Brooke and Jeffrey: Second Date Update - Second Date Update: 30 for 30

Episode Date: November 5, 2025

One of our listeners is experimenting in a new dating strategy, all about the YEAR she was born. Find out what she’s doing in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

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Start your love story on Bumble. On the podcast Health Stuff, we are tackling all the health questions that keep you up at night. I'm Dr. Priyankawali, a double board certified physician. And I'm Hurricane Dabolu, a comedian and someone who once Googled, Do I Have Scurvy at 3 a.m? And on our show, we're talking about health in a different way, like our episode where we look at diabetes. In the United States, I mean, 50% of Americans are pre-diabetic.

How preventable is type 2? Extremely. Listen to Health Stuff on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. And she said, Johnny, the kids didn't come home last night. Along the Central Texas Plains, teens are dying, suicides that don't make sense, strange accidents, and brutal murders. In what seems to be, a plot ripped straight out of Breaking Bad.

Drugs, alcohol, trafficking of people. There are people out there that absolutely know what happened. Listen to Paper Ghosts, the Texas Teen Murders, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas, and destructive companies in the history of business. First episode, How Southwest Airlines used. cheap seats and free whiskey to fight its way into the airline is.

The most Texas story ever. Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, I'm Cal Penn, and on my new podcast, here we go again, we'll take today's trends and headlines and ask, why does history keep repeating itself? Each week, I'm calling up my friends like Bill Nye, Lily Singh, and Pete Buttigieg, to talk about everything from the space race to movie remakes to psychedelics. Put another way, are you high? Look, the world can seem pretty scary right now.

But my goal here is for you to listen and feel a little better about the future. Listen and subscribe to here we go again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, it's Brick and Jeffrey and we've got a brand new second date podcast for you. And just a quick check in, we'd love to hear how you found our podcast. Yeah, are you from TikTok, Facebook? YouTube. Maybe you're on YouTube right now. We love it. Let us know in the comments.

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Second Date Update. It's Brooke and Jeffrey in the morning. And when you turn 30 years old and you're still single, Some people handle it just fine, but others, not so much. They start looking around wondering, why am I the only single person at the bar right now? You're not. You just feel that way. No, I am. Everybody else is making out except me.

Oh, my gosh. That doesn't mean they're together with anyone. All my friends are getting married now and they're having kids. Maybe I should start thinking about adopting my seventh cat. Uh-huh. Just to keep the other six company, you know. I want to be a good cat mom. Seven's lucky.

Yeah, but it's easy. You can get self-conscious and down about it, or you can be proactive and do something. And apparently, that's what our listener, Angela, has decided to do when she turned 30 recently. And she said, I got to switch up my dating tactics. So let's learn about it. Angela, welcome to the show. Hi, guys. Hey, Angela.

Happy 30th birthday. Oh, my God. Thank you. I'm so old. Dude, you're not. You're not, but I get it. So you said in your email that you switched up your dating tactics at 30. What did you do?

So, like, I've been single for way too long, and I was like, okay, let me try something different. So I thought, all right, I'm obviously not going to be like a Forbes best three people in the world. So why don't I do my own version of that? And I came up with 30 for 30. dating. Oh, 30 for 30 dating. That means I have vowed to go out on 30 dates before the end of the year. Oh, okay.

30 dates while you're 30 years old. Okay. It's like the 30 before 30 bucket list that's trending. Yeah, yeah. 30 guys, wow. Yeah, yeah. Okay. So, it's a horrible.

It's been rough. I mean, I've had to, like, speed it up. I'm on 19 or, like, I think. I've completed 19. Okay. But the thing is that, I don't know if I want to go on 20 because I really like 19. Oh, okay. That's good.

I mean, I feel like you should have some fine print in this that if any of the numbers turn out awesome, you don't have to continue because that's the whole point. Yeah. So I'm assuming that we're calling one particular guy here. But before we get to that, real quick, just because this is so interesting, your situation is so unique, could you tell us like some of the highlights and low lights from your 30 for 30 experience? Okay, four was a nightmare. Okay, he took me ax, and I beat him. And, like, the rest of the date, he was kind of just sulking.

