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Brooke
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Hari Kondabolu
On the Podcast Health Stuff we are tackling all the health questions that keep you up at night.
Jeffrey
I'm Dr. Priyanka Wali, a double board certified physician.
Hari Kondabolu
And I'm Hari Kondabolu, a comedian and someone who once googled Do I have scurvy at 3am and on our show we're talking about health in a different way. Like our episode where we look at.
Jeffrey
Diabetes in the United states. I mean 50% of Americans are pre diabetic.
Hari Kondabolu
How preventable is type 2?
Jeffrey
Extremely. Listen to Health Stuff on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Angela
She said Johnny, the kids didn't come home last night.
Brooke
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 PL ripped straight out of Breaking Bad. Drugs, alcohol, trafficking of people.
Jeffrey
There are people out there that absolutely know what happened.
Brooke
Listen to Paper Ghosts, the Texas Teen murders on the iHeartRadio 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 business. The most Texas story ever. Listen to business history on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Jeffrey
Hey, it's Brigand 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, TikTok, Facebook, YouTube, maybe. You're on YouTube right now. We love it. Let us know in the comments. And what do you see right now on the board? Well, Kalen Banks Lovelady found our podcast this way. My husband introduced me to your podcast on our honeymoon. We listened to hours and hours while in the car. And now six months later, we're still listening together on Road Trip. Oh, they're still married six months later. Congrats. I love it. I love it. Well, your brand new episode starts right now.
Brooke
Second date update. It's Brooke and Jeffrey in the morning. And when you turn 38 years old and you're still single, some people handle it just fine.
Jeffrey
Yeah.
Brooke
But others, not so much. They start looking around, wondering, why am I the only single person at the bar right now?
Jeffrey
You're not. You just feel that way?
Brooke
No, I am. Everybody else is making out except me.
Jeffrey
Oh, my gosh. That doesn't mean they're together with anyone.
Brooke
All my friends are getting married now and they're having kids.
Jeffrey
Oh.
Brooke
Maybe I should start thinking about adopting my seventh cat.
Jeffrey
Oh.
Brooke
Just to keep the other six company. You know, I want to be a good cat mom.
Jeffrey
Seven's lucky.
Brooke
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 gotta switch up my dating tactics. So let's learn about it. Angela, welcome to the show.
Angela
Hi, guys.
Brooke
Angela, happy 30th birthday.
Angela
Oh, my God, thank you.
Damon
I'm so old.
Jeffrey
Dude, you're not. You're not, but I get it.
Brooke
So you said in your email that you switched up your dating tactics at 30. What did you do?
Angela
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 gonna be on, like, 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.
Jeffrey
Oh, 30 for 30 dating.
Angela
That means I have vowed to go out on 30 dates before the end of the year.
Brooke
30 dates while you're 30 years old.
Jeffrey
Okay. It's like the 30 before 30 bucket list that's trending. Yeah. This is 30, guys. Wow. Yeah. Yeah.
Brooke
It's a month.
Angela
It's been rough. I mean, I've had to, like, speed it up. I'm on 19. I completed 19. But the thing is, I don't know if I want to go on 20, because I really, like.
Jeffrey
Okay, 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.
Brooke
Yeah. So I'm assuming that we're calling one particular guy here. But before we get to that real quick, because just because this is so interesting, your situation so unique, could you tell us, like, some of the highlights and lowlights from your 30 for 30 experience?
Angela
Okay. Four was a nightmare. Okay. He took me accidentally, and I beat him. And, like, the rest of the day, he was kind of just sulking like. Yeah, four was a nightmare. 12 brought his mom.
Brooke
Oh, yikes.
Jeffrey
All you need to say.
Angela
And she was only supposed to stay for, like, 30 seconds, and she ended up seeing the whole date.
Brooke
Oh.
Jeffrey
She said the whole time she hold his hand and tell me he was being a good boy. I really liked you.
Angela
Yeah, absolutely. Her and I still talk.
Jeffrey
Oh.
Brooke
Oh, okay.
Jeffrey
Out of the. The last 18 dates, you got a mom out of it. Hey, that's cool.
Angela
What can I say?
Brooke
Do these dudes know that you are on a challenge, or do you just go on the dates naturally?
Damon
So it doesn't.
Brooke
That's a really good question.
Angela
So, like, when I first started, I was telling them, like, trying to be all transparent. Like, one, two. I told. 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.
Brooke
It'd be a good litmus test to see how the guys are about it. If they're chill.
Jeffrey
I mean, I don't know how chill they'd be about it, Jeff. They don't really want to be considered a number. Oh, yeah.
Brooke
Unless you're a 10 out of 10.
