Worth Winning

Worth Winning

Year: 1989

Runtime: 103 mins

Language: English

Director: Will Mackenzie

RomanceComedy

A light‑hearted comedy follows Taylor, a self‑assured bachelor who prides himself on his success with women. When his friends dare him to win marriage proposals from three women they each choose, he embarks on a series of humorous misadventures, juggling dates, misunderstandings and unexpected chemistry to prove his confidence.

Warning: spoilers below!

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Timeline & Setting – Worth Winning (1989)

Explore the full timeline and setting of Worth Winning (1989). Follow every major event in chronological order and see how the environment shapes the story, characters, and dramatic tension.

Time period

Late 1980s

The story unfolds in a contemporary late-1980s setting, reflecting the era’s media culture and dating mores. The use of a hidden camera and a televised bet plays into the era’s fascination with public displays and screens. Fashion, technology, and social expectations of the time shape how characters respond to deception and heartbreak.

Location

Philadelphia, Weekend cabin, Grand hall (benefit auction)

Philadelphia serves as the practical backdrop, anchoring Taylor’s career as a local TV weatherman and the social world around him. The weekend cabin functions as a private staging ground for his schemes and the film’s more intimate moments. The grand hall used for a charity auction later becomes the public arena where truth and reputation collide, wrapping up the bet with a dramatic public apology.

🏙️ Philadelphia 🎬 TV industry 🏞️ Urban settings

Last Updated: October 04, 2025 at 13:53

Main Characters – Worth Winning (1989)

Meet the key characters of Worth Winning (1989), with detailed profiles, motivations, and roles in the plot. Understand their emotional journeys and what they reveal about the film’s deeper themes.

Taylor Worth (Mark Harmon)

A devastatingly handsome and charming weatherman whose bet drives him to pursue three women. His manipulation reveals a calculating, self-centered streak, though he gradually experiences genuine emotion for Veronica. The finale shows him confronting his flaws and attempting a sincere public apology.

✨ Charismatic 🕵️‍♂️ Manipulative 💔 Self-centered

Veronica Briskow (Madeleine Stowe)

A career-minded concert pianist who challenges Taylor’s world and grows to care for him. She values honesty and commitment, and the deception tests her resolve. Her heartbreak and eventual acceptance of Taylor’s gesture underscore a hard-won, genuine connection.

💼 Career-driven 🛡️ Independent 💖 Sincere

Erin Cooper (Maria Holvoe)

A sexy receptionist who longs to start a family, pulled into the bet and torn between desire and possibility. She faces heartbreak when the relationship ends as part of the wager, highlighting the human cost of manipulation.

💋 Seductive 🎯 Ambitious 💔 Heartbroken

Eleanor Larimore (Lesley Ann Warren)

An attractive married woman who becomes entangled in Taylor’s schemes. She relishes the thrill of the affair and ultimately participates in the deception, contributing to the web of complications surrounding the relationships.

💍 Married 🔥 Sensual 🧭 Opportunistic

Ned Broudy (Mark Blum)

Taylor’s friend who bets he cannot win three women, a gambler with a keen appetite for schemes. He watches the chaos unfold with a mix of bravado and detached curiosity.

🎲 Gambler 🧠 Schemer 💼 Wealthy

Clair Broudy (Andrea Martin)

Ned’s wife, initially supportive and unaware of the full deception. She remains invested in the outcome and celebrates Veronica’s acceptance, adding emotional stakes to the bet’s resolution.

🎭 Socialite 🧠 Insightful 💖 Loyal

Tarry Childs (Tony Longo)

A football player who guards Erin’s happiness and adds competitive tension to the relationships. He cares for Erin’s future and serves as a counterpoint to Taylor’s manipulative schemes.

🏈 Athlete 🔥 Protective 🤝 Loyal

Last Updated: October 04, 2025 at 13:53

Major Themes – Worth Winning (1989)

Explore the central themes of Worth Winning (1989), from psychological, social, and emotional dimensions to philosophical messages. Understand what the film is really saying beneath the surface.

💘 Love and Deception

The central wager hinges on manipulating affection, exposing how charm can mask selfish motives. Taylor’s pursuit of love through manipulation tests the boundaries between flirtation and exploitation. As genuine feelings emerge, the film critiques treating people as means to an end rather than ends in themselves.

🎭 Public Image vs Reality

A hidden TV camera turns private scheming into visible spectacle, collapsing the illusion of romance. Characters contend with the gap between who they pretend to be and who they are in real life. The narrative uses this tension to show the far-reaching consequences of living a double life.

⚖️ Consequences and Redemption

Deceit leaves relationships in ruin, jealousy and heartbreak following the unraveling truth. Taylor’s climactic public apology signals a shift from manipulation toward accountability. The ending frames love as something earned through honesty and personal growth rather than a clever ruse.

Last Updated: October 04, 2025 at 13:53

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Worth Winning Summary

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Worth Winning Summary

Worth Winning Timeline

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Worth Winning Timeline

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