Brooke and Jeffrey: Second Date Update - Second Date Update: Till Date Do Us Part

Episode Date: September 17, 2025

For one of our listeners, the hottest thing that happened on her date was a game of CHARADES! Yeah, Charades! We’ll dive into that coming up in a new Second Date Update podcast!See omnystudio.com/listener for privacy information.

Hey, everybody, this is Matt Rogers. And Bowen-Yang. And you're never going to guess who's our guest on Las Culturistas. It is Elle Woods, Tracy Flick, herself. Reese Witherspoon. Louise, it must go in a girl's trip. I have to have a tequila. We must.

Oh! Whoever said orange is the new pink. We seriously disturbs. Listen to Las Culturistas on the I-HeartRadio app, Apple Podcast, or wherever you get your podcasts. Hi, my name is Enya Umanzor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie and you love crimes, we're not the podcast for you.

But if you have unmedicated ADHD... Oh my God, perfect. And want to hear people with mental illness, psycho babble. Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app. Search Emergency Intercom and listen now. Hey, it's your favorite jersey girl, Gia Judice.

Welcome to Casual Chaos, where I share my story. This week, I'm sitting down with Vanderpump Rule Star, Sheena Shea. I don't really talk to either of them, if I'm being honest. There will be an occasional text, one way or the other, from me to Ariana. Maybe a happy birthday from Ariana to me. I think the last time I talked to Tom, it was like, congrats on America's Got Talent. This is a combo you don't want to miss. Listen to Casual Chaos on the IHeart Radio app.

Apple Podcasts or wherever you get your podcasts. Betrayal Weekly is back for season two with brand new stories. The detective comes driving up fast and just like screeches right in the parking lot. I swear I'm not crazy, but I think he poisoned me. I feel trapped. My breathing changes. I realize, wow, like he is not a mentor. He's pretty much a monster.

But these aren't just stories of destruction. They're stories of survival. I'm going to tell my story and I'm going to hold my head up. Listen to Betrayal Weekly on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Bridget Armstrong,

host of the new podcast, The Curse of America's Next Top Model. I've been investigating the real story behind that iconic show. I ended up having anorexia issues, bulimia issues, by talking to the models,

the producers, and the people who profited from it all. We basically sold our souls, and they got rich. If you were so rooting for her and saw her drowning, what did you help her? Listen to the curse of America's Next Top Model on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Hey, it's Brick and Jeffrey, and this is your brand new second date podcast. Thanks so much for being here. And yesterday's awkward Tuesday was really a lesson on why you should never hire your friends.

It actually turned out great for him. He wasn't doing the job, but then somehow got promoted above her. Whatever he's doing, he's doing it, right? Yeah, I guess. Apparently. Hopefully she'll take the time to figure out that she is happy for him in the end. But we definitely got some comments on the situation, Alexis. Yeah, well, someone said, in all caps, we need an update from that awkward Tuesday phone call to know what happens to her.

And someone else said, I love awkward Tuesdays. Please consider doing awkward Wednesdays, Thursdays, Fridays. I need one more awkward day in the week. week. Oh, man. God, that would be a lot. Yeah. And then a lot of other comments saying, why is she not happy for her best friend? And then other people saying, wait, what kind of company promotes a guy that sounds like he never shows up? Yeah, it was all over the place. I saw one one that said, hey, I hired my best friend as my manager and I work with my husband as my boss. Oh, my God. I was like, it's great. But I was like, for now. For now. It's a very, very tight knit.

Yeah, you got to be careful with that one. It's a careful balance there. Sensitive situation. Yeah, for sure. Well, we always love reading your comments. So thank you so much for being here and for participating and for subscribing. We love that too. We're going to start your brand new second date right now. Second Date Update. We've been doing second date updates on our show for what now?

Over 10 years? Yeah. No longer. It feels like 100 years. 50, 75. Somewhere around there. And it's interesting because when we first started, we found it so weird that more and more people we're meeting strangers from online.

And now we find it odd that more and more people are choosing to go back to meeting up in person again. Yeah. Who wants to do that? It's so weird. We've kind of come full circle. Yeah. I know. I met her at a bar and we're like, was it scary?

Yeah. And that's exactly how I'm feeling about today's listener who reached out to us. Mia, she needs our help. Mia, what were you thinking? Meeting a guy in person? It must have been terrifying for you. Well, I mean, it was at a friend's housewarming party, so, you know, there were a bunch of people there. So you didn't, you didn't scream and run until 30 minutes into the...

