May 4, 2026

Dear Treehouse #22 | Valentine’s Day Stories: Best, Worst & Dating Disasters

Show Notes
Transcript

Valentine’s Day brings out the best—and the absolute worst—in dating and relationships. In this episode of The Treehouse Show, we share our best Valentine’s Day memories, the worst dating fails, and Trey tells a heartbreak story that sets a new standard for bad Valentine’s experiences. If you enjoy comedy podcasts about relationships, dating stories, and real-life humor, this episode delivers. Topics include:

Best Valentine’s Day moments
Worst Valentine’s Day disasters
Funny dating and relationship stories
A brutal heartbreak story you won’t forget

About the show:

Leave your worries outside and join Dan O'Malley, Trey Trenholm, and their hilarious guests for laughs about funny news and viral stories with ridiculous commentary inside the Treehouse Show.

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WEBVTT

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It is time to leave your worries outside and laugh

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with us inside the Treehouse. I'm Daniel Malley along with

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Trade Trendholm and Raj Sharma. Here we have a very

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special edition of Deer Treehouse. Trey take it away.

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Well, this is a very special edition because this is

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constitutes a first Now full disclosure, we're recording this on

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Friday the thirteenth, but and this will drop on Monday

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the sixteenth, which, by the way, my girlfriend Brandy's birthday.

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Happy birthday, baby, I love you.

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And I'm sorry so.

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But first time we've all been in relationships.

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So my god, You're right, the planets have aligned.

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So my first question is what do you all have

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planned for Valentine's Day for your significant others?

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Raj uh, My, my girl's out of town, so we'll

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do it when she gets back.

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All right, what are you gonna do when she gets back?

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We usually just.

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Go out, uh to like Antonio's. I love that place

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and just grab some Italian food and some wine.

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And yeah, you.

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Make it sound like you've done this before on previous

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Valentine's But isn't this your first Valentine's Day together?

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That's kind of where we go on like special occasions.

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Okay, so so nothing special then for Valentine's Day.

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No, I mean, I mean not a big holiday person.

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She's not a big no commercial holiday or you know,

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like you know, Trey was saying, like the Christmas Thanksgiving,

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Like Thanksgiving is a different one, but Christmas and Valentine's

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Day and stuff like that, she's not really big into.

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So you know, I'll buy her. I'll buy her like

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some jewelry or something. But that's about it.

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See, my wife is not into Valentine's Day, and because

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of that, I celebrate by celebrating the fact that I had.

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I don't have to get her anything, never have, and

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I keep waiting for that shoe to drop. We're being honest.

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I still get a little anti every Valentine's Day. But

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so far, so good. She hasn't you know, murdered me

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yet for not getting her something for Valentine's Day. So

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she was true to her word. That first Valentine's Day.

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She's like, I don't like Valentine's Day. You don't have

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to get me anything? Cool?

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Yeah, I mean when I say, Jeuelie, she just wanted

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like a really light like silver chain. It's nothing like extravagant.

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So we'll do that and have some dinner and it'll be.

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It and a coupon for some raj lovin.

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I already gave her the book.

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And Dan, I think you could have just done an

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all stop as my wife hasn't killed me yet.

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Yeah, but I'm still waiting. Could this be the year?

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Yeah? Just won't happen on Valentine's Day?

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The day after be the day after Valentine's Day massacre.

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Oh, I am a. This one's a weird one. I'm

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planning on getting up and I'm going to cook brandy breakfast,

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bake some blueberry muffins, stuff like that. Uh, then if

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she wants to, she's expressed interest. I bought a sour

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dough starter kick kit, so we're gonna make bread.

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Is that an that? Any window for something else?

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Literally tell the story? Kay? Can you tell the story

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again and make it an innu window.

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All you have to do is go, hey, baby, let's

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make some bread.

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You want to stick your hands and some yeast together,

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But that's what it is. That is what it is.

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You're going to celebrate Valentine's Day by you know, molesting

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some yeast.

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Maybe you've got to you gotta make this thing rise.

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So that needs to be on a shirt, sour dough

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starter thing. I make this rise. There you go.

