Holly a professor at a college that is smaller, has had a long history of choosing the guy that is wrong. She's accomplished quite a bit in her life, but once her younger sister announces she's pregnant, so Holly decides she is going to make a bid to meet Mr. Right. Meanwhile, David, another professor, is one dad, kind and very smart, however, not the type that Holly takes note of when the two have been delegated to plan the Christmas Formal. At the insistence of the best friend, Holly signs up for the dating internet site"Cupid's Arrow," where she meets Josh, a lawyer just hired by the faculty. He's everything she wants on the surface, but has little to say beyond his work and also appearances. David and josh were roommates in college, therefore Josh recruits David to write messages in an endeavor to acquire Holly over.