Oh, okay. Yeah, four was a nightmare. Twelve brought his mom. Oh, yikes. All you need to say. And she was only supposed to stay for, like, 30 seconds, and she ended up seeing the whole date. Oh, she stayed the whole day. Oh, no.

She holds his hand, didn't tell me he was being a good boy. I really liked you. Yeah, absolutely. Her and I still talk. Oh. Oh, you still talk. Okay. Out of the last 18 dates, you got a mom out of it.

Hey, that's cool. Slash bestie. What can I say? Do these dudes know that you are on a challenge, or do you just go on the dates naturally? That's a really good question. So, like, when I first started, I was telling them, like, trying to be all transparent.

Like, one, two, I towed, and then they acted all weird and everything was just weird about the date. And so, like, three and on, I haven't said anything about what I'm doing. It'd be a good litmus test to see how the guys are about it if they're chill. I mean, I don't know how chill. be about it, Jeff. They don't really want to be considered a number. Oh, yeah.

Unless you're a 10 out of 10. Oh, okay. But that's what date 19 was. Does he get a name or do we just call him 19? 19 is a 19 out of 19. His name is Damon. Oh, wow. And he gave him a 19 rating out of a 19.

That's really good. Dinner was like really good. Like, he's a genuine guy. Like, he's has a really nice smile, no pressure. We went for a wall. We kids. We had like a really nice kiss. It was super cute.

And I thought he would be calling, and I don't really want to go on a 20. Like, I really want to go out with him again. And if I'm asking you guys, can you please help? Okay. Well, hold on. You skipped really fast. What's the deal with Damon's mom? Are you an aunt at us?

I know. I hope I meet her next date. Okay. You want to meet this mom. That's good. Did anything weird happen on your date with Damon or awkward? No. I mean, we ain't dinner on a Mexican.

in place he paid and I mean all as well like yeah he was fine I think like maybe almost 200 bucks like it was really like everything was chill that's a nice salsa I know that's a big plate of nachos

that's guac not salsa for sure oh my god okay listen he got a kiss out of it and I want to see him again do you think there's any chance he could have found out about the 30 for 30 like are you posting about it on your TikTok or

Yeah, and then he went and saw our socials. Alexis said that some of these are trending. Yeah. Okay, I am posting about it on my Insta, but I don't ever give my, but I never give my socials out to anybody. I just started dating, right? Okay. I don't know how he would find out about that because it's like not my name on my

Insta, but. Oh, that's what I was going to say. You can search your name. But if you heard you're the latest one and it was a good date, I wouldn't be that upset. That's a good point. You didn't post a bad post about it. Yeah.

That's a compliment, right? Thank you. So how long has it been since you and Damon hung out? Oh, my God, it's been like a week and a half, and I haven't heard from him. Okay. Oh, sounds up. Like you've texted, you've called, or? I don't really double text, but I did text and I did do a call, and like, that's plenty, right?

Yeah. Yeah, yeah, that's funny. Yeah, I don't do anymore. That's the problem is some people don't get that hint, and then they keep going. What you need to do is have a radio station call him. Yes. What if he's doing a 30 for 30, and he's only on number 17, and that's why. That would be amazing. Oh, my God.

That would be the pits. Wait, screw him. I'm like, that's not even at. You guys can do double dates side by side. Well, we'll try to figure out what's going on with Damon when we come back, call him, and hopefully get some answers on your 30-for-30-second date update, 30 dates with 30 men on your 30th birthday. Before your 30. 30th year.

We got it. That doesn't sound as sexy. No. You can't do it all in one day. But they get it. You understand what we're doing. Second date update right after this. Hold on.

Second Date Update. Welcome back to a special second date update, 30 for 30 edition. And what is 30 for 30? Yes. It's a little dating challenge. Our listener, Angela, gave herself when she turned 30 years old. Where she decided, I'm going to go out on 30 dates with 30 different men before she turns 31. Yeah, because she wants to be in a relationship.

Like, the goal is not to just do this, but it's also to find someone. Yeah. And also a little brag, too. It's kind of fun. The thing is, she hasn't even reached 30 guys yet. She's stopped at 19 after she met Damon, who has turned out to be everything she was looking for. In fact, she sounds fully ready to go all in on him

if she could just get him to answer her damn calls. So we're going to step in and try and make that happen. Now, Angela, do you have a guy number 20 lined up just in case? Because we might need to put a little pressure on Damon with a little, hey, if you don't, somebody else will. Okay. I don't have a 20. I don't have a 10.

