Brooke and Jeffrey: Second Date Update - Second Date Update UPDATE Classic: 8 Trees A Trimming

Episode Date: November 27, 2025

The holidays nearly broke up the couple on the phone today when they first dated a year ago. But now with the yuletide season coming up were going to reconnect with them for a special update!See omnystudio.com/listener for privacy information.

Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc and send me the link. Thanks. Hey, just finished drawing up that quick one page business plan for you. Here's the link. But there was no link. There was no business plan. I hadn't programmed Kyle to be able to do that yet. I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people. Check out the second season of my podcast, Shell Game, on the IHeart Radio app or wherever you get your podcasts. On this week's episode of Next Chapter, I, T.D. Jake, sit down with Denzel Washington, a two-time Academy Award-winning actor and cultural icon.

I don't take any credit for it. I just didn't put me first. I just put God first and he's carrying me. Listen to the next chapter podcast on the I Heart Radio app, Apple Podcast, or wherever you get your podcast. New episodes drop weekly. Hi, I'm Dr. Priyanko Wally. And I'm Hurricane Dibolu. On our new podcast Health Stuff, we demystify your burning health questions.

You'll hear us being completely honest about her own health. My residency colon was like a cry for help, honestly. And you'll hear candid advice and personal stories from experts who want to make health care more human. I feel like they never felt like I truly belonged in medicine. We want to make health less confusing and maybe even a little fun. Find Health Stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history.

And some of the worst people, horrible ideas and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. most Texas story ever. Listen to Business History on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA, and I want to tell you about my new podcast called The Mail Room. And I'm Jordan, the show's producer. And like most guys, I haven't been to the doctor in way too long. I'll be asking the questions we probably should be asking, but aren't. Every week, we're breaking down the world of men's health from testosterone and fitness to diets and fertility. We'll talk science without the jargon and get your

real answers to the stuff you actually wonder about. So check out the mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows. You know, one thing that you could give thanks for today is that your dating life isn't so bad that you're on our show yet. Oh, that's true. That's true. Good point. Hey, welcome to it. It is a Thanksgiving edition of your second date.

And we do have an episode for you just to make you laugh this morning. Maybe you're prepping meals. Maybe you're avoiding family. Maybe you're traveling. Maybe you're one of those unlucky ones that have to be stuck at work. Oh, yeah. We're grateful that you're there and for all you do. And we truly give thanks to our listeners today.

Hopefully we're helping you somehow. Yeah, if your family's fighting over something petty, let us know in the comments what it is. Yes. I love that. I love that. Custody of a dog? That's right. We're all in it together.

Happy Thanksgiving from Brooke and Jeffrey in the morning. Ready or not, here it comes. The holidays are fast approaching. Oh, my. There's just something about the Christmas season that brings out the romantic side of people. Oh, I think that's true. Thank you, eggnog and office party mistletoe. But that was definitely not the case for two of our listeners who appeared on our show almost a year ago.

Oh. Because in their case, the holidays nearly broke them on their very first date. Oh, no. Thankfully, we were able to help out. And now that we're coming up on the Yuletide season, we're going to check back in on that same. couple for a special holiday second date update update right after this second date update brook swears she's never used the dating apps before i haven't is that true or because she knows that her family listens to the show sometimes oh i really haven't but with the way we've been doing

our second date updates lately it's kind of like brook you're getting the online experience anyway Because we've been asking people to open up their dates profiles and read us some of the stuff that they've wrote on there. And I'll say, I have flipped through my single friends at dating profile. Now our stories changed all of a sudden. What about a test, Brooke? If you want to match with someone, which direction do you swipe? Everyone knows that. You swipe right.

Oh, wow. Suddenly she's an expert. Wow, Brooke. Anyway, now that Brooke has schooled us on how online dating works, Maybe you can talk to Shana, who wants our help today, and we want to get into Shana's dates profile, too. Shana, welcome to our happy little slice of morning radio. Hey, thanks. You're welcome, Shana.

So who did you swipe right on? I swipe right on a guy named Hunter. Hunter, okay. He says he's looking for a lady to match his energy. Okay. Jose, you should put that on your dating profile. Oh, man, we would be high-energy dating. We would be exhausted.

