Nellie has had a crush on her coworker Kent ever since she started working at the company. But Kent thinks of her as a little sister. While Nellie secretly hopes that her feelings will be reciprocated, she learns that he's being promoted to a spot at the international branch of the company. In a mere two weeks, no less! Having spent a year unable to attract Kent's attention, Nellie decides to do away with her introverted self and formulate a last-ditch plan to marry her dreamboat!

Meteorologist and college professor Jake is far too busy with his research for romance. So his father, worried for Jake's future, decides to play matchmaker for him. Jasper makes a deal with a young waitress named Cheri, promising that if she stays married to Jake for a year while living on a private island with him, he'll give her one million dollars. Dumbfounded as to why his father is so fond of Cheri, Jake resolves to expose her for the wolf in sheep's clothing that she really is!