Cass is a successful business woman that appears unsuccessful in her personal life and decides to try The Daters Handbook at her sisters encouragement and dates several guys to test the process.Realizing she has a recurring habit of picking the wrong type of guy, Cassandra Barber turns to relationship expert, Dr. Susie, and her latest self-help book, "Dater's Handbook" to help with her ailing love life. She follows the advice in Dr. Susie's book to evaluate potential suitors, and then must ultimately choose between reliable George and fun-loving Robert.