Smitten with his longtime girlfriend yet uncertain of how to express his deep-rooted feelings, a young record executive misinterprets a post-coital sigh as a sign he's not leaving her satisfied, and sets out on a misguided quest to discover the secret of pleasing women. Andy Conners (Josh Meyers) may not be the most experienced lover on his block, but his love for Lauren (Krysten Ritter) is the one thing that keeps him sane in a crazy world. But Andy's lovemaking skills aren't the problem; it's his lack of communication skills that are slowly driving Lauren away. As Andy consults with his best friend Layne to learn the secrets of driving women wild, Lauren airs her grievances to her sympathetic girlfriends and falls under the charms of her handsome ex. Later, Lauren is offered a job in Chicago, and prepares to start a new life without Andy. By the time Andy realizes his mistake, Lauren is already on a flight to the Windy City. Perhaps now that he's learned the truth about his shortcomings as a communicator, Andy can find a way to convince the love of his life to give him a second chance.