Yeah. I mean, he might be the one who screamed and ran. I'm totally into him. Okay. You met him at a house party. You had mutual friends there clearly. What's the guy's name? Owen is his name.

Can I ask her quick? Was this like a mutual... setup type of sitch? No, I don't think so. I mean, she certainly didn't say anything to me if it was. Okay. Stay with me because this sounds a little nerdy, but he was dominating charades. Yes.

Brooke, it's exciting. Yeah, it's hot. Show me how you mime that word, okay? When you say house party, I was picturing like beer pong and games like that. The game, Fishbowl is so popular. I pay out every party with my friends. You could drink fish bowls at the same time you play it. Yeah, there was a bit of alcohol going around for sure.

Well, that's good here. So tell us about the connection that you and Owen, like, have that happen. Well, I went up to him afterwards and was just like, wow, that was pretty impressive. You're really great at that. I'm like, I'm a terrible mime. So I was just like, wow, you know. And then the very next day, he reached out to me through our mutual friend, Julia. He got my number through her.

I know, yay. Okay. He took the initiative. Yeah, and he took an extra step to even make it happen. Yeah, he took initiative, and we were just sort of texting kind of casually back and forth, but pretty quickly he turned it into a date. He was like, let's go to this retro arcade. Oh, like a barcade?

Do they serve drinks there? Yeah, it's like a bar, but then there's like, you know, video games and there's like pinball and stuff. What was it like between you, you two, and it was just one-on-one? I thought it was really good I mean we met there but he had dressed up you know he looked really great and that's kind of cute

to the bar or to the arcade yeah what do you mean dressed up yeah like in a tuxedo or no not like touch but like I don't know just like I could put some care into it yeah the fact that he has pants on that's a big win or a big loss depending on what kind of date you want if it's going that well

you might want them off so for first date I'll take the pants okay fair fair so I mean what were the highlights or low Let's, like, paint the picture for us. Well, I'm really good at pinball, so it meant that I kind of got to show off that time. Yeah.

Oh. Is this really a flex? Yeah, she's a flipper queen. Is that the name? I don't know. It took over the high score. Is that where we're at, where we're looking for in a significant other? I just think any time someone can nerd out about something that they're excited about is a positive.

Their passion. Yeah. Was he rooting you on at the pinball? machine? Totally. Yeah. And it was just really fun. He had that same kind of energy as the first night that I'd seen him of just being really funny and really upbeat. And he shows me this picture of himself from high school that a friend had sent to him. And I'm like, oh, yeah, you know, he's kind of dorky then. But he goes, no, no, no, look over there. The bartender has my same haircut. That's awesome. You know, you can kind of just like poke fun at himself.

I was confused. I thought you met bartender in the photo. And I'm like, wow. How did you get into a... I'm sorry. No, I still think... Bartender in the arcade has the same photo... Has the same hair cut as him in high school. I thought it was in the picture. No, no.

I get it. Okay. So you both went over to the bartender and gave him a wedgie. Yeah. To get back into the mode. Oh, she liked that. Okay. Tell us, how did it end that night?

There was a nice kiss at my car as I was leaving. Good. Cute. Yeah. I mean, it seems like a really good date. Like, there's no red flag, but that was six days ago. Six days. And he didn't ghost me, but he's not initiating any conversation.

And he's like, one word responses. Like, I'm like, hey, how was your day? He's like, good. Oh, man. That feels so bad. Sometimes I'm like, I just wish they just leave you alone then. Yeah. You know, like, why even write the one word?

I mean, sometimes I'll say that, but then I'll follow it if I'm really busy with being like, good. And then be like, sorry, it's short text. I'm really busy. Like, we'll talk later. You know, like, just to clarify, because it does feel kind of. Well, I don't know. Mia, what did you think he meant by good? Well, I'm just figuring.

He doesn't want to hear from me, but he's not ghosting me because we have this mutual friend. I asked her about it, and she's like, oh, he didn't see anything to me. Oh, I forget about the friends. So he can really ghost you because you guys are going to see each other maybe some day. All right. You're getting the vibe that he's kind of politely trying to avoid you now. So we need to figure out what's really going on. We're not going to let that happen.

No. No. No, no politeness here. That's his answer, though. That's his answer. Like, oh, I'm not interested. No, we're going to make fun of him for that answer. Thank you.

