Brooke and Jeffrey: Second Date Update - Second Date Update: Bachelor Party of One

Episode Date: January 26, 2026

This may be the BIGGEST RED FLAG we’ve ever heard on a first date… yet somehow, they still hooked up afterwords?? See omnystudio.com/listener for privacy information.

Hey, it's Joel and Matt from How to Money. If your New Year's resolution is to finally get your finances in shape, we've got your back. Prices, they're still high and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Yeah, each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence. Listen to how to money on the IHeart Radio app, Apple Podcasts, or wherever you get your

Podcasts. This is Dr. Jesse Mills, host of the Mailroom podcast. Each January, men promise to get stronger, work harder, and fix what's broken? But what if the real work isn't physical at all? I sat down with psychologist, Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the Valley of Despair is realizing this has happened, and you have to make a choice whether you're going to stay in it or move forward. Our two-part conversation is available now. Listen to the mailroom on the I-heart radio app, Apple podcasts or wherever you get your favorite shows. This season on Dear Chelsea with me, Chelsea Handler, we've got some incredible guests like

Kumail Nanjiani. Let's start with your cat. How is she? She is not with us. Okay, great, great, great way to start. Maybe you will cry. Ross Matthews. You know what kids always say to me?

Are you a boy or girl? Oh my God. That's so funny. I love it. So I try to butcher it up for kids so they're not confused. Yeah, but you're butching it up is basically like Doris Day. Right? No, I turn into Be Arthur. Listen to these episodes of Dear Chelsea on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts.

This show contains information subject to, but not limited to personal takes, rumors, not so accurate stats, and plenty more. What's up, man? This is your boy, Nav Green, from the Broken Play Podcast. Look, it's the end of the season, the playoffs are here. But guess what? It ain't the end of your season. You can always tune in with Broken Play Podcasts with Nav Green on the Black Effect Podcast Network. Not a team who ain't going to the playoffs. The chief.

It's time to rebuild. Listen to Broken Play with Nav Green from the Black Effect Podcast Network on the Iheart Radio app. Apple Podcasts or whatever you get your podcast. You know Roll Doll. He thought up Willie Wonka and the BFG. But did you know he was a spy? In the new podcast, The Secret World of Roll Doll, I'll tell you that story, and much, much more. What?

You probably won't believe it either. Was this before he wrote his stories? It must have been. Okay, I don't think that's true. I'm telling you. I was a spy. Listen to the secret world of Roll Dahl on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

All right, it's Monday time for a brand new second date update. And Jose Mu Karama commented, the second date pissed me off and the second date update pissed me off. So, you know, I'm concerned that this person's going to feel what they hear about today's Bachelor Party guy. Yeah, well, at least we don't have. have an update, update, update. Yet.

That's true. That's true. So I don't know how today will affect your emotions, but let us know in the comments after you hear it. You will be moved. It'll be emotional for you. Moved is the word. Yep.

Your brand new second date update right now. Broken Jeffrey in the morning. Second date update. Out of all the crazy places we've heard of people meeting each other on this segment. Yeah. Mid-convenience store robbery. We're in the colonoscopy prep area. Oh, that one was cute.

Very sweet. I mean, we've definitely heard some strange meetups before that you'd tell stories about for years if it ended up working out. Yeah. I don't know about this one. Because one of our listeners says he met a woman while attending his own bachelor party. Oh, no. His words, not mine. Should we have him on the phone, Jeff?

Well, I'm curious to hear what the story is, at least. Hopefully he's single now or something. Maybe he was an open marriage. I don't know. Oh, that's true. I would never think about that. We have a lot of questions, so we need to talk to this guy. Rick, hey man, welcome to the show.

How you doing? We're confused. I feel like you needed to come in with more than just how you're doing. Like, hey, big misunderstanding. Did I read this right? This is your bachelor party? It was my bachelor party. Oh, wow.

Honestly, I'm pushing 40, and I've been to all of my friends' bachelor parties. I spend tons of money on them. And I felt like it was time to. celebrate me. Wait. You threw yourself your own bachelor party, bro. But that means you're getting married. Were you getting married?

No, I'm celebrating that I'm a bachelor. It's a bachelor party. That is, I just had this combo with a friend. I was like, you guys, I'm never going to have a bachelor party, but their bachelor parties have always been fun. That is funny because bachelor parties are always, are typically celebrating the end of being a bachelor, but you're actually celebrating currently being a bachelor. Exactly.

