Doug has never been very comfortable with big changes in his life. When his girlfriend Patricia suddenly leaves him and has him fired from his job, Doug's life is turned upside-down. With the help of his good friend CJ, he finds another job where Randy and Mukesh his new wacky co-workers convince him to try Internet dating. Not wanting to complicate matters, he decides to take every date to the same restaurant, Vinny's Grill where Juanman the crazy busboy adds to the mayhem. Following his friends' advice, Doug experiences one hilarious dating disaster after another before finding what seems to be the perfect woman. But just as Doug starts to get involved with Angela the waitress at Vinny's Grill, Patricia decides to come back and chaos ensues.