With Valentine’s Day rapidly approaching, Steve and Joel we gathered up some real embarrassing stories from our readers. If you’ve ever made a fool of yourself for love, don’t worry, these guys got you beat!
Comedy of Errors
Most embarrassing Valentine’s Day? It’s a lock. So I fall head over heels for this hot broad from the house of Capulet. I am big pimping, showing up at her window for a booty call, knocking mad boots, even wife-ing this chick. I mean, I know I have a bit of a reputation for womanizing, but not this time. I was FEELING it.
Then my buddy Mercutio gets murdered and then I gotta go kill the guy who killed him, blah blah blah. Listen, long story short, we both drank poison in this dumb plan a priest thought of and died. Most embarrassing Valentine’s Day EVER.
Same Old Song
So I’m sitting in my pub, just trying to get my bud Sam to play this song I like, when this babe I used to know back in Paris shows up. I’m giving her the cold shoulder because she ran out on me, but who am I kidding? It’s just a run-around, I’m all over getting back together. So we fall in love all over again. Whatever, I’m a sucker for a monochromatic girl, what can I say?
I end up having to send her off and then I get to die at the hands of some Nazis. So embarrassing. At least I got to say my favourite line: “We’ll always have Paris.” Someone arrest me, I’m too bad-ass!
Balling in Brokeback
Boy, it’s tough being a gay cowboy. I mean, do you know how hard it is to tell if someone’s gay when everyone wears tapered boots? I was settling for mannish brothel whores until I ran into this bro of a ranch hand, and so I start making eyes at him and whatnot.
Anyways, one thing leads to another and we hug and look intensely in each others eyes and all that. Sounds pretty good, right? Yeah man, it really is. I’m a gay cowboy and I can lasso the hat off your head. Nothing embarrassing about that.
Just Your Average Patient
I spent last Valentine’s day hopelessly burned and disfigured, lying on a dirty hospital bed and just thinking about stuff. Tell me how a dude is going to pick up a hot nurse when his face is totally bandaged up? Yeah, I got an accent going for me, but brother, let me tell you, being on your deathbed gets you a lot more points if you don’t look like someone melted you.
Whatever, I actually like being alone on Valentine’s Day. I think people in relationships are so lame. You couldn’t get me in a relationship if you paid me a million dollars.
That being said, if you know anyone, these scars are healing up pretty good. Hook me up!
No Class
So I’m Ryan Gosling right? I’m really poor and I get with the wealthy girl this one night. It was hot and sex happened of course, but then she had to go and our different backgrounds and class sort of made things weird and we didn’t speak. I went to war after that and I guess that was alright. Then I’m restoring my dad’s house and I see her again. We hooked up and the whole time she’s engaged. NOT MY PROBLEM, right? Yeah. They break it off and we hook up like, forever. We got old and then died at the same time. Thing was, I didn’t want to die so that kind of sucked.
Man, I’ll never get caught up in something like that again.

Love Boat
So I’m on this huge freak’n boat, like the biggest ever. I meet this girl and I tell her I do portraits. She’s so into that it’s scary and kind of weird. Next thing I know I’m totally drawing her naked and it takes me a while of course. We had super steamy sex in a car after. Literally steamy as in I fogged up the god damn windows. Yeah man. It was all going great till the god damn boat sank. Just my luck. I get with this hot babe, and now I’m probably going to die.
We didn’t get on one of the rafts which really sucked. We just had this chunk of debris to float on. I let her lie on it by herself, being a gentlemen and crap. Crazy thing is, she never offers me to jump on with her. I TOTALLY DIED!
Never get with a picky dame. They’ll just let you die like a chump.