Okay. That's good, but you probably have to explain that to women when you're out. Yeah. Hey, I'm not actually getting married. You think you found the reason he's not going to call back? Yeah, maybe. He came off as a fiancee that's cheating. Well, we don't know. We don't know what the story is or who we met. Like, we need to hear it from you, Rick. Tell us what happened.

So, yeah, we had a, I threw the party downtown and there was lots of drinks and fun. And we went to a bunch of clubs. It was a great time. And this is you and, like, what, a group of your guy friends? Yeah, it was about six of us total. And is there anything indicating Bachelor Party as you're out? You know, like girls will wear sashes and white dresses. Oh, yeah. We just kind of wear like suits and stuff, I guess.

Do you have any of that? I mean, we all dressed up nicely, but yeah, we didn't have coordinating outfits or anything. And carrying her girlfriend, her fiance's head around on a stick. Yeah, yeah. Like the girls threw the bar. Yeah, yeah. Is that what you guys do? I got to love to our friends, boyfriends.

I'll show you. Yeah. All right. We'll do that after we talk to Rick more about his bachelor party. So apparently you ended up meeting a. a girl while you were out? Yeah. At one of the clubs I met this girl

name is Riley. She's great. And we hit it off right away. But as you can imagine, she was immediately skeptical thinking that I'm about to get married when she found out about the bachelor party. Oh.

It's because you're calling it a bachelor party, bro. So everyone's assuming you're getting married. Exactly. Well, it wasn't my fault. Like, I was talking to her. And then one of my buddies comes up behind me. And he's like, dude, congrats on the bachelor party. And then he, like, runs off.

Oh. No, accidentally blocked you. And I assume you try to explain, but then you would just come off as a bigger liar. Yeah, that's bad. No, no, no, no. I've been single for way too long. No, I'm celebrating being single. Yeah.

Never being married. It's not an easy explanation. I'm like, no, this is a branding issue. You know, I finally, I brought another friend over, and he explained the whole thing, and she got it. She did. Yeah, she did. Or at least she pretended to get it. Well, I mean, if she stayed around, then she probably believed you.

She went to the bathroom, did a quick Google search, checked your insoling. So was there more to the evening after that? There was. So I got in a hotel room because it's my bachelor party. And at some point, Riley and I decided to sneak off and I ditch my own party. Oh, okay. Nice though. That's awesome.

Riley went to the hotel? Yeah. And she stayed the night. Okay. Wow. None of this. I mean, it sounds really fun, really fun. Uh-huh.

It does not sound like something you'd expect to call back from. Yeah. That's a good point. Why not, Brooke? Why wouldn't you get a callback after such a romantic evening? I mean, did you indicate to her how interested you were in her? I did. Like in the morning, you know, we had had all these, like, lots of long, deep conversations.

I really felt like we connected. So in the morning, I was like, we need to see each other again. We need to continue this. Oh, okay. You were really direct. I was, and I thought she was on the same page. But that was four days ago. and she hasn't responded since.

I've sent her texts and I've gotten nothing. Maybe she's still nursing her hangover. Yeah. Like the bright light of my phone is too much. Yeah. I mean, we didn't drink a ton to be honest. We drank, sure, but it wasn't like blackout drunk or anything. Okay.

Yeah, there was romance, but we talked a lot. We really got to know each other. So maybe that's the problem then. Oh. I mean, if Brooke's going back to a guy's hotel, she does not want to talk. That's for sure. Well, I mean, after a night of the club, I don't think anybody does. I think what you experienced is unusual for sure and special. Like, I could understand why you're upset. I'm just confused because I know people and I could read her and she had strong feelings

for me. I could tell. So I just don't know what to make of this whole thing. Huh. Maybe she's not being fully honest with you about where she is in life. Well, she did a bachelor at party. Yeah. Wait a minute. It was a birthday party, she said, so. Okay. All right. Who knows what that means?

