Olive Moore has been avoiding her hometown for three years now. But a phone call with her mom has her agreeing to spend the holidays back home with her family, she lets it slip she will be bringing a boyfriend with her. The only problem with that is she has no boyfriend. That is until she meets a handsome-albeit annoying-stranger on the plane who makes her an offer she can't refuse. Finn Beckett has always had good luck, as demonstrated by the gorgeous blonde he's seated next to on a flight to Aspen. One drink too many leads to Olive spilling her problems in his lap, and he feels compelled to help. So he makes her an offer: he'll pretend to be her boyfriend to keep her family off her back and make this the best Christmas ever. Olive and Finn spend the next two weeks going on spirit-filled Christmas dates with her family. Their ruse is working perfectly, but Finn can't help but notice Olive is holding something back. Something that could ruin everything. Their relationship may have taken off smoothly, but with all this turbulence, will they ever make it to baggage claim?