Second Date Update: Bachelor Party of One

Summary

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Podcast Summary: Brooke and Jeffrey – Second Date Update: "Bachelor Party of One"

Original air date: January 26, 2026
Hosts: Brooke & Jeffrey (with Bowen Yang and others)
Guest Participants: Rick and Riley

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Overview

In this "Second Date Update" episode, Brooke and Jeffrey help Rick, a self-proclaimed "bachelor," figure out why Riley, a woman he hit it off with on the night of his own self-hosted bachelor party, hasn’t been returning his texts. The episode explores misunderstandings, "test" questions in dating, and hilarious but all-too-relatable confusion on both sides after a memorable first meeting.

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Major Discussion Points & Insights

1. Rick's Unusual Bachelor Party

• Rick clarifies he hosted a bachelor party for himself (03:54), not because he’s getting married but to celebrate being a bachelor at 40.
  • Quote (Rick, 04:45): "Honestly, I'm pushing 40...I felt like it was time to celebrate me."
  • Reaction (Jeffrey, 04:59): "You threw yourself your own bachelor party."
• Rick and friends (six in total) went out clubbing, no sashes or costumes, just a night of fun (05:52, 06:04).
• The concept initially weirds out the hosts but is also received with some admiration.
  • Quote (Brooke, 06:23): "[You] probably have to explain that to women when you're out..."

2. Meeting Riley

• Rick meets Riley at a club. She’s skeptical when she hears about the “bachelor party” ("assumes he's about to get married").
  • Quote (Rick, 06:42): "It wasn't my fault...[a friend] comes up behind, 'Dude, congrats on the bachelor party.'"
  • He explains it’s a "single guy's celebration," not an engagement event. Eventually, she accepts—at least outwardly (07:04).

3. The Night Together

• The chemistry is strong. After continued clubbing and talking, Rick and Riley leave together and spend the night in Rick's hotel room—talking, connecting, and being intimate (07:39).
  • Rick insists it wasn’t just a hookup; they had "long, deep conversations" (08:02, 08:32).
  • Rick is confused why she hasn’t responded to his follow-up messages ("she hasn't responded since," 08:15).

4. The Hosts Speculate

• Brooke posits Riley may have nursed a hangover; Jeffrey wonders if the confusion about the party scared her off (08:25).
• Rick insists it was a meaningful, sober-leaning night. He genuinely considers Riley special (09:01).

5. Riley’s Side of the Story

• When the show reaches out to Riley, she’s hesitant but opens up after some coaxing (12:02).
• Riley reveals she left Rick’s hotel room that night angry—not because of the state of the room or the party explanation, but due to a key moment during their late-night conversation (13:05).
  • Riley had asked a "test" question: "If we were together and broke up, would you date someone like me after?" (14:16).
  • Rick responded: "No, that's impossible. You're a one of one."
    • Riley interprets this as him assuming they’d break up, not “you’re my person forever.”
  • Quote (Riley, 14:47): "He should have been like, 'No, we'd never break up because you're my person.'"

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Notable Quotes & Memorable Moments

• Riley, on Rick's “test" failing answer (14:47):
  "He should have been like, 'No, of course not. We'd never break up because you're my person.'"
• Hosts’ reactions to Riley's expectations:
  • Brooke (14:54): "For me, that would have freaked me out if someone would've said 'we're never gonna break up' on the first night."
  • Jeffrey (15:02): "To totally cut him off after that...[is] pretty harsh."
• Hilariously tense "redo" of the test question (16:43):
  • Rick: "Just ask me again. Ask me the same damn question again."
  • Riley: "The answer isn't going to matter now that you know what I want to hear."
• Multiple, comically botched attempts at the right answer:
  • Brooke, to Rick, 17:09: "Rick, you're supposed to say 'No, we're never going to break up.'"
  • Riley: "I told you what to say, and you still didn't do it."
• Tension and comedy in the resolution (18:52):
  • Riley: "I will give you one more night. Anything that goes wrong, it's over."
  • Brooke: "He won't be walking on eggshells at all, Rick."

