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Warren Schmidt (Jack Nicholson) has arrived at several of life's crossroads all at the same time. To begin with, he is retiring from a lifetime of service as an actuary for Woodmen of the World Insurance Company, and he feels utterly adrift. Furthermore, his only daughter Jeannie (Hope Davis) is about to marry a boob. And his wife Helen (June Squibb) dies suddenly after 42 years of marriage.