Someone with the energy of 10,000 sons. I'm like, hi, hi. Oh, my God, what's your name? What's your name? Oh, I love you. Someone's out there for you. What else? That's a lot.

Okay, so we have sports picks on here. Like, he's in different, like, jogging attire. Okay. So he's an active guy. And also says he's an old soul that is dreaming of moving to a tiny town in the middle of nowhere. Oh. All right. Now you lost me.

I grew up in a tiny town in the middle of nowhere. Nothing romantic about it. That's a really sad story while your parents listened to this. It's like the opposite of Hallmark. Oh, they know. Yeah, they thought it was going to be more picket fences, less meth-meth-methlaps. They didn't plan on what small-town life is actually like. Are you into that?

Yeah, well, because I think I love gardening and I would love to have some animals and stuff like that. You know what I mean? And it's like, I don't think math labs have played it. And I hope not. But anyway. No one plans on it. We'll call it a plan B for you in case doesn't work out. Anything else on there?

And then he ends it with he's unapologetically me. So this is great. So it's like, okay. That's a red flag. I'm sorry. But guys or girls that say that, it's always like. It basically says I'm drama. Yeah.

And I'm not going to apologize. Well, it worked for her. I know. She swiped on him already. It's good. Sorry. Shannie, you're much more forgiving than any of us are. So tell us about the date that you went on.

Okay, so our day was great. He took me to a pro hockey game. Oh, fun. And I kind of like hockey, so it was kind of a good thing. I think, yeah, so anyway. But that thing about it is that there was no parking. We, like, literally circled the parking lot for 20 minutes. Did you say the best thing about it was there was no parking?

The worst thing about, yeah. Like one of the worst things about it, there was no parking. Yeah. So we looked for like 20 minutes, and then I realized that I didn't have my gloves. And so I made him take me home Are you going to get in the gold box? What do you need the gloves for? You just mean like regular questions?

No, I understand. You guys, I'm always cold. Like right now my hands are freezing. I just have cold hands all the time. You say you made him take you home? Yeah, yeah. We haven't found parking at that point anyway. So I'm like, just take me home and get my gloves.

Oh, yeah. It's okay. So you missed the whole first period, it sounds like. Probably. Yeah, but we did come back and we saw the rest of the most of the game, which was great. And then. That didn't ruin his mood, like having a demand like that. No, he was so sweet about it.

He's like, I get it. It's very nice. Plus, he doesn't want to get hugged by her if she has cold hands, too. So it's probably made a bad. Find me a woman that doesn't have cold hands. Cold hands, I know. Cold hands, warm heart. Anyway, the game was great.

And then he took me home because, you know, games are long. And then he was like, can I come in to my apartment? I was like, well, you can totally come in. But it's really cluttered if I'm doing this home project. but I kind of just discourage him because I really didn't want him in my mess because it's embarrassing. Trying to be polite, but you're like, yeah, if you come in, though, it's going to be the worst experience of your life. But you can. So he didn't come in.

No, he did not come in. Oh, good. He got the head. Yeah. So then, you know, I texted him, and he was like, I had a great time. He texted me. I had a great time. But then there's been no, let's get together again.

Let's go out on another date. There's been, like, just, hi. How are you? I think she does match my energy. Yeah, that's what I was going to say. You are definitely a lot of energy, I can tell you. It's a good thing, I think. I'm not sure if it matches his energy, though, because I don't know what he's like.

I'm telling, yeah, I don't know. I mean, I'm telling you guys, it really did have a good time. All right. He was really nice, and I had such a great time. It's just kind of, wat, wat, wat, what. It's kind of like, you know. Well, I want to hear this wat, wah, wah, in person when we call him. We're going to dial his number in just a few minutes.

First we'll play a song. We'll come back, and then we'll try and get you a second day. update right after this okay okay all right hold on second date update you're in the middle of a second date update update and we're going to find out how the couple is doing right after you here part two if you're just joining us for the second date we're on the phone with shana who clearly has a lot of personality yes she's got high energy with freezing cold hands and a messy apartment filled with secret projects that she doesn't want her date to see.

I think it was just the mess that she didn't want him to see, not the project. Well, because after the hockey date, Shauna told Hunter, in no uncertain terms, no, you cannot come inside and see my place. I mean, it's a pretty bold ask for a guy to go, can I come in? True. I mean...

