At the theatre, the ticket checking guy...
Ticket guy: Enjoy the movie
Me: You too! Oh ####, sorry, I mean thanks.
Ticket guy: No swearing!
Me: *mumbles* sorry...
Went to a club with a few buddies. Girls wander off (as they always do in groups) and 3 of us are just standing around waiting for them. My buddy starts getting groped, humped from behind and hardcore molested by a drunk (not very good looking) cougar while her friend (also not good looking) is taking a bunch of photos with a phone (he was about 19 ish at the time). Awkwardness was the two of us staring at him in horror, shock and confusion, then slowly backing away from the situation. I believe that was the last time he went clubbing in Calgary.
A few years back at the Stampede. Hot day, so I use a paper fan to cool down. A lady walks up to me and says, "My son really loves your fan, where did you get it?" I reply that I didn't buy it at the Stampede and it likely wouldn't be available at any venue on the grounds, but she could probably try a dollar store or Chinatown. This leaves a small boy in tears in front of me. In a panic, I offer to give the boy the fan. But the mother refuses, twice, and finally saying something odd like, "It's ok. He needs to learn to be an adult about it." and walking away holding the hand of a sobbing 5 or 6 year old boy.
Trying to win something at the Stampede so I play the carny game, the ball in the basket. I promptly lose $5 and so the carny in pity gives me a practice throw for free. My next two practice throws don't even hit the basket...

The carny tells me, "I'm trying to help you out! But I think you really should play a different game instead."
Ha..... thanks?