Hmm most awkward for me at a con. Well there was two actually ha ha ha. The first year I cosplayed one of the costumes I had was the Red Engie from Team Fortress 2. So I go down in the evening. Things are winding down a little so I'm just chilling and and walking around and then I go get dinner. I'm standing in line, plate in hand ready to go pay then I hear my name called. I turn around and then there is one of my class mates. I just stare and say "ahhhhh....." no I didn't really want people from school to see me dressed up.
Second moment was I was dressed as Turkey from Hetalia. Anyways long story short I'm hanging around the other Hetalia cosplayers and then this Northern Italy walks up to me and asks me "Hey do you want to play the pocky game?" I'm just staring in disbelief not quite sure if I heard right. I mean it came completely out of the blue, I have no idea who the heck this is and what baffled me is I'm Turkey...why would an Italy ask this. As you can see I was propelled into a world of awkwardness...it got more awkward when I said sure I'd play not really knowing what the pocky game was... I do now...