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Uh. And then and this is the uh, the weird one.

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She's making me dinner.

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Oh nice, So you're bookending meals for Valentine's Day.

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Yeah, but I'm doing She literally was like, now, granted

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her birthdays Monday and and but she was like, I

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want to make you dinner for Valentine's Day. It's like,

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guys always do it for the girls. I want to

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do something for you.

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That's pretty cool.

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Have you had her cooking before? I have? It's good? Okay,

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it's a good.

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Okay.

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So there's also a trend by the way of uh,

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you know, doing some role reversal type stuff in relationships.

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So her wanting to make you dinner for Valentine's Day

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as a you know, that's a traditional gender role swap

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kind of the thing. Let's take it a couple of

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steps ahead. What would you do if she proposed, because

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that's the new trend as well.

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I'd say yes, and then they would eat bread after

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she made it rise. Mm hmm, Well you would say yes.

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Wow?

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All right, man, It's fascinating the strap On King talks

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about role reversals.

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Clearly I know a thing or two about it.

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That sounds like the name of an adult toy store

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mattress King. I'll just eat the spitty arm guy twelve twelve,

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loop twelve everything half off from the strap on King.

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Oh god, quick disclaimer, that's not true anyway. All right,

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back to back to Valentine's Day spectacular inside the treas.

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So this leads me to my second question, best and

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worst Valentine's Days.

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In history or just with ourselves?

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With yourselves?

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Oh, okay, the best Valentine's Days have been every single

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one with my wife.

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Good answer, good answer. She's in the room, right, yeah,

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look at him. Yeah, yeah, that's a solid answer. She

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knows that's bullshit.

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But yeah, she's not even acknowledging. Yes, oh there is.

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Uh.

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The worst was there's one Valentine's Day with an ex

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clearly that I. I made dinner and and it did

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not go over well. I didn't the you're cooking or

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just the it was a lackluster. It was a lackluster meal.

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Apparently I didn't put enough effort into it. Keep in mind,

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that was back when I really didn't cook good. Well,

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I meant, well, how I said it. The cooking was

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so poor, as was my grammar.

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Was this something she that she pointed out or just

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you felt like you had underdelivered.

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That's probably a little bit of both. I mean, uh,

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we were on trying to be on a healthy kick

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at the time. So I had made dinner. I said,

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I'll make dinner, and I just you know, it was

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a salad. At the end of the day, it was

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a salad with some shrimp. And no, it's it's it's

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a very underwhelming me e for Valentine's Day. But then again,

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I mean, yeah.

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He's not even like a Christini or something, just shrimp.

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It was two thousand and six, two thousand and seven,

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I didn't even know what a Christini was.

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Wow, shrimp salad. I think I had that on an

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American Airlines flight once.

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I think that's I think that was my inspiration.

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Was it American Airlines or American Eagle?

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It was Eagle, were right.

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Even Spirit, even Spirit would look down on that. Spirit

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wouldn't let it on the flight, and.

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The only way to get her to eat it was

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to make the airplane noise.

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So yeah, I just thought of it and I had

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the best Valentine's Day and the worst Valentine's Day in

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the same day. I was dating this awful, awful human

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being in Los Angeles. She was just like Even my

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manager at the time was like, get a new girlfriend, like,

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because we'd go to the club and I would have

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her sit next to him and she's like, she's the

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worst person. But we would break up every three months

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and she would come to my door and had a

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sobbing and have a letter. And I can't stand to

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watch a woman cry. I can't stand it. So I'm like,

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we'll figure it out. Come on in, We'll figure it out.

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But I came home. She had a key to my

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place and I came home. I had an audition or

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something like that that day. And I came home and

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she had cooked like home cooked Indian food, Indian girl,

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So only Indian girl ever dated, and I'll never do

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it again, hopefully never have to. And she made like

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chicken curry and rice and fresh non like the whole

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nine yards and it was great. And we were having

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dinner and then she started talking and I was like,

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you always screw it up, yep, I was like you

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I started talking about my set from the night before

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and how she found it underwhelming even though sold out

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show followed.

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Dane cook and nobody left.

