An shy writer has to go out on a date with a different man every month in order to write an article for her company's 'Man for Every Month' blog.

Bob is a landscape gardener and handyman with a typical American family. But his ailing father, Buster, is hiding a secret past while his sister, Stephanie, holds onto a secret of her own. When Bob proposes to his girlfriend and gets involved in a get-rich quick scheme, a series of events unfolds which changes their lives forever.