bad poetry, setting off a major scandal. We break down the truth, the lies, and the poetry in between on hoax, a new podcast hosted by me, Lizzie Logan, and me, Dana Schwartz. Every episode, Hoax explores an audacious fraud or ruse from history.

Listen to hoax on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Why are TSA rules so confusing? You got a hood of you. I'll take it off. I'm Manny. I'm Noah. This is Devin. And we're best friends and journalists with a new podcast called No Such Thing, where we get to the bottom of questions like that. Why are you screaming?

I can't expect what to do. Now, if the rule was the same, go off on me. I deserve it. You know, lock him up. Listen to No Such Thing on the I Heart Radio. app, Apple Podcasts, or wherever you get your podcasts. No such thing. Your entire identity has been fabricated.

Your beloved brother goes missing without a trace. You discover the depths of your mother's illness. I'm Danny Shapiro, and these are just a few of the powerful stories I'll be mining on our upcoming 12th season of Family Secrets. We continue to be moved and inspired by our guests and their courageously told stories. Listen to Family Secrets Season 12 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. It's your second date podcast with Brooke and Jeffrey in the morning. We got a brand new one for you today.

A guy waited three days to send the first post-date text. Alexis says way too long. Too long, but he claims he has a good reason why. So, I mean, you know. Even you will hear him out. Yeah. Okay. We're going to listen to that here in just a second.

But we love to highlight your comments. Yes. Okay, Olivia said hello from Santa Fe, New Mexico. Oh, cool. We're best friends. We love listening to your show together. You really need to read this comment because we had a huge epiphany. Oh.

We think that Jeff and Jose are secretly in love. It makes sense. That's why they're always so embarrassed around each other. Jeff and Jose, we just want to let you know we 100% support you as a couple. Jeff is the closest thing I'll ever have to a relationship. I accept this. Isn't that sweet that they're shipping you? Yeah.

Someone likes me. I love that. I love it too. Love it, too. All right. Your brand new second date starts right now. Second date update. You know, we've talked about bringing a gift to a first date before.

Oh, yeah. And that could include flowers, maybe a stuffed animal, or a real animal. This baby bear was over by the garbage cans near my house. It's yours now. That's so nice. You're welcome. Yeah. Yeah, bring me a raccoon next week, please.

Yeah, but what about buying them a gift during your date? Is that still a strong move? Yeah, that's cute. I like it. Might be better. That's what our listener, Isaac, did. So, Isaac, clearly, you're one of those generous daters. Congratulations.

Welcome to the show. Hey, thank you, guys. But let's not get too caught up. It wasn't anything that crazy. Well, we're impressed because Jeff only gives away free wildlife. He finds in his backyard. You want a possum? We've got a whole, like, cage of animals ready for you.

Maybe after this is done, you could take something home. But let's get to what happened with this girl you met. What's her name? Her name's Elisa. Elisa. Where'd you meet her? So we met on one of the dating apps, and we ended up connecting over stand-up comedy. Oh, no.

Okay. Are you a stand-up comedian, or you just like to watch? I like to watch, but man, I really want to one day. Oh, you should. You should, man. That's a good thing to bond over, stand-up comedy. What did you decide to do for your date? So, like, we talked a bunch, and we didn't end up going to a comedy show.

You did not. Oh, no. We didn't. But I did end up sending her some clips because she wasn't too familiar with Jim Gaffick. One of my favorites. He's so good. We've actually interviewed him. He's so nice, too.

So funny. I was just talking about how I don't love his comedy. Oh, my God. I don't even know what I was. He's like a dad. In hot pockets if you get it. Like, it's the funniest joke ever. He talks about being a dad a lot.

And we don't support that on this show. No fatherhood talk. I mean, I feel like those are safe, though. I mean, I haven't heard anything. You know, offensive. He's a pretty family friendly. Yeah. Because that's always a risk, too.

Like, if you send a joke that maybe you find funny, that is not fine. Yeah. That's why I felt like, oh, he's the perfect person to send. Like I said, I love the guy and who doesn't. I mean, well, Brooke, now we know who. I'm sorry. I don't hate him.

just not my favorite. So how did you parlay talking about Jim Gaffigan into a first date? So I think the laughter kind of made it just was fun. So I asked her if we could go out on a date and we, it was simple. We went to a chili. A chili. Oh, nice. Okay.

