In order to get two timing date, you must not have any succesful date. So, to trigger two-timing acquire more than 2 girlfriends, but do not date them. After going on date, on your way back to home after 7seconds next girlfriends should appear. There is 50% chance to have two-timing date, if you haven't disabled it before. Two-timing dates can be disabled with completing of any date succesfully, or if CJ goes on date, when he has only 1 girlfriend. Gimp-suit dates do not disable two-timing dates.