lol that would be a good one, or right before he has to go somewhere important tape them all over his car, so he can either be late and have his car look fine, or be on time driving around town with condoms taped all over his car //content.invisioncic.com/y282845/emoticons/smile.gif.1ebc41e1811405b213edfc4622c41e27.gifThe paper dots are a good one.
Another funny is going and buying about 100 condoms and randomly placing them (opened) in his room. Put some in the medicine cabinet, on in his shoe, some under his clothes....ah you get the picture.