Brooke and Jeffrey: Second Date Update
Second Date Update UPDATE: Gucci First Questions Later
05 Mar 2026
Chapter 1: What dilemma does the woman face in choosing between love and wealth?
I'm Bailey Taylor, and this is It Girl. This podcast is all about going deeper with the women shaping culture right now. Yes, we will talk about the style and the success, but we are also talking about the pressure, the expectations and the real work behind it all. As a woman in the industry, you're always underestimated.
So you have to work extra hard in a way that doesn't compromise who you are and your integrity. You know, I like to say I was kind of like a silent ninja. Listen to It Girl with Bailey Taylor on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. In the middle of the night, Saskia awoke in a haze. Her husband Mike was on his laptop.
What was on his screen would change Saskia's life forever. I said, I need you to tell me exactly what you're doing. And immediately, the mask came off. You're supposed to be safe. That's your home. That's your husband. Listen to Betrayal Season 5 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Hi, it's Jill Winterstein, 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 podcasts. I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast. This is a story about a horrendous lie that destroyed two families. Late one night, Bobby Gumpright became the victim of a random crime.
The perpetrator was sentenced to 99 years until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Good people, what's up, what's up? It's Questlove.
So recently I had the incredible opportunity to have a real conversation with actress and producer Jamie Lee Curtis from Routines to Recovery, True Lies, and a certain Jermaine Jackson music video. Jamie's real and raw, and it's something I really admire about her.
I am so happy that I'm the head in charge at 67, that I have the perspective that I have at my age to really be able to put all of this into context. Listen to The Questlove Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Out of all the people in 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. 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.
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Chapter 2: How did Isaac and Elisa connect over stand-up comedy?
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. 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. God, 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. 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 away 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 Gaffigan, one of my favorites. Oh, 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. He's like a dad. Text him to 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. He's pretty clean. Yeah. Because that's always a risk, too. Like if you send a joke that maybe you find funny. Someone 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, now we know. 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. So I asked her if we could go out on a date and we, it was simple.
We went to 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. 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 the dude. 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. Timing's important there, Alexis. Yes. And that was the big thing. We watched like a little bit together, but then I kind of segued 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
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Chapter 3: What unique gift did Isaac give Elisa during their date?
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 girls weekend. Yeah, we did go for a girls 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 spree. Wait. He took you and all your girls shopping. Like, he took us to Gucci and Louis Vuitton, all these stores. We got shoes, purses. And he just was, I guess, being really generous. I mean, he didn't ask us to do anything weird. 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'm back, things just, I don't know, seem different. 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. 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, he 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 moon 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 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 you 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, 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. Cause he's on the other line right now, listening to this conversation. Oh God. Okay. Isaac, are you there? Yeah. Um, Man, I think it was an awesome weekend. He's jealous, man. Alisa, look, I really liked you. I had a lot of fun.
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Chapter 4: Why has Elisa not been responding to Isaac after their date?
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 podcasts. I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast. This is a story about a horrendous lie that destroyed two families. Late one night, Bobby Gumpright became the victim of a random crime.
The perpetrator was sentenced to 99 years until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Good people, what's up, what's up? It's Questlove.
So recently I had the incredible opportunity to have a real conversation with actress and producer Jamie Lee Curtis from Routines to Recovery, True Lies, and a certain Jermaine Jackson music video. Jamie's real and raw, and it's something I really admire about her.
I am so happy that I'm the head in charge at 67, that I have the perspective that I have at my age to really be able to put all of this into context. Listen to The Questlove Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
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