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Brooke and Jeffrey: Second Date Update

Second Date Update: Leave Wicky Alone

16 Jan 2026

Transcription

Chapter 1: What is the main topic discussed in this episode?

0.031 - 16.531 Brooke

Hey, it's Joel and Matt from HowToMoney. 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 That's right. Yeah.

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16.611 - 32.67 Brooke

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. Hi, I'm Dr. Priyanka Wally.

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32.79 - 33.891 Hari Kundabolu

And I'm Hari Kundabolu.

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34.051 - 38.536 Brooke

It's a new year, and on the podcast Health Stuff, we're resetting the way we talk about our health.

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38.597 - 54.955 Hari Kundabolu

Which means being honest about what we know, what we don't know, and how messy it can all be. I like to sleep in late and sleep early. Is there a chronotype for that, or am I just depressed? Health Stuff is about learning, laughing, and feeling a little less alone.

55.236 - 60.902 Brooke

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

61.321 - 78.206 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.

78.626 - 85.236 Unknown

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.

85.267 - 93.218 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.

Chapter 2: What unusual situation did Ricky face during his date?

515.651 - 521.678 Brooke

It sounds like the middle of the date actually wasn't that bad, but how you start and end a date is probably the most important piece.

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521.758 - 523.861 Unknown

Good point. Last impression and first impression.

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523.881 - 536.195 Brooke

You don't want to bookend it with mom talk. Unless you play it off good, but I don't know. Maybe your mom cursed you by saying good luck. She should have said, break a leg, sweetie. Yeah. I don't know about that.

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536.215 - 538.397 Unknown

Remember that for when you drop your kids off on dates, Brooks.

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538.377 - 548.16 Brooke

So when you said you think you know the reason why, is it because the whole situation with your mom? Yeah, she said she was okay with it, but I don't know if she really was.

548.822 - 550.125 Unknown

Have you heard from her at all?

550.763 - 554.287 Brooke

Uh, no. If you can get a hold of her, that would be the first.

554.327 - 554.508 Unknown

Okay.

555.108 - 563.959 Brooke

Okay. Well, let's find out when we call Annette for you and see if your mom is the person who actually blocked you from finding true love. Another mom block.

Chapter 3: How did Ricky meet Annette and what was their date like?

688.774 - 690.216 Unknown

Okay, we are here.

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690.236 - 692.619 Brooke

Hi, Annette. Good morning. I liked that idea, though. When it's happening?

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692.759 - 694.02 Unknown

One of these times, we should be quiet.

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694.04 - 716.264 Brooke

Yeah. What's happening is you're part of a segment that we're doing now. It's called the Second Date Update. Welcome to it. Yeah. Okay. I know it's probably weird to getting this call, but it's not supposed to be a scary thing. We're just trying to help one of our listeners who went out on a date with you recently, a guy named Ricky. Oh, seriously?

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717.847 - 720.591 Unknown

Yeah. That was a reaction. It was.

720.911 - 741.305 Brooke

Ricky told us about your hangout and said he had a great time with you. Oh, and he even told us about the app that you guys met on. That was kind of cool where you like draw pictures of who you're looking for. That's interesting. This is very strange that he's like calling you about this and talking about my life. Well, his life, too. Yeah.

741.325 - 742.447 Unknown

Yeah. It's a shared life.

743.188 - 746.093 Brooke

No, it's not.

746.133 - 747.736 Unknown

You're right. You shouldn't have said that.

Chapter 4: What role did Ricky's mom play in the date scenario?

976.291 - 1001.499 Brooke

I have a job. You said that. I'm an accountant. You're an accountant. You're a child accountant. But you told her, Ricky, I choose to live my life like a child. She said those were your words. Maybe she misunderstood what you were saying, Ricky. Maybe re-explain it so she gets it. Look, I understand I'm fully grown. I'm not in denial about that. It's just that being an adult sucks.

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1001.68 - 1003.904 Brooke

Everybody hates it. Amen to that.

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1005.047 - 1005.247 Unknown

Yeah.

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1005.588 - 1025.333 Brooke

I have the opportunity to just not pay rent, not pay mortgage, and just... Whoa. Okay, that makes it sound more like you're freeloading of your parents. No, I... What are you working for then? Like... Uh-huh. I save money for things that I like, you know, like big Lego sets or... Hey, Legos speak to adults, too.

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1025.573 - 1026.214 Unknown

Yeah.

1026.234 - 1030.159 Brooke

That's true. That's probably not the best example of what you spend your money on right now, Ricky.

1030.179 - 1034.304 Unknown

But it's not impressive to be like, this is a $1,000 Lego set. Still. It's not as impressive.

1034.344 - 1057.9 Brooke

Not if you don't have a real house to put it in. But financial planning is financial planning, and that's an adult skill set. That's true. I told you that this is just temporary, and... That one day I will get my own place and I'll be able to afford it because this whole time I've been choosing to live like a child. And again, it's because people are so stressed out. People are so upset.

1058.08 - 1083.534 Brooke

And I'm a happy person and I choose to be. Well, that's good. I have a hard time arguing with the logic. Ricky, you can be happy and still be a man. You need to prove to her that you're a man to get another chance. Brooke, he's happy. Why are you trying to take away his happy childlike happiness? Stop yelling at children, Brooke. Come on. It's not your kids, Brooke.

Chapter 5: Did Ricky feel a connection with Annette during their date?

1393.363 - 1406.906 Dr. Jesse Mills

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.

0

1407.346 - 1413.957 Unknown

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.

0

1413.937 - 1421.905 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.

0

1422.644 - 1440.049 Josh Zeman

A decade ago, I was on the trail of one of the country's most elusive serial killers. But it wasn't until 2023 when he was finally caught. The answers were there, hidden in plain sight. So why did it take so long to catch him? I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer.

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1440.309 - 1451.385 Josh Zeman

The investigation into the most notorious killer in New York since the son of Sam, available now. Listen for free on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

1452.513 - 1469.098 Mike Della Rocha

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.

1469.639 - 1481.997 Mike Della Rocha

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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