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

Episode Date: March 5, 2026

Is it better to find true love or a rich guy with a big boat? Today we’ll finally learn the answer in a special Second Date Update UPDATE!See omnystudio.com/listener for privacy information.

Getting ready for a game means being ready for anything, like packing a spare stick. I like to be prepared. That's why I remember, 988, Canada's suicide crisis helpline. It's good to know, just in case. Anyone can call or text for free confidential support from a train responder anytime. 988 suicide crisis helpline is funded by the government in Canada. Hi, it's Joe Interesting, host of the Spirit Daughter podcast, where we talk about astrology, natal charts and how to step into your most vibrant life. And today I'm talking with my dear friend

Krista Williams. It can change you in the best way possible. Dance with the change. Dance with the breakdowns. The embodiment of Pisces intuition with Capricorn power moves. So I'm like delusionally proud of my chart. Listen to the Spirit Daughter podcast starting on February 24th on the IHeart Radio app, Apple Podcasts, or wherever you listen to your podcast. Hey, I'm Jay Shetty, host of the On Purpose podcast. I'm joined by Luke Combs, award-winning country music artist and one of the most authentic voices in music today. The guy that says he's always going to be there and that will do anything to be there is the only guy that's not there. No matter what, I'm going to prioritize my wife and my children.

I dread the conversation with my son. Listen to On Purpose with Jay Shetty on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. Ready for a different take on Formula One? Look no further than No Grip, a new podcast tackling the culture of motor racing's most coveted series. Join me, Lily Herman, as we dive into the under-explored pockets of F-1, including the astrology of the current grid, the story of the sports most consequential driver's strike, and plenty of other mishaps, scandals, and sagas that have made Formula One a delightful, decadent, gumster fire for more than 75 years. Listen to No Grip on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

I'm Amanda Knox, and in the new podcast, Doubt, the case of Lucy Letby, we unpack the story of an unimaginable tragedy that gripped the UK in 2023. But what if we didn't get the whole story? Evidence has been made to fit. The moment you look at the whole picture, the case collapsed. What if the truth was disguised by a story we chose to believe? Oh my God, I think she might be innocent. Listen to Doubt, The Case of Lucy Letby on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Out of all the people and all the world that's been on this show, this is not who I thought we'd get an update from.

Yeah. I don't think they expected it either. Yes. Yes. Definitely listen to the whole thing. Remember, oh, by the way, this is brand new. We're getting a check-in from a couple that was previously on the show as to what has happened since. And so we're going to get them back on in part three. So stick around for that.

But first comments. Yeah, Autumn, the Taylor Stan, said, I listened to you guys. over 20K minutes after a breakup last year. Wow. And I just got dumped again. So I'll see you guys in my 2026 wrapped IG. Yay! All right.

So we rely on you having failed relationships. Yeah. That kind of follows the pattern of our show. Yeah, I guess you're right. Everybody, we hope all of you fail. Yeah. You're going to feel better about being single after listening to this. Yeah.

That's for sure. Your brand new update, update starts right now. There comes a time in every young woman's life when she needs to decide, do I want to try and find true love with a sweet guy who genuinely cares about me? Or do I want to party on a billionaire's yacht with a bunch of creepy old rich guys serving me champagne? That's the answer, Jeff. I always pick that.

Happiness now or happiness later. It is a tough, tough choice. But that was the big question occupying the mind of one woman. And today, we finally get to learn her answer. Did she pick the nice guy or the billionaire? Hey, who's to say the billionaire on a boat isn't true love? That's fair, Jose. Or the nice guy.

Sure, we'll find out in a special second date update update right after this. Brooke and Jeffrey in the morning. Second date update. You know, we've talked about bringing a gift to a first date before. 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. Bring me a raccoon next week, please. 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 it wasn't anything that crazy. Well, we're impressed because Jeff only gives that way free wildlife. He finds in his backyard. I've got a whole like cage of animals ready for you.

