Nathan is happily engaged in his playboy lifestyle with girlfriend Jessica and best friend and ski buddy, Travis. His plans for a ski holiday are abruptly derailed when his parents decide to take a lengthy vacation and he is expected to return to the family homestead to babysit his elementary-aged siblings. He, and his younger brother and sister, grudgingly accept their plight only to shortly discover that their parents will never return. A plane crash has left them as orphans. This story is set around Nathan's frequent visits to the psychiatrist in his attempts to cope with siblings who give him no personal space, a girlfriend demanding that he send them away to a boarding school as she pressures him to marry her, school authorities telling him to get help or they will have the children taken away, an attorney who tells him he has to settle down and take care of his father's business, nannies with strange habits and personal ambitions, and his unexpected emotions for a Christian girl