Kate Wells (Famke Janssen) is a beautiful and talented magazine writer who turns to her own life for inspiration when she is given an impossible assignment. Within twenty-four hours, Kate must write a single woman's guide to love and sex. A stranger to both since her break-up with Adam Levy (Jon Favreau), Kate conducts her research by recalling her many calamitous relationships with men, beginning with her first kiss and her first betrayal on the sixth-grade playground. More heartbreaks follow over the years, with married men, Mama's boys, and a multitude of disappointing bachelors. But the man who seems to have had the most impact on her life is Adam, an artist who does not look -- or behave -- like a typical Prince Charming.