Josie, who works at a large hotel in Chicago, goes home for Christmas to her parents, who run a small inn in her hometown. She is taken aback to discover that her former boyfriend, Miles, is staying there with his wife and their daughter. As if that weren't enough, another ex-boyfriend, Ellis, has also checked in. When it then turns out that the final booking is Sam - another of Josie's former partners - things become truly complicated. Both Miles and Ellis also seek Josie's advice about their new relationships. In the midst of all this, preparations are underway for the town's Christmas celebrations, in which the inn is involved. Sam, however, is more than happy to help out. It becomes a Christmas to remember, to say the least.