Plot Synopsis

Still suffering from the awkward phase that plagued his youth, accountant Harold White hires Annie Hayes, the pretty and popular girl he had a crush on in high school, to be his dating coach. He hopes with her help he can shed his wallflower approach to romance. Annie also enlists her friend Kim, a waitress at a local diner, to be Harold's practice date. Thanks to Annie, he soon comes out of his shell and wins over a beautiful woman he's had his eye on for some time. But things get complicated when he discovers his old feelings for Annie have been reawakened. Not realizing the feelings are mutual, he finds himself unable to act on them due to his fear of being rejected by the one woman he truly loves.