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Brooke and Jeffrey: Second Date Update

Second Date Update: First Timers Club

21 Jan 2026

Transcription

Chapter 1: What is the 'First Timers Club' mentioned in the episode?

0.031 - 16.846 Unknown

A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della 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.

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17.386 - 29.717 Unknown

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 Della Rocha on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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30.153 - 46.451 Brooke and Jeffrey

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.

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46.471 - 60.733 Brooke and Jeffrey

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.

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Chapter 2: Why is Sam reaching out for help with his first date?

61.118 - 69.205 Chelsea Handler

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?

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69.846 - 71.888 Unknown

She is not with us anymore.

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71.908 - 73.729 Chelsea Handler

Okay, great, great, great way to start.

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73.909 - 85.279 Ross Matthews

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.

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Chapter 3: What challenges does Sam face as a first-time dater?

85.299 - 89.303 Ross Matthews

It's basically like Doris Day. Right? No, I turn into Bea Arthur.

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89.283 - 96.205 Chelsea Handler

Listen to these episodes of Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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96.792 - 113.719 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.

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114.14 - 120.69 Brooke and Jeffrey

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.

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120.772 - 128.682 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.

129.022 - 141.058 Nav Green

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 your boy, Nav Green, from the Broken Play Podcast. Look, it's the end of the season, the playoffs are here.

Chapter 4: How did Sam meet Witty, the girl he went on a date with?

141.298 - 160.778 Nav Green

But guess what? It ain't the end of your season. You can always tune in with Broken Play Podcast with Nav Green on the Black Effect Podcast Network. Not a team who ain't going to the playoffs. The Chiefs. It's time to rebuild. Listen to Broken Play with Nav Green from the Black Effect Podcast Network on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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160.799 - 182.581 Brooke and Jeffrey

Hey, it's Brooke and Jeffrey, and this is the Second Date Podcast. And today, honestly, like, it's incredible to be part of anyone's love journey, period, right? That they invite us in. But today we've got a guy who has never been on a date before. Aww. So wholesome, so innocent. Yes, he's 25 years old. It's his very first date.

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Chapter 5: What was the setting and atmosphere of Sam's first date?

182.862 - 201.229 Brooke and Jeffrey

And he called us for help. I don't know if he should have. We'll be talking in probably the next five years and see how dating goes for him. So you got that brand new episode about to start. But first, comments. Yeah, Pop Tartatouille said the other day, this is one of the best episodes I've heard.

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201.249 - 207.781 Unknown

I listen to you guys every time I'm driving somewhere, and this had me dying. I genuinely hope you guys never stop making these.

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207.801 - 226.312 Brooke and Jeffrey

I can see myself being 70 and still listening to this podcast. I hope we're in your guys' lives that long. I'll be 120. So tell me, did he have teeth? Did he slide into your DMs? That's not even a thing anymore. Yeah, come on.

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Chapter 6: What awkward moments occurred during Sam's date with Witty?

226.332 - 252.184 Brooke and Jeffrey

Did he holograph into your mind? Okay, listen. We got a brand new episode starting right now. You know, personally, I like the second date updates where people haven't really been dating for a while and they need to jump back on the horse. Yeah, you know. Or slide back into the hot tub. No time like, wait, the present. Whatever the saying is. I think that's it. Put your key back in the bowl.

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252.264 - 267.064 Brooke and Jeffrey

Yeah, exactly. And I'm assuming that's the case for our listener, Sam, because he said in his email, dating is foreign to him. Does that mean he just likes foreign chicks? I don't blame him. Hard for me to read between the lines here, so let's find out.

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Chapter 7: Why did Witty feel the date was strange?

267.164 - 292.835 Brooke and Jeffrey

Sam, est-ce que vous avez moi? Is that from Moulin Rouge? Guys, I'm talking to Sam. He's into foreigners. Sam, can you understand what I'm saying? I don't speak that language. French people don't speak that language either. So what do you mean when you say dating is foreign to you? How long has it been since you went on a date? Uh, forever. Oh. Wait, wait, no, wait.

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292.895 - 298.622 Brooke and Jeffrey

Honestly, like, have you ever been on a date? That's not, I'm not being sarcastic. No, I mean forever.

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Chapter 8: What insights can be gained from Sam's experience as a first-time dater?

298.682 - 317.905 Brooke and Jeffrey

This is the first date I've ever been on. Oh, that's so cute. Okay, you're telling us. Oh, that's awesome. You're saying you've never been on an actual date with a woman before in your entire life. No, I've always wanted to, but at 25, I finally got my first taste, and then it vanished again, so. Oh, no.

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319.036 - 341.188 Brooke and Jeffrey

I mean, it makes sense. Like, you're 25. Like, the COVID era, like, really screwed your guys' social lives up. You know, like, postponed everything. So here we are. Yeah. So who are we going to be calling here? What's her name? Her name is Witty. Witty? Witty, yes. Okay, cool. How'd you meet her? So I'm a graduate assistant at a chemistry lab for a local university.

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342.07 - 361.159 Brooke and Jeffrey

And we had a situation working with this company. They have people come in a few times a week to use our lab facilities. And she's one of those people. So I got to know her a little this way. That's good because you're naturally learning about each other, right? I have to know, how long did it take you to work up the nerve to ask her out?

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361.932 - 380.116 Brooke and Jeffrey

Um, I couldn't really pick up that she was interested the first few times, you know, and then she hinted at wanting to get together and then I asked her out. Okay. Oh, that's good that she kind of stepped up a little bit for you. How did you do it? What was your approach?

381.437 - 392.682 Brooke and Jeffrey

I mean, I just basically, I wrote on a piece of lab paper and I wrote, what would you say to a cute guy in a lab coat if he wanted to take you out to dinner? And she said yes.

393.664 - 393.865 Unknown

All right.

393.885 - 417.284 Brooke and Jeffrey

This is great, man. This is all going off to a good start, especially for your first date. So where did you guys go? So it was weird because it was actually the same day she was working at the lab. So we kind of clocked out at the same time and she asked, Like, where are you taking me to? And I realized I kind of forgot about that part. Oh. You didn't pick a place? Oh.

417.724 - 419.307 Chelsea Handler

Because it was happening right then, the date.

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