Foolproof (2003)

Watch Foolproof: Twenty-something Torontonians and friends Kevin, Sam and Rob play a game they call Foolproof: they plan foolproof heists, but without the intention of actually carrying them out. They have a few rules in the game, including the three having the necessary technical and physical abilities to carry out the tasks required for the heist, the plan cannot include loaded guns, and there is no violence meaning that no one gets hurt. They try to be as meticulous if not more so than the best high stakes thieves. The fun is in knowing they could do it if they truly wanted. Their collective lives change when someone breaks into Sam's apartment and steals their latest plan for a jewelry warehouse...