So once we got to the Chili's, that's where I showed her some of the clips, especially my favorite one. But you would... Ooh. Wow, even more? Yeah, you'd sent her some and now we're watching him together.

Look, it might have been overkill, but I just love to do. I mean, I will say watching stand up together is always funnier than when you watch it by yourself. Okay, but if you got a chance to talk about yourself on the date already first. Not just straight into the clips. That's a good point. That's a good point. Timing's important there, Alexis. Yes, and that was the big thing.

We watched like a little bit together, but then I kind of segue that into learning things about each other. That's great. So is all this happening in the parking lot outside of the Chili's, or are we sitting down for dinner yet? No, we're sitting down and we're eating. So at the start of this, we were talking about how you bought her a gift during the day. Where does that come into play? Oh, yeah.

Oh, okay. So we had a great dinner, and we still felt like hanging out. So there was a mall that was pretty close. So we go to one of these stores that just sells a bunch of, like, cute little knick-knack. I love a knick-knack store. Oh, my God. And they're always, like, overloaded with stuff. Yes.

You know, way too much stuff for you to take in. So many knacks. Uh-huh, and Knicks. Now, the good thing is, though, I got to see how she reacted when she saw this pair of socks. They were like little bumblebee socks, but she loves. That's really cute. I'm literally picturing the same brand of funny socks. I see every one of those nicknack stores.

It's the same company. Right. They're not very comfortable, but sometimes they have cuss words. Yeah, you always, yes. The girls seem to think socks are a good first date gift idea. When I saw how excited she got about them, I said, I'm going to grab those. And she was like, oh, my God, you don't have to. to do that. I said, hey, if you love

them, I want you to be happy. I want you to enjoy the socks. You really like them. What a nice guy. That's cute. Now put these on for me. Nice and slow. Let me watch you wear them. Okay. I hope we didn't do that because that gives real, like, feet guy. I heard it's one in five guys have one.

Yeah. I'm just checking. That did not happen? No, that's not what happened. Strong move. Okay. Good work. So, she liked the socks. She did. She liked them. And this was the thing, too, when we were at the Chili, she took a selfie with me. And I'm thinking, okay, well, if I was a girl and I'm out on a first date with a guy,

I'm not taking a selfie with him if I don't want to see him again. Totally. You only want the picture if you think there's potential. Or we're in the group chat and she's like, guys, stay away from this one. Yeah. Just like, I need to make sure I have evidence on my phone of this man. Just in a Facebook group. But I'm sure it's not that.

I'm sure she, like you said, was just enjoying herself, wanted to have a memory of the night with you. Well, we did kiss at the end of the night. Oh, that's cute. Okay. How is it that you're not getting a call back because all of this sounds really good? That's the thing, too. Like, she did say she was getting ready to go on a girl's trip. So I was all right, cool.

Didn't want to bother her while she was there. She said that was only going to be like a couple days. It's like a long weekend. Okay. But now it's been like a week and I'm still not hearing from her. Okay. I sent her like one text when she should have been back from the trip, but left it. Maybe she thought, I just not thought about it.

She might maybe thought I wasn't that interested because I didn't text her while she was on the trip. That's not a bad thought. As long as your text was, let me see those tootsies in those bumblebee socks, girl. Then you're probably going to be okay. But we'll find out we'll call Elisa for you and try and get you your second date update when we come back right after this. Hold on. Second date update. If you miss part one of the second date update, let's just hit the highlights here real quick.

Our listener, Isaac, bonded with his date, Elisa, over stand-up comedy. Yeah. Specifically, the comedian Jim Gaffigan, which, that's great. He's got a big head. Love that. Took his date to Chili's for dinner. Awesome egg rolls there. Thumbs up.

Egg-olds? Do they? I don't even know they had Egg rolls at Chili. I don't think they do. Just check the menu. It's okay. You don't have to believe me. Bought her some bumblebee socks at the mall that she liked.

Bees are dope. We approve. Yeah. Even got a kiss at the car. Oh, and it sounds sweet. It sure did. So the weird part is he hasn't really heard from her since then. So why on earth would Elisa be avoiding him?