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Usually there's a mass exodus after Dane is done and

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nobody left, and it was a great set, and she's like,

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I just don't understand why people think you're funny. And

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I was like, bitch, if this food wasn't as good

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as it is, i'd throw you off my balcony right now. Yeah,

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And I ended that very quickly. But after you ate, oh,

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in mid food, I was like, you can leave now,

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and asked her to leave. And so the food was spectacular,

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you can leave the non yeah yeah, oh, I mean

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she left everything. I was like, the food was amazing,

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the ambiance was great. Like she like candles, and like

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she brought me flowers, which I thought was weird.

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Was that to soften the blow of her critique of

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your Oh I.

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Don't know, but I gave her those flowers on the

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way out the door.

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I was like, take these good. I don't want these

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to die in my house. Like this relationship just did.

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What was that the last of their relationship?

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It was there was one more month and we had

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to come to Dallas for a wedding and she embarrassed

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me in front of my family and friends, and she

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flew back. We flew back separately, and she picked me

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up from the airport and we're driving them like, how

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do I get out of her spending the night?

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And I was like, hey, I just got a call.

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I have a set at the laugh Actor.

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She's like, oh, okay, and We're pulling into my parking

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garage and I was like, She's like, I just want

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to come up for a bit. I was like, I gotta,

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I gotta go now immediately, and I had It's the

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first time, and this is so awful, and I know

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you guys are gonna think it's awful. But I broke

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up with her in the laugh Factory. Like I'm sitting

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in the laugh Actory having a drink and y a text.

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She said good night and I said good night. I

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can't do this anymore, and she goes, we'll talk about

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it in the morning. I go nothing to talk about

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mail me my key. Never heard from her again.

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It was the saing is how you have a weakness

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when it comes to a crying woman. And you should

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have dumped her a month before. I'm fine with it, okay, good.

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Yeah, because a lot of just my friends that are

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girls were like, that's just mean. And I'm like, you

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don't know this girl like she's been she was married.

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I didn't find this out until later from one of

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her friends. She'd been married three times and none of

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them over a year. Yeah, none of them. And one

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she moved to Ireland for this guy. And so it was.

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It was.

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It was the best of times in the worst of times.

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Like that's what That's what that Valentine's Day was.

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But the food was.

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Man, if she would have just been a nice person,

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I would have locked it down.

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Yeah.

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So that was yours. That was your best and your

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worst Valentine's same day. All right, what about you, Trey?

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Hm hmm, you tell someday.

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I'm I'm thinking tomorrow will be the best of the

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Valentine's Day. Yeah, my worst though, it's a doozy Okay.

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So back in uh So, this is two thousand and five.

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I've been dating a girl about I don't know, six

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seven months, and uh everything was going pretty well. Uh

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and in January she had uh she was pregnant, and

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uh so I was nervous but excited and on Valentine's day,

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we went and got the first sonogram of the baby.

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Go in there and you know, they pittch you off

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a little picture, had it in my front pocket my shirt.

236
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Spent the day trying looking for places for us to

237
00:14:25.240 --> 00:14:28.639
you know, live, and we're supposed to meet that night

238
00:14:28.679 --> 00:14:36.600
for dinner and seven o'clock, no show, eight, no show.

239
00:14:38.000 --> 00:14:42.440
At this point, I am now after eight, I'm getting

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00:14:42.519 --> 00:14:50.200
very very agitated. Finally, about nine o'clock, after numerous calls

241
00:14:50.200 --> 00:14:54.080
and text she finally turns my call and I'm like,

242
00:14:54.159 --> 00:14:59.440
you know what's going on? Where are you? And no,

243
00:14:59.519 --> 00:15:05.360
buffer know nothing. Their next sentence is, we need to

244
00:15:05.360 --> 00:15:06.600
have a paternity.

245
00:15:06.120 --> 00:15:13.559
Test after the baby's born, correct, because you can't have

246
00:15:13.639 --> 00:15:16.159
it then and there.

247
00:15:15.960 --> 00:15:19.759
You could have a pre It was very difficult at

248
00:15:19.759 --> 00:15:21.720
that time and very dangerous.

