The game is simple. Your objective is to make Dan lose everything. 

Many ways to lose money. Black Jack, Slot Machines, Roulette, anything you find in a casino. But be tread carefully, some don’t like it when you lose their money

Besides the occasional mafia encounters, Dan’s awareness becomes higher when his wife or children try to reason with him. Keep them at bay while you lose as much money. If you lose too much to fast, he will realize his addiction. Fortunately for Dan. Unfortunate for you.