We're going to find out when we call her and hopefully get some answers. And maybe if this goes well, we can throw you another real Bachelor party somewhere down to live. Dude, I'd love to join your bachelor party. We'll find out when we come back for your second date update. I'll do it right after this. Hold on. Brooke and Jeffrey in the morning, second date update. Our listener, Rick, has given us a whole new definition.

for the term bachelor party. Yeah. Because he threw one for himself recently, even though he's not getting married. No, not even in a relationship. No, he did it to celebrate his status as a single, eligible young man, an actual bachelor. Okay, most people would just call it single guy's night out. That doesn't have the same ring to it, though. You don't get people to buy you drinks if you say that.

Yeah, but you don't have this terrible misunderstanding that he had. I don't know if there was a misunderstanding because while he was out partying with his buddies, that's where he met a woman named Riley and ended up bringing her back to his hotel room, where they spent the rest of that night talking and having deep, meaningful conversations. It sounds like Jeff is using his sarcasm voice, but that was real. Yeah, really, which again, total opposite of your typical bachelor party, end of the night affair. But that's why he's so confused about why Riley's been completely ignoring him afterwards. I mean, Alexis, you would call him back, right, after a night like that?

I mean, to be fair, when you just said, like, men's bachelor hotel room, I kind of got chills of how dirty it might be. Not going to lie. I mean, Rick, what was the state of your hotel room? It wasn't that dirty. I mean, we did pre-party there, but I tried to hide the shop bottle, so it wasn't that bad. Okay. So then, yeah, I would call him back. Oh, okay.

Well, let's see if Riley, first of all, answers our call. And second of all, she has an explanation for why she's been ignoring you for the past four days since your intimate hangout. I hope so. Hopefully we could turn this around for you, Rick. Don't be so sad. Yeah, man. I'm just nervous.

Okay. You guys know you had chemistry. You have that, bro. Yeah. And remember, you are a confident single bachelor. Yeah. Any woman would be lucky to have you. Did you guys hear what I said before?

I'm pushing 40s, so this might be my last chance. Oh, you're a guy. You got easily a good 15 years left, you know? You can date well into your 70s and still catch like a 20 or 30s. with enough money, that's true. That is true. We all have faith in you. Let's see if Riley picks up the phone.

I'm going to dial the number right now. Here we go. Hi, is this Riley? This is. Hi, Riley. Hi, good morning. Hi. What is this in regards to?

Yeah, this is, we're a radio show. We're called Brooke and Jeffrey in the morning. And we're doing a segment called the second date update. And we would love if you could be a part of it. Yeah, yeah. Just yeah. Okay. You're able to be convinced of anything, aren't you?

You're going to go with the flow type of person. So is this about one of my friends then? No, not really. This is more about you and why you're not calling back one of our friends, a listener to our show named Rick. Actually, I've changed my mind. I don't want to participate anymore. Wait.

Hold on. Oh, gosh. This is, that's a crazy reaction. Yeah. Yeah, I mean, I just, I don't really know what to tell you. I was really upset in his room. So, I mean, if he didn't already mention that to you, I guess that that means that I hit it pretty well. The way that he told it to us was that you two went back to his room and basically spent the entire night talking and getting to know each other.

And he felt like the two of you connected on a deeper level. Honestly, I don't really want to talk about it because if I do, I think it might make me mad again. You sound mad already. So I feel like we're past that point. Was this hotel room at home? Total mess. Is that what it was? No, that honestly would have been way better. Oh, shit.

I tried. Okay. Would you mind sharing with, I mean, we don't want to pry too deep into your personal life, but it would really help Rick if we could know just a little bit about what he did wrong or? Well, I mean, we had been together probably three hours at this point and we, you know, we were really connecting. And honestly, like, my intuition was like, oh, my God, like, this could be the one. I mean, I feel stupid now that I was thinking that, because obviously he wasn't. And I was like, I want this to be more. And so we were talking for like a really long time. And I asked him, like, if we were together, like, we were boyfriend and girlfriend.

And we broke up, would you date someone similar to me afterwards? Oh, God. You asked a theoretical. Okay. Would you get into a hypothetical question? I'm getting together and then breaking up. So what did he say? Yeah, his answer is important.

That you didn't like. He said, no, that's impossible. You're a one of one. Aw, that is. No, that feels like a good response. Because he immediately went to we would break up. And that was the point. Like, he should have been like, no, of course not.

We would never break up because you're my person. For me, that would have freaked me out if someone would have said, well, never going to break up on the first night I met them. I'd be like, whoa. Yeah, that's a great point. But Brooke, they had hung out for three whole hours. Yeah. I mean, don't you think that, man, that's pretty harsh.

