Jane Goodale (Ashley Judd) has everything going for her. She's a producer of a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray (Greg Kinnear). When Ray unexpectedly dumps her, she begins an extensive study of male behavior to try to find out what makes men tick. Her "research leads her to become an overnight sensation/guru for single women everywhere. When Jane begins to use her womanizing roomate and co-worker Eddie (Hugh Jackman) as fodder for her research, she finds both humor and answers where they were least expected.