Would pretty woman work with a male hooker?
Rich middle aged white woman meets attractive 21 year ago old male hooker and convinces him to stop providing sexual services to men and instead be her date for the next few days.
Guy "Girl you sure you know what I do?
Instead of teaching him to be "a gentleman", it's also teaching him to be more masculine, and less gay.
(Picture reworked shopping spree where he ditches the short-shorts and see-through tshirt for a nice suit).
Of course her douchebag business partner (a gay man) has to assault him and say he will hire him (curiously again played by Jason Alexander), but in the end, true love wins out, with former rent boy bagging himself a rich cougar.