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May 4, 2026

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

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

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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0:00 It is time to leave your worries outside and laugh with us inside the Treehouse. I'm Daniel Malley along with Trade Trendholm and Raj Sharma. Here we have a very special edition of Deer Treehouse. Trey take it away. Well, this is a very special edition because this is constitutes a first Now full disclosure, we're recording this on Friday the thirteenth, but and this will drop on Monday the sixteenth, which, by the way, my girlfriend Brandy's birthday. Happy birthday, baby, I love you. And I'm sorry so.

0:42 But first time we've all been in relationships. So my god, You're right, the planets have aligned. So my first question is what do you all have planned for Valentine's Day for your significant others? Raj uh, My, my girl's out of town, so we'll do it when she gets back. All right, what are you gonna do when she gets back? We usually just. Go out, uh to like Antonio's. I love that place and just grab some Italian food and some wine. And yeah, you. Make it sound like you've done this before on previous Valentine's But isn't this your first Valentine's Day together?

1:24 That's kind of where we go on like special occasions. Okay, so so nothing special then for Valentine's Day. No, I mean, I mean not a big holiday person. She's not a big no commercial holiday or you know, like you know, Trey was saying, like the Christmas Thanksgiving, Like Thanksgiving is a different one, but Christmas and Valentine's Day and stuff like that, she's not really big into. So you know, I'll buy her. I'll buy her like some jewelry or something. But that's about it. See, my wife is not into Valentine's Day, and because of that, I celebrate by celebrating the fact that I had. I don't have to get her anything, never have, and I keep waiting for that shoe to drop. We're being honest.

2:10 I still get a little anti every Valentine's Day. But so far, so good. She hasn't you know, murdered me yet for not getting her something for Valentine's Day. So she was true to her word. That first Valentine's Day. She's like, I don't like Valentine's Day. You don't have to get me anything? Cool? Yeah, I mean when I say, Jeuelie, she just wanted like a really light like silver chain. It's nothing like extravagant. So we'll do that and have some dinner and it'll be. It and a coupon for some raj lovin. I already gave her the book. And Dan, I think you could have just done an all stop as my wife hasn't killed me yet. Yeah, but I'm still waiting. Could this be the year?

2:57 Yeah? Just won't happen on Valentine's Day? The day after be the day after Valentine's Day massacre. Oh, I am a. This one's a weird one. I'm planning on getting up and I'm going to cook brandy breakfast, bake some blueberry muffins, stuff like that. Uh, then if she wants to, she's expressed interest. I bought a sour dough starter kick kit, so we're gonna make bread. Is that an that? Any window for something else?

3:39 Literally tell the story? Kay? Can you tell the story again and make it an innu window. All you have to do is go, hey, baby, let's make some bread. You want to stick your hands and some yeast together, But that's what it is. That is what it is. You're going to celebrate Valentine's Day by you know, molesting some yeast. Maybe you've got to you gotta make this thing rise. So that needs to be on a shirt, sour dough starter thing. I make this rise. There you go. Uh. And then and this is the uh, the weird one.

4:26 She's making me dinner. Oh nice, So you're bookending meals for Valentine's Day. Yeah, but I'm doing She literally was like, now, granted her birthdays Monday and and but she was like, I want to make you dinner for Valentine's Day. It's like, guys always do it for the girls. I want to do something for you. That's pretty cool. Have you had her cooking before? I have? It's good? Okay, it's a good. Okay. So there's also a trend by the way of uh, you know, doing some role reversal type stuff in relationships. So her wanting to make you dinner for Valentine's Day as a you know, that's a traditional gender role swap kind of the thing. Let's take it a couple of steps ahead. What would you do if she proposed, because that's the new trend as well.

5:23 I'd say yes, and then they would eat bread after she made it rise. Mm hmm, Well you would say yes. Wow? All right, man, It's fascinating the strap On King talks about role reversals. Clearly I know a thing or two about it. That sounds like the name of an adult toy store mattress King. I'll just eat the spitty arm guy twelve twelve, loop twelve everything half off from the strap on King. Oh god, quick disclaimer, that's not true anyway. All right, back to back to Valentine's Day spectacular inside the treas.

6:11 So this leads me to my second question, best and worst Valentine's Days. In history or just with ourselves? With yourselves? Oh, okay, the best Valentine's Days have been every single one with my wife. Good answer, good answer. She's in the room, right, yeah, look at him. Yeah, yeah, that's a solid answer. She knows that's bullshit. But yeah, she's not even acknowledging. Yes, oh there is.

6:54 Uh. The worst was there's one Valentine's Day with an ex clearly that I. I made dinner and and it did not go over well. I didn't the you're cooking or just the it was a lackluster. It was a lackluster meal. Apparently I didn't put enough effort into it. Keep in mind, that was back when I really didn't cook good. Well, I meant, well, how I said it. The cooking was so poor, as was my grammar. Was this something she that she pointed out or just you felt like you had underdelivered.