They've already been there twice that day for the first time after she had to go pick up the gloves. She found her gloves in the clutter. It's true. I'm curious, Jose, as a guy, would You take that personally if a girl turned you away at the door? I would definitely read into it. I mean, it's like most of the time if a girl says it's messy in there, it's nothing compared

to a, like, a guy's mess. What you live with. Exactly. There are some clean men. I don't know them. Yeah. Brooke, I would ask you, but I know you've never turned away a guy at the door. So let's forget it.

Never had to, Jeff. Never had to. Jump in the clutter. Shana, how are you doing? Are you okay before we call? Hunter here? I'm good. You guys are hysterical.

Okay. Oh, good. Nobody else has ever said that. No, I hope we can get you a date. I mean, maybe he's just been busy or something. Yeah, I hope so. All right. Let's find out for sure.

We're going to dial Hunter's number right now and we'll see what he has to say, okay? Okay. And just for the record, we think you're hysterical, too. Yeah. We're matching energy. You're welcome. All right. Let's just call him. Here we go.

Hello? Hey, is this Hunter? Yes, this is him. Who is this? Hey, this is Jeff from the radio show Brooke and Jeffrey in the morning. Is this the same hunter that went out with a girl recently named Shana to a hockey game? Who's asking? I'm sorry? Me?

Yeah. What is your name? Who are you here? He already said that. I said my name. You guys say you're from the radio? Yeah, yeah, we do a morning radio show. Yeah.

It's called Brooke and Jeffrey in the morning. Okay, so wait. I'm really confused right now. I'm sorry. This has never happened to me before. Well, we'd like to ask you questions about the date because Shauna reached out to us afterwards and said she had a really nice time with you. Oh. It's part of a thing that we do call the second date update.

And we're trying to help her get some answers for why afterwards you two aren't reconnecting. well uh she's she's something that's for sure is she being too eager like were you going to get back to her I'm assuming you spoke to her right so I'm guessing you kind of got the feel from her that she's a a lot of energy she's a lot yeah but she said I mean she told us on your dating profile it says you're looking for someone to match your energy I mean people who write that are only people who are like high energy right And no, don't be wrong, I'm all for matching energies, but there's levels to these sort of thing. And the date itself was fine.

I mean, albeit that there were minor inconveniences having to go out of my way to get her gloves, and it's the whole thing. Okay, yeah. We heard about that. And from what we understand, she felt kind of bad that she left her gloves and made you leave and missed part of the game. She even called you a total gentleman about the whole thing. She told me about that. And I understood it's fine. It's whatever.

That's not what the deal breaker was for me. Oh, so there is a deal breaker? Yes. One specific reason? And that was kind of like the cherry on top. And I was just kind of like, okay, now I can't go through it. But the gloves were at the beginning. Like, what was it then?

Yeah. The tail end of it. Okay. Yeah, the very, very, very end of it when we went back to her place and she's telling me about this project that she's working on. It's a mess. You know, she's telling me, I don't think it's, you know, you might feel comfortable it's a little cramped in there and I asked I was what's this project that you're working on and she told me that she has Christmas trees she's you know like okay well Christmas

time is coming and what she said plural trees I'm like wait you have more than one oh yeah some people do that or you have a bunch of small trees that'd be cute yeah what's the problem well she has five of them and she's working on three more she's eight trees are she does she like make them for other people and then deliver them or something? It's for her. Just to have around the household. Full-sized trees? Like every room in the house is a full-sized tree? I don't know if it's all in one

room or if it's in one room and one's in a bedroom, one's in a... I don't know. One in each corner of every room. So you you hate Christmas? Is that what it is? No, yeah. I'm not trying to be the Grinch here. I'm just saying that you know, and then she seemed a little compulsive, obsessive over it to the point where it's kind of creepy.

So it sounds to me like You might see her as a little bit high maintenance? Well, I'll tell you this much. I've been on enough dates through the apps to know that when someone obsesses over something like this, it's a major red flag. I like to call red flags fun facts. Sometimes it turns out, you know, good. Look at this. Red is a color of Christmas.