After all that good news, we may never know the answer. No, that's the whole point of this, Jeff. We're going to find out right now. Right, unless she answers the phone. Yeah, then we'll know. That's step one. Did the egg rolls go to your head, Jeff? Isaac, can you confirm that the egg rolls do exist at Chili's?

Honestly, I can. They are pretty good. Yay. Wow. Yeah, let's give some love to Chili's egg rolls right now. Who are the best egg rolls in the city? We're in Chili. Yeah.

Jeff went to Chili. I'm still stuck on that. When did you go? This is about Isaac, you guys. Not about Jeff's dietary dining habits. Okay. Well, we'll make that the second point of conversation after we hopefully get a lease on the phone here. I'm going to dial her number right now.

Let's see how this goes. Here we go. Hello? Hi, is this Alisa? Yeah, who's this? Hey, Elisa. Hey, Elisa. There's a whole room of people here.

Sorry, I'm coming in hot. I forgot. We are excited to talk to you because you're on the radio right now with Brooke and Jeffrey in the morning. Uh, okay. Yeah. Radio show and a podcast. Yeah. Um, all right.

Okay. We're just calling her brag. And you don't. Bye. Okay, click. No, we're kidding. Just kidding. Yeah, we're doing a segment from our show.

It's called a second date update. Okay. Okay. And that's where we help out listeners who've gone out with somebody and they're not hearing back after their date. We try to help that person figure out the reason why. Okay, I got to. I just don't know why you'd be calling me. Well, because there is a guy that went out with you recently who really would love to see you again, a guy named Isaac.

Oh, yeah, Isaac, right. How could you forget him? You just went out like a week and a half ago. I'm sorry, my life has just been crazy lately. Oh, okay. Oh, is that why you're not getting back to him? You've just been, I mean, he did mention you had, like, a girl's weekend. Yeah, we did go for a girl's weekend down to Miami.

Fun, right. Yeah, it was a lot of fun. And, yeah, the craziest thing happened. Wait, on your trip? Yeah, on our trip. What? Well, I mean, Brooke, should we be asking her about the date with Isaac? I don't know.

I'm kind of interested in what wild thing happened on a girls weekend in Miami. Oh, yeah. We could get to Isaac, but. Spill the tea, girl. What happened in Miami? That was so crazy. So we met this guy at the pool, and he was, like, a billionaire or something, and he took us on a $30,000 shopping spree.

What? Wow. He took you and all your girls shopping, and I'm sure he's, like, didn't want anything in return. Don't trust him. No, he didn't. Like, he took us to Gucci and Lee Viton, all these. stores. We've got shoes,

purses, and he just was, I guess, being really generous. I mean, he didn't ask us to do anything weird or... Wow. How does that relate to... Yeah, can we bring it back to Isaac? Because the whole reason that we're calling is he thought he'd be hearing back from you by this

point after you returned from your trip, but he hasn't heard anything. Well, now that I back, things just... I don't know seem different. I don't know. I don't know really how to explain it. Oh, you met a guy. You mean, like, you were interested in him until the Miami trip and now you're not

interested in Isaac? Well, I guess I didn't realize that there were just so many generous people out there like that. When you say generous, you mean rich, right? Well, yeah, he just made me see that there's a whole

other world out there. And, um, oh. But that world's a little superficial. Like, you're going to be on yachts and in cars, but is it going to be finding love? Yeah, I mean, those all sound really good to me, Jose. So, you know, it's sold me. Wait, are you still talking to the billionaire dude from Miami?

Is that it? Oh, no, no. I'm not interested in him or anything. Oh, okay. The thing is, my girlfriends and I decided to go back to Miami for the next few weekends, you know, to just hang at the pool again. Has he been flying you out? No, he didn't not, like, offer to fly us out or anything. We're just going, you know, because we want to go.

You're hunting for more billionaires and more pools to buy your shopping. Now, I get it. You're not going back for him. You're going back to just scout. That can't happen that often. Like, that has to be like a once-in-a-blue situation. Where you don't have to do anything back. Yeah.

Yeah. I feel like you're going down a path that you're not going to be thrilled with. I mean, maybe, but, you know, we're at the age now where we just kind of want to have fun and see what happens and hang. Yeah. I mean, honestly, like, look, that's your life and you're a lot. to do whatever you want to do to have fun with your girlfriends, that's all great. But

we're just, like, calling on behalf of Isaac because he has no idea that this is happening. He feels like he's being left totally ghosted with no communication. I say, who needs a $30,000 shopping spree when you got a guy who got your bumblebee socks. Yeah.

