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Brooke and Jeffrey

Second Date Update Classics: The Boy Who Cried Tree + Deck The Mall

20 Dec 2025

Transcription

Chapter 1: Why is Brian back for a second date update?

0.031 - 13.197 Jeff

It's Brooke and Jeffrey in the morning. This is Technical Director Ashton coming at you with another classic second date update. And just for all of you ladies out there, if you like this second date, you like what the guy did on this second date, give me a call.

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14.122 - 27.264 Jose

Most of the time, if you go to a business for some help and they provide horrible service, completely let you down and leave you off worse than when you came in. Wow. That would be the end of it. You would never go back again.

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27.304 - 30.73 Unknown

Yeah. You go places for help. Right. Not the other way.

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30.71 - 39.803 Jose

That's why we were so surprised after we totally botched a second date for a guy a few months ago. And he's asking us for another one today.

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39.823 - 41.665 Unknown

I take back my statement. Yeah, but we're free.

Chapter 2: What happened during Brian's date at the Christmas tree farm?

41.846 - 45.21 Unknown

He's not paying for it, so maybe that's why he's still here.

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45.231 - 63.638 Jose

I mean, at this point, I'm not sure if he's just trolling us or if he really, really enjoys the punishment. But his name's Brian, and we're going to hear about his holiday that he had at a Christmas tree farm the other day. Okay. And we promise to give at least 30% effort. Well, Brooke, 22%.

0

63.698 - 64.86 Unknown

Okay, all right.

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64.88 - 66.783 Jose

We don't want to stretch ourselves too far for this.

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66.803 - 69.969 Unknown

I'm pretty tired right now during the holidays. Can I just 17?

70.329 - 74.156 Jose

Okay, yeah. We're going to muster whatever little strength that we have left.

74.176 - 75.157 Unknown

Okay, let's do this.

75.177 - 79.364 Jose

In your second date update that's coming up next.

79.384 - 80.967 Unknown

Second date update.

Chapter 3: How did Brian's date with Aubrey unfold?

82.027 - 86.838 Jose

Today, we actually have a repeat customer for a second date update.

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86.859 - 91.85 Unknown

What? No way. Okay. Is that allowed? I just don't think things are going very well for them, Ben.

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92.091 - 98.065 Jose

Well, he called in about five months ago. Okay. When he got side-eyed during sushi by another woman that he ghosted.

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98.727 - 98.787 Unknown

Oh.

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98.767 - 120.502 Jose

remember that i don't remember we do so many well i guess we couldn't get him another date there but apparently there's a new lady who's caught his attention and he wants our help again so we're welcoming back brian brian welcome back man you must really have faith in us for some reason i know we couldn't I believe in you guys. I believe in you.

120.842 - 123.625 Unknown

I feel like we cursed your love life and you're just stuck with us.

125.547 - 128.531 Jose

He's like, I'm trying other morning shows, but you're the only ones that like me.

Chapter 4: What unexpected situation occurred with a crying child?

129.011 - 132.215 Unknown

Actually, I emailed all of them, but you're the only ones that responded.

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134.117 - 141.885 Jose

Yeah, we have very low standards here. So welcome back. Tell us about the girl that you met this time. What's her name?

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142.22 - 163.953 Unknown

All right. So her name is Aubrey. I saw a picture on my coworker's Instagram. She was tagged in it. Oh, nice. I got into detective mode and clicked the tag and went on her page. I love it when girls tag their friends because some girls will have a really hot friend, but they won't tag them. And I'm like, how am I supposed to creep on your friend if you don't tag her?

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163.993 - 166.637 Unknown

Okay, so remind me not to tag my friend.

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166.677 - 169.161 Jose

So that's not okay from a woman's perspective?

Chapter 5: What was Aubrey's reaction to the Christmas tree incident?

169.181 - 170.944 Jose

Is it cool if a guy reaches out to you?

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170.924 - 174.95 Unknown

I mean, it depends on how hot he is, right? That's always the answer.

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175.031 - 178.917 Jose

Brian, I know you're super handsome, so you're safe. What did Aubrey say when you reached out?

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179.458 - 195.062 Unknown

Well, I slid in a DM. She didn't seem to be attached to anyone. And I found out this is going to be her first Christmas alone because she's actually moved and she's going to be away from her family. Oh, that's too bad. She should get used to being alone like me.

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195.724 - 197.927 Jose

Was she sad about that or was she happy about it?

198.245 - 202.109 Unknown

She was a little distraught. Okay. Yeah, I can see why. Okay.

Chapter 6: How did Brian justify his actions during the date?

202.129 - 224.213 Unknown

So you're like, this is my moment. I'm going to do something holiday for her. Is that what you're thinking? Of course. I offered to take her to a Christmas tree farm to get her a tree. Aww. So at least she had the season to be jolly filled with a tree in the house. That's cute, too. And I feel like you can be vouched for, right? It's not just some rando coming into her DMs.

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224.293 - 226.255 Unknown

It's her co-worker's friend.

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226.315 - 228.117 Jose

So how did the Christmas tree farm go?

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228.434 - 233.646 Unknown

It was great. It was great. So what we did, we wore our silly Christmas sweater.

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Chapter 7: What was the outcome of the call with Aubrey?

233.686 - 258.442 Unknown

Oh, nice. And I wore my sweater that said, jingle and single. I love it. This is great. I want to do this now. Her said, Santa's favorite, ho, ho, ho. Nice. I knew it was going to be an awesome time, so I bought a little bit of those, you know those small bottles they have on the airplane of alcohol? Yeah, shooters. Yeah, I bought a couple of those.

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258.462 - 270.186 Unknown

I bought like four or five whiskey bottles, and it loosened both of us up. We had such a great time. Okay. I mean, that's a really cute date. I mean, what was the highlight of it all for you?

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Chapter 8: What lessons can be learned from this second date update?

271.027 - 275.818 Para

Well, she found a tree that she loved, loved, loved, so I offered to buy it for her.

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275.838 - 284.597 Unknown

Dang. And then I saw the price tag and was like, whoa. Yeah. How much do trees cost? Oh, my God. We just got one this weekend. It was $85. Whoa.

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284.847 - 287.711 Jose

It was like in three figures. It was pretty high.

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288.232 - 289.313 Unknown

Oh, okay.

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289.333 - 289.694 Jose

Oh, yeah.

289.714 - 294.26 Unknown

Ours was only, like, five foot tall. Like, if you're thinking eight feet or something. That's expensive.

294.28 - 299.327 Jose

Oh, that's not a good look when you offer to pay for something and you're, like, going back on it afterwards. Yeah, I know. Actually.

299.347 - 316.353 Unknown

That's like being, like, all day for dinner, seeing the bill. Actually, you are. He just saw, you know, a foot off the top. Yeah. This was actually a three-footer now. Yeah. Well, it's funny because she saw the look on my face when I saw that price tag. And she was like, alright, we're definitely splitting this. And I was like, yeah, we are.

316.393 - 318.938 Jose

Alright.

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