Jeffrey
But that's what. That's what date 19 was. Does he get a name or do we just call him 19?
Angela
19 is a 19 out of 19. His name is Damon.
Brooke
Oh, wow. And he gave him a 19 rating out of a 19.
Jeffrey
That's hot.
Angela
I like Damon. Dinner was, like, really good. Like, it was. He's a genuine guy. Like, he has a really nice smile. No press. We went for a walk. We kissed. 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?
Brooke
Okay, well, hold on. You skipped really fast. What's the deal with Damon's mom?
Jeffrey
Are you in that close? No.
Angela
I hope I meet her next date.
Brooke
Okay, you want to meet this mom? That's good.
Jeffrey
Did anything weird happen on your date with Damon or awkward?
Angela
No. I mean, we ate dinner at a Mexican place. He paid and, I mean, all was well. Yeah, he was fine. I think, like, maybe almost 200 bucks. Like, it was a really nice. Everything was chill.
Brooke
That's a nice salsa. I know.
Jeffrey
Oh, my God.
Angela
Okay, listen, he got a kiss out of it, and I want to see him again.
Jeffrey
Oh, okay. 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 Tick tock? Alexis said that some of these are trending.
Angela
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 start dating. Right.
Jeffrey
Okay.
Angela
I don't know how he would find out about that because it's like, not my name on my insta, but.
Brooke
Oh, that's what I was gonna say. Search your name.
Jeffrey
But if you heard you're the latest one and it was a good date, I wouldn't be that upset.
Damon
Upset?
Brooke
You didn't post a bad post about.
Angela
Yeah, that's a compliment, right? Thank you.
Brooke
So how long has it been since you and Damon hung out?
Angela
Oh, my God, it's been like a week and a half and I haven't heard from him.
Jeffrey
Okay, like, you've texted, you've called, or.
Angela
I don't really double text, but I did text and I did do a call and, like, that's plenty, right?
Jeffrey
Yeah, yeah, yeah, yeah.
Brooke
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.
Jeffrey
What if he's doing a 30 for 30 and he's only on number 17? That's why.
Brooke
Amazing.
Angela
That would be the pits. Wait, screw him? Like, that's not even it.
Brooke
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.
Jeffrey
30Th year.
Brooke
We got it. That doesn't sound as sexy.
Jeffrey
You can't do it all in one day.
Brooke
Okay, 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. 30 years old, where she decided, I'm going to go out on 30 dates with 30 different men before she turns 31.
Jeffrey
Yeah, cuz she wants to be in a relationship. Like the goal is not to just do this, but it's also to find someone.
Brooke
Yeah, and also a little brag too. The thing is, she hasn't even reached 30 guys yet. She 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 gonna 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.
Angela
I don't have a 20. I don't.
Jeffrey
Okay. You really are committed to this guy.
Angela
I am. I am. I hope so.
Brooke
Okay, well, if. I think we're all in agreement though, that's 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.
Jeffrey
Right. Unless he saw her Instagram or something.
Brooke
We just go by number 19.
Jeffrey
Yeah, sure, 19.
Brooke
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 up. And here we go.
Damon
Hello?
Brooke
Hey, is this Damon?
Damon
Yeah, it is. Who's this?
Brooke
Hey, man. This is a radio show, actually, called Brooke and Jeffrey in the Morning.
Jeffrey
Hi, Damon. Hey.
Brooke
Hey, good morning.
Jeffrey
Sounds like we caught you. Maybe you're busy right now or something.
Damon
I mean, it's not that I'm busy. I just don't. I don't know why the radio station's calling me.
Brooke
Oh, that's funny, because we Know you at least.
Jeffrey
Okay, we've heard about him.
Brooke
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 okay, you're right. We. We've heard glowing reviews about you from one of our friends, a listener to our show, a woman named Angela.
Damon
Oh, the girl I went out with? That Angela?
Brooke
Yeah. Cuz what we're doing here, it's called the 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 bit.
Damon
Yeah, I've been. I've been blowing her off a lot. Like, kind of don't want to hang out with her no more.
Brooke
Oh, okay.
Damon
All right.
Jeffrey
That sounds like something wrong.
Brooke
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.
Jeffrey
Yeah.
Brooke
Yeah.
Jeffrey
Sounds like from the way you're talking, it should be obvious, huh?
Damon
Well, I feel more taken advantage of.
Jeffrey
Than taking advantage of.
Brooke
And not in the good way. Like the bad way.
Damon
Yeah, I feel violated. My pocket.
Jeffrey
Wait, she said that you paid for dinner. Is that what you mean?
Damon
Yeah, I paid 200. She doesn't tell y' all that?