And for that bad haircut he had in high school. Exactly. We're going to bully him into a second date with you, whether he wants it or not. When we come back, call him and get you a second date update. Go get him. We'll do it next. Second date update. Every man knows if a woman tells you it's fine.

Yeah. Uh-oh. Things are not. fine at all. So when our listener, Mia, texted her date, Owen, asking how his day was going, and he replied, good, she knew instantly, yikes, good, that's bad. Right, Mia? Yeah, I think so.

I'm laughing because every single person in the room is totally following along. The girls are like, yep, that's right. It's true. She says that's right. You say that's right. Doesn't everyone agree with that? I mean, even I have to agree, but come on guys. That's a little better than fine, though.

There's hope. Yeah. It is better. It's weird because your arcade date, the way you described it to us, sounded like it went just fine. Like, I would go as far to say it went good. But maybe that's bad. It's good bad.

I don't know. It went great because there was a kiss at the end. Oh, yeah, yeah, yeah. Okay, that is undeniably a good sign. That's a good point. But who knows what words mean anymore. So it's safer to just call Owen and ask for his thoughts directly on it. You know, sometimes you got to read between the lines, Jeff.

It's not just black and white. all the time oh i see what you're saying i'm reading in between the lines of that sentence right that's right should you be yeah see do is she wants you to read i'm thumbs downing this message okay i don't know what to do other than just dial owen's number and pray that he answers welcome to be a man okay mea good luck to us on this good luck to you what about me yeah it's more about her than you or me you have to read between the lines of what i said too no we only take you literally We're only one-dimensional, Jim.

You know what? It's fine. I'm just going to dial the number. Here we go. Hey, Owen. Thanks for answering. We're a radio show. We're called Brooke and Jeffrey in the morning.

Hey, Owen. Welcome to the show. How's it going, Owen? I've been saving that one. That's pretty good. However, I'm on you there? Yeah, I just, what's going on? Sorry.

Hey, man. So, yeah, this is, it's a segment we do. It's called the second date update. Okay. Okay. I don't know if you're familiar with it, but. I'm not familiar with it now. Okay.

Well, just to clue you in, it's basically where we help out our listeners. If they've gone out with somebody on a date recently and they're not getting a call back for a second meetup, they come to us to try and reach out and figure out if there's a reason why. Okay. Okay. And so we heard through the grapevine that you are really good at charades. Oh, yeah. It is so disappointing this is a radio show because there's no way for us to tell.

Oh, yeah, we can't let you prove it. So, um, what are that charades now? I'm sorry. This is still pretty random. Yeah, so I know that's a little bit of a deep cut, but we heard that from Mia, the girl that you went on a date with after the housewarming party you met her at. Yeah. Did you like Mia?

Did you guys have a good time? The date was pretty good But a few days later I did look her up on social media Okay Yeah that's very normal How does that change things Look I don't know if I'm comfortable

Telling you guys I mean if it's on social media It's obviously not something she's trying to hide What did you see? Like a picture or a post Um Okay I guess I'll just tell you guys

Um So she was in like a wedding dress and doing, like, wedding things. Doing what? Wedding things. I mean, I didn't see her, like, with a groom or anything, but she was there in a wedding dress. What?

Oh, whoa. And so how are you reading that as she's obviously married? Yeah, you don't just put on a wedding dress, usually. Well, modeling people do. Wedding dress Wednesdays at the office we do that sometimes. Wedding dress Wednesday? Why do I always have to hold Jeff's veil? Right.

How are you reading that, Owen? I'm not sure exactly how to read it. Yeah, but that's so weird. It's a lot. You think about it. Oh, and you got her phone number from your guys' mutual friend. Like, why wouldn't your mutual friend

have given you a heads up if she was married? Yeah. There's no chance. I did speak to our mutual friend and she's only known her for a few months. So she doesn't know about it. I mean, I don't know if that means it did or didn't happen. We're not sure.

Well, you can't write her off. You got to just ask her. You know, I don't really want to be a part of any kind of drama. I mean, if she got married, I mean, if it's new or old, it's just not something I don't think I'm going to be into. But you don't know what it is yet. Yeah. And the good news is these second date calls, usually very low drama.

And we can prove that to you by introducing you to Mia on the other line of this call, who's been quietly listening the entire time. Hey. Well, what's going to? Hey, Owen. Why is she on the phone? Well, that's kind of how we make this segment work. Yeah.

