One of my older brothers has made messing with people an art form. He doesn't even have to plan ahead anymore. He just goes for it. Here's an example I witnessed the other day that involved my older brother and a coworker:
Brother: "Okay, I'm going to say some texting abbreviations and you tell me what they mean.... B-R-B."
Coworker: "That's Be Right Back."
Brother: "Okay, B-T-W."
Coworker: "By The Way."
Coworker: "I Don't Know."
Brother: "Ha! Stumped you!"
Coworker: "No. I. Don't. Know."
Brother: "I know. I stumped you."
Coworker: "No! I-D-K. I Don't Know."
Brother: "Well look it up and tell me what it means, then."
One person ended up impossibly frustrated. The other ended up super-proud of himself for setting such an easy trap. The coworker is an idiot, so I don't really feel any pity in this instance. But I am proud of my brother for pulling that one off.