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.

Resort developer Madison Lane is tasked with finding a location for a new ski resort. Her boss tells her to take a trip to Christmas, Colorado, to consider the location. On her way into town, Madison has a minor fender-bender with the town’s welcome sign. Town Sheriff Gage McBride gives Madison a ride into town so she can attend her meeting with the mayor while the car is towed and repaired. Little does Madison know that the town is on a mission to convince Madison that Christmas is the best place for the new ski resort.

In the frenzy before Christmas, two single parents accidentally mix up their toys at a crowded department store. As a result, both of their Christmases appear to be ruined. Although the two can’t stand each other, the only way to get things back on track is to help each other salvage their holiday plans – not realizing they’re falling for each other in the process.

As Christmas approaches, Paula, a St. Louis antique appraiser, reluctantly accepts a marriage proposal from her boyfriend, Daniel, a career-focused attorney. When her Aunt Jane senses she has mixed emotions over the engagement, she invites Paula to her Nantucket home. Upon her arrival, Paula plans a trip to the nearby island of Martha's Vineyard where she meets a charming inn owner.