And 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. And 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 to. So funny. I was just talking about how I don't love his comedy. Oh my God. He's like a dad. Text in the 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. Oh, yeah. You know, offensive. He's a pretty family friendly. He's pretty clean. 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. He's 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. And so I asked her if we could go out on a date. And we, it was simple. We went to a Chili. A Chili's. 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, 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. 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 loved. 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. Yeah. I heard it's one in five guys have one. Yeah. Hot to hot. 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. Nice. 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. But 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. Brooke and Jeffrey in the morning. Second Date Update. You're in the middle of a second date update update, and we're going to find out how the couple is doing right after you here, part two.

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 rolls? Do they? I don't even know they had egg rolls at Chili. I don't think they do. I 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. Aw, 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. Yeah, let's give some love to Chili's egg rolls right now. Who are the best egg rolls in the city? We're at Chili's.

Yeah. Jeff went to Chili. I'm still stuck on that. When did you go to airports? 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 Elisa on the phone here.

I'm going to dial her number right now. Let's see how this goes. Here we go. Hi, is this Elisa? Hi, Lisa. There's a whole room of people here. Sorry, I'm coming in a 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. Okay. We're doing a segment from our show. It's called a second date update. 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 you.

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 is. It's 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 girls 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. 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 free. What? He took you and all your girls shopping. Like he took us to Gucci and Levitron, all these stores.

Wow. We 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. Like, 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, host. So, you know, it's sold me.

Wait, are you still talking to the billionaire dude from Miami? Is that it? Oh, no, 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. You're hunting for more billionaires and more pools. to buy you shopping screens.

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 mood situation. Where you don't have to do anything back. Yeah. 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 allowed 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. And 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.

Isaac, are you there? Yeah. Man, this was like it was an awesome weekend. He's jealous, man. 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 the time with you. He is so stinking cute. He's like a genuinely nice 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. I'm glad what it was. I should have got that egg rolls. 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. With that said, Elisa, 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. right in front of you. Jeff, just say the best things in life are free.

That's the saying. He's just never hurting. Yeah, I don't know what that is. 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, everything's better in Miami.

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. A bag of a purse at the time. Yeah, well, if you get the shower to her with gifts. Yeah. Yeah, anything. No, more bag. Four years.

12 bags. You only had 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 Alicia, 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 podcast. Yeah. Yeah, I think so. Brooke and Jeffrey in the morning.

Getting ready for a game means being ready for anything. Like packing a spare stick. I like to be prepared. That's why I remember 988, Canada's suicide crisis hubline. It's good to know just in case. Anyone can call or text for free confidential support from a trainer's spot. anytime. 988 suicide crisis helpline is funded by the government in Canada. Hi, this is Joe Winterstein, host of the Spirit Daughter podcast, where we talk about astrology,

natal charts, and how to step into your most vibrant life. And I just sat down with a mini driver. The Irish traveler said when I was 16, you're going to have a terrible time with men. Actor, storyteller, and unapologetic Aquarian visionary. Aquarius is all about freedom-loving, and different perspectives. And I find a lot of people with strong placements in Aquarius are misunderstood. A son and Venus and Aquarius in her seventh house spark her unconventional approach to partnership.

He really has taught me to embrace people sleeping in different rooms on different houses and different places, but just an embracing of the isness of it all. If you're navigating your own transformation or just want to chart side view into how a leading artist integrates astrology, creativity, and real life, this episode is a must listen. Listen to the Spirit Daughter podcast, starting on February 24th, on the IHeartRadio app, Apple Podcasts, or wherever you listen to your podcast.

Well, this is a surprise that we're getting an update, update from a couple. I think nobody in studio really thought would go out again. Well, they said they wouldn't. That's why we thought that. There was a maybe in there somewhere after the two-week Miami trip. I guess. Let's welcome back, Isaac and Elisa. And let's just start with Elisa.

Tell us what's going on with you, too. So, obviously, last time I was going after my goal of exploring men with money. Yeah, yeah. Wait, did it all backfire? No, it didn't backfire. And I just had a realization the last time I was in Miami. Why? What happened?