Okay. You really are committed to this guy. I am. That's so cute. Okay. Well, I think we're all in agreement, though, that if we get him on the phone, we're not bringing up the 30 for 30 challenge to him unless he already knows about it. Right.

Unless he saw her Instagram or something. We just go by number 19. Yeah. Yeah. Sure. Yeah. It's really, it's your business, Angela. If you want to bring it up to him, that's your decision.

We're not going to say anything. But let's just call his number. We'll see if he picks him. up, and here we go. Hello? Hey, is this Damon? Yeah, it is. Who's this?

Hey, man, this is a radio show, actually, called Brooke and Jeffrey in the morning. Hi, Damon. Hey. Hey, good morning. Sounds like we caught you. Maybe you're busy right now or something. I mean, it's not that I'm busy.

I just don't, I don't know why the radio station is calling me. Oh, that's funny, because we know you, at least we've heard about you. Don't creep him out. Well, not in a creepy way, in a good way. We've heard a lot about you. I don't think that's how I said it, but we've heard glowing

reviews about you from one of our friends, a listener to our show, a woman named Angela. Oh, the girl I went out with, that Angela? Yeah, because what we're doing here, it's called a second date update, and we're just trying to help out Angela. She feels like after your hangout, you've been blowing her off a little

it? Yeah, I've been, I've been alone and her off a lot. Like, I don't want to hang out with her no more. Oh, okay. That's all on purpose. That sounds like something wrong. Well, that's really interesting to hear because when we delved into your date, she couldn't figure out anything that went wrong that night. Yeah, it sounds like from the way you're talking, it should be obvious. Uh-huh. Well, I feel more taking advantage of than... Oh, really? And not in the good way. the bad way. Yeah, I feel violated my pocket. What?

Your pockets. Wait, she said that you paid for dinner. Is that what you mean? Yeah, I paid $200. She doesn't tell y'all that? Yeah. She said $200, but she made it seem like that was totally agreeable and that you were happy to offer that.

That's totally not true. I mean, I was actually kind of coerced into it. Coerced. Yeah, like, she does videos. She records videos. Videos of what? Oh, she's like an influencer. Like on the date, she was recording videos?

She was doing full reviews. That's why she ordered $200. It wasn't that we were caught up having a great time. Oh, my gosh. No. Also, wait, she, like, ordered one of everything on the menu so she could try it? Yeah, and I mean, it's like the whole menu and not the happy hour menu. It was.

Oh, my God. And then, I mean, the weird part is you're at dinner and then. They're just on their phone recording. Yes. Yeah. Like, did she even talk to you? No, she told me to kind of be quiet So I don't interrupt

I'm sorry, I don't mean Now I understand a little bit more Why you feel like you were used Yeah, but though you kissed I thought she's told us that you had a great kiss I mean, hell yeah I'm not going to turn it down Okay

After what he suffered through the least he did Yeah You deserve a review on how your kiss was Because In fact we might be able to give it to you Right now since Angela has been On the other line listening Wanting to talk to you

Oh, God. Why? Why? Okay. Okay. Angela, are you there? I'm here. Oh, you sound embarrassed. Don't be embarrassed. I'm upset. Why didn't you tell us that this was for a food review? Well, it wasn't for a food review. That's what he's just assuming. But hi, Damon. Damon, Damon, talk to Angela here.

Hi. I mean, you, hey, yeah, whatever. You. I'm kind of faking the funk right now. You know that you had your phone out the whole time. We really didn't connect on anything, and you didn't even eat all the food. It was just like you were ordered the most expensive dish to take one bite and move on to the next dish.

No, my gosh. Like, I know I had my phone out, but it wasn't a food review. And honestly, David, we had, like, it was $200. You had an appetizer. I had an appetizer. You had an entree. You had an entree. No, no, no, no.

No, chose, wait, slow down. You had all of that alone yourself. Oh. And I remember because I was the cameraman, remember, you told me, hold it for me. I know. Oh, my God. I'm so sorry. I feel really crappy about that part.

