Ugh, I've got quite a few of these, but I'll throw in my most memorable one:
I was at lunch with some friends, including a girl that I really liked. The conversation turned to wierdness, and The Girl said something like "Oh yeah, if he's got a beard he's a pedo" - fortunately, she seemed genuinely shocked when she remembered that I had a beard.
Uh, anyway, that wasn't the embarrassing part. At dinner that night (at a pub), we were talking about IDs and their photos - she asked us whether her ID photo looked underage, and another of my 'friends' - he's never been one for subtlety - blurted out "Well, heyyyy, if you look underage and he's a pedophile...eh? eh? :D".
Ugh.
Oh, and then later that night, admiring the fact that he'd hooked two of our friends up, he turned to me and said "Ok, *insert my name here*, you're going to be my next project". to which she replied "Oh, really? Who're you going to hook him up with?". Awkwardness. :P
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