7:42 That's probably a little bit of both. I mean, uh, we were on trying to be on a healthy kick at the time. So I had made dinner. I said, I'll make dinner, and I just you know, it was a salad. At the end of the day, it was a salad with some shrimp. And no, it's it's it's a very underwhelming me e for Valentine's Day. But then again, I mean, yeah. He's not even like a Christini or something, just shrimp. It was two thousand and six, two thousand and seven, I didn't even know what a Christini was. Wow, shrimp salad. I think I had that on an American Airlines flight once. I think that's I think that was my inspiration.

8:23 Was it American Airlines or American Eagle? It was Eagle, were right. Even Spirit, even Spirit would look down on that. Spirit wouldn't let it on the flight, and. The only way to get her to eat it was to make the airplane noise. So yeah, I just thought of it and I had the best Valentine's Day and the worst Valentine's Day in the same day. I was dating this awful, awful human being in Los Angeles. She was just like Even my manager at the time was like, get a new girlfriend, like, because we'd go to the club and I would have her sit next to him and she's like, she's the worst person. But we would break up every three months and she would come to my door and had a sobbing and have a letter. And I can't stand to watch a woman cry. I can't stand it. So I'm like, we'll figure it out. Come on in, We'll figure it out.

9:24 But I came home. She had a key to my place and I came home. I had an audition or something like that that day. And I came home and she had cooked like home cooked Indian food, Indian girl, So only Indian girl ever dated, and I'll never do it again, hopefully never have to. And she made like chicken curry and rice and fresh non like the whole nine yards and it was great. And we were having dinner and then she started talking and I was like, you always screw it up, yep, I was like you I started talking about my set from the night before and how she found it underwhelming even though sold out show followed.

10:10 Dane cook and nobody left. Usually there's a mass exodus after Dane is done and nobody left, and it was a great set, and she's like, I just don't understand why people think you're funny. And I was like, bitch, if this food wasn't as good as it is, i'd throw you off my balcony right now. Yeah, And I ended that very quickly. But after you ate, oh, in mid food, I was like, you can leave now, and asked her to leave. And so the food was spectacular, you can leave the non yeah yeah, oh, I mean she left everything. I was like, the food was amazing, the ambiance was great. Like she like candles, and like she brought me flowers, which I thought was weird.

10:57 Was that to soften the blow of her critique of your Oh I. Don't know, but I gave her those flowers on the way out the door. I was like, take these good. I don't want these to die in my house. Like this relationship just did. What was that the last of their relationship? It was there was one more month and we had to come to Dallas for a wedding and she embarrassed me in front of my family and friends, and she flew back. We flew back separately, and she picked me up from the airport and we're driving them like, how do I get out of her spending the night? And I was like, hey, I just got a call. I have a set at the laugh Actor.

11:38 She's like, oh, okay, and We're pulling into my parking garage and I was like, She's like, I just want to come up for a bit. I was like, I gotta, I gotta go now immediately, and I had It's the first time, and this is so awful, and I know you guys are gonna think it's awful. But I broke up with her in the laugh Factory. Like I'm sitting in the laugh Actory having a drink and y a text. She said good night and I said good night. I can't do this anymore, and she goes, we'll talk about it in the morning. I go nothing to talk about mail me my key. Never heard from her again. It was the saing is how you have a weakness when it comes to a crying woman. And you should have dumped her a month before. I'm fine with it, okay, good.

12:22 Yeah, because a lot of just my friends that are girls were like, that's just mean. And I'm like, you don't know this girl like she's been she was married. I didn't find this out until later from one of her friends. She'd been married three times and none of them over a year. Yeah, none of them. And one she moved to Ireland for this guy. And so it was. It was. It was the best of times in the worst of times. Like that's what That's what that Valentine's Day was. But the food was. Man, if she would have just been a nice person, I would have locked it down. Yeah. So that was yours. That was your best and your worst Valentine's same day. All right, what about you, Trey?

13:09 Hm hmm, you tell someday. I'm I'm thinking tomorrow will be the best of the Valentine's Day. Yeah, my worst though, it's a doozy Okay. So back in uh So, this is two thousand and five. I've been dating a girl about I don't know, six seven months, and uh everything was going pretty well. Uh and in January she had uh she was pregnant, and uh so I was nervous but excited and on Valentine's day, we went and got the first sonogram of the baby.

14:13 Go in there and you know, they pittch you off a little picture, had it in my front pocket my shirt. Spent the day trying looking for places for us to you know, live, and we're supposed to meet that night for dinner and seven o'clock, no show, eight, no show. At this point, I am now after eight, I'm getting very very agitated. Finally, about nine o'clock, after numerous calls and text she finally turns my call and I'm like, you know what's going on? Where are you? And no, buffer know nothing. Their next sentence is, we need to have a paternity.

