Brooke and Jeffrey: Second Date Update - Second Date Update: High Steaks Heartbreak

Episode Date: March 11, 2026

One of our listeners found the ULTIMATE HACK to take a woman out, without breaking the bank. It requires a tad bit of deception though… find out more in your Second Date Update podcast!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. Next Monday, our 26 IHeart Podcast Awards are happening live at South by Southwest.

It's the biggest night in podcasting. We'll honor the very best in podcasting from the past year and celebrate the most innovative talent and creators in the industry. And the winner is... Creativity, knowledge, and passion will all be on full display. Thank you so much. IHeartRadio. Thank you to all the other nominees. You guys are awesome.

Watch live next Monday at 8 p.m. Eastern, 5 p.m. Pacific free at veeps. Or the Veeps app. 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. I'm Clayton Necker. In 2022, I was the lead of ABC's The Bachelor. But here's the thing. Bachelor fans hated him. If I could press a button and rewind it all I would.

That's when his life took a disturbing turn. A one-night stand would end in a courtroom. The media is here. This case has gone viral. The dating contract. Agree to date me, but I'm also suing you. This is unlike anything I've ever seen before. I'm Stephanie Young. Listen to Love Trapped on the IHeart Radio app.

Apple Podcasts or wherever you get 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 Gumpbright 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 the IHeart Radio 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. Oh, yeah. It's a brand new second date. Yeah, her second date podcast. And, well, I mean, it is a scam. We all liked it for the guy, honestly. Yeah.

He figured out how to take a lady out to a high-end restaurant without paying for it. Yeah. Pretty much, yeah. So, 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.

Hey, there you go. Blurie. Out of the wild, man, that must have been fun. Back in the day. 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? Uh-oh, Jeff, that's a loaded question. There's an entitled to every person. Okay, cool. Well, without looking directly, in the mirror. What does that look like? What are the characteristics that you're trying to describe there? I knew this.

Someone entitled feels like they're owed something, right? That's, I mean, kind of the definition. Yeah, like the type of woman who would scoff if you paid with a non-platinum credit card. That reflects poorly on a horror. 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 3-60s. Unless you're entitled. Yeah. And they can be hard to date, I mean, almost impossible. But one of our listeners, Zique, 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, Zique, welcome to the show, man. Hey, thank you good for having me, guys. Yeah. Where did you meet this entitled woman? So I matched with her, like, on dating with fight. Her name is Chalette. Chalette.

Sorry, Chaless with, like, a CH in it? Yeah, I thought that was interesting. Like Celeste, but like Chaleste. Sounds pretty high maintenance. I like her already. What did you like about her? I mean, she's just dropped 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. So she sounds like what my friend group would call the fancy pants. Okay. We're not judging you at all. So tell us more about you and Chalest.

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, the dating profile? Well, I hope you had already exchanged phone numbers at that point. No, we were only talking, like, to the app. You do know that we have to be able to contact her in order for this segment to work. Yeah, wait.

And the producers have her numbers now? 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. No, but that's how the station works. It's how we record. 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. Because I remember talking about going and meeting up for dinner, like on a day 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? And she picks the fanciest, most expensive steakhouse in the city. And she says we should both get tomahawks there.

What? Is it that 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 yourself. Well, this could just be a test. Like she wants to see how you react.

How'd you react? I said, sure, done. It's already books next Monday. You need there six 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 day? 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. 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.

Oh, cute. 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 T.P.S? You're thinking what I was thinking.

So I chose the one day out of the week that I knew it wasn't going to be open. Oh, you did. I did do it on purpose. That's smart, girl. 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. Oh. Was that believable you playing dumb? I mean, I just blamed it on the restaurant. They just must have screwed up or something. That's kind of smart.

Like, they misheard me on the phone. That 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 be prepared. Right. Because you knew that this was going to happen. 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? I just was just going to say, what's what I mean? You know, like, not like a food course that has like subways.

It's like more high-end food. Okay. I think we do have one of these in the mall in the nice part of town. Oh, yeah, yeah, yeah. Where it's like local restaurants and artisan pizza. They're like making handmade dog wings. 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. 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. Yeah.

