Molly Mahoney (Aubrey Dollar) is flying home to Chicago for her mom's wedding, bringing a 'Mystery Man' home to meet her family. But when she discovers this Mystery Man has a Mystery Wife, she dumps him at the curbside check-in. She ends up crying on the shoulder of childhood friend Josh Shiffman (Shane McRae), who is flying home for the same wedding. Emotionally drained, Molly passes out in Josh's arms just as he gets a phone call from his parents. Josh learns that his father is dying and his only regret is that he will not get to meet the woman who will one day become his son's wife. Desperate to fulfill his dad's final wish, Josh claims that his dad has already met that woman, close childhood and family friend: Molly Mahoney. When Josh sheepishly confesses his ruse in mid-flight Molly is furious, making him promise to right the wrong the moment they land. Only when they arrive - it's too late! Word has leaked out and they are swarmed at the airport by BOTH FAMILIES with well wishes and congratulatory banners. Josh convinces Molly to play fiancé by using a deadly combination, her Catholic guilt and his Playboy charm. But as they plan their phony wedding, the two of them start to fall in love for real. This turns their dating lives, and family's interactions hilariously upside down tugging on every heartstring in the process.