You know, that's what I'm talking about. No, I mean, they were really cute. It was a really sweet thing. It was awesome. But I just, I don't want to hurt his feelings. I mean, he was a really nice guy. Okay, well, instead of telling that to us, you should probably just tell it directly to Isaac

because he's on the other line right now listening to this conversation. Oh, my God. Oh, God. Okay. Isaac, are you there? Yeah. I mean, at least you like the socks I got. What were the socks? Like, gosh, gosh, bag gosh. Yeah, I mean, they're definitely not yacht on Miami-level size. I mean, yeah.

Dude, you need to tell her, Isaac. Tell her why you're a better catch. Like, why you're better than some billionaire, like, buying people's affection in a pool somewhere. That guy's lonely. If that guy had real friends, he'd be buying his friend's stuff, you know? He brought some of his friends, and he was buying them things, too. Oh, shit.

It just to keep everyone happy around. We have a group of girls. You have to bring your friends because that's how he impresses them. But he has friends. I was going for he wasn't. He sucks. Isaac, you're better. Tell her.

Yeah, I mean, look, hey, I, man, this is I think it was an awesome weekend. He's jealous, man. I mean, Lisa, look, I really liked you. I had a lot of fun. But, I mean, if you're not interested because you're focused on wealthier people, I'm not going to be able to compete with that. I think I really enjoy spending time with you. He is so stinking cute. He's like a genuinely nice dude.

Dude, Lisa, you're going to be missing out. Think of how sweet that mall parking lot kiss was. Seriously, Isaac, you're selling yourself short to her. Remember, you took her to dinner at Chili's. Oh, yeah, a brand name. Maybe he didn't order the egg rolls that time. Oh, probably not. That's what it was.

I should have got that egg roll. Totally. You need to go back. Lisa, you got to go back with him. I think that's a great idea. If you'll let me take you back to Chili, this time we will get egg rolls. Oh. With that said, Alisa, we would like to offer to send you on another date with Isaac that we would pay for it.

And just remember, like, not all great things in life come with an expensive price tag. Sometimes the best stuff is actually really affordable and right in front of you. Jeff, just say the best things in life are free. That's a saying. He's just never hurting. Yeah, I don't know what that is. What, you don't pay for moments with your family? So what do you think, Elise?

Are you willing to give Isaac a second chance? Come on. Well, guys, I'm going to be gone the next couple weekends, and I'm just going to be really busy, so I can't really promise that right now. Oh, I thought we were going to get a date. Oh, my God. You're going to think about this three months from now and regret this moment. Maybe, but I will probably be in Miami. Yeah.

You're going to be on that yacht with your Gucci purse and your prod a bag, and you're just going to be crying. And her bumblebee socks. Too bad. A bag of a purse at the time. Yeah. If they showered her with gifts. She could have gotten shoes or something. Yeah, anything.

There's another, like a jacket. No, four bags. You only have 30,000. That's not that much. All right. Well, Isaac, man, I'm sorry. I can't believe she said no to that. You're a real catch.

I mean, if it's not Elisa, you're going to find somebody who's great for you. Yeah, man. Thanks, guys. I appreciate it. Okay. And make sure you call us back when you own a yacht and it'll be a lot easier on our part.

Yeah, I think so. Brooke and Jeffrey in the morning. Hey, guys. It's Azee Fud. may know me as a gold medalist. You may know me as an NCAA national champion and recent most outstanding player. You may even know me as a People's Princess, but now you're also going to know me as your favorite host. Every week on my new podcast, fud around and find out, I'll give you an inside look at everything happening in my crazy light as I try to balance it all, from my travels

across the globe to preparing for another run at the Natty with my Yukon Huskies to just try to make it to my midterms on time. You'll get the inside scoop on everything. I'll be talking to some special guests about pop culture, basketball, and what it's like to be a professional athlete on and off the court. You'll even get to have some fun with the fud family. So if you follow me on social media or watch me on TV, you may think you know me. But this show is the only place where you can really fud around and find out. Listen to fud around and find out, a production of Iheart women's sports and partnership with unanimous media on the Iheart radio app, Apple podcast, or wherever you get your podcast. Have you ever looked at a piece of

