Worth Winning (1989)

Worth Winning is a 1989 American film starring Mark Harmon, Madeleine Stowe and Lesley Ann Warren, directed by Will Mackenzie. It was written by Josann McGibbon and Sara Parriott, based on the novel by Dan Lewandowski.
---- Taylor Worth is a devastatingly handsome and charming weatherman for a Philadelphia television station. A confirmed bachelor, he sees a lot of women and gains the envy of his closest friends.
One of them, Ned Broudy, offers Taylor a wager, that he cannot get three randomly chosen women to fall in love with him over a three-month period of time and accept a proposal of marriage.
Taylor takes the bet, putting up his weekend cabin against a valuable painting that Ned and Clair Broudy own.

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