I believe you should try everything once. Some thing possibly twice. I believe someone should do whatever they want to do and a true friend will accept them no matter what. I am happy to talk about anything so long as it is light-hearted, etc. Craziest thing I have done = Flipping my jetski in the surf and having it not start. Swimming a jetski into the beach in heavy surf isn't a good idea :) Most Painful thing = either breaking a rib or losing a bet and getting waxed. Both are up there on the pain level. Most fun = doing something adventurous with friends ie paintball, sports, etc.