of abstract art or music or poetry and thought, that's just a bunch of pretentious nonsense? Well, that's exactly what two bored Australian soldiers set out to prove during World War II. When they pulled off what was either a bold literary hoax or a grand poetic experiment, publishing over a dozen intentionally bad but highly acclaimed works of expressionist poetry under the name Earn Malley in an incident that caused a media firestorm and even a criminal trial. The Earned Malley episode made fools of believers and critics alike and still fascinates poetry lovers to this day. We break down the truth, the lies, and the poetry in between on hoax, a new podcast hosted by me, Lizzie Logan, and me, Dana Schwartz. Every episode, hoax explores an audacious fraud or ruse from history from forged artworks to the original fake news to try and answer why we believe.

Listen to hoax on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. We've definitely had people on this show who've lost out to past ex-boyfriends or hunky firefighters that showed up on the scene. Rarely has somebody ever lost out to an entire state before. And I can officially say now, Isaac has lost his date to Florida. Specifically, Miami and all the generous wealthy men who live over there, but Florida, you win. Here's the thing. I really predict that she is going to. go to pool after pool and not meet one more billionaire.

Oh, no, I disagree. I walked out of my lobby last time I was in Miami and Lil Nasex was standing there. Maybe it won't happen. Maybe it will. Or maybe Miami Tourism Board is going to contact us as this is their new campaign. It probably should be. The weird part is it sounded like she really liked him, though. He didn't do anything wrong. She had a great time on the date. She just decided I'm into Florida more right now. It's hard to top a single girl's trip to Miami. Yeah. Didn't work out for our friend, I But it could work for you if you want to email the show. We'll call that person who's not calling you back.

And did you know these second date updates are up on YouTube? Yeah, Jeff, we knew. Who's putting them up there? Jake. Jake did the YouTube, sorry. Our digital producer. Our digital producer, does he have permission to do that? Oh, okay.

Is YouTube not? I actually think he has more permissions than you do. Yeah. Go check them out. They're up on YouTube at Brooke and Jeffrey. Make sure you subscribe. The stuff you should know, guys, have made their own summer playlist of their must listen podcasts on movies.

It's me, Josh, and I'd like to welcome you to the stuff you should know summer movie playlist. What Screams Summer? More than a nice, darkened, air-conditioned theater, and a great movie playing right in front of you. Episodes on James Bond, special effects, stunt men and women, disaster films, even movies that change filmmaking, and many more. Listen to the Stuff You Should Know Summer Movie playlist on the IHeart Radio app, Apple

podcasts, or wherever you listen to podcasts. Have you overlooked at a piece of abstract art or music or poetry? and thought, that's just a bunch of pretentious nonsense? That's exactly what two bored Australian soldiers set out to prove during World War II when they tricked the literary world with their intentionally bad poetry, setting off a major scandal. We break down the truth, the lies, and the poetry in between on hoax, a new podcast hosted by me, Lizzie Logan, and me, Dana Schwartz. Every episode, Hoax explores an audacious fraud or ruse from history.

Listen to Hoax on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey guys, it's AZ Fudd. You may know me as a gold medalist. You may know me as an NCAA national champion. You may even know me as the People's Princess. Every week on my new podcast, Fud Around and Find Out, I'll be talking to some special guests about pop culture, basketball, and what it's like to be a professional athlete on and off the court.

Listen to Fud Around and Find Out, a production of IHeart Women's Sports in partnership with unanimous media on the IHart Radio app, Apple Podcast, or wherever you get your podcast. Why are TSA rules so confusing? You got a hood of you. I'm take it all. I'm Manny. I'm Noah. This is Devin. And we're best friends and journalists with a new podcast called No Such Thing, where we get to the bottom of questions like that.

Why are you screaming? I can't expect what to do. Now, if the rule was the same, go off on me. I deserve it. You know, lock him up. Listen to No Such Thing on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. No.

Thank you. Your entire identity has been fabricated. Your beloved brother goes missing without a trace. You discover the depths of your mother's illness. I'm Danny Shapiro. And these are just a few of the powerful stories I'll be mining on our upcoming 12th season of Family Secrets. We continue to be moved and inspired by our guests

and their courageously told stories. Listen to Family Secrets Season 12 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.