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An uptight, conservative businesswoman accompanies her boyfriend to his eccentric and outgoing family's annual Christmas celebration and finds that she's a fish out of water in their free-spirited way of life.

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Will Freeman is a good-looking, smooth-talking bachelor whose primary goal in life is avoiding any kind of responsibility. But when he invents an imaginary son in order to meet attractive single moms, Will gets a hilarious lesson about life from a bright, but hopelessly geeky 12-year-old named Marcus. Now, as Will struggles to teach Marcus the art of being cool, Marcus teaches Will that you're never too old to grow up.

Will Freeman lives a charmed existence as the ultimate man-child. After writing a hit song, he was granted a life of free time, free love and freedom from financial woes. He's single, unemployed and loving it. So imagine his surprise when Fiona, a needy single mom and her oddly charming 11-year-old son, Marcus, move in next door and disrupt his perfect world. When Marcus begins dropping by his home unannounced, Will's not so sure about being a kid's new best friend, until, of course, Will discovers that women find single dads irresistible. That changes everything and a deal is struck: Marcus will pretend to be Will's son and, in return, Marcus is allowed to chill at Will's house. Before he realizes it, Will starts to enjoy the visits and even finds himself looking out for the kid. In fact, this newfound friendship may very well teach him a thing or two that he never imagined possible - about himself and caring for others.