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Shortly after he retires from a lifetime of service as an insurance company actuary, Warren Schmidt's (Jack Nicholson) wife dies suddenly, leaving him feeling desperately alone. Trying to put his life back together, he embarks on a road trip to Denver, where his only daughter (Hope Davis) is preparing to marry an underachieving waterbed salesman named Randall (Dermot Mulroney). Warren disapproves of his daughter's groom-to-be and decides he must save his daughter from making the biggest mistake of her life. Throughout his journey, Warren shares his experiences in the letters he writes to Ndugu Umbo - a six-year old Tanzanian orphan whom he sponsors - and Warren begins to catch a glimpse of who he really is.