It's a few days before Christmas. As they have always done, widowed schoolteacher Tom Pullman, his thirteen year old daughter Hilly Pullman and their pet dog Toby are driving from their home in Chicago to Vail to spend Christmas with his mother, Rheudel Pullman. Although loving her grandmother, Hilly would rather have a more exciting Christmas than spending it in the country. She would also prefer to fly than to drive in Tom's aged pickup truck, which is not guaranteed to last the trip. Tom, on the other hand, finds taking the back roads seeing the countryside as part of the adventure. Meanwhile, Chicago-based fashion photographer Claire Jamison, a pampered city girl, has one more assignment, after which she will fly to Aspen to join her Italian fiancé Lorenzo at his chalet where they will get married on Christmas Eve. Although they have known each other for some time, the romance, engagement and wedding are recent phenomena, Lorenzo who is handling the bulk of the wedding plans with the help of his personal assistant Michele. Almost everyone who Claire tells about the wedding is skeptical, if only because of the stereotype of Italian men being Latin lovers, meaning that Lorenzo will have a wandering eye if it hasn't wandered already. As Claire's assignment is canceled at the last minute, she plans to fly to Aspen early to surprise Lorenzo. But Claire's trip is anything but smooth, the first big bump being her flight being diverted to Lincoln, with no guarantee of any form of transportation being able to get her to Aspen in time. As Claire and Hilly have seen each other from afar a few times on this trip, they believe it may be kismet when they cross paths in Ogallala, Nebraska, when Tom offers her, at that time in total distress, a ride. There are the existing issues of Tom's failing pickup truck and Claire needing to keep in constant contact with Lorenzo but not having reliable cell phone service, but the biggest issue in their trip may be their outward differences, which each assumes makes the other a specific type of person not copacetic with their self. But Hilly can see that there are feelings developing between the two. Even if Tom and/or Claire do eventually acknowledge those feelings, there still is the fact of Claire's imminent wedding which may prevent a happily ever after for Tom and Claire.