CUPID, the god of love, is burned out. He wants desperately to retire and hand the bow and arrow over to his protégé: the well-meaning, romantic, and completely hapless Ruby.

Holly, a professor at a small college, has had a long history of finding the wrong guy. She’s accomplished quite a bit in her life, but after her younger sister announces she is pregnant, Holly decides she is going to make an effort to meet Mr. Right. Meanwhile, David, another professor, is a single father, very smart and kind, but not the type that Holly takes notice of when the two are assigned to plan the Christmas Formal. At the insistence of her best friend, Holly signs up for the dating website “Cupid’s Arrow,” where she meets Josh, an attorney just hired by the school. He’s everything she wants on the surface, but has little to say beyond his work and good looks. Josh and David were roommates in college, so Josh recruits David to write poetic messages in an attempt to win Holly over.

Following an unexpected breakup weeks before Christmas, Hannah, tech wiz and creator of the dating app, Perfect One, heads home for the holidays, challenged to save her failing business by re-conceiving a new romantic dating model. Upon her return she runs into her high school boyfriend, Sam, who she has carefully avoided for years and reluctantly makes a deal with her dad to sign up for the town’s Christmas Cupid, an anonymous holiday pen pal service. As the season progresses, Hannah is smitten by each beautifully written letter she receives and starts to believe that her Christmas pen pal could be her soul mate.