I'm not sure if this is the biggest wtf moment that I had in this game, but just yesterday I was playing and I was stuffing kids in trashcans for an errand. So I went to grab Algie and I accidentally tackled him instead, and when I got up I realized he had a bottle rocket launcher! He started chasing me with it and firing at me. I got owned by a pants-wetting nerd.
Oh I thought of another one. I was talking to Johnny Vincent after I had to take pics of Lola and Gord together, and this lady drives up and runs me over. Then I get up and she runs me over again!. I was like "WTF?!" So I smashed her window and ran away. That'll teach her.