Probably back in the 5th grade when I tried to make my crush laugh while she was in a bad mood, then she said I wasn't funny.
Edit: More of an awkward moment but I was pretty embarrassed. A cute girl was walking past me while I was resting after my set at the gym, we both locked eyes quickly, she smiled, I quickly turned my head because I'm a little *****, I had no idea she was about to stare at me but I felt pretty bad afterwards.
