Worth Winning is a 1989 American romantic comedy film directed by Will Mackenzie and starring Mark Harmon, Madeleine Stowe and Lesley Ann Warren.

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.

The remaining two women Taylor must persuade to fall in love with him are Erin Cooper, a sexy Philadelphia Eagles receptionist, and Eleanor Larimore, an attractive older woman.

It turns out she is unsatisfied at home and a willing participant when Taylor flirts with her while posing as a shoe salesman, engaging him in dangerous sex in public places.

Erin finds solace in the arms of her football player while Eleanor takes pleasure in Taylor's humiliation at being exposed for what he really is, but Veronica is genuinely heartbroken.

As a grand gesture, he makes a public apology to Veronica at a benefit auction in a giant hall, expressing his love and his desire to be with her for everybody to hear.