Matthew Flanagan is in 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 colorful 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.