I'm going to tell you. It wasn't a food review. Angela, you got to explain why were you making him film you while eating the food? It wasn't for a food movie. Like, honestly, I like you. And the reason why you're on the show today is because I turned 30, as you know, earlier this year. And I just made a personal goal to go out on 30 dates for my 30th year of life. Oh.

And I wanted to do a video for Instagram and you're number 19. Okay, Danlin, that's what's going on. You're number 19. And I don't want to go on the 20th, though. I don't like, I'm trying to tell you I like you. I don't want to go on a 20th. I like you a lot. And that's what the video was about.

It wasn't like trying to order a bunch of food. It was just doing my own little silly 30 for 30. That's it. Okay. So what happened to the other 18 dudes? The other 18 are wherever they are. I didn't go out on a second date with them. I didn't like them.

I wasn't interested. And now this is where it's stuck. So none of it was actually about reviewing the food. It was just kind of B-roll content to talk about the date. If that's the case, why wasn't I in the video at all? I was just filming you eating. Because I respect your privacy. Like, I wouldn't be going to put you on black like that.

It's actually true. I am curious, Angela, did the other. 18 dudes all have to pay for your meals too and film you eating also? Great question. So the thing is there's no have to, right? No way he's making anybody get it. Strongly suggested that they do. I get it.

Oh my God. I mean, David, where are you at knowing that this was all part of a challenge? I mean, I don't like being a part of somebody's elaborate game that they're trying to have to like boost their own self-esteem because, you know, I have my own.

It's not games, though. It's not games. It's goals. It's goals and objectives. Yeah. I'm number 19. Like, you got 10, 15 more people to go. Like, come on. I don't have anybody else to go. I want to stop with you, Damon.

Yeah, that's the point. She's doing good. That was a good line. This may have all started out as, like, a fun experiment for her, like, an interesting way to meet people. But once she met you, Damon, she decided I'm out. I'm fully committed to Damon if he's willing to give me another chance. Yeah.

And she didn't even want to tell you about it because she knew that it probably wouldn't feel good. That's true. She didn't say that. Like, it'd be weird. In fact, she rated you. you a 19 out of 19, which is the highest rating you can have. Yeah. Up to 20.

You know. If we went out again, there would be like no phone. Like, I wouldn't do any of it. I mean, that was literally just some social stuff, Damon. Like, it's not anything like that. Like, I'm just trying to. Oh, wait. Oh, wait.

Okay. I like this. Damon's taking charge. What do you need to say? If we go out again, no phone, how about this? We go out again, you spend it $200 on me. Okay. Wow.

There's a challenge for you. I like that, too. That's a challenge. How about you and your challenge on that? Okay. So it's a yes from Damon. Now it's up to Angela. Will you accept his terms and conditions?

No, I don't like his energy now. What? What? You've got to be kidding me. Dude, Angela, we work so hard for you. You better pay for that date. No, I'm not. Like, I don't, like, first of all, like, just slowed out.

I didn't make you pay for anything. Oh. But this whole, this whole added, like, that energy is not going to work for me. Like, you say, okay, why don't we make it? Like, be a little more polite about it. Like, he's been a little, I don't do, I didn't know you as gangsta. That was ridiculous. Oh, man.

He's matching your challenge. That's all he's doing. No, he's not. It's my challenge. Find your own challenge. All right. Time is running out on this segment. So, Damon, any last words before we let you go?

Wow. Don't let the game play. You play the game. Hey. Okay. Well, he kind of got played, bro. Says the guy that's out $200. Yeah.

Brooke and Jeffrey in the morning No one can resist A rule of culture, so here's one for the dating files. Rule of culture number 72. Chemistry isn't just vibes, it's values. Because what's the point of matching with someone if you can't talk about the shows you binge,

the books you dog ear, or all the hot takes you'll defend it brunch? I mean, you definitely have friends who have met their partners on Bumble, and it makes sense. It's not just about matching with someone. It's about finding someone who gets your references, your obsessions, your whole vibe with shared interests and problems. You don't just see a profile.

