Realizing she has a recurring habit of picking the wrong type of guy, Cassandra Barber (Meghan Markle) turns to relationship expert, Dr. Susie, and her latest self-help book, “The 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 (Jonathan Scarfe) and fun-loving Robert (Kristoffer Polaha). It’s hard to change old habits and place your faith in the experts, especially when your heart tells you something different.