249
00:15:22.720 --> 00:15:25.120
That would be the amniocentesis, right, that's what they would

250
00:15:25.200 --> 00:15:25.480
have to do.

251
00:15:26.279 --> 00:15:27.879
At the time, there was only a place in Houston

252
00:15:27.879 --> 00:15:36.080
that was doing it, and so that uh, that was

253
00:15:36.120 --> 00:15:36.720
life changing.

254
00:15:37.399 --> 00:15:37.919
Mm hmmm.

255
00:15:39.399 --> 00:15:41.799
I told her.

256
00:15:41.759 --> 00:15:45.000
That, you know.

257
00:15:45.159 --> 00:15:47.600
I it was like, if it's mine, I'll be a

258
00:15:47.639 --> 00:15:50.399
great father. If it's not, you can funk all the

259
00:15:50.440 --> 00:15:50.840
way off.

260
00:15:54.120 --> 00:15:54.240
Uh.

261
00:15:55.039 --> 00:15:57.120
And then I was the really nice guy and I

262
00:15:57.440 --> 00:16:01.200
actually she decided at that point that she did not

263
00:16:01.279 --> 00:16:03.480
want to risk it if it was the other guys,

264
00:16:04.679 --> 00:16:11.320
and uh decided to have an abortion. And I took

265
00:16:11.320 --> 00:16:13.440
her to and held her hand through the process because

266
00:16:13.519 --> 00:16:14.919
I thought I was being a nice guy.

267
00:16:16.000 --> 00:16:21.639
Oh and this is so that that happened Valentine's Day

268
00:16:21.639 --> 00:16:23.720
and this happened the same night.

269
00:16:25.000 --> 00:16:27.639
No, this was just the aftermath of it. Nomet know.

270
00:16:27.679 --> 00:16:29.240
What I'm saying, is she called the same night for

271
00:16:29.279 --> 00:16:30.159
the coternity test.

272
00:16:30.240 --> 00:16:31.799
No, I know, but in my head it's like good

273
00:16:31.840 --> 00:16:34.120
drive on through with the Valentine's Day special here at

274
00:16:34.120 --> 00:16:34.519
the clinic.

275
00:16:35.039 --> 00:16:38.120
Yeah. Yeah, No, that was how she she why she

276
00:16:38.200 --> 00:16:41.919
was late for dinner. As she said, she'd, instead of

277
00:16:41.919 --> 00:16:43.559
saying we need to talk or anything else, said we

278
00:16:43.559 --> 00:16:44.600
need to have a trinity test.

279
00:16:45.279 --> 00:16:45.759
Wow.

280
00:16:46.039 --> 00:16:48.720
Okay, yeah, I see most people agree that we need

281
00:16:48.759 --> 00:16:52.679
to talk. Sentence is bad. Yeah, but you learned that

282
00:16:52.720 --> 00:16:53.919
there is a worst sentence.

283
00:16:54.639 --> 00:16:56.080
Yeah, that we need to talk at least as a

284
00:16:56.080 --> 00:16:58.039
buffer that you know something bad is coming.

285
00:16:58.440 --> 00:17:00.919
Yeah, As opposed to her just straight up saying and

286
00:17:01.080 --> 00:17:03.120
so we needed to do a paternity Yeah.

287
00:17:03.240 --> 00:17:06.079
That that that was the o g raw dogging.

288
00:17:09.640 --> 00:17:11.720
That's that's when Maury gets on the phone with you

289
00:17:11.759 --> 00:17:13.400
and it's like, all right, we got the we got

290
00:17:13.400 --> 00:17:14.000
the results.

291
00:17:14.319 --> 00:17:17.200
Yeah, are you ready. I would like to point out

292
00:17:17.200 --> 00:17:18.839
that this is one of the few times I kept

293
00:17:18.839 --> 00:17:23.079
my mouth shut because when you mentioned that your girlfriend

294
00:17:23.119 --> 00:17:25.039
at the time was pregnant, the first thought in my

295
00:17:25.119 --> 00:17:27.480
mind was being a dick, was is yours? So I'm

296
00:17:27.480 --> 00:17:28.319
glad I didn't ask that.

