One time, I told my coworker that I’ll be driving up to SFO (from LA) again for the weekend. She said, “That’s a long drive. Don’t you get tired?”

I replied, “Not really. I usually drive behind an 18 wheeler and hook up my car to it and take a nap until I’m close to the Bay Area.”

She took off after that and I thought that was probably the stupidest joke she heard.

A few months later, she came to me in the morning telling me “You’re such a jerk! I told my sister about hooking up the car to a truck on our trip to SD and my entire family laughed at me!”