Love for the First Time (2008)

Bob Smith lives a quiet, simple life. With a modest apartment in the San Fernando Valley, a job, and a bicycle, he wants for little else. But when his young co-workers discover that middle-aged Bob is still a virgin, they feel obligated to get him laid. Having been dragged out to a local strip club one evening, he meets May Singleton, a shy 25-year-old bartender. May lives an equally quiet, uneventful, and somewhat lonely life, but all of that changes when she meets Bob and together they discover love... for the first time.