Male - 21 Years Old
I can beat that one. Before my current girlfriend and I had sex, we were just hooking up for a few days (just making out and shit, I was roommates with my sister and her bf and she's my sister's best friend so we wanted to keep it quiet at first) until one night she said "Wait, nobody's home. Why aren't we having sex?" I agreed and, trying to be smooth, picked her up to carry her into my bedroom from the living room. I opened the door to my pitch black room, closed the door behind us, walked towards the bed and proceeded to trip over an Xbox controller that was plugged in. That took both of us down, as well at the tv stand, and of course, my flat screen.
I ended up with a fucked up ankle for a few weeks, she bruised her tailbone, and my 2-month old tv now had a huge crack in the middle of the screen. Least boss thing I've ever done in my life. Still got laid, but at quite the cost.
Haha damn. I think the fact that you still got some after that makes it a little more boss