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Key Timestamps for Important Segments

• Introduction & Rick’s Bachelor Party Concept: 03:43–06:14
• Rick & Riley’s Club Encounter/Hotel Night: 06:23–08:32
• Rick's Post-Date Confusion: 08:43–09:41
• Calling Riley, Her Reluctance & Revelation: 12:02–14:47
• The “Test Question” Scene & On-Air Mediation: 14:16–18:47
• Decision—Second Chance or Not?: 18:47–19:20
• Hosts’ Postmortem & Banter: 21:43–22:48

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Tone & Language

• The tone is a lively blend of light mockery, exasperation, and real empathy, true to “Brooke and Jeffrey” style.
• The hosts bring humor ("you probably have to explain that to women when you’re out," 06:23), but show concern for Rick’s feelings and Riley’s emotional honesty.
• Riley is blunt, occasionally defensive, and has a notably all-or-nothing approach; Rick is earnest but awkward, genuinely confused by dating "tests."
• Conversations read like “reality TV radio”—fast-paced, packed with jokes, but grounded in very real dating dilemmas.

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Conclusion

• Rick and Riley agree, somewhat reluctantly, to a second date—Riley warns she has zero tolerance for mistakes this time ("Anything that goes wrong, it's over," 18:52).
• The hosts express doubt about the future, joking it's only a matter of time before Rick is back for another update ("He's gonna blow it in the first, like, 30 minutes," 21:52).

Final thought from hosts (21:57):

Jeffrey: "But how? How could anyone not blow it with her?" Brooke: "Like, how is she ever gonna be in a relationship? ... That was nuts."

The episode closes with hosts looping back to their signature banter and a reminder of the absurd highs and lows of modern dating.

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[All timestamps in MM:SS; transcription segments edited for focus and clarity.]

Transcript

[Bowen Yang]

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[Dr. Jesse Mills]

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.

[Jeffrey]

Part of the way through the valley.

[Rick]

Of despair is realizing this has happened and you have to make a choice.

[Jeffrey]

Whether you're gonna stay in it or move forward.

[Dr. Jesse Mills]

Our two part conversation is available now. Listen to the mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite.

[Jeffrey]

A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike De la Rocha, host of Sacred Lessons, a space for men to pause, reflect and heal. This year we're talking honestly about mental health, relationships and the patterns we're ready to release. If you're looking for clarity, connection and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroch on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. 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 iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

[Brooke]

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?

[Bowen Yang]

She is not with us anymore.

[Brooke]

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. I know. So I try to butch it up for kids so they're not confused. Yeah, but you're butching it up basically, like an angry woman Doris Day. Right now I turn into Bea Arthur. Listen to these episodes of Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. All right, it's Monday. Time for a brand new second date update. And Jose Mukarrama commented, the second date update pissed me off and the second date update update pissed me off. So, you know, I'm concerned how this person's gonna feel when they hear about today's bachelor party guy.

[Jeffrey]

Yeah, well, at least we don't have an update, update, update yet.

[Brooke]

That's true. That's so. I don't know how today will affect your emotions, but let us know in the comments after you hear it.

[Jeffrey]

You will be moved. It'll be emotional for you.

[Brooke]

Moved is the word. Yep. Your brand new second date update right now. Brooke and Jeffrey in the morning Second date update.

[Jeffrey]

Out of all the crazy places we've heard of people meeting each other on this segment. Yeah, mid convenience store robbery or in the colonoscopy prep area.

[Brooke]

Oh, that one was cute.

[Jeffrey]

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.

[Bowen Yang]

Oh, no.

[Jeffrey]

His words, not mine.

[Brooke]

Should we have him on the phone, Jeff?

[Jeffrey]

Well, I'm curious to hear what the story is at least. Or he's single now or something.

[Brooke]

Maybe it was an open marriage. I don't know.

[Bowen Yang]

Oh, that's true.

[Jeffrey]

I never. I would never think about that. We have a lot of questions, so we need to talk to this guy.

[Bowen Yang]

Rick.

[Dr. Jesse Mills]

Hey, man.

[Jeffrey]

Welcome to the show.

[Rick]

How you doing?

[Jeffrey]

We're confused.

[Brooke]

I feel like you needed to come in with more Than just how you doing? Like, yeah, big misunderstanding.

[Jeffrey]

Okay, did I read this right? This is your bachelor party?

[Rick]

It was my bachelor party.

[Brooke]

Oh, wow.

[Rick]

Honestly, I'm pushing 40 and I've been to all of my friends vaginal parties. I've spent tons of money on them, and I felt like it was time to celebrate me.

