Les and Sly embark on separate holiday road trips from Phoenix back home to Chicago. Neither knows that the magic of the season will intervene to make them lovers by the time the parallel journeys are over.

Both Les and Sly are still aching from recent breakups, and they vow to avoid romantic entanglements for the foreseeable future. Fate has other plans. By the time they unexpectedly cross paths for a third time, they suspect it might be more than a coincidence.

Good-natured happy-go-lucky Les is great at friendships and a failure at love. He moved to Phoenix to stick by his best friends and immediately jumped into another painful dating relationship that ended in a parking lot Christmas tree market.

Sly is eager to leave one of the worst years of his life behind. The end of a two-year romance and the death of his stepfather cast a cloud of gloom over his December. He decides to visit his mom in Chicago for a bit of guaranteed Christmas cheer.