Holly, a professor at a small college, has a track record of choosing the wrong partners. Despite her many achievements, she decides to actively search for Mr. Right after her younger sister reveals her pregnancy. At the same time, David, a fellow professor and single father, is intelligent and kind but doesn’t initially catch Holly’s eye when they are paired to organize the Christmas Formal. Encouraged by her best friend, Holly joins the dating site “Cupid’s Arrow” and meets Josh, a newly hired attorney at the college. Although Josh seems perfect on the surface, he lacks depth beyond his career and appearance. Interestingly, Josh and David were college roommates, and Josh enlists David’s help to craft poetic messages to charm Holly.