Brooke
Yeah, she said 200, but she made it seem like that was totally agreeable and that you were happy to offer that.
Damon
That's totally not true. I mean, I was actually kind of coerced into it.
Jeffrey
Coerced?
Damon
Yeah, like, she does videos. She records videos.
Jeffrey
Videos of what?
Brooke
She's like an influencer. Like, on the date she was recording.
Damon
Videos, she was doing food reviews. That's why she ordered $200. It wasn't that we were caught up having a great time.
Brooke
Oh, my gosh, no.
Jeffrey
Oh, so wait, she, like, ordered one of everything on the menu so she could try it?
Damon
Yeah, and I mean, it's like the whole menu and not the happy hour menu. It was.
Jeffrey
My God. And then, I mean, the weird part is you're at dinner and then they're on their phone. Yeah. Recording. Y me. Like, did she even talk to you?
Damon
No, she told me to kind of be quiet so I don't interrupt.
Jeffrey
Sorry.
Brooke
Now I understand a little bit more why you feel like you were used.
Jeffrey
Yeah. Wait, but though you kissed? I thought she told us that you had a great kiss.
Damon
I mean, hell yeah. I'm not going to turn it down.
Jeffrey
After what he suffered through, the least he.
Brooke
You deserve a review on how your kiss was. Because she should have videoed it. 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.
Damon
Why? Why? Okay.
Jeffrey
Okay. Angela?
Brooke
Angela, are you there?
Angela
I'm here.
Jeffrey
Oh, you sound embarrassed.
Brooke
Don't be embarrassed. You. I'm upset. Why didn't you tell us that this was for a food review?
Angela
Well, it wasn't for a food review. That's what he's just assuming, but. Hi, Damon.
Brooke
Damon, Damon, talk to Angela here.
Damon
Hey. Yeah, whatever. You 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 will order the most expensive dish to take one bite and move on to the next dish.
Angela
No, Damon. Oh, my gosh. Like, I know I have my phone out, but it wasn't a food review. And honestly, Damon, we had like. It was $200. You had an appetizer. I had an appetizer. You had an entree. I had an entree.
Damon
Wait, slow down. You had all of that alone yourself? Oh, and I. I remember because I was the cameraman, remember? You told me. Hold your phone.
Angela
I know. Oh, my God. I'm so sorry. I feel. I feel really crappy about that part. But I'm going to tell you, it wasn't a food review.
Brooke
Angela, you got to explain. Why were you making him film you while eating the food?
Angela
It wasn't for a food review. 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. And I wanted to do a video for Instagram. And you're number 19. Okay, Dalen, 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, like, I'm trying to tell you I like you. I don't want to go on the 20th. I like you a lot. And that's 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.
Damon
Okay, so what happened to the other 18 dudes?
Angela
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 Stops.
Brooke
So none of it was actually about reviewing the food. It was just kind of B roll content to talk about the date.
Jeffrey
Yeah.
Damon
If that's the case, why wasn't I in the video at all? I was just filming you eating because.
Angela
I respect your privacy. Like, I wasn't going to put you on black like that.
Brooke
I am curious, Angela. Did the other 18 dudes all have to pay for your meals too and film you eating also? Great question.
Angela
So the thing is, there's no have to, right?
Brooke
Like, making anybody strongly suggested that they do. I get.
Jeffrey
Oh, my God. I mean, David, where are you at knowing that this was all part of a challenge?
Damon
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 games, though.
Angela
It's not games, it's goals. It's goals and objectives.
Brooke
Yeah.
Damon
I'm number 19. Like, you got 10, 15 more people to go. Like, come on.
Angela
I don't have anybody else to go. I want to stop a few damage.
Brooke
Yeah, that's, that's the point is 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.
Jeffrey
Yeah, and she didn't even want to tell you about it because she knew that it probably wouldn't feel good.
Brooke
You know, like, it'd be weird. In fact, she rated you a 19 out of 19. Which is the highest rating you can have. Yeah, up to 20.
Angela
You know, if we went out again, there would be like, no phone. Like, I wouldn't do any of. I mean, that was literally just some social stuff, Damon. Like, it's not anything like that. Like, I'm just.
Damon
All right, enough.
Jeffrey
Okay? I like this. Damon's taking charge. What do you need to say if.
Damon
We go out again? No phone. How about this? We go out again, you spending 200 on me.
Jeffrey
Okay. Wow. There's a challenge for you.
Brooke
I like that too, because that's a challenge.
Damon
How about you end your challenge on that?
Brooke
Okay, so it's a yes from Damon. Now it's up to Angela. Will you accept his terms and conditions?
