The Sweetest Thing is a romantic comedy film that revolves around a woman attempting to reconnect with a man she is smitten with. Christina Walters (Cameron Diaz) goes out one night with her friend, Courtney Rockcliffe (Christina Applegate). That night Christina meets a man named Peter (Thomas Jane) and is instantly attracted to him. She is led to believe that Peter's brother, Roger (Jason Bateman), is about to get married when in reality it is Peter who is the groom-to-be. A short time later, Christina sees how much her friend is enamored with Peter so she decides to get Courtney and Peter reconnected. The girls set out on a road trip to San Francisco to find Peter. During this trip, Christina and Courtney experience many hilarious but unfortunate events. However, they do eventually arrive in San Francisco, on the day of Peter's wedding. Will Christina discover the truth about the man she loves?