Ben Bonner is an uptight, conservative lawyer who has everything except for love. After one heart break too many, his best friend Carey arranges for him to move in with a magical character named Jack. Urban legend has it that whoever lives with Jack will immediately find their soul mate and live happily ever after. However this match comes with a catch because Jack is also a middle-aged party animal. And although he finds his roommates love, Jack also ruins every other aspects of their life.
Desperate to find his special one, Ben moves in and immediately meets Anna Henderson, a smart, beautiful woman who takes Ben's breathe away. Anna, though, isn't the type to sit around waiting for a man. She's witty, spirited and she has a few secrets of her own. In fact, she isn't even sure how much she likes Ben... which makes it too bad that in his frustration, Ben breaks Jack's Cupid-like powers. With his powers gone, not only is Jack unable to get Anna to fall in love, but no one else in the world will be able to fall in love either.
So now with his life crumbling around him and the love of his life fading away, it becomes essential for Ben to get Anna's help so that together they can; fix Jack, help the world to love again, and just maybe, live happily ever after.