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A group of thirtysomethings who all went to the same high school are reunited and realize that their lives didn't turn out as they had planned.

Gordon Stiles' life is not easy. He's an executive whose boss, Mr. Peterson, is overbearing, demanding, and insufferable. His brother Jimmy is an actor but he can barely spell it, let alone actually do it; while he waits for his big break, he relies on Gordon for all his necessities. As if that's not enough, Gordon's wife has left him to raise their son Dan on his own, since Jimmy isn't exactly reliable. Fortunately, he meets grad student Kelly O'Malley, who has a way with Dan, so he hires her to be Dan's nanny. Now Kelly can't help but get involved in Gordon's personal life--and vice versa--and they come to rely on each other as they both nurture Dan.