It's by having them quietly listening to hear the reason they're not getting called. Well, you need to tell me stuff that if I'm going to say stuff like that. Well, that's going to make it more dramatic. I'm trying to give it low drum. And would you have been honest if you knew she was on the line, bro? It's on her social media. She knows it's there. Yeah, you could have said much worse.

Yes. Now she has a chance to explain. So go ahead, Mia, jump in. And what's the deal with your wedding dress picture that you have online? Okay, I did do a photo shoot in a wedding dress. Why? Why? What's the point of that?

She's like, it was for a wedding that I was in. But, you know. Wedding dresses are typically worn at weddings. But I'm not married. Well, it was sort of a wedding without a groom, you know? Like, I want to get married sometime. I love love. And my friend was like, look, you have been wanting this for so long and you're not doing anything

about it. You need to do more to manifest it in the world, you know, to like put the desire out there. So I just did this little wedding and a photo. shoot had a little party like we cut cake we I dance with my dad I mean you paid for a fake wedding oh yeah it's like I wanted the party and I wanted to like just put it out into the world that I'm ready for that that's like kind of cute I mean what is owen okay yeah oh and that's not weird right she had a wedding for herself yeah I think that's pretty weird I mean I'm not conventional that's for sure yeah but weird I mean she's manifesting right they always say like dream boards and

stop. Brooke, it seems like you're a little bit on the fence about this. Where's your head at? I don't know. I mean, I could see both sides. Like, that's a lot to give any other single person all at once. I think you need to edit the caption on that photo to say, I am not married. Disclaymer. You know? I don't know that that helps.

Or like my future wedding. I don't know. Owen, where are you out with this? Well, I don't know. I mean, like you said, the guy or guys that you're going to date, you're going to see this. So that could put a lot of pressure on a person. Okay. Oh, she's, yeah. That makes sense.

Clearly, we need to get you into a tuxedo and have you slow dance with your mom for you to really understand what's going on here. I just feel like, my doing this means I got the party, so it actually takes the pressure off of any guy that I'm dating. Sure. No. Wait, that's your second wedding, then, if you ever get married, it doesn't even count then. Hey, second weddings count. Wait. People have second weddings all the time.

Do you divorce yourself then and then start over? It's not a legal marriage, Jose, so you don't have to worry about all the minutia of it. The bottom line we're trying to figure out is fake wedding pictures aside. Do you feel like you have a connection with each other? You guys sounded so cute together. Like you bonded, you had a great, you had great chemistry. You got to the bottom of this really quickly. A good first kiss.

And if any of that is true, then it's worth pursuing another date and we would pay for it. I got to be honest with you, I don't think this is going to work out between us. And I'm just going to bow out. Oh, okay. Wow, he's got cold feet. But, Owen, she's good at pinball. You can't forget that. She's actually great at pinball, and I wish she would have posted that on social media instead.

Oh, she still can if you're willing to give her a shot. She'll just be in a wedding dress. Owen, I had a really fun time on our date. I thought we had a really good connection, and I just don't know why this feels so weird, because I want to be married, and that's not that unusual. Well, I mean, the picture is a little bit unusual, especially the photo of you dancing with your dad and cutting the wedding cake and throwing the bouquet. I bet you had a lot of likes, though. Yeah, that's true.

My wedding photos got me so many likes. Oh, maybe I should take some. Yeah, seriously. But, Owen, I mean, this is the last time I'll ask, will you give Mia one more chance? It sounds like you're asking. Will you give Mia? I'm down on one knee. Will you take Mia to be your lawfully wedded date?

date for one more night and we'll pay for it. Smooth. I hate to say it again, but just no. Oh, man, we tried. Oh, man, Mia. Well, I don't have to wonder anymore, so thank you guys. You still sound so nice.

I don't know. Maybe make your social media private and that way you can explain it before people see it. My goal is to put it out in the universe. It's not to be private. It's going to be out there public for everybody to see. and maybe that's my screening mechanism. If a guy can't handle it, then he's not right for me.

Oh, it's going to be your new standard. Her new handle is when Mia gets married. Oh, I love it. I'm going to follow. Good luck for the next 20 years of dating, Mia. Brooke and Jeffrey in the morning. Hey, everybody, this is Matt Rogers. And Bowen Yang. And you're never going to guess who's our guest on Lost Cultureistas.

