When students all flee an elite university in Vermont for winter break, the locals and faculty hunker down for their favorite time of year - the annual Christmas Bar Trivia Tournament! For Celeste (Sursok), a Type-A astronomy professor, this event combines the magic of Christmas with her greatest comfort in life: knowing the right answer. But when her colleague drops out of the tournament to do a month-long lecture tour in Asia, Celeste’s team must adopt Max (Daugherty), the football team’s new offensive coordinator. To Celeste, Max seems like nothing more than a grown-up class clown - though he brings an undeniable knowledge of sports trivia (a category their team has always fallen short in). Initial clashes between the two eventually turn into mutual appreciation as the team enjoys scavenger hunts on campus, decorating the international house with Christmas lights, baking Christmas cookies, and advancing toward the championship trivia game. Celeste can't help but delight in Max's infectious enthusiasm, love for all things Christmas and perhaps most importantly, his comfort with the unknown. And after a romantic wintery night at the campus observatory with Max, Celeste starts to wonder if being open to life’s surprises is more important than knowing the answer to everything.

When Olivia, a successful interior designer, finds an old letter from Santa promising she’ll meet the love of her life by Christmas Eve—and that his name will be Nick—she’s stunned to meet not one, but three guys named Nick. As she navigates these holiday romances, Olivia also finds herself drawn to her charming co-worker, Chris, throwing her magical Christmas quest into question. With the clock ticking toward Christmas Eve, Olivia embarks on a heartwarming and humorous journey to uncover her true soulmate.

Rose tries to flip a house in Ireland but is blocked by Sean, a handsome local who wants to preserve the historic cottage.