297
00:17:31.200 --> 00:17:34.400
Wow, that is wild. Now it makes my chicken curry

298
00:17:34.400 --> 00:17:43.799
story look like shit. Turns out my Valentine's Day was great. Yeah.

299
00:17:43.880 --> 00:17:45.799
I need to call up my ex and say, see,

300
00:17:45.839 --> 00:17:46.839
could have been way worse.

301
00:17:51.160 --> 00:17:59.440
Listen to this from Salad bitch. Wow, that is wild.

302
00:17:59.480 --> 00:17:59.880
That is.

303
00:18:01.519 --> 00:18:04.640
Again that I wouldn't even know how to react to that.

304
00:18:04.839 --> 00:18:10.160
Like I drank a lot, Yeah there was, Oh you

305
00:18:10.200 --> 00:18:10.599
were drinking.

306
00:18:11.200 --> 00:18:14.440
This is twenty one years ago, Trey, and years ago

307
00:18:14.559 --> 00:18:16.720
Tray was yeah.

308
00:18:16.519 --> 00:18:17.119
But I'm back.

309
00:18:17.920 --> 00:18:20.240
Uh well, I drink with Tray one time at the

310
00:18:20.279 --> 00:18:24.000
loon when we were all there and you left and

311
00:18:24.079 --> 00:18:26.119
he we we stuck around. That's how the that's the

312
00:18:26.119 --> 00:18:29.759
first time we ever just kind of chatted like about nothing,

313
00:18:30.079 --> 00:18:31.279
you know, everything and nothing.

314
00:18:32.799 --> 00:18:37.799
Yeah, I'll have to say this fueled my alcoholism.

315
00:18:38.920 --> 00:18:42.039
Oh wow, I wouldn't doubt it. I would not dapt

316
00:18:42.079 --> 00:18:42.400
with that.

317
00:18:44.440 --> 00:18:48.200
Uh yeah, there's nobody's I can tell you right now,

318
00:18:48.480 --> 00:18:51.279
every listener, nobody's got a better story than this, Like,

319
00:18:51.440 --> 00:18:52.519
nobody's got a worse.

320
00:18:52.480 --> 00:18:55.079
No, that was hard to top.

321
00:18:55.440 --> 00:18:56.079
It really is.

322
00:18:56.519 --> 00:19:00.640
Yeah, and I don't say that, you know, boastfully.

323
00:19:01.519 --> 00:19:03.559
Yeah, this is not one of those one upping stories

324
00:19:03.559 --> 00:19:05.400
where you're like, ha ha scoreboard bitches.

325
00:19:05.519 --> 00:19:08.799
No, I'd prefer not to have won that competition.

326
00:19:09.680 --> 00:19:12.160
Oh, I know, but when people listen to the show

327
00:19:12.240 --> 00:19:15.200
or watch it, then we were like I got a store.

328
00:19:15.240 --> 00:19:17.519
Look from the beginning, when you're like what's your best

329
00:19:17.559 --> 00:19:19.519
and worst, people are like, oh, I got a good one.

330
00:19:19.920 --> 00:19:22.720
By the time they get to yours, we'll be like, nope,

331
00:19:22.880 --> 00:19:23.880
I don't got a good one.

332
00:19:26.640 --> 00:19:33.279
The good news is for tomorrow's Valentine's Day, I really

333
00:19:33.279 --> 00:19:37.720
do believe it's going to turn out better that So

334
00:19:37.759 --> 00:19:40.000
it's just you know what, It's kind of like Cradick

335
00:19:40.079 --> 00:19:42.200
used to stay, just keep looking up because that's where

336
00:19:42.200 --> 00:19:42.799
it all is.

337
00:19:46.559 --> 00:19:48.039
Tell us how the muffins turn out.

338
00:19:51.319 --> 00:19:54.599
And Uh, the other thing I'm gonna do is I'm

339
00:19:54.640 --> 00:19:58.920
going to Uh, I'm gonna send Brandy this tomorrow just

340
00:19:58.960 --> 00:19:59.880
to start the day off.