And then you paid with a non-platinum credit card, I'm assuming. Yeah. Uh-oh. I just paid with like a normal card. I don't think she even noticed. But she's definitely a type of woman who probably gets like 50 likes a day by guys on this app. So really pretty. Okay.

So we should pretend we're like a high-end service calling to help you that you spent a lot of money on. Good, you guys? I mean, I mean, I think it's kind of obvious. We're free when you listen to us. We can 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.

Oh, 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? I mean, I don't mind the feisty, the high maintenance. Like, she's just also really beautiful. So, like, I kind of know what I'm getting herself into. But how are you going to keep up?

Yeah. Sounds expensive. I'll just eat booking restaurants that are closed on Monday. Ah, hey, 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, call this Chaleste. set her up with the man of her dreams when we do your second date update

coming up right after this. Hold on, ma'am. Thank you, guys. Brooke and Jeffrey in the morning. Second date update. If you were just joining us, our listener, Zique just finessed his way into a first date with a self-described

entitled woman named Chalest. Yeah. Yeah, she's like the chillest. 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 and tour? 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. When he was like, oh, I booked it's 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. How did that happen? Dorn it.

Did he do that on purpose? Yes. A hundred percent 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. I mean, she ended the day asking about the Tomahawk. Right. She was disappointed.

Did she figure out the whole plan? Did she find somebody else to go buy her Tomahawk steaks? Of course she did. I'm sure, yeah. But Zieg's still holding out hope that maybe he can get a second chance. How you feeling, Zieg? I mean, I'm feeling pretty confident. 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 Brooks wrong. I'm going to keep my hopes high for now. You really probably shouldn't do that because it's going to hurt when she says she's looking for a 60-ounce steak out of this. Let's find out.

I'm going to dial Chaless number. Let's see if she actually answers the phone. I mean, here or worse again, I'd get tingles. Oh, wait a minute. All right, we're going to put you on mute then. Yeah, I don't want to know what tingles are. I don't want to hear it. But, yeah, let's talk to Chaleste and see what happens.

Here we go. Hey, is this Chalest? This is she? Hey, we're a radio show. We're called Brooke and Jeffrey in the morning. Thank you for answering. Yeah. Hi, good morning.

Did I win something or? Why do people always ask that? Because that's usually what radio stations call about. Usually they call you because you want. I just want stuff from us. Okay. No. I mean, if we had the budget, that would be great.

Sure. But we might have something even better to offer you. Okay. A chance to meet up one more time with one of our listeners, a great guy that we've spoken to named Zeke. Oh, man. Hey, wait a minute. That's what this is about? Yeah.

Yeah. This is called a second date update. She's laughing. We're trying to help Zeke figure out why you two haven't met up a second time. Yeah, I've heard of this type of thing before. Okay. Okay. Yeah.

We heard about the Steakhouse Miner. mishap where, gosh, it was closed? Mishap. Is that what he said? He called it a mishap? I mean, what would you call it? Yeah. Well, I looked it up later and it said the restaurant was closed on that day. So it wasn't a mishap.

Oh. Well, then, I mean, it was a mistake, right? He got confused with another restaurant. Look, he took me in the restaurant. It was closed. And then he ends up taking me to some food court that he keeps telling me is this high-end food court, which there's no such thing, by the way. And I'm sorry, if a place,

says Mexican sushi. I mean, I don't even know, I don't even know what that is. That's what we call fusion. That sounds really good, actually. Yeah, I mean, I would take some. Some carnitas inside of a sushi roll? In sushi form? Yeah, not good. Let me just say it was not good. Oh, no. You were, okay, so the food wasn't great, but what about his sparkling personality? That must have won you over in some way. I mean, the moment I was in a food court, I was like half listening to him, so I don't, a shining personality. I couldn't see past like, the disappointment.

And the whole thing just felt weird and I was suspicious of the whole thing. So, I mean, it just nothing was, nothing was right. Why were you suspicious? It just seemed convenient that we have this, like, wonderful reservation and then the place was closed. Like, if you made a reservation, they would tell us. And then I called the next day,

and that's when I found out that they were already closed under that day. Wait. So you called and kept investigating whether or not, what, faked the reservation? Is that what you're saying? Absolutely. Because if it, you know, he said it was a mistake,

so I called them to see if there was any other day with his name on the reservation or a mistake that they could have made. And there was absolutely no record of his name in his system at all. I mean, he totally lied. He's such a cheap ass. I know it. Wait. Wait. I thought you were going to be upset about the lie, but you're upset about the cheap part of it.

