I have a friend who is in his late eighties who has three girlfriends at all times...each has her role. One he dances with (late sixties), one he takes to dinner (late fifties), and one he gets busy with (late thirties). When asked what he does to be so successful in finding women to meet his needs at his age, he says he asks, "Would you like for me to make your car payment this month? Electric bill?" etc...
As he likes to explain, "we all pay for it anyway, so why not be upfront and make things easier?" Makes sense in a jaded sort of way and...he has still never been arrested as he is certainly within the law.