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Brooke and Jeffrey: Second Date Update

Second Date Update: High Steaks Heartbreak

11 Mar 2026

Transcription

Chapter 1: What is the ultimate hack for a budget-friendly date?

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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.

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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.

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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.

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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. Let's go.

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Our iHeartRadio Music Awards are coming back Thursday, March 26th, live on Fox. Watch as we honor the biggest stars from all genres of music that you loved listening to all year long on your favorite iHeartRadio station and the iHeartRadio app. Hosted by Ludacris. Icon Award recipient, John Mellencamp. Innovator Award recipient, Miley Cyrus.

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With performances by Alex Warren, Kehlani, Laney Wilson, Ludacris, Ray, TLC, Salt-N-Pepa, and En Vogue.

Chapter 2: How did Zeke meet the entitled woman named Celeste?

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Plus, Taylor Swift makes her first award show appearance this year. Also, gold medal Olympian Alyssa Liu, Neo, Nicole Scherzinger, Nikki Glaser, Sombra, Weezer, and more. Watch live on Fox Thursday, March 26th at 8, 7 central. And listen on iHeartRadio stations across America and the free iHeart app. Hey there, this is Josh from Stuff You Should Know with a message that could change your life.

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The Stuff You Should Know Think Spring podcast playlist is available now. Whether spring has sprung in your neck of the woods yet or not, the Stuff You Should Know Think Spring playlist will make you want to get your overalls on, get outside, and get your hands in the dirt.

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You can get the Stuff You Should Know Think Spring playlist on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Oh, I love a good hack on how to get stuff for cheap. It's Brooke and Jeffrey. It's a brand new second date podcast. And well, I mean, it is a scam. We all liked it for the guy, honestly.

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He figured out how to take a lady out to a high end restaurant without paying for it. Yeah. Yeah. You're going to hear that in just a second. But we always love to feature your comments. Yes. Okay. Dominic said, glad to have met my wife the old fashioned way. At a bar with more alcohol than either of us should have legally been sold. Out of the wild? Man, that must have been fun. Back in the day.

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All right. Listen, your brand new episode starts right now. Brooke and Jeffrey in the morning. Second date update. Brooke, is there such a thing as an entitled woman?

Chapter 3: What were Zeke's initial impressions of Celeste?

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Uh-oh, Jeff, that's a loaded question. There's an entitled every person. Okay, cool. Well, without looking directly in the mirror, what does that look like? Like, what are the characteristics that you're trying to describe there? I knew this was happening. Someone entitled feels like they're owed something, right? That's, I mean, kind of the definition.

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Yeah, like the type of woman who would scoff if you paid with a non-platinum credit card. Oh. That reflects poorly on horror. Yes. Or gets upset that her hotel room with ocean view doesn't face both oceans. That's a good point. Well, unless it's a 360. Unless you're entitled. Yeah. And they can be hard to date. I mean, almost impossible.

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But one of our listeners, Zeke, went out with someone and says even though she's definitely entitled, he still wants another date with her. Okay. I mean, if he knows what he's getting himself into, then cool. Yeah. So, Zeke, welcome to the show, man. Hey, thank you for having me, guys. Yeah. Where did you meet this entitled woman? So I matched with her like on a dating website.

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Her name is Celeste. Sorry, Celeste with like a C-H in it?

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Chapter 4: What was Celeste's reaction to the dinner invitation?

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Yeah, I thought it was interesting. Like Celeste, but like Celeste. Sounds pretty high maintenance. I like her already. What did you like about her? I mean, she's just drop-dead gorgeous. Like, she's so beautiful. And she's also a professional stylist with, like, a very busy schedule. But, like, I don't mind that at all. Did you meet her on Raya? Okay.

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So she sounds like what my friend group would call a fancy pants. Okay. We're not judging you at all. So tell us more about you and Celeste. How did you guys interact? So, I mean, we started talking on the app, but then, like, in the middle of us, like, almost getting to hang out, she deletes her profile. Oh. Oh. Oh, the dating profile?

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Well, I hope you had already exchanged phone numbers at that point. No, we were only talking, like, through the app. You do know that we have to be able to contact her in order for this segment to work. Yeah, wait. Do the producers have her number? That's a very entitled thing to think, Brooke. The only way we'll call someone is via phone. There's plenty of other ways to do it.

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No, but that's how the station works. That's how we record.

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Chapter 5: How did Zeke handle the unexpected restaurant closure?

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Okay, okay. The whole room's entitled now. All right. So when was that? I want to say like a few months ago because now she actually came back on the app. So we matched again. Oh, that's funny. Okay. So like I just jump and I say, hey, are we still going to hang out? Like my first question. Cool.

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Because I remember talking about going and meeting up for dinner like on a date and like getting some steaks. That's cool. Okay. So what did she say to dinner and steaks? She throws out, you know what I would love to do? Hmm. And she picks the fanciest, most expensive steakhouse in the city. And she says we should both get tomahawks there. What?

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Isn't the tomahawks like the huge ones that cost like $500 or something? Yeah, you do it just for Instagram. Yeah, exactly. And I'm thinking there's no way I'm going there on a first date. I'm thinking there's no way a woman can eat a whole tomahawk by herself. Well, this could just be a test. Like she wants to see how you react. How'd you react? I said, sure, done.