[Jeffrey]

Wait.

[Brooke]

Oh, wait.

[Jeffrey]

You threw yourself your own bachelor party.

[Brooke]

But that means you're getting married? Were you getting married?

[Rick]

No, I'm celebrating that I'm a bachelor. It's a bachelor party.

[Jeffrey]

That is. I just had this combo with a friend. I was like, you guys, I'm never gonna 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.

[Rick]

Yeah, exactly.

[Brooke]

Okay, that's good. But you probably have to explain that to women when you're out actually getting married. You think you found the reason he's not getting a call back? Yeah, he came off as a fiance. That's cheating.

[Jeffrey]

Well, we don't know. We don't know what the story is or who he met. Like, we need to hear it from you, Rick. Tell us what happened.

[Rick]

So, yeah, we had a. I threw the party downtown, and there's lots of drinks and fun and we went to a bunch of clubs. It was a great time.

[Jeffrey]

And this is you and, like, what, a group of your guy friends?

[Rick]

Yeah, it was about 6 of us total.

[Brooke]

And is there anything indicating bachelor party as you're out? You know, like, girls will wear sashes and white dresses.

[Jeffrey]

Like, do you kind of wear, like, suits and stuff? I guess.

[Brooke]

Do you have any of that?

[Rick]

No. I mean, we all dressed up nicely, but yeah, we didn't have coordinating outfits or anything.

[Brooke]

Carrying her girlfriend, your fiance's head around on a stick.

[Riley]

Yeah.

[Brooke]

Yeah. Like the girls.

[Rick]

Yeah.

[Brooke]

Yeah.

[Jeffrey]

Is that what you guys do?

[Brooke]

I got some leftover friends, boyfriends.

[Bowen Yang]

I'll show you.

[Jeffrey]

Yeah, all right, we'll do that after we talk to Rick more about his bachelor party. So apparently you ended up meeting a girl while you were out.

[Rick]

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.

[Jeffrey]

Yeah, it's because you're calling at a bachelor party, bro. So everyone's assuming you're getting married. Exactly.

[Rick]

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.

[Jeffrey]

Oh, no. Accidentally blocked you.

[Brooke]

And I assume you try to explain. Explain. But then you would just come off as a bigger liar.

[Jeffrey]

Yeah, I've been single for way too long.

[Brooke]

No, I'm celebrating being single.

[Jeffrey]

Yeah. Never being married.

[Rick]

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.

[Brooke]

She did?

[Rick]

Yeah, she did.

[Jeffrey]

Or at least she pretended to get it.

[Brooke]

Well, I mean, if she stayed around, then she probably believed she went to the bathroom. Did a quick Google search, checked your Insta.

[Jeffrey]

So was there more to the evening after that?

[Rick]

There was. So I. You know, 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 ditched my own party.

[Brooke]

Oh, okay.

[Jeffrey]

Nice, though.

[Dr. Jesse Mills]

Awesome.

[Jeffrey]

And you and Riley went to the hotel?

[Rick]

Yeah, and she stayed the night.

[Brooke]

Okay.

[Jeffrey]

Wow.

[Brooke]

None of this. I mean, it sounds really fun. Really fun. It does not sound like something you'd expect to call back from.

[Jeffrey]

Yeah, that's a good point. Why wouldn't you get a call back after such a romantic evening?

[Brooke]

I mean, did you indicate to her how interested you were in her?

[Rick]

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.

[Brooke]

Oh, okay. You were really direct.

[Rick]

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 got nothing.

[Brooke]

Maybe she's still nursing her hangover. Like the bright light of my phone is too much.

[Jeffrey]

Yeah.

[Rick]

I mean, we didn't drink a ton, to be honest. We drank, sure, but it wasn't, like, blackout drunk or anything. And, yeah, there was romance, but we talked a lot, and we really got to know each other.

[Jeffrey]

So maybe that's the problem then. I mean, if Brooke's going back to a guy's hotel, she does not want to talk. That's for sure.

[Brooke]

Well, I mean, after a night at the club, I don't think anybody did. I think what you experienced is unusual, for sure. And special. Like, I could understand why you're upset.

[Rick]

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.

[Bowen Yang]

Huh.

[Brooke]

Maybe she's not being fully honest with you about where she is in life. Was she at a bachelorette party?

[Rick]

Yeah, she was on a. It was a birthday party. She said so.

