A career oriented woman, Sarah Bloom, who ran away from her small town life in Massachusetts, is now living in New York City and poised to become the next big wedding planner of the famed NY social scene when she’s hired to plan the most anticipated wedding of the season. The problem: The groom is from Sarah’s home town of Williamstown, MA and wants the wedding on the family farm which is now being run by the older brother who happens to be Sarah’s first love. So, can the sophisticated city girl navigate the pitfalls of her past, possibly find true love in her future, and pull off the wedding of the season even though it might not be the one she planned for?

At the height of her career, investigative journalist Hannah Dunbar finds herself wondering what would have been had she stayed with the love of her life, Ben, 10 years before. When Santa Claus hears her “what ifs?” as a Christmas wish, he transports Hannah to a version of her life where she and Ben started a family.