It is Bradley Jackson, L. Woods, Tracy Flick herself. Reese Withers. Spoon. It must go in a girls' trip. I have to have a tequila. We must. Oh! The Q rating.

When they run diagnostic on you guys. I'd be scared. I'll run the Q rating. No, on the Q rating. My resiliency score is down to adequate because we were on a red eye. My resiliency score. Where's your grit? My grit.

I got to get my grit score up. Now, don't think that you're going to come out Los Culturistas to the podcast, and we're not going to at least bring up Big Little Lies season three. Whoever said orange is the new pink. We seriously disturbs. Listen to Las Culturistas on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Jorge Ramos. And I'm Paola Ramos. Together we're launching The Moment, a new podcast about what it means to live through a time as uncertain as this one.

We sit down with politicians. I would be the first immigrant mayor in generations, but 40% of New Yorkers were born outside of this country. Artists and activists, I mean, do you ever feel demoralized? I might personally lose hope. This individual might lose the faith, but there's an institution that doesn't lose faith. And that's what I believe in.

To bring you death and analysis from a unique Latino perspective. There's not a single day that Paola and I don't call or text each other. sharing news and thoughts about what's happening in the country. This new podcast will be a way to make that ongoing intergenerational conversation public. Listen to The Moment with Jorge Ramos and Paola Ramos as part of the MyCultura Podcast Network on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Man, I don't know if I can do these much longer.

What? Did they break you? I get too invested, so when they say no, I feel like I'm getting rejected for a second. I do kind of feel like she should have got a date or she should still. I don't know. I can also understand his side though. It'd be a lot to see that. Like if I saw a dude in a tux pretending to have a wedding on Instagram after I went out with him,

it'd be hard for me. Yeah, but it is a bummer because Mia was, and I'm going to actually use Brooks words here, she was just being her authentic self. Yeah. She said, I'm not going to hide my real ambitions. I'm just going to put it out into the universe and see what comes back to me. I agree with that, but I didn't ever use those words. But, yeah. You've used those words at some point. Yeah.

So, that's tough. We'll edit it together. Yeah. And I just really hope that Mia finds love and stays far, far away from our show as long as possible. Because I can't take any more rejection. Oh, sorry. I can't do it. Wow.

You're so fragile. Remember. She finds a guy who just has a tucks in his picture. That would be great. Do it on somebody else's show. Remember, you can listen to all of our second date updates, wherever you get your podcast on Apple, on Spotify. We even have them up on YouTube. Join in the millions who listen each month just by searching Brooke and Jeffrey in the morning.

Hey, everybody. This is Matt Rogers. And Bowen-Yang. And you're never going to guess who's our guest on Las Culturistas. It is L. Woods, Tracy Flick, herself. Reese Witherspoon. Louise, it must go in a girl's trip. I have to have a tequila.

We must. Oh. Whoever said orange is the new pink. We seriously disturbs. Listen to Las Culturistas on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. Hi, my name is Enya Humanzor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom.

If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect. And want to hear people with mental illness, psychobabble. Yes. Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app.

Search Emergency Intercom and listen now. Hey, it's your favorite Jersey girl, Gia Judice. Welcome to Casual Chaos, where I share my story. This week, I'm sitting down with Vanderpump Rural Star, Sheena Shea. I don't really talk to either of them, if I'm being honest. There will be an occasional text, one way or the other, from me to Ariana. Maybe a happy birthday from Ariana to me. I think the last time I talked to.

Tom, it was like, congrats on America's Got Talent. This is a combo you don't want to miss. Listen to Casual Chaos on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Bridget Armstrong, host of the new podcast, The Curse of America's Next Top Model. I've been investigating the real story behind that iconic show. I ended up having anorexia issues, bulimia issues, by talking to the models, the producers, and the people who profited from it all. We basically sold our souls. and they got rich.

If you were so rooting for her and saw her drowning, what did you help her? Listen to the curse of America's Next Top Model on the IHeart Radio app, Apple Podcast, or wherever you get your podcast.

Betrayal Weekly is back for season two with brand new stories. The detective comes driving up fast and just like screeches right in the parking lot. I swear I'm not crazy, but I think he poisoned me.

I feel trapped. My breathing changes. I realize, wow, like, he is not a mentor. He's pretty much a monster. But these aren't just stories of destruction. They're stories of survival. I'm going to tell my story, and I'm going to hold my head up. Listen to Betrayal Weekly on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.