What was your biggest "D'Oh!!!" moment in your love life?

One day my brother and me were in a small accident. So as he pulled over to get infomation and such, I was standing by the car. Then this limo pulls up full of girls and they ask if I need a ride. They're going the opposite way I was, and I didn't want to leave my brother. So I said "I'm fine, Thanks". They drove off, and right away I smacked my forehead and thought " Just like in Dumb and Dumber. i'm such a idiot!".

What's worse, is I was the most unlucky guy when it comes to girls, so to pass this up makes me extra retarded.

To be fair, I doubt they were going to invite you to join their lesbian orgy.

Yeah, you would probably wake up naked in a hotel room with a stitched wound in your side and the taste of donkey dick in your mouth.

Although the imagery was disturbing, it still made me laugh out loud, good stuff. (the humour, not the taste of donkey dick....not that I know what thats like...)

Ah yes, I have a "D'Oh!" moment (well actually, I have more, but here are two).

I had just begun dating my present boyfriend and we were fooling around. You know, the usual, me naked, him fully clothed, etc... when suddenly the phone rings. So I get up and try to rush to answer and I didn't see his size 14 shoes next to the bed. Of course, being the blind clutz that I am, I trip on his shoes and go flying across the room almost hitting my head on the computer desk where my phone was. I guess it was funnier to him because I am, uhh, shall we say, well endowed in the chestal area... Needless to say, his fucking shoes stay hidden now. He still laughs at me over this.

and a painful one...

Same boyfriend, same setting, later date... I'm going down on him and I notice this tiny little scratch under his head (yeah that one). I asked him how he got it, he says he doesn't know... I asked him if it hurt and he said no, so I continue doing what I do best when it suddenly occurs to me that I'm the one that scratched him with one of my teeth. It wasn't painful until we had sex (that kevin smith story he delivered during his university speech comes to mind)... It really was like battery acid for him. So my solution: Aveeno hand jobs will cure cuts and bruises

It's ok though, he forgave me when he accidentally cut my inner lips with his long fingernails...

God, can you say clumsy???

About 5 years back I was working for Club Med resorts, doing tech in their theaters. I met this goddess in Cancun who was an incredibly hot receptionist from Quebec (sexy accent alert). We flirted all the time, but I never really made my move. I couldn't really tell if she was in to me, or just being friendly, and then I was shipped out to a ski resort in Colorado about three weeks after she arrived. Oh well.

So, fast forward about nine months, and I'm in the Dominican Republic, and a bunch of girls from C.M. Resorts all over the Carribean show up for a training session for something or another. And I get to talking with one of them, and she says she worked the reception desk at Cancun for the last six months or so. So I say, "okay, so you must have known Nancy."

She stops. She looks again at my employee badge.

She says "Oh, you're that Josh. She talked about all the time!"

D'oh!

I enjoy your stories the best. But without all the boyfriend nonsense.

Edited to say: I hope you're a girl, otherwise, I'll feel all confused inside (again) after writing that post.

Not horribly stupid on my part, but definitely a "D'oh!" moment...

I'm home from college for Christmas, and I meet this girl I had a thing for since high school at a bar. She's having a family reunion this weekend, and a bunch of her family, several of whom I know at least casually, are staying at a hotel down the street from the bar. We have a few drinks, flirt around, and she invites me back to her room. I tell my buddies not to worry about me and finally get her alone, and we start fooling around. As things progress, my not having a condom becomes an issue. So I tell her, wait a minute, I'll go grab one. I run down the hall in my socks, trying to figure out where I can find one in the hotel. No luck there, so I go outside and hurry to a gas station on the corner. No dice. There are closing and won't even let me into the bathroom. I almost make a scene, but there is a cop right there in the parking lot, so I extend my search. Eventually I buy a condom for $10 from a guy on the street, and consider it a bargain. So I get back to the room, and...about 8 of her cousins, aunts and uncles, in various stages of inebriation, are hanging out, laughing it up and talking about old times. And there I am, with no shoes and my shirt on inside-out, trying to play it off like I wasn't about to penetrate anyone's god-daughter or anything.

And thus, I'm the only one I know who has ever been cock-blocked by the girl's entire extended family.

Well the thread is about love life, so it applies.

And yes, I'm a girl.

Man, you must have sharp teeth. You must be scratching your own tongue all the time.

Well, look on the bright side... The drunken extended family could have walked in WHILE you were doing the deed if you had a rubber.

Back when I was significantly younger and infinitely more stupid:

I had just been introduced to the wonderful world of SEX! This was like... my third time. My girlfriend at the time (she was 3 years older than me) and I were flirting around my room waiting for my mom to leave the house so we could 'get it on'. We heard a car leave, and got down to business in short order. This was in an older, farm-style house, and honestly, my door didn't even have a lock, but whatever, no one was home, right? Thin walls, no walls, whatever, no one around.

Well, we're getting into it hot and heavy, and the bed starts squeaking, when suddenly my phone rings (I had a separate house line because I was using dial-up to lynx through a university system then), and it's my mother on the other line. She says, "You know... I'm still downstairs..."

Ok, So I turned 22 and I'm on a cruise with all of my friends (like 12 of us) and I'm being all rico suave talking to all kinds of different women (ages 18-35). There's something about being in international waters that gives a fat nerd like me all kinds of confidence. There was this one girl that i dubbed: The Goal. If you met her you would know why she was the Goal of my cruise. Anyway, The Goal was probably the most incredible looking girl on the cruise. She was 19, from Las Vegas, short blonde hair, blue eyes, and to quote Bill Paxson in True Lies "ass like a ten year old boy!" So I talked to her, we chit chat by the pool, whatever.
One night we're in the club, they're playing some song, when she hits the dance floor and starts heading my way. I'm like "Oh shit! this is the hottest girl here and she wants to dance with me?" so I'm walking towards her and she is motioning for me to come closer, and when I am about 5 feet away, some freaking nasty, 16 year old, slutty girl that was trying to hook up with all of my friends gets in front of me and starts dancing all sensualy right in between me and the Goal. I froze, I had no idea what to do for a split second. I come to my senses moments later, and right when I start going around this lil nasty slut, The Goal looks at the slut and says, "I'm sorry. I didn't know he was your boyfriend." and walks away. I try to follow her and explain but she isn't hearing it. she thinks i was going to cheat on my girlfriend, when i tried to explain that i didn't even know the girl! She said, "I've seen her hanging around all of your friends the whole week"

The next day i saw some good looking crew member dude flirting with The Goal and within hours he was in, like Flynn.

So the moral of the story is, make sure your friends won't sell you out and just laugh when some ugly slut interupts a once in a lifetime opportunity with a goddess like the Goal.

D'Oh!!

I once forgot to shave the "courtesy 10" off a snap guess of my wife's weight.

I spent the next month hearing about how much farther she ran that day than I did.