You get a glimpse of someone's personality, which makes it even easier to start conversations that actually lead somewhere. Plus, with photo and ID verification, you can trust that the person you're talking to is real. With that added piece of mind, it's so much easier to show up as your full self. So whether your rule of culture is,

the best first dates start with the shared hot take on Renaissance or compatibility as having the same hometown bodega order, download Bumble, and turn those connections into something bigger. Download Bumble and start your love story. On the podcast Health Stuff, we are tackling all the health questions that keep you up at night. Yes, I'm Dr. Priyanka Wally, a double board certified physician. And I'm Hurricane Dibolu, a comedian and someone who once Googled, Do I Have Scurvy at 3 a.m?

On Health Stuff, we're talking about health in a different way. It's not only about what we can do to improve our health, but also what our health says about us and the way we're living. Like our episode where we look at diabetes. In the United States, I mean, 50. percent of Americans are pre-diabetic. How preventable is type 2? Extremely.

Or our in-depth analysis of how incredible mangoes are. Oh, it's hard to explain to the rest of the world that, like, your mangoes are fine because mangoes are incredible, but like, you don't even know. You don't know. You don't know. It's going to be a fun ride. So tune in. Listen to health stuff on the IHeart Radio app, Apple Podcasts, or wherever you.

you get your podcasts. Oh, imagine, Brooke, one day you end up going 60 for 60. Oh, my gosh. 60 dudes in your 60th year. Dude, I do not want to enter the dating game again. That's true. It does go up as you get older, Jack. Challenge gets harder.

Dude, she said no. I know. What is that? Now I'm like, there's a reason she's been on 19 and no. Her intentions were a little shady at the end there. I thought it was like so cool. He was like matching her energy. He was put in a person that will push back a little bit.

You know, the give and the take. Gave too much, took too little. Darn it was. But looks like Angela has to move on to guy number 20 in her 30 for 30 quest. And I just hope whoever that guy is has a good job and steady hands. Because clearly dinner's not going to be cheap. And he's going to have to hold the camera the entire night. You know what?

I don't even want to follow her on socials. He doesn't have to, remember? Right. It's a choice. That's right. Maybe that's what modern shiver. is it's not about opening doors and pulling out chairs anymore it's holding their cameras and choosing to pay the bill oh i'm just going to ask that on the next date excuse me but do you think

i could use your phone and take a picture of you oh what a gentleman the dating world's weird and that's why we're here to help if you ever need it reach out to the show we'll call that person who's not calling you back and go check out all of our second date updates they're online wherever you get your podcast at brook and geoffrey on the podcast health stuff we are tackling all the health questions that keep you up at night. I'm Dr. Priyankawali, a double board certified physician. And I'm Hurricane de Bolu, a comedian and someone who once Googled, do I have scurvy at 3 a.m.

And on our show, we're talking about health in a different way, like our episode where we look at diabetes. In the United States, I mean, 50% of Americans are pre-diabetic. How preventable is type 2? Extremely. Listen to health stuff on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. And she said, Johnny, the kids didn't come home last night.

Along the central Texas planes, teens are dying. Suicides that don't make sense. Strange accidents and brutal murders. In what seems to be, a plot ripped straight out of breaking bad. Drugs, alcohol, trafficking of people. There are people out there that absolutely know what happened. Listen to paper ghosts, the Texas teen murders. the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas, and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The Most Texas Story ever. Listen to Business History on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, I'm Cal Penn, and on my new podcast, here we go again. We'll take today's trends and headlines and ask, why does history keep repeating itself?

Each week, I'm calling up my friends, like Bill Nye, Lily Singh, and Pete Buttigieg, to talk about everything from the space race to movie remakes to psychedelics. Put another way, are you high? Look, the world can seem pretty scary right now. But my goal here is for you to listen and feel a little better about the future. Listen and subscribe to Here We Go again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Big Take podcast from Bloomberg News keeps you on top of the biggest stories of the day. My fellow Americans, this is Liberation Day. Stories that move markets.

Chair Powell opened the door to this first interest rate cut. politics, change businesses. This is a really stunning development for the AI world. And how you think about your bottom line. Listen to the big take from Bloomberg News every weekday afternoon on the IHeart radio app, Apple Podcasts, or wherever you get your podcasts.