No, I know why he lied. He lied because he didn't want to have to pay for anything. Okay. It sounds like the nicest restaurant in the city. Oh, so you say it's okay to be. lied about it then. No. No. We're just saying what happened to the good old days of women just taking a man at his word and not questioning everything that he did and the motives behind it. Right, Brooke? No, you shouldn't have lied. That was the grossest statement.

I'm sorry. It's a pretty outlandish thing. I'm sorry. I don't know why men are considered trustworthy these days, especially when we have them waiting on the other line, listening in on these phone calls, waiting to talk. Wait, what? Yeah. Yeah, that is kind of how this works. Zika is on the phone right now, I think. Yeah, I'm here. Way to come in with some confidence, Zique. Yeah. What's up?

Exactly. It's a nice to hear your voice again. It's not nice to hear your voice. I don't know why we're on here right now. I think it was pretty obvious what my thoughts were on our last date. Okay. Oh, that hurt. I mean, I like you and I like your vibe, and I wanted to be with you because of that.

I just, I felt like it was just too much for a first date. And if I said that, you wouldn't have gone out with me. Yeah. Well, of course, I'm awesome and I'm gorgeous and I deserve all of that. So you're right. I would not have gone out with you had you been honest with me and just said that we weren't going to go to that restaurant. So you're saying that if he said, I'm sorry, I can't afford a $700 steak, that would have been like a turnoff for you. He didn't even say that.

He just said that's too much for a first date. He didn't tell me that ahead of time. He's telling us that now after he'd already lied. So it's a small problem of timing is what we're having. Yeah, and I kind of just wanted you to get to know the real me, you know? Like I thought you liked that. Well, you know, the real you is broke and I don't like that. Oh, wow.

Okay, well, now it's a little more super much. That's not true. I make above the average median salary for a men my age. Hey. And, you know, go have some Mexican sushi with other men because you're not going to attract any, like, high value woman with, you know, a bait and switch game. I would actually argue, Chalas, that a high-value woman is someone who looks beyond whatever the economic situation is into a person's potential and their personality. Oh, God. I almost threw up in the room.

I didn't even listen to the second half of that. I thought what I said was bad. That was horrible. That's really sweet that you think that way, but we have to give ourselves a leg up. We have to take our standards up higher because otherwise we're just going to get stuck with people who drag us down. No broke boys. Why can't you just make the money? I do make money.

There you go. Okay, so you take him out to tomahawk steaks, you know? You be the sugar mama or whatever. Brooke wouldn't do that herself in her own dating life, but everybody else definitely should. I never dated someone who made more money than me, and that was true when I was making 17 grand a year. Well, it's financially impossible to make more money than you, Brooke. So how was it supposed to compete? When I was making $17,000 a year, I was still dating someone.

You made $17K? Jeez, bro. Bragger. Anyway, Chaless, listen, I apologize on behalf of my co-host coming after you and your high standards for what women deserve. But speaking to Zique, I think Zieg, what she's looking for is like a full admission of guilt. You messed up, like a total apology. Really? I think she's just looking for a bank statement. Well, that's secondary.

If you had that too, that'd be great. Honestly, I'm just trying to get off the phone at this point. Okay. Okay, but just give Zeeke one last chance to state his point. What if I did apologize? And what if I actually did take you to dinner there for real? And then these guys will pay for it. What?

Wait, wait, no. We didn't say that. No, we don't. This is a radio budget, my friend. No, I thought you guys, like, that's your whole, like, ding. Like, you guys pay for, like, the date. Yeah, maybe at, like, a red robin. But not, like, the most expensive steakhouse in the entire city.

Yeah, we don't even go to that place. You want to do I-hot breakfast for dinner's always fun. Besides, Zeeke, I want you to pay for it yourself, like a man should, in fact. That's right, Zeeke. Yeah. I'm actually agreed with her now. We all want you to feel it, Zeeke. I'll give you my address right now,

and you can door dash a tomahawk to me tonight, and then maybe I'll consider giving you a chance. Wow. The doors cracked back open for you, Zique. This is your chance. I mean, I would, but I already looked at all the places that sell those, and they're, like, closed right now. Oh, yeah.