I know to totally cut him off after that. I just feel like when you know, you know, and he obviously didn't know that I was his person. And so why would I waste my time? Rick told us that you guys talked for hours. And I don't know if that question even, like, resonated with him in the same way that it did with you. But we can ask. I can't stop thinking about it. Okay.

See, he may not even remember. Maybe an opportunity for test corrections. Yeah, this is a good chance because Rick is on the line right now listening in on this call waiting to talk to you. Hey, Riley. I would love to, hello. Just the tone shift. Oh, my God. I don't even know what to say.

Yeah, there's no surprise there because you didn't know what to say that night either. Oh, my God. Wait, Rick, do you remember that moment in your guys' conversation? Yeah, but I'd no idea was a test question. Yeah, that's the point of a test. You're not supposed to know what's happening. I thought his answer was pretty good. Like, you're one of a kind.

There's no one in the world like you. Wiley, look, I just want to try to fix this. I really like you, and I just wanted to get to know you. That's what I thought was happening that night. I mean, I thought that we were getting to know each other as well, and I did. I got to know that I am not important to you. What? That you would be willing to just, that you would automatically assume that we would not make it.

You're reading it wrong. Just because I answered one question wrong doesn't mean that we can't be together. I said you're one of a kind. Yeah. Yeah, one of a kind. But after we broke up. Oh, my God. Just give me another chance.

Just ask me again. Ask me the same damn question again. The answer, the answer isn't going to matter now that you know what I want to hear. Yeah, but it's important to study before a test. You know, every teacher would want that. Yeah. Okay, fine. If you're a boyfriend and girlfriend and we broke up,

would you date someone similar to me afterwards? Okay. Here we go. No, absolutely not. Oh, so you would date somebody different than me? No. Rick, you're supposed to say, no, we're never going to break up. Yeah.

Were you not paying attention? I gave you the answer. He's tricking me again. I can't do that. Just ask me again. Ask me again. I'm not going to ask you again. I already asked you twice.

You were supposed to say we would never break up. I told you what to say, and you still didn't do it. I'm kind of switching to her side of the second round. She's not a good listener. Hey, listen, we're back under pressure, you guys. There's a lot happening right now. Rick was fully invested in what was happening with you, too. You can't see me right now, but I am sweating, right?

My shirt is soaking wet. Ew. That's not attractive. Okay. Dude, I can't believe you're going to throw this all away because of one silly question that you don't even, like. And my guy, fine. I agree. There's two hours and 59 minutes of really great conversation. And greatness after that.

All I'm doing right now is living my feelings. Okay. You don't get to tell me how to feel. I'm not trying to tell you how to feel. Just give me one more chance, okay? And I will listen. I will be there for you. I would not break up with you.

I would not date someone else that looks like you. I would always just be there for you. Rick, did you just answer all three options there all at the same time? I thought it was a smart move, Jeff. I don't know. He forgot to just say yes. You know what? True and false. Both correct.

All of you above. Riley, whatever you want to hear, that's what he has to say. So at this point, we'd like to ask, Riley, if you would be willing to give Rick a second chance and meet up with him for another date. If you are, we would pay for that. Please. And this is a test. There is a correct answer to it, Riley, just so you know. A good one, Jeff.

Riley, don't be so. Come on. Everybody deserves another shot. I will give you one more night. But anything that goes wrong is it. It's over. Oh, on the edge. Yeah, it sounds like he won't be walking on eggshells at all.

Oh, no, Rick, that sounds like so much fun, doesn't it? She's like, hi, how are you doing? He's like, I don't know how to answer this. No comment. Listen, I know who I am. I know what I bring to the table, and you either want it or you don't. Okay. Well, I think he wants it.

You want it, Rick? Absolutely. Nothing is going to go wrong. Okay. Wow. It better not. Okay. Oh, that's a threat.

Because you don't get to call the radio station to ask me back for a third time. Okay. This call just keeps getting sweeter and sweeter as we go on. So, you know what? We're going to say it took over. It really did. We're going to set you two up on a lovely date and you just have the best time together, okay? We will and we won't and all the above.