15:06 Test after the baby's born, correct, because you can't have it then and there. You could have a pre It was very difficult at that time and very dangerous. That would be the amniocentesis, right, that's what they would have to do. At the time, there was only a place in Houston that was doing it, and so that uh, that was life changing. Mm hmmm. I told her. That, you know. I it was like, if it's mine, I'll be a great father. If it's not, you can funk all the way off.

15:54 Uh. And then I was the really nice guy and I actually she decided at that point that she did not want to risk it if it was the other guys, and uh decided to have an abortion. And I took her to and held her hand through the process because I thought I was being a nice guy. Oh and this is so that that happened Valentine's Day and this happened the same night. No, this was just the aftermath of it. Nomet know. What I'm saying, is she called the same night for the coternity test. No, I know, but in my head it's like good drive on through with the Valentine's Day special here at the clinic.

16:35 Yeah. Yeah, No, that was how she she why she was late for dinner. As she said, she'd, instead of saying we need to talk or anything else, said we need to have a trinity test. Wow. Okay, yeah, I see most people agree that we need to talk. Sentence is bad. Yeah, but you learned that there is a worst sentence. Yeah, that we need to talk at least as a buffer that you know something bad is coming. Yeah, As opposed to her just straight up saying and so we needed to do a paternity Yeah. That that that was the o g raw dogging. That's that's when Maury gets on the phone with you and it's like, all right, we got the we got the results. Yeah, are you ready. I would like to point out that this is one of the few times I kept my mouth shut because when you mentioned that your girlfriend at the time was pregnant, the first thought in my mind was being a dick, was is yours? So I'm glad I didn't ask that.

17:31 Wow, that is wild. Now it makes my chicken curry story look like shit. Turns out my Valentine's Day was great. Yeah. I need to call up my ex and say, see, could have been way worse. Listen to this from Salad bitch. Wow, that is wild. That is. Again that I wouldn't even know how to react to that. Like I drank a lot, Yeah there was, Oh you were drinking.

18:11 This is twenty one years ago, Trey, and years ago Tray was yeah. But I'm back. Uh well, I drink with Tray one time at the loon when we were all there and you left and he we we stuck around. That's how the that's the first time we ever just kind of chatted like about nothing, you know, everything and nothing. Yeah, I'll have to say this fueled my alcoholism. Oh wow, I wouldn't doubt it. I would not dapt with that. Uh yeah, there's nobody's I can tell you right now, every listener, nobody's got a better story than this, Like, nobody's got a worse.

18:52 No, that was hard to top. It really is. Yeah, and I don't say that, you know, boastfully. Yeah, this is not one of those one upping stories where you're like, ha ha scoreboard bitches. No, I'd prefer not to have won that competition. Oh, I know, but when people listen to the show or watch it, then we were like I got a store. Look from the beginning, when you're like what's your best and worst, people are like, oh, I got a good one. By the time they get to yours, we'll be like, nope, I don't got a good one. The good news is for tomorrow's Valentine's Day, I really do believe it's going to turn out better that So it's just you know what, It's kind of like Cradick used to stay, just keep looking up because that's where it all is.

19:46 Tell us how the muffins turn out. And Uh, the other thing I'm gonna do is I'm going to Uh, I'm gonna send Brandy this tomorrow just to start the day off. Hey, that dayre's coming gap and I'm going to wish for buy heart to oh my friends family, Happy Valentide Day. Be sure to give love, because we can give love, it's eesier to receive love. Hey, and he says Valentine's. Well, he doesn't. He doesn't say Valentines.

20:30 The fact he can still pronounce it. I mean, come on, and and can I just without seeming just so insensitive? Which eye is real? And I think it's the one that's more closed. Saying the small one. It's gonna be my first one. Did he not get the other one? Fitted? I don't know how this works. Or just has he done so many drugs They only work on on his you know, one side of his brain, because his left eye looks like it's so dilated. He you know, did an eight ball.

21:10 He snorts it in that eye. He's the only one I know that does eye cocaine. I do love, though, how you've managed to you know what? Leave it to Gary Busey to bridge the gap between Friday the thirteenth and Valentine's Day, because he's really both days wrapped up in One Man. Yeah, he looks like he can be in both horror movies. Absolutely, he could be under your bed, but also with a lot of love in his heart. Yeah. I think Raj hit it though. I think you know, if you put lines of cocaine in front of Bucy, he would have to take his eye out, and his eye would do one line and he'd do the other.

21:57 Then, and then as he puts it back in, he would say sharing. His Karen pat. For all things Treehouse, go to Treehouse on Air dot com. Also check out the Treehouse Show podcast. Regular episodes of the Treehouse Show are available everywhere you get your podcasts. Also extra Treehouse in Your Life Patreon dot com, slash Treehouse on Air. We will see you next time right here inside the Treehouse. Happy Valentine's Day on Monday,