Angela
No, I don't like his energy now.
Jeffrey
What?
Brooke
What? You gotta be kidding me.
Jeffrey
Dude. Angela, we work so hard for you, you better pay for that date.
Angela
No, I'm not. I gotta. Like, first of all, like, just slowed. I didn't make you pay for anything. But this whole, this whole attitude, 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. I don't do. I didn't know you was gangster.
Jeffrey
That was ridiculous. You know what? He's matching your challenge. That's all he's doing.
Angela
No, he's not. It's my challenge. Find your own challenge.
Brooke
Time is running out on this segment. So, Damon, any last words before we let you go?
Jeffrey
Wow.
Damon
Don't let the game play. You play the game. Okay.
Brooke
Well, you kind of got played, bro.
Jeffrey
Says the guy that's out 200 bucks. Yeah.
Brooke
Brooke and Jeffrey in the morning on.
Hari Kondabolu
The podcast Health Stuff. We are tackling all the health questions that keep you up at night.
Jeffrey
Yes. I'm Dr. Priyanka Walley, a double board certified physician.
Hari Kondabolu
And I'm Hari Kundabolu, a comedian and someone who once googled do I have scurvy at 3am on health stuff, we're.
Jeffrey
Talking about health in a different way.
Hari Kondabolu
It's not only about what we can do to improve our health, but also.
Jeffrey
What our health says about us and the way we're living.
Hari Kondabolu
Like our episode where we look at.
Jeffrey
Diabetes in the United states. I mean, 50% of Americans are pre diabetic.
Hari Kondabolu
How preventable is type 2?
Jeffrey
Extremely. Or our in depth analysis of how incredible mangoes are.
Hari Kondabolu
Oh, it's hard to explain to rest of the world that, like, your mangoes are fine because mangoes are incredible, but, like, you don't even know.
Jeffrey
You don't know.
Brooke
You don't know.
Jeffrey
It's going to be a fun ride. So tune in.
Hari Kondabolu
Listen to health stuff on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Angela
She said, johnny, the kids didn't come home last night.
Brooke
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.
Jeffrey
There are people out there that absolutely know what happened.
Brooke
Listen to paper ghosts, the Texas teen murders on the iHeartRadio app, Apple Podcast, or wherever you get your podcasts. Oh, imagine, Brooke, one day you end up going 60 for 60.
Jeffrey
Oh, my God.
Brooke
60 dudes in your 16th year.
Jeffrey
Dude, I do not want to enter the dating game again. That's true.
Brooke
It does go up as you get older.
Jeffrey
Yes.
Brooke
Challenge gets harder, dude.
Jeffrey
She said no. I know. What is that? Now I'm like there's a reason she's been on 19 and nobody.
Brooke
Her intentions were a little shady at the end there.
Jeffrey
I thought it was like so cool. He was like matching her energy. You know, you want a person that will push back a little bit. You know, the give and the take.
Brooke
Gave too much, took too little.
Jeffrey
Darn.
Brooke
But looks like Angela has to move on to guy number 20 in her 30 for 30 quest. And I just hope, I hope whoever that guy is has a good job and steady hands. Cuz clearly dinner's not going to be cheap and he's going to have to hold the camera the entire night.
Jeffrey
You know what? I don't even want to follow her on socials. He doesn't have to remember.
Brooke
Right, right, right.
Jeffrey
It's a choice.
Brooke
That's right. Maybe that's what modern chivalry is 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 gonna ask that on the next date. Excuse me, but do you think I could use your phone and take a picture of you? 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.
Hari Kondabolu
Brooke and Jeffrey on the podcast Health Stuff, we are tackling all the health questions that keep you up at night.
Jeffrey
I'm Dr. Priyanka Wali, a double board certified physician.
Hari Kondabolu
And I'm Hari Kondabolu, a comedian and someone who once googled do I have scurvy at 3am and on our show we're talking about health in a different way. Like our episode where we look at.
Jeffrey
Diabetes in the United states. I mean, 50% of Americans are pre diabetic.
Hari Kondabolu
How preventable is type 2?
Jeffrey
Extremely. Listen to Health Stuff on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Brooke
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.
Jeffrey
There are people out there that absolutely know what happened.
Brooke
Listen to paper the Texas teen murders on the iHeartRadio 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 ide 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 business. The Most Texas Story ever. Listen to Business history on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Angela
The murder of an 18 year old.
Jeffrey
Girl in Graves County, Kentucky went unsolved for years until a local housewife, a journalist and a handful of girls came forward with a story.
Damon
America, y' all better wake the hell up.
Hari Kondabolu
Bad things happens to good people and small towns.
