Not too long ago I went to a small gathering and we decided to play Monopoly with real money (we're university students). There's an ATM nearby so everyone withdrew about a hundred dollars, went to the convenient store to exchange them into smaller denominations and went back to the apartment. The basic rules were: -All prices on the board were divided by 10 (this was the original Monopoly with the most expensive property being Mayfair at 400 Monopoly dollars or 40 irl dollars). -$120 starting money -Passing Go meant you took a shot. Obviously you can choose something else since you don't want to involve drinking. You really think about your choices three times more carefully when you're playing with your own money.