In "The Bachelor" (1999), Jimmie Shannon, played by Chris O'Donnell, is a charming and carefree bachelor who enjoys his life of freedom and fun. However, everything changes when he learns that his wealthy grandfather has passed away, leaving him a substantial inheritance. The catch? Jimmie must be married by the time he turns 30 to claim the fortune. With the clock ticking, he finds himself in a race against time to find a bride.

As he navigates the complexities of love and commitment, Jimmie enlists the help of his friends and family, leading to a series of comedic and heartfelt encounters. Along the way, he discovers what true love really means, ultimately leading him to reevaluate his priorities and the relationships in his life. The film blends humor with romance, showcasing the challenges of modern relationships and the importance of genuine connection.