341
00:20:00.960 --> 00:20:04.359
Hey, that dayre's coming gap and I'm going to wish

342
00:20:04.400 --> 00:20:11.640
for buy heart to oh my friends family, Happy Valentide Day.

343
00:20:12.279 --> 00:20:14.920
Be sure to give love, because we can give love,

344
00:20:15.279 --> 00:20:17.480
it's eesier to receive love.

345
00:20:18.359 --> 00:20:23.240
Hey, and he says Valentine's.

346
00:20:25.319 --> 00:20:26.039
Well, he doesn't.

347
00:20:26.079 --> 00:20:33.039
He doesn't say Valentines.

348
00:20:30.440 --> 00:20:31.799
The fact he can still pronounce it.

349
00:20:31.839 --> 00:20:34.960
I mean, come on, and and can I just without

350
00:20:35.240 --> 00:20:37.240
seeming just so insensitive?

351
00:20:37.880 --> 00:20:38.960
Which eye is real?

352
00:20:42.920 --> 00:20:47.279
And I think it's the one that's more closed.

353
00:20:47.319 --> 00:20:49.359
Saying the small one. It's gonna be my first one.

354
00:20:50.920 --> 00:20:52.200
Did he not get the other one?

355
00:20:52.279 --> 00:20:52.640
Fitted?

356
00:20:52.799 --> 00:20:54.480
I don't know how this works.

357
00:20:56.240 --> 00:20:58.400
Or just has he done so many drugs They only

358
00:20:58.440 --> 00:21:00.960
work on on his you know, one side of his brain,

359
00:21:01.640 --> 00:21:06.400
because his left eye looks like it's so dilated. He

360
00:21:06.519 --> 00:21:07.799
you know, did an eight ball.

361
00:21:10.599 --> 00:21:14.200
He snorts it in that eye.

362
00:21:15.720 --> 00:21:19.079
He's the only one I know that does eye cocaine.

363
00:21:19.759 --> 00:21:23.319
I do love, though, how you've managed to you know what?

364
00:21:23.480 --> 00:21:27.160
Leave it to Gary Busey to bridge the gap between

365
00:21:27.200 --> 00:21:31.599
Friday the thirteenth and Valentine's Day, because he's really both

366
00:21:31.759 --> 00:21:33.640
days wrapped up in One Man.

367
00:21:34.200 --> 00:21:36.880
Yeah, he looks like he can be in both horror movies.

368
00:21:37.079 --> 00:21:42.799
Absolutely, he could be under your bed, but also with

369
00:21:42.839 --> 00:21:43.920
a lot of love in his heart.

370
00:21:44.519 --> 00:21:44.960
Yeah.

371
00:21:45.440 --> 00:21:47.880
I think Raj hit it though. I think you know,

372
00:21:48.039 --> 00:21:51.079
if you put lines of cocaine in front of Bucy,

373
00:21:51.680 --> 00:21:53.119
he would have to take his eye out, and his

374
00:21:53.119 --> 00:21:55.000
eye would do one line and he'd do the other.

375
00:21:57.640 --> 00:21:59.519
Then, and then as he puts it back in, he

376
00:21:59.559 --> 00:22:00.680
would say sharing.

377
00:22:00.480 --> 00:22:01.359
His Karen pat.

378
00:22:10.880 --> 00:22:16.279
For all things Treehouse, go to Treehouse on Air dot com.

379
00:22:16.279 --> 00:22:19.759
Also check out the Treehouse Show podcast. Regular episodes of

380
00:22:19.799 --> 00:22:23.319
the Treehouse Show are available everywhere you get your podcasts.

381
00:22:23.960 --> 00:22:28.240
Also extra Treehouse in Your Life Patreon dot com, slash

382
00:22:28.240 --> 00:22:30.160
Treehouse on Air. We will see you next time right

383
00:22:30.200 --> 00:22:41.279
here inside the Treehouse. Happy Valentine's Day on Monday,

Dear Treehouse #22 | Valentine’s Day Stories: Best, Worst & Dating Disasters

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