Ralph is a retired police officer who has worked as a New York cop for over 38 years. He plans on visiting his niece Jennifer in Chicago for the holidays. Jennifer is a successful businesswoman and the single mother of her young son Brian. She grew up all her life mostly at Ralph's, as her mother was constantly traveling and her father died when she was very young. Since then, she has lost her Christmas spirit. At the airport, Ralph has no idea where he has to be and he is helped by co-traveller Morgan Derby, a 30-year-old chef who has trouble accepting his age. When it turns out his second flight to Denver is cancelled, Ralph offers Morgan to stay at Jennifer's place.
Initially, Jennifer is reluctant to take in Morgan, but she allows him to stay, since he is a top chef and she needs someone to make her son a turkey. They soon come to the conclusion that they are two completely different people. Jennifer is irritated by his careless and adventurous behavior and Morgan feels that she is a cynical control freak, which is mostly the result of dating the successful but materialistic businessman Richard Windom. Ralph, however, feels that they are perfect for each other and tries to prevent Jennifer from sending Morgan away.
When Jennifer is about to set him off at the airport, it turns out Ralph has stolen his passport. Jennifer and Morgan end up spending the entire day together and bond. With a lot of trouble and some illegal activities, Morgan is able to get Brian the one Christmas gift he wished for: rocketwheel, a very rare bicycle. Later that night, on Christmas Eve, Morgan makes Brian believe in Santa Claus again, by climbing on the roof and pretending to be one of Santa's helpers. Meanwhile, Jen and Richard attend a formal party and get engaged.
Upon hearing the news, Morgan feels disappointed and leaves. Jennifer is mad when she finds out, but softens up when Ralph tells her that Morgan nearly killed himself on the roof, trying to make Brian believe in Christmas again. Finally convinced by Ralph and Morgan's opinion on Richard and realizing she is in love with Morgan, she breaks off the engagement. She rushes to the airport, trying to stop Morgan from leaving. In the end, they become a couple.
The film was released on DVD on October 13, 2009.
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