Maybe you could be the green flag to go with her. And I'm sure there's a perfectly good explanation she could give you right now when we put her on the other line. because she's actually been there the whole time, Hunter. Well, what? Yeah. Yeah, she's been listening to this conversation. Hi, Hunter. Hi, Hunter.

Oh, my gosh. Oh. Yeah. So, okay, so I'm listening to this. My head is about to explode. First of all, you haven't even been in my house. How have been in my house? To see.

This energy. Well, I mean, not for nothing, you sounded like you didn't even want me to come in. So. Well, I didn't because I had, like, I had, like, ornaments everywhere and everything. They're so cool. I have, like, a forest. Yes, I do admit. You have, like, poor in my living room.

It's kind of like a forest. I have, like, little elves and stuff. You know, I put one in my garage, and I have it decorated, like, with, like, little tools, like with little nuts and bolts, a little wrenches. Oh, see, Hunter, there. You definitely overreacted. Not a red flag at all. Oh, yeah.

And then I have one in the back. I actually put one in the bathroom, like, in the corner. I take out my hamper and put, like, it in the bathroom. Wait, like, a full-sized tree? But why? Yeah, it's great. You have a big bathroom. Yeah.

It's pretty big. It's tall and skinny. Can you all the shape trees are like different shapes and sizes and whatever? This is my tall skinny tree. I'm how to decorate it. Shana, Shana, thank you for sharing so much. I think we get the picture now.

You love Christmas. You love all the trees in your house. I love Christmas. He sounds like a grinch. And are you baahumbugging. You're a baahumbug. That's not what he's saying. I would just like to give Hunter a chance to respond to you a little bit about what he thinks

about all the trees in your house. Hunter? Well, let him get out. Shana, hold on a second. Let him get out maybe more than two words this time. Hunter, give it a shot.

Don't get me wrong. I'm all for Christmas spirit. I love nature. Foliage, you name it. But outside the house, you know, maybe one Christmas tree suffices. Standard creation.

Awesome about Christmas for you. I just can't get over and you put up eight trees, which means you take down eight trees. I'm kind of hearing that she's rich. Those are expensive. Big houses. She's got a lot of energy. Eight trees is probably the equivalent of one tree for us.

What do you do for New Year's? What do you do for Valentine's? Like, now you have me thinking. Well, you know, Valentine's is great. I have a whole, like, a separate storage unit for all of my decorations for every holiday of year. Hunter was asking her about Valentine's Day, which makes me think he was planning ahead. He is interested. Hunter, we would love to send you on that pre-valentine's Day date and we will pay for it.

Oh, yes, my friend. I mean, you've got to give her, she is fun, she is spirited. Fair enough, fair enough, fair enough. And we know from your dating profile, Hunter, that you're unapologetically yourself. And you can continue to unapologetically be yourself on that next date. You have my profile pulled up right now or she? No, not to say that. But I will say the majority of people in this room thought that was a red flag.

So maybe you could look over her red flag. Shana's sure did. Come on, Hunter. One more chance. We'll pay for it, man. Red flag, green flag, put them together. Christmas. Is that a mer-

What color is that made? It's like a purple flag? No, it's like brown. It's like a bad NASCAR. Oh, I'll see yucky. What do you say, Hunter? You're paying, definitely. Oh, that's what does it for you.

All right, he's unapologetically cheap, too. So congratulations, you get another day. Brooke and Jeffrey in the morning. Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc. the link. Thanks. Hey, just finished drawing up that quick one-page business plan for you. Here's the link. But there was no link. There was no business plan. It's not his fault. I hadn't programmed

Kyle to be able to do that yet. My name is Evan Ratliff. I decided to create Kyle, my AI co-founder, after hearing a lot of stuff like this from OpenAI CEO Sam Aldman. There's this betting pool for the first year that there's a one-person billion dollar company, which would have been like unimaginable without AI and now will happen. I got to thinking, could I be that one person? I'd made AI agents before for my award-winning podcast, Shell Game. This season on Shell Game, I'm trying to build a real company with a real product run by fake people.

