Your Most Un-Smooth Moments

Ah, I did something like this to a girl I had been dating for probably (and I cringe to remember this) a week, if that. I was dropping her off at her house and giving the parting/goodnight kiss and whatnot, and the following dialogue takes place...

"I love you."
"..."
"Erm..."
"..."
"...bye"

We ended up breaking up less than a week later.

Different girl (whom I wasn't dating at the time, but had dated in the past), much more recently: a couple friends of hers just moved into a new house, and the four of us (the girl, the two guys living in the house, and me) are touring the house. No furniture yet except for a sparsely furnished bedroom with only a mattress and a computer. She goes out of her way to send the other guys out of the house to run various errands for long periods of time, leaving her alone with me. We end up in the bedroom watching porn (yes) together on the computer, and she starts getting into it. She starts getting closer to me, being more physical, etc, eventually at one point she was on top of me. At one point she asks "What are you thinking about right now?" and I only managed a stuttered "Uh...welll...ummm..."

I suck.

This isn't me, but a friend of mine, who we'll call Matt, who happens to also be a goon.

Matt's out at a club and somehow finds out the name of a girl at the bar. So he wanders up to get a drink and makes a bet with the cute girl serving him that he can guess her name. Thinking hes onto a sure think, he goes "is your name [name he was told earlier]?". To which she just gives him a funny look - turns out it isn't her name but the OTHER bargirl.

Theres a break in the music for some reason and overhearing this, another friend behind him in the line decides to pipe in in a voice loud enough for the entire bar to hear "Sure fucked that one up, dickhead!". And everyone just turned around to look at Matt standing there in his moment of shame.

I turn into a retard around chicks I find attractive. Even when I'm not trying to hit on them. One time I was waiting in line at the movie theater with a friend and we were just talking and not really paying attention to where we were in line. Before I knew it I at the ticket window and the girl selling tickets was rather attractive.

Caught off guard I managed to tell her what movie I wanted a ticket to, gave her the money and she smiled, handed me my ticket and said "Enjoy your movie." I replied with "Yeah, you too." About half a second after those words left my mouth I realized what I had said and I quickly ducked into the movie theater laughing my ass off.

My friend told me that he didn't even see me go into the movie theater because I moved so fast. Not only had I made my friend break into laughter but some dude that was standing near us got a good laugh out of it too.

I hooked up with this girl at a party and took her into my friends room, excited that I was finally hooking up with this girl I had been interested for a while I dived under the sheets, I don't know if it was the alcohol or the bed was just so damn comfy but I fell aleep straight away. I was only awoken when she stormed out of the room saying she had to go to work.

Same girl a couple months later, I message her to see what she is up to.

Me: "Hey what you up to?"
Her: "Im drunk and horny as fuck"
Me: "Hahaha sounds fun, have a good night"

I guess it's still fine between us because she messaged me at 1am in the mourning to say she was thinking of me.

Freshman year of high school I got a huge crush on the girl behind me in English. Seeing as how I had no game back then, I got no where, but we did become friends, remaining so over the next 4 years of high school.

Flash forward 4 years. Being a senior and less game challenged, I grasp an opportunity and smoothly reveal my old crush, ask her out, she accepts, it somehow goes awry before the date, things kinda left at that for a few weeks.

Flash forward a few weeks later to the start of the glorious Senior trip! Four days to wander Washington, D.C. with minimal supervision, good times to be had by all. Before the bus trip she asks me if I'll walk her to her locker to get something she forgot. Being the gentleman I am, I accept and when we are alone she reveals to me that (and I quote) "I am in love with you." HOLY SHIT! My normally quick mind is completely thrown into chaos over this bit of info. Much like the OP, that fucking red button is hit and what I spit out is, "uhhh, ok." Awkward silence. I knew I fucked that up, shit, I better say something fast or the moment will be gone! Not quite looking at her I stammer, "Prove it." Yah well that wasn't quite the romantic or even human response she expected. On the bus ride I try and get back into normal ride with her but she was pissy and ended up hooking up with a different guy at the end of the trip. Fucking bastards started dating. No love for me.