Following an unexpected breakup weeks before Christmas, tech wiz Hannah (Drew), creator of the dating app Perfect One, heads home for the holidays, challenged to save her failing business by creating a new romantic dating model. Upon her return she runs into her high-school boyfriend Sam (Matter), whom she had carefully avoided for years, and reluctantly makes a deal with her dad Ted (Gross) 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. It's not until Christmas Eve that everyone must reveal their true identities to their pen pals, even if it means coming face-to-face with the last person they ever expected.