Oh, hey, Evan. Good to have you join us. I found some really interesting data on adoption rates for AI agents and small to medium businesses. Listen to Shell Game on the IHeart Radio app or wherever you get your podcasts. A decade ago, I was on the trail of one of the country's most elusive cereal. 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, the investigation into the most notorious killer in New York, since the son of Sam, available now. Listen for

free on the IHeart Radio app, Apple podcasts, wherever you get your podcasts. Well, it's been almost an entire year since we've had them on, but apparently Hunter and Shana are still dating, which is great. But the holidays are

coming up again. I wonder if that's going to cause any tension in their relationship. I would say it already has. This girl has already decorated. There is no way she's waiting. Hunter, Shana, how are you guys doing? Oh, we're so good. Merry Christmas. Can you hear us in the forest in your house?

Oh, we haven't even started yet. No. Oh, you haven't. Oh, why? Is that normal for you? Or are you trying to be considerate of him? No, totally normal. Oh, okay, good. All right.

Hunter, how are you doing? Are you excited for the holidays this season? Yeah, yeah, I'm excited. I'm actually more excited for her, you know, so her being excited makes me excited. Aw, that's a good boyfriend. I mean, where are you guys are? Are you living together or what? Yeah, we're together.

I mean, we're actually upping the ante this time around. You're upping the ante? What does that mean? So we're actually, instead of eight trees, we're doing nine. Oh, another one. Is that ninth tree, like your tree, the couple's tree? It's like the band cave tree? Is that how it works?

There's actually something really special about this extra tree because this one, we're actually going into the forest to get it ourselves. We're going to cut it down. Oh. It's going to be totally like a Hallmark movie. I'm so excited. Oh, that's cute.

Also, check for squirrels. Hunter, I'm curious, is Shana like this on any other holiday of the year now that you've almost spent like a whole one together? Is she like this for anything else? Well, at first I thought it might But no, it's actually only Christmas She has a spreadsheet That she has prepared in July

Oh, in July Is it? Yeah, okay It has to be that way Because I've got to keep it all organized And I have to write it down Like all the themes of the trees And what goes on each tree

Yeah, I have to be that way Wow At least we keep it simple I feel like you should start your own business Yeah, exactly You know? Santa should hire you to actually run the work set. You need to go and set up the North Pole.

I know. Oh, it sounds like you guys are in a really great relationship. It's really great. He's amazing. Oh, you guys, if you ever get married, will you get married at Christmas time? Amongst our forests. Yes. I love it. I love it. I will keep us updated on your relationship. Happy to hear from you. Yeah, congratulations. It's Brooke and Jeffrey in the morning. Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page. As a Google Doc and send me the link. Thanks. Hey, just finished drawing up that quick one-page business plan for you. Here's the link. But there was no link. There was no business plan. I hadn't programmed

Kyle to be able to do that yet. I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people. Check out the second season of my podcast, Shell Game, on the IHeart Radio app or wherever you get your podcasts. on this week's episode of next chapter i t d jake sit down with denzil washington a two-time academy award-winning actor and cultural icon for a conversation about change identity and the moment everything shifted i mean i don't take any credit for it is nothing i did as special you know I didn't knock down a few pegs and recognize it, but I just didn't put me first.

I just put God first, and he's carried me. Whether you're rebuilding, reimagining, or just trying to hold it together, this one will speak to you. Listen to the next chapter podcast on the I Heart Radio app, Apple Podcast, or wherever you get your podcast. New episodes drop weekly.

Don't miss one of them. Hi, I'm Dr. Priyanko Wally. And I'm Hurricane DeBolu. On our new podcast Health Stuff, we demystify your burning health questions. You'll hear us being completely honest about her own health. My residency colon was like a cry for help, honestly. And you'll hear candid advice and personal stories from experts who want to make health care more human.

I feel like I never felt like I truly belonged in medicine. We want to make health less confusing and maybe even a little fun. Find health stuff on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people. horrible ideas and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is.

The most Texas story ever. Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What do you get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconic sitcoms of all time? You get Desi Arness. On the podcast star in Desi Arnaz and Wilmer Valderrama, I'll take you in a journey to to Desi's life, how he redefined American television and what that meant for all of us watching from the sidelines, waiting for a face like hours on screen. Listen to starring Desi Arnaz and Wilmer Valderrama on the IHard Radio app, Apple Podcasts, or wherever you get your podcast.