For all his life, wealthy businessman Wesley Deeds has done what's expected of him and has settled into a predictable routine. His scripted life begins to change, however, when he meets Lindsey Wakefield, a struggling single mother who works as a night janitor for his corporation and has just been evicted. He offers to help Lindsey get back on her feet and, though he's already engaged, romantic sparks begin to fly. Suddenly, he finds himself torn between what is expected of him and what he really wants.