Jeffrey
Listen to Graves county on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts and to binge the entire season ad free. Subscribe to Lava for Good plus on Apple Podcasts.
Brooke
Hey, I'm Kyle McLaughlin. You might know me as that guy from Twin Peaks, Sex and the City, or just the Internet Stand. I have a new podcast called what Are We Even Doing? Where I embark on a noble quest to understand the brilliant chaos of youth culture. Each week I invite someone fascinating to join me to talk about navigating this.
Hari Kondabolu
High school speed roller coaster we call reality.
Brooke
Join me and my delightful guests every Thursday and let's get weird together in a good way. Listen to what Are We Even doing on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Date: November 5, 2025
Podcast: Brooke and Jeffrey: Second Date Update
Hosts: Brooke, Jeffrey
Guests: Angela (the dater), Damon (the date)
In this episode, Brooke and Jeffrey delve into the modern dating challenge of their listener, Angela, who created her own “30 for 30” dating experiment: going on 30 dates with 30 different men during her 30th year. After stopping at date 19, having met Damon—her favorite so far—Angela is ghosted and enlists the show’s help to find out what went wrong and if there’s hope for another date.
The episode offers an engaging, comedic, and surprisingly candid look at dating in today’s social media age, highlighting the intersection of digital content and real-world connections.
Angela’s Premise: Freshly 30 and single, Angela vows to try new tactics; "I came up with 30 for 30 dating," she explains. "That means I have vowed to go out on 30 dates before the end of the year." (04:37)
Memorable Moments from Her Dates:
Notable Quote:
Damon: “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 would order the most expensive dish to take one bite and move on to the next dish.” (14:50)
Her Defense: Asserts it wasn’t a food review, but "just doing my own little silly 30 for 30. That’s it." (15:43)
Host Inquiry: “Did the other 18 dudes all have to pay for your meals too and film you eating?” (16:49)
Damon Stance: He’s frustrated with “being part of somebody’s elaborate game...I mean, I have my games though.” (17:09)
Notable Exchange:
Damon: “Don’t let the game play you, play the game.” (19:13)
Brooke: “Well, you kind of got played, bro.” (19:16)
Jeffrey: “Says the guy that’s out 200 bucks.” (19:18)
At 21:12
Angela (describing her challenge):
"I came up with 30 for 30 dating. That means I have vowed to go out on 30 dates before the end of the year." — Angela (04:37)
Angela recounting bad dates:
"Twelve brought his mom. She was only supposed to stay for like 30 seconds, and she ended up seeing the whole date." (06:10)
Damon, on being used:
"I feel violated. My pocket." (12:54)
"You had your phone out the whole time...you will order the most expensive dish to take one bite and move on to the next dish." (14:50)
Angela defends herself:
"It wasn’t for a food review...I turned 30...just made a personal goal to go out on 30 dates for my 30th year of life. And I wanted to do a video for Instagram. And you’re number 19." (15:43)
Negotiation standoff:
Damon: "We go out again, you spending 200 on me." (18:14)
Angela: "No, I don’t like his energy now." (18:32)
Damon’s parting philosophy:
"Don’t let the game play you, play the game." (19:13)
| Time | Segment | |-----------|-----------------------------------------------------------------| | 03:20 | Show and Angela’s challenge introduced | | 05:58 | Angela shares date horror/comedy stories | | 07:16 | Angela describes the date with Damon | | 08:54 | Angela reveals she's been ghosted, asks for help | | 11:33 | Call to Damon, he gives first reaction | | 12:25 | Damon explains why he ghosted Angela | | 13:26 | Damon details "food review" and feeling used | | 14:27 | Angela joins, clarifies her intentions | | 18:14 | Damon’s counter: “You spend $200 on me.” | | 18:32 | Angela refuses, cuts off the possibility | | 21:17 | Hosts recap, analyze and joke about modern dating |
The conversation is playful, direct, and candid. Brooke and Jeffrey provide supportive but humorous commentary, poking fun at dating challenges while acknowledging both guests’ feelings. Angela is energetic, defensive but honest; Damon is blunt and a bit wounded but good-natured.
This episode dives headfirst into the realities of contemporary dating, social experiments, and the expectations (and pitfalls) of mixing content creation with real relationships. Angela’s “30 for 30” approach is ambitious, but her surprise at Damon’s pushback after feeling used highlights the complications of dating in an age where every experience might be performance. Ultimately, neither is willing to budge, and both part ways—Angela onto date #20, and Damon $200 lighter but a little wiser. The hosts deftly balance comedy and empathy, making this a must-listen for anyone navigating, or simply bemused by, the modern dating scene.