Christmas Pen Pals follows tech wiz Hannah (Drew), creator of the dating app Perfect One, who faces an unexpected breakup weeks before Christmas. She heads home for the holidays, determined to save her failing business by creating a new romantic dating model.
Upon her return, Hannah encounters her high-school boyfriend Sam (Matter), whom she had avoided for years. Reluctantly, she 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 captivated by the beautifully-written letters she receives from her Christmas pen pal, leading her to believe that he 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 facing the last person they ever expected.