[Jeffrey]

Okay, all right, well, who knows what that means? We're gonna 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. I'll do it right after this. Hold on.

[Brooke]

Brooke and Jeffrey in the morning. Second date update.

[Jeffrey]

Our listener Rick has given us a whole new definition for the term bachelor party. Because he threw one for himself recently. Even though he's not getting married?

[Brooke]

No. Not even in a relationship.

[Jeffrey]

No, he did it to celebrate his status as a single, eligible young man. An actual bachelor.

[Brooke]

Okay. Most people just call it single guys night out.

[Jeffrey]

It doesn't have the same ring to it though.

[Brooke]

You don't get people to buy you drinks if you.

[Jeffrey]

If you say that.

[Brooke]

Yeah, but you don't have this terrible misunderstanding that he had.

[Jeffrey]

True. I don't know if there was a misunderstanding, cuz 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.

[Brooke]

It sounds like Jeff is using his sarcasm voice, but that was real.

[Jeffrey]

No, 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?

[Brooke]

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 gonna lie.

[Jeffrey]

I mean, Rick, what was the state of your hotel room?

[Rick]

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.

[Brooke]

Yeah, okay, so then, yeah, I would call him back.

[Jeffrey]

Yeah, well, let's see if Riley first of all answers our call. And second of all, if she has an explanation for why she's been ignoring you for the past four days since your intimate hangout.

[Rick]

I hope so.

[Brooke]

Hopefully we can turn this around for you, Rick. Don't be so sad.

[Rick]

Yeah, man, I'm just nervous.

[Jeffrey]

Okay. You guys know you had chemistry, so you have that, bro. Yeah. And remember, you are a confident single bachelor. Yeah. Any woman would be lucky to have you.

[Rick]

Did you guys hear what I said before? I'm pushing 40, so this might be my last chance.

[Brooke]

Oh, you're a guy. You got easily a good 15 years left, you know.

[Jeffrey]

Yeah, you can date well into your 70s and still catch like a 20.

[Brooke]

Or 30, so with enough money. That's true.

[Jeffrey]

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.

[Riley]

Hello?

[Jeffrey]

Hi, is this Riley?

[Riley]

This is.

[Brooke]

Hi, Riley.

[Rick]

Hi.

[Bowen Yang]

Hi.

[Riley]

What is this in regards to?

[Jeffrey]

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.

[Riley]

Yeah. Yeah.

[Brooke]

Just. Yeah. Oh, you're able to be convinced of anything, aren't you?

[Jeffrey]

You're real go with the flow type of person.

[Riley]

So is this about one of my friends then? Because.

[Jeffrey]

No, not really. This is more about you and why you're not calling back. One of our. Our friends. A listener to our show named Rick.

[Riley]

Actually, I've changed my mind. I don't want to participate anymore.

[Jeffrey]

Hold on, hold on. This is.

[Brooke]

That's crazy. That's a crazy reaction.

[Jeffrey]

Yeah.

[Riley]

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 hid it pretty well.

[Jeffrey]

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.

[Riley]

Honestly, I don't really want to talk about it because if I do, I'm. I think it might make me mad again.

[Brooke]

You sound mad already, so I feel like we're past that point.

[Jeffrey]

Was this hotel room a total mess? Is that what it was?

[Riley]

No, that honestly, would have been way better.

[Brooke]

Oh, I tried.

[Jeffrey]

Okay. Fix that.

[Rick]

Right.

[Jeffrey]

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 can know just a little bit about what he did wrong or.

[Riley]

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?

[Brooke]

Oh, God.

[Jeffrey]

You asked a theoretical.

[Brooke]

Okay, hypothetical question. Those are getting together and then breaking up. Okay, so what did he say? His answer is important that you didn't.

[Riley]

Like, he said, no, that's impossible. You're a one of one.

[Brooke]

Oh, yeah, that feels like a good one.

[Riley]

Because he immediately went till 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.

[Brooke]

For me, that would have freaked me out. If someone would have said, we're never gonna break up on the first night I met them, I'd be like, whoa.

[Jeffrey]

Yeah, that's a great point. But, Brooke, they had hung out for three whole hours.

[Brooke]

Yeah, I. And don't you think that. Man, that's pretty harsh.

[Rick]

I know.

[Jeffrey]

To totally cut him off after that.

