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When Richard and Hugh both fall in love with Celia, they decide to use their skills as insurance salesmen to compete for her affections. They create a bet, with the winner being the man who is able to successfully court and marry Celia within a year. The loser must pay the winner $25,000.As the year progresses, Richard and Hugh use a variety of tactics to woo Celia, including elaborate romantic gestures, intrigue, and deception. However, they soon realize that they may have underestimated Celia's own intelligence and cunning.