The situations Jimmie Shannon gets in with his ex are hilarious. Will he be well succeeded? "The Bachelor" is an absolutely underrated comedy, with an entertaining and delightful story based on a play. Now his only chance is to find one ex-girlfriend that accepts to marry him. But his birthday is one the next day and Jimmie believes Anne is in Greece. His friend and lawyer shows a videotape where James tells that Jimmie must be married until 6:00 PM on his 30th birthday to inherit one hundred million dollars.
Meanwhile Jimmie´s grandfather James Shannon (Peter Ustinov) dies. Anne decides to travel to Greece bur she changes her idea and travels to her parents´ home with her sister Natalie Arden (Marley Shelton). They go to a fancy restaurant but the clumsy Jimmie get into trouble when he unintentionally offends her. Meanwhile each of his friends get married and Jimmie decides to propose Anne to marry him.
When he meets the independent Anne Arden (Renée Zellweger), she becomes his girlfriend along three years. In San Francisco, Jimmie Shannon (Chris O'Donnell) is a confirmed bachelor.
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