[Riley]

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?

[Jeffrey]

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.

[Riley]

Yeah, well, I can't stop thinking about it.

[Brooke]

Maybe an opportunity for test corrections.

[Jeffrey]

Yeah, this is a good chance because Rick is on the line right now listening in on this call, waiting to talk to you.

[Dr. Jesse Mills]

You.

[Rick]

Hey, Riley, I would love to.

[Riley]

Hello?

[Jeffrey]

It's the tone shift. Oh, my God.

[Rick]

I. I don't even know what to say.

[Riley]

Yeah, there's no surprise there because you didn't know what to say that night either.

[Brooke]

Oh, my God. Wait, Rick, do you remember that moment in your guys's conversation?

[Rick]

Yeah, but I had no idea it was a test question.

[Riley]

Yeah, that's the point of a test. You're not supposed to know what's happening.

[Jeffrey]

I thought his answer was pretty good. Like, you're one of a kind. There's no one in the world you.

[Rick]

Riley, look, I. I just want to try to fix this. I really like you, and I just. I just wanted to get to know you. That's what I thought was happening that night.

[Riley]

I mean, yeah, 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, that you would automatically assume that we would not make it.

[Rick]

Oh, 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.

[Riley]

Yeah, yeah, one of a kind. But after we broke up.

[Brooke]

Oh, my God.

[Rick]

Just give me another chance. Just ask me again. Ask me the same damn question again.

[Riley]

The answer isn't going to matter now that you know what I want to hear.

[Brooke]

It's important to study before a test. Yeah, you know, every teacher would want that.

[Riley]

Yeah, okay, fine. If you're a boyfriend and girlfriend and we broke up, would you date someone similar to me afterwards?

[Jeffrey]

Okay, here we go.

[Rick]

No. Absolutely not.

[Riley]

Oh, so you would date somebody different than me?

[Brooke]

Rick, you're supposed to say no, we're never gonna break up.

[Dr. Jesse Mills]

Yeah.

[Brooke]

Were you not paying attention?

[Riley]

I gave you the answer.

[Rick]

She's tricking me again. I can't do. Just ask me again. Ask me again.

[Riley]

Okay, I'm not gonna 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.

[Brooke]

I'm kind of switching to her side of the second round. You guys, there's a lot happening right now. Rick was fully invested in what was happening with you, too.

[Rick]

You can't see me right now, but I am sweating, all right? My shirt is soaking wet.

[Riley]

That's not attractive.

[Brooke]

Okay, I can't believe you're going to throw this all away because of one silly question that you don't even like.

[Jeffrey]

And my guy finally went on a limb. I agree. There's 2 hours and 59 minutes of really great conversation and greatness after that.

[Riley]

All I'm doing right now is living my feelings. Okay? You don't get to tell me how to feel.

[Rick]

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.

[Jeffrey]

Rick, did you just answer all three options there all at the same time?

[Brooke]

I thought it was a smart move. And false. Yeah, all of the above.

[Jeffrey]

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, Jeffrey.

[Brooke]

Riley, don't be so like. Come on. Everybody deserves another shot.

[Riley]

I will give you one more night. Anything that goes wrong.

[Brooke]

Is it.

[Riley]

It's over.

[Brooke]

Okay.

[Jeffrey]

On the edge.

[Brooke]

Yeah. It sounds like he won't be walking on eggshells at all, Rick.

[Jeffrey]

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.

[Bowen Yang]

No comment.

[Riley]

I know who I am. I know what I bring to the table, and you either want it or you don't.

[Jeffrey]

Okay, well, I think he wants.

[Dr. Jesse Mills]

You want it, Rick.

[Rick]

Oh, absolutely. Nothing is gonna go wrong.

[Dr. Jesse Mills]

Okay.

[Brooke]

Wow.

[Riley]

It better not.

[Jeffrey]

Okay, that's a threat because you don't.

[Riley]

Get to call the radio station to ask me back for a third time.

[Jeffrey]

Okay. Okay. This call just keeps getting sweeter and sweeter as we go on. So you know what we're gonna say took over. It really did. We're gonna set you two up on a lovely date, and you just have the best time together.

[Rick]

Okay, we will and we won't. And all the above.

[Jeffrey]

All right, that's my man, Rick.

[Brooke]

He's Gordon. Yes.

