The most awkward moment I can think of was during my junior year of highschool. I had just gotten my new camera phone and a buddy of mine wanted to fuck around with it so naturally I let him. Come lunchtime he hands it back, giggling like a little school girl. I shrug it off. I shared this lunch period with my girlfriend at the time so I let her use the phone to call whomever and off she went to the bathroom to make the call. Unbeknownst to me, my friend had taken a handful of photos of different girls in their gym outfits in provocative positions (one of them actually being her younger sister). As if that wasn't enough, he set the wallpaper to one of the pictures of the girls. Needless to say, she came back furious with tears coming down her face. I honestly didn't know what she was complaining about but she made a big scene. My friend shortly confessed to her what had happened, but I don't think she ever bought it because she dumped me 2 or 3 weeks later. I didn't even get to tap it. Ain't that a bitch?