Chapter 1: What unusual situation leads to a bachelor party confession?
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.
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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 anymore.
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 a girl? Oh my God.
All the time. That's so funny. I know.
So I try to butch it up for kids so they're not confused. Yeah, but you're butching it up. It's basically like Doris Day.
Right?
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Chapter 2: How does Rick explain his self-hosted bachelor party?
Was she at a bachelorette party?
Yeah. It was a birthday party, she said.
Okay. All right. Well, 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 the line.
Dude, I'd love to join your bachelor party.
We'll find out when we come back for your second date update. Thank you. We'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. Oh, 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.
Yeah.
An actual bachelor. Yeah.
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Chapter 3: What was the initial reaction of Riley upon meeting Rick?
Cracked under pressure, you guys. There's a lot happening right now. Rick was fully invested in what was happening with you two. You can't see me right now, but I am sweating, all right? My shirt is soaking wet. Ew. Oh. 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 finally went out on a limb. 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. Oh, God. 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.
You forgot to just say yes. You know what? True and false. All of the 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.
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. On the edge. Sounds like he won't be walking on eggshells at all. Rick, that sounds like so much fun, doesn't it? She's like, hi, how you doing? He's like, I don't know how to answer this. No comment.
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. Great answer. 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?
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Chapter 4: What unexpected twist occurs during Rick and Riley's conversation?
I just was like, damn.
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It's an amazing conversation. One you definitely don't want to miss. So listen to The Questlove Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
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?
He's going to blow it in the first like 30 minutes.
I promise. could anyone not blow it with her? How is she ever going to be in a relationship? I mean, maybe she doesn't want to be, right?
Maybe 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. Uh, excuse me. They broke up. Yeah. After the three hours. No, they are never going to break up. Oh yeah. I don't know. I would have failed her test. Yeah. Who wouldn't?
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Chapter 5: How do Rick and Riley's perspectives on their night differ?
Listen to Sacred Lessons with Mike Della Rocha on the iHeartRadio 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 iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows.