Worth Winning

Taylor Worth is a devastatingly handsome and charming weatherman working for a Philadelphia TV station. He enjoys the attention of many women and resents the envy that his friends feel about his single lifestyle. This sets the stage for the bet that will drive the rest of the story.

Ned Broudy challenges Taylor with a dare: he must win three randomly chosen women to fall in love with him and accept a marriage proposal within three months. The stakes are high: Taylor's weekend cabin goes against a valuable painting owned by Ned and Clair Broudy. The challenge is set to test Taylor's charms and endurance.

Clair is unaware of the bet, but she is pleased when her husband arranges a match between Taylor and Veronica Briskow, a concert pianist. Veronica is independent and career-focused, which makes her a tricky target. Taylor sets out to attract her interest despite the odds.

Taylor seduces Erin Cooper, a sexy Philadelphia Eagles receptionist, and proposes marriage to her on the air via a hidden TV camera. The moment sparks a cascade of jealousy and complications as Erin's friends react to the staged engagement. The televised proposal marks the first victory toward the three-win requirement.

Taylor learns Erin is still a virgin and, despite his early triumph, chooses not to sleep with her. The revelation shapes how their engagement unfolds and underscores Taylor's evolving conscience. Erin remains engaged, but the relationship remains fragile and guarded.

Taylor targets Eleanor Larimore, who is married and dissatisfied at home. He flirts with her while posing as a shoe salesman and takes her on a dangerous sexual journey in public places. Eleanor agrees to a secret marriage proposal that is captured on video.

As Taylor spends more time with Veronica Briskow, he feels a real pull to keep her beyond the wager. Veronica's career focus makes the union unlikely, but Taylor pursues a genuine bond. He contemplates proposing to Veronica as the wager progresses.

Taylor finally proposes to Veronica at his cabin, and she accepts, transforming the wager into a real relationship. Clair is delighted, while Ned is devastated by the turn of events. The two hopeful couples move toward a possible future together.

With two engagements in the air, Taylor must break off with Erin to focus on Veronica. He tricks Erin by pretending to be impotent to avoid starting a family and ending the engagement. The ruse deepens the emotional fallout among the involved parties.

Meanwhile Eleanor revels in the newfound intimate life and brags to Clair and Veronica about it, revealing Taylor's manipulative plots. The bragging heightens suspicion and trust begins to crumble among the women. The deception at the heart of the bet starts to unravel.

It becomes clear that three women are seeing the same man, and each relationship falls apart. Erin seeks solace with her football teammate Tarry Childs, while Eleanor revels in exposing Taylor's deception. Veronica is heartbreaking affected as the truth comes out.

A broken Taylor makes a grand, public gesture to Veronica at a benefit auction, apologizing for his actions and declaring his love. He asserts his desire to be with her, hoping to repair the damage done by the bet. Veronica, though heartbroken, sees his honesty and the possibility of a real relationship.