All right. That's my man, Rick. He's sorted. Brooke and Jeffrey in the morning. New year, new goals, and in this economy, a better money plan is more necessary. than ever. I am Matt and I'm Joel. We are from the How to Money podcast and every week we help you to spend smarter, save more, and make sense of what's going on out there. If you want 2026 to be the year you finally feel in control of your money, we're here to give you the tools and advice

to help you make it happen. Listen to How to Money on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey there, this is Dr. Jesse Mills, Director of the Men's Clinic at UCLA Health and host of the Mailroom podcast. Each January guys everywhere make the same resolutions. Get stronger, work harder, fix, what's broken? But what if the real work isn't physical at all? To kick off the new year, I sat down with Dr. Steve Polter, a psychologist with over 30 years' experience, helping men unpack shame, anxiety, and emotional pain they were never taught to name.

In a powerful two-part conversation, we discuss why men aren't emotionally bulletproof, why shame hides in plain sight, and how real strength comes from listening to yourself and to others. Guys who are toxic, they're immature, or they've got something they just haven't resolved. Once that gets resolved, then there comes empathy and some compassion. If you want this to be the year, you stop powering through pain and start understanding what's underneath. Listen to the mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows. What do you think is the percentage that we're going to get an update update from Rick and Riley somewhere down the road? Not at all, dude.

Maybe just him on the phone. Yeah. Are there percentages less than zero? Dude, he's going to blow it in the first, like, 30 minutes, I promise. But how could anyone not blow it with her? Exactly. Like, how is she ever going to be in a relationship? I mean, maybe she doesn't want to be, right?

Yeah, she's lying to herself. I don't know. That is, that was nuts. He's in a tough position at this point, but I will say it is impressive that after just three hours, they went from complete strangers to arguing like a married couple of 20 years. Excuse me, they broke up. Yeah. Yeah.

After the three hours. No, they are never going to break up, Brooke. I don't know. I would have failed her test. Yeah. Who wouldn't? But remember, the one test you can't fail is finding us on our second date update podcast. It's easy to find.

We're never breaking up, are we? No, we're not. And we're in all of your favorite podcast platforms. We're there. Search Rick and Riley in the morning. No, it's Brooke and Jeffrey. In the morning. Although it does have a good ring to it.

Hey, it's Joel and Matt from How To Money. if your New Year's resolution is to finally get your finances in shape. We've got your back. Prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Each week we break down what's happening with your money, the most important issues to focus on,

and the small moves that make a big difference. Kick off the year with confidence. Listen to How to Money on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. This is Dr. Jesse Mills. host of the Mailroom podcast. Each January, men promised to get stronger, work harder, and fix what's broken? But what if the real work isn't physical at all? I sat down with psychologist, Dr. Steve Poulter, to unpack shame, anxiety, and the emotional pain men were never taught

how to name. Part of the way through the Valley of Despair is realizing this would happen, and you have to make a choice whether you're going to stay in it or move forward. Our two-part conversation is available now. Listen to the Mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows. This season on Dear Chelsea with me, Chelsea Handler, we've got some incredible guests like Kumail Nanjiani. Let's start with your cat. How is she? She is not with us.

Okay, great, great, great way to start. Maybe you will cry. Ross Matthews. You know what kids always say to me? Are you a boy or girl? Oh my God. All the time. That's so funny.

I know. So I try to butcher it up for kids so they're not confused. Yeah, but you're butching it up is basically like Doris Day. Right? No, I turn into Be Arthur. Listen, to these episodes. of Dear Chelsea on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. This show contains information subject to, but not limited to personal takes, rumors, not so accurate stats, and plenty more.

What's up, man? This is your boy, Nav Green from the Broken Play Podcast. Look, it's the end of the season, the playoffs are here. But guess what? It ain't the end of your season. You can always tune in with Broken Play Podcasts with Nav Green on the Black Effect Podcast Network. Not a team who ain't going to the playoffs. The Chief. It's time to rebuild. Listen to Broken Play with Navgreen from the Black Effect Podcast Network on the Iheart Radio app. Apple Podcasts or whatever you get your podcast. You know Roll Doll. He thought up Willie Wonka and the BFG.

But did you know he was a spy? In the new podcast, The Secret World of Roll Doll, I'll tell you that story, and much, much more. What? You probably won't believe it either. Was this before he wrote his stories? It must have been. Okay, I don't think that's true. I'm telling you.

I was a spy. Listen to the secret world of Roll Doll on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.