Leah Meyer (Arlook) is a bonafide lover of Christmas – the trees, the ornaments, the eggnog! But she has always admired the holiday from afar because she’s Jewish. Though her family celebrates Hanukkah, Leah has longed to experience a traditional Christmas. When her boyfriend Graham (Roderick) invites her to spend the holidays with his classic Connecticut family, she eagerly accepts. Excited to dive into the quintessential Christmas she’s always dreamed of, Leah quickly discovers that fitting in with Graham’s uptight family and his not-so-welcoming mom (Niven) is easier said than done. As holiday traditions clash and awkward moments pile up, it is not quite the cozy Christmas that she expected.

One week before Hanukkah, corporate lawyer Tory (Farber) finds herself unexpectedly unemployed and questioning the career she’s dedicated years to. As she helps her Bubby prepare for the holiday, she embarks on a quest across Chicago to find the last box of coveted Hanukkah candles. Her search leads her to Rocky’s, an Old Town bar, where she encounters Jay (Kagasoff), a charming doctor from Florida, his grandfather Sam (Summers) and a cast of quirky regulars who make her rethink everything. Torn between keeping her job loss a secret and embracing a newfound sense of belonging, Tory ends up bartending at Rocky’s, transforming it into the vibrant “Hanukkah on the Rocks” celebration. Through festive food, drinks, and games, she revitalizes the bar, bonds with Jay, and finds the courage to pursue her true calling. As Tory navigates the holiday, she learns that sometimes a detour can lead you exactly where you’re meant to be, lighting the way to a future filled with joy, romance, and self-discovery.

Kate North (Sustad) finds herself reluctantly taking over her father’s once acclaimed and now struggling Santa School. In the weeks leading up to Christmas and the school’s next session, Kate and her new co-worker Dan (Ayres) discover who they believe to be the real Santa Claus, lost and without his memories after his sled steered off course and crashed near the school. They decide to help him remember who he is by inviting him to participate in the intense Santa training program. There’s a lot at stake this year with Kate’s school needs to best the rival St. Nicholas School or be forced to close their doors, and Nick (Santa Claus) needs to remember who he is, or the fate of Christmas might be at stake.