Annie is a kindergarten teacher who gets the shock of her life when Duncan, the famous entrepreneur who all the newspapers have labeled "Meanest CEO in the Country," tells her that her little brother embezzled money from his company! He says that if he can't get his money back he's going to take her house and throw her brother in jail. Annie's in such deep shock that when he proposes an alternative that will forgive her of her debts, she takes him up on his offer. All she has to do is help him change his stone-cold image by pretending to be his girlfriend for the month leading up to Christmas. They both live in such completely different worlds, such a thing shouldn't even be possible...or so she thought!