I heard a female pilot ask the controller if her transmission was a little fuzzy. Some unknown pilot responded with, "That depends on how old you are".

Another one I heard was a pilot asking for a direct routing through a MOA which sounded like a womans name, something like candy moa. The controller responded by saying candy is hot, and not allowing any penetrations. Some pilot responded with "I think I used to date her"

And the last one I heard was while talking to Kansas City Center, they were very busy. Some airline pilot thought he was on the aircraft intercom giving the cabin brief, thanks for flying with us, we will be turning off the seat belt sign, and begin beverage service, ect. After blocking centers freq for a good minute and a half, he shut up. All the pilots on the freq began placing their drink orders, I'll have a double vodka on the rocks, ect. It was hillarious. Finally the guilty pilot responded with a simple oops.