Oh, wow. What are the odds? I heard that, too. Every single place. I just looked. I just looked. It's the reverse of last time. Yeah.

This is the same story. He just broke. That's it. Yeah, but have you tried the Applebee's egg rolls? Because we heard those were good. High end. Okay, the highest we go is cheesecake factory. What do you say?

I say I have to go. I'm done. Okay. I'm sorry, D. I'm sorry. I tried. Thank you guys. Well, now we know.

You just got to stay in your lane, buddy. Is that the thing? The bus lane. Mexican sushi. Yeah, it's a food court. 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 train responder. Anytime. 988 suicide crisis helpline is funded by the government in Canada. Next Monday, our 2026 IHeart Podcast Awards are happening live at South by Southwest. It's the biggest night in podcasting.

We'll honor the very best in podcasting from the past year and celebrate the most innovative talent and creators in the industry. And the winner is creativity, knowledge, and passion will all be on full display. Thank you so much. IHeart Radio. Thank you to all the other nominees. You guys are awesome. Watch live next Monday at 8 p.m. Eastern, 5 p.m. Pacific free at vips.com or the Veeps. You know, Zeeks probably in his 20s right now, but I feel like down the road when he's 80 or 90,

he's going to look back on this and appreciate that he just got the opportunity to go on one date with an entitled woman at a food court. Not a lot of people can say that. You know, I bet they looked out of place. Like she's dolled up ready to go to the nicest restaurant in the city. Oh, I'm sure. Beautiful, he said, right? We didn't even ask him if he dressed up for the occasion since he didn't, he knew he wasn't going to the steakhouse.

Why? Did he have a collared shirt? I don't know. I mean, like there was so much other stuff going on. I doubt he could afford even a collared shirt from the way that we heard. I do have a feeling this was the peak of his dating life. What? Oh, no. It was.

This is the best he's going to do. And now he's going to have to learn how to settle for a woman who just appreciates him for who he is. Ew, personality. That's the peak. That's the peak. The other one's the valley. No. Enjoy your spiral down into normalness.

I feel terrible for him, but that doesn't have to be your story. We can help you date way above your means by reaching out to the show and we'll call that person who's not calling you back. Remember how we just set expectations too high for being able to afford a tomahawk for people's dinner? Never quit on your dream. Yeah, we can get you rejected. That's Brooke and Jeffrey in the morning. Next Monday, our 2026 IHeart podcast awards are happening live at South by Southwest. It's the biggest night in podcasting.

We'll honor the very best in podcasting from the past year and celebrate the most innovative talent and creators in the industry. And the winner is creativity, knowledge, and passion will all be on full display. Thank you so much. IHeart Radio. Thank you to all the other nominees. You guys are awesome. Watch live next Monday at 8 p.m. Eastern, 5 p.m. Pacific free at Veeps.com or the Veeps Hi, it's Joe Interestine, 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. I'm Clayton Eckerd. In 2022, I was the lead of ABC's The Bachelor. But here's the thing. Bachelor fans hated him. If I could press a button and rewind it all I would.

That's when his life took a disturbing turn. A one-night stand would end in a courtroom. The media is here. This case has gone viral. The dating contract. agree to date me, but I'm also suing you. This is unlike anything I've ever seen before. I'm Stephanie Young. Listen to Love Trapped on the IHeart Radio app, Apple Podcasts, or wherever you get 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 90. years until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Ego Wota is your host for the 2026 IHart Podcast Awards, live at South by Southwest.

Hello, is anybody there? Raised by a single mom, Ego may have a few father-related issues. Are we supposed to talk about your dad? Her podcast, Thanks, Dad, is full of funny, heartfelt conversations. with actors, including fellow S&L alums, comedians, musicians, and more about life and their wonderfully complicated relationships with their fathers. I think and hope that's a good thing. Get to know Ego.

Follow Thanks, Dad, with Ego Wodom, and start listening on the free IHeart Radio app today.