When Leah, a Jewish girl is invited home to celebrate Christmas with her boyfriend Graham's family, she is excited to experience her first Christmas. However, it doesn't take long for her to clash with Graham's uptight mother and as a result traditions begin to expand to include new experiences.

After being promoted to partner, workaholic lawyer Lucy Miller plans to celebrate by working over the Christmas holiday, despite her sister Alexa urging her to come home to Milwaukee to spend time with family. However, thanks to a mysterious rideshare, Lucy is transported back to 1999 and has to relive the first major event in her life following the death of her father.