Josie Moore has given the opposite sex and love plenty of chances. Four exactly, if you count all her failed engagements, and five if you include the absentee father who kept her existence a secret until very recently. So when her father decides to announce his retirement with a splashy magazine piece about the family, Josie realizes her romantic history is a complicated PR issue.
 
Matthew Flanagan is the mud, literally. Not only has he been fired from his job, but also the tires of his car are stuck in the muck after taking a wrong turn as he enters Green Oak, North Carolina. So, he grabs a duffel with his essentials and goes in search of a place to crash until he gets his life back on track. But instead, he finds his best friend’s sister, Josie, greeting him as her fiancé.
 
What starts as a big messy misunderstanding quickly turns into an arrangement with Matthew playing a new role as doting fiancé. A fifth engagement and a stunt, at that makes Josie’s stomach turn, but every dilemma requires a choice between equally undesirable alternatives, and Matthew doesn’t seem to mind becoming one more number in a colourful list of grooms-that-never-were. Despite the ring on her finger, Josie knows this is only temporary, even if the rest of the small town believes that the fifth time’s the charm.