It wasn't as much fun the second time around. Really? The first time was spontaneous and exciting. What happened on time, too? Well, we and a few of my girlfriends wound up on this rich guy's yacht. But the guys on there were so weird. A lot of times they're like nerdy, techy, socially awkward kind of people. But what's weird about that?

It's interesting when you have to pay for people to hang out with you that you wouldn't be someone that's super likeable. No. Yeah, this time around, they wanted to sign NDAs and give up our cell phones. I mean, it was really creepy and I didn't feel comfortable at all. So you didn't sign the NDA? No, I got off of there real quick. Okay. So then you went back home and then you met up with Isaac again?

Not exactly. Oh. I did realize I'm not into chasing billionaires. Okay. Now I'm just into regular millionaires because they're not as weird. Yeah, there's a lot of them So you're not to poor boys yet She's got standards

She's still on yachts They're just a little smaller yachts Give it another five years She'll work her way down But Isaac is on the phone right now too Have you guys hung out, Isaac? Yeah, yeah We've hung out

But it hasn't really been like that Oh Not different vibe You guys are just friends I mean that's cool Like we love to start a friendship Sure Yeah I mean like sometimes

She'll let me dog fit or whatever, so it's not that big a deal. Isaac, that sounds like she's using you. You work for her now. Hey, it sounds like I'm working for her, but she pays pretty well, and I needed a side hustle. Oh, she does pay you. Okay.

I thought it was for free. That's cool. Oh, God, no. Oh, no, no. He's not an idiot. Are we counting this as a win-win, Isaac? Hey, it is to me. All right.

Okay. Cool. You may be on the boat party and too, but he's serving drinks. Yeah, that's fine. He's got a good side hustle out of this now. So, all right, kind of a weird, happy ending to this story, but I'm glad you two are friends. And thanks for keeping us updated on your romantic journey. Yeah, congrats.

Thank you. They're happy. Hi, it's Joe Interesting, host of the Spirit Daughter podcast where we talk about astrology, natal charts, and how to step into your most vibrant life. And today I'm talking with my dear friend, Krista Williams. It can change you in the best way possible. Dance with the change. Dance with the breakdowns.

The embodiment of Pisces intuition with Capricorn power moves. So I'm like delusionally proud of my chart. Listen to the Spirit Daughter podcast starting on February 24th on the IHeartRadio app, Apple Podcasts, or wherever you listen to your podcast. Ready for a different take on Formula One? Look no further than no grip. a new podcast tackling the culture of motor racing's most coveted series. Join me, Lily Herman, as we dive into the under-explored pockets of F1, including the astrology of the current grid,

the story of the sports most consequential driver's strike, and plenty of other mishaped scandals and sagas that have made Formula One a delightful, decadent, gumster fire for more than 75 years. Listen to No Grip on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, I'm Jay Chetty, host of the on-purpose podcast. I'm joined by Luke Combs, award-winning country music artist and one of the most authentic voices in music today. The guy that says he's always going to be there and that will do anything to be there is the only guy that's not there. No matter what, I'm going to prioritize my wife and my children. I dread the conversation with my son.

Listen to On Purpose with Jay Chetty on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Amanda Knox, and in the new podcast, Doubt, the case. of Lucy Letby, we unpack the story of an unimaginable tragedy that gripped the UK in 23. But what if we didn't get the whole story? The moment you look at the whole picture, the case collapsed. What if the truth was disguised by a story we chose to believe? Oh my God, I think she might be innocent.

Listen to Doubt, the case of Lucy Letby on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. This is Special Agent Regal, Special Agent. Bradley Hall. In 2018, the FBI took down a ring of spies working for China's Ministry of State Security, one of the most mysterious intelligence agencies in the world. The Sixth Bureau podcast is a story of the inner workings of the MSS, and how one man's ambition and mistakes opened its fault of secrets.

Listen to the Sixth Bureau on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.