[Riley]

Brooke and Jeffrey in the morning.

[Bowen Yang]

This is Bowen Yang from Lost Culture Research with Matt Rogers and Bowen Yang. We all know the feeling when life gets really busy. Taking care of yourself can feel impossible. That's why Premier protein shakes are my go to. They have 30 grams of protein, 160 calories, no added sugar, and they taste amazing. So they're a healthy choice you'll actually want to make. It's not just for fitness. It's for getting after life. 30 grams of protein gives you the fuel you need. It's not just for intense gym sessions. It's for life. With the wide variety of flavors, from cafe latte to cake batter, it never feels boring. It's a flavor for everyone. I personally love the peaches and cream, but maybe you're a root beer floater, cinnamon roll kind of person. Premier Protein empowers me to say yes to more. Find your favorite [e-mail]. that's P R E M I E R protein.com. or at Amazon, Walmart and other major retailers.

[Dr. Jesse Mills]

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 Poulter, 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.

[Rick]

Guys who are toxic, they're immature, or.

[Jeffrey]

They'Ve got something they just haven't resolved.

[Rick]

Once that gets resolved, then there comes empathy and some compassion.

[Dr. Jesse Mills]

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 iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows.

[Jeffrey]

What do you think's the percentage that we're gonna get an update update from Rick and Riley somewhere down the road? Not at all, dude.

[Brooke]

Maybe just him on the phone?

[Jeffrey]

Yeah. Are there percentages? Less than zero. Dude, he's gonna blow it in the first, like, 30 minutes, I promise.

[Brooke]

But how? How could anyone not blow it with her?

[Jeffrey]

Exactly.

[Brooke]

Like, how is she ever gonna be in a relationship? I mean, maybe she doesn't want to be.

[Jeffrey]

Right? She's lying to herself.

[Brooke]

I don't know. That is. That was nuts.

[Jeffrey]

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.

[Brooke]

Excuse me. They broke up?

[Jeffrey]

Yeah.

[Brooke]

After the three hours.

[Jeffrey]

No, they are never gonna break up.

[Brooke]

Oh, yeah. I don't know. I would have failed her test. Yeah, who wouldn't?

[Jeffrey]

But remember, the one test you can't fail is finding us on our second date update podcast. It's easy to find.

[Brooke]

We're never breaking up, are we?

[Jeffrey]

We're not. And we're in all of your favorite podcast platforms. We're there. Search Rick and Riley in the morning.

[Brooke]

No, Brooke and Jeffrey.

[Jeffrey]

Oh, Brooke and Jeffrey in the morning. Although it does have a good ring to it.

[Bowen Yang]

This is Bowen Yang from Lost Cultureistas with Matt Rogers and Bowen Yang. We all know the feeling when life gets really busy. Taking care of yourself can feel impossible. That's why premier protein shakes are my go to. They have 30 grams of protein, 160 calories, no added sugar, and they taste amazing. So they're a healthy choice you'll actually want to make. It's not just for fitness. It's for getting after life. 30 grams of protein gives you the fuel you need. It's not just for intense gym sessions, it's just for life. With the wide variety of flavors, from cafe latte to cake batter, it never feels boring. There's a flavor for everyone. I personally love the peaches and cream, but maybe you're a root beer floater, cinnamon roll kind of person. Premier Protein powers me to say yes to more. Find favorite [e-mail] that's P R E M I E R protein.com or at Amazon, Walmart and other major retailers.

[Dr. Jesse Mills]

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.

[Jeffrey]

Part of the way through the valley.

[Rick]

Of despair is realizing this has happened and you have to make a choice.

[Jeffrey]

Whether you're going to stay in it or move forward.

[Dr. Jesse Mills]

Our two part conversation is available now. Listen to the mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows.

[Jeffrey]

A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike De La Rocha, host of Sacred Lessons, a space for men to pause, reflect and heal. This year, we're talking honestly about mental health, relationships and the patterns we're ready to release. If you're looking for clarity, connection and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. 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 iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

[Brooke]

This season on Dear Chelsea with me, Chelsea Handler. We've got some incredible guests like Kumail Nanjiani. Let's start with your ca. How is she?

[Bowen Yang]

She is not with us anymore.

[Brooke]

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. 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 an angry woman. Doris Day, right? No, I turn into Bea Arthur. Listen to these episodes of Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.