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It's already booked next Monday.

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Chapter 6: What was the outcome of Zeke's date at the food court?

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Be there at 6 o'clock. Oh. Would you? I mean, isn't it kind of the thing that you don't want to go that fancy on a first date? I was going to say, I wonder if you failed the test by saying sure. Like you should have said. The test is, oh, I love that place, but I'm going to take you to this other steakhouse first. We're so jaded.

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We think every question is definitely a test and that there's a right way to do this and a wrong way to do this. Well, he's on the phone with us, so we might be right. That's fair. I mean, she was very excited. We meet there and it's closed. It's closed? Wait, what? Oh, I bet you're so happy. That's how you know. Is that why you suggested Monday at 3 p.m.? You're thinking what I was thinking.

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So I chose the one day out of the week that I knew it wasn't going to be open. Oh, you did. You did do it on purpose. I thought smart, bro. That's genius level. Like, darn it. But you kind of look like an idiot. Yeah, but he saved a bunch of money. I mean, yeah, she was shocked and asked, didn't you make reservations? And I just had to play dumb. Was that believable, you playing dumb?

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Chapter 7: What does Celeste think about Zeke's dating strategy?

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I mean, I just blamed it on the restaurant. They just must have screwed up or something. That's kind of smart. They misheard me on the phone. It would work on us, but we said she's entitled, so I don't know that. Yeah, wait a minute. But the customer is always right, so as the customer. So open up this restaurant right now. Yeah. I mean, you obviously had a plan B prepared. Right.

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Because you knew that this was going to happen. Oh, yeah. So where did you actually take her? I ended up just, like, taking her to this high-end food court, I mean, in a nearby building. What's a high-end food court? What does that even mean? You know, like, not like a food court that has, like, subways. Just, like, more high-end food. Okay.

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I think we do have one of these in the mall in the nice part of town. Oh, yeah. Where it's like local restaurants and artisan pizza. They're making handmade dumplings. Why are you saying it like that? I love getting grilled cheese from there. I know. I know. I'm a huge fan of that place. She's all dressed up for a high-end steakhouse and now she's in a food court.

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Chapter 8: What lessons can be learned from Zeke's dating experience?

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But now she gets to know the real you. And that must have been a good thing. I don't know if that was enough. She's not calling me back. Oh, man. How did you guys end the date? Can I ask? Good question. She looked at me and said, well, I thought we were going to get tomahawks. She didn't get over it. Yeah. And then you paid with a non-platinum credit card, I'm assuming. Yeah. Uh-oh.

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I just paid with, like, a normal card. I don't think she even noticed. But, like, she's definitely the type of woman who probably gets, like, 50 likes a day by guys on this app. Really pretty. So we should pretend we're like a high-end service calling to help you that you spent a lot of money on. Could you guys? I mean, I think it's kind of obvious we're free once you listen to us.

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We could be investment bankers. We're calling because we hear you're rich and we want to help you with your money. Yeah, that would be super believable. We're still trying to get a date. I wanted to be a character for this. I am curious, though. The way you're describing her seems very high maintenance, very demanding and needy. If she's like that, what makes you want to date her so badly?

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Oh, yeah. I mean, I don't mind the feisty, the high maintenance. She's just also really beautiful. So I kind of know what I'm getting myself into. But how are you going to keep up? Yeah. Sounds expensive. Uh-huh. I'll just keep booking restaurants that are closed on Monday. Your favorite date night. A lifetime of happiness, that sounds like. But we'll try and get a hold of her when we come back.

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Call this Celeste and set her up with the man of her dreams when we do your second date update coming up right after this. Hold on, man. Thank you, guys. Brooke and Jeffrey in the morning. Second date update. If you're just joining us, our listener Zeke just finessed his way into a first date with a self-described entitled woman named Celeste. Yeah, she's like the chillest.

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I think she's the highest maintenance. Kind of the opposite, yeah. But she suggested that they go eat tomahawk steaks together at the fanciest restaurant in town. And so did he talk sense into her? Absolutely not. That's right. Zeke said, sure, let's do it, and told her he booked a reservation. Which makes sense. Usually it takes months to get into those places.

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When he was like, oh, I booked us a resi, I was like, oh, wow. But his hack is kind of genius. Yeah. Because they showed up on the one day when that restaurant was closed. What? How did that happen? Darn it. Did he do that on purpose? Yes. 100% he did. And he also pivoted then to a high-end food court, which was much more in his price range. But now he's not getting a call back.

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I mean, she ended the day asking about the tomahawk. Right. Still disappointed. Yeah. Did she figure out the whole plan? Did she find somebody else to go buy her tomahawk steaks? Yeah. Of course she did. I'm sure, yeah. But Zeke's still holding out hope that maybe he can get a second chance. How you feeling, Zeke? I mean, I'm feeling pretty confident.

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I hope that my personality was enough, honestly. Well, it hasn't been so far. But I do like the optimism. I just don't think that personality is what she's searching for. I could be wrong. I mean, maybe we can convince her that's a good way to go. We hope Brooke's wrong. I'm going to keep my hopes high for now. Okay.

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