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When his rich granddad, Howard "Red" Stevens (portrayed by James Garner) died, Jason (Drew Fuller) thought he was going to inherit a piece of the old man's multi-billion dollar estate, but it came with a condition. In order to get his share of the willed inheritance, Jason must complete 12 separate assignments within a year. Each assignment is centered around a "gift". Gifts of Work, money, friends and learning are among the dozen that Jason must perform before he is eligible for the mysterious "Ultimate Gift" his grandfather's will has for him. Throughout his trials and tribulations, the family attorney, Mr. Hamilton (Bill Cobbs), and his secretary Miss Hastings (Lee Meriwether) attempt to guide Jason along the path his grandfather wishes him to travel. However, the problem they have is that Jason has lived leisurely using his grandfather's money as an under-achiever who has never had to genuinely work, and who believes through a young adulthood of loneliness that money is the only pathway to making life decent. For instance, to carry out the first task he has to fly to Texas, and naturally assumes he has a first-class seat, and is annoyed when he discovers he has a coach class seat, complaining to the steward "Don't you know who I am?"

On his return after completing the first task in Texas, everything he values is suddenly taken away from him - luxury apartment, his restored muscle car (a 1970 Dodge Coronet R/T) and money - and he is left homeless. His trendy girlfriend, Caitlin (Mircea Monroe), ditches him when his credit card is rejected at a fancy restaurant and she is mortified when he asks her if she could pay the bill. After his mother (Donna Cherry) tells her son she cannot give him help as part of the agreement, Jason miserably finds himself being ejected from private property he wishes to rest on, and wanders the city for the first time truly alone.

It is while sleeping in a park that he encounters a woman, Alexia (Ali Hillis), and her extrovert daughter Emily (Abigail Breslin) - a side story that was not in the novel. Jason befriends the two but then tells them that he needs them to come along to the attorney's office and confirm themselves as his "good friends" in order to pass the "gift of friends" assignment. Alexia and Emily still believe that Jason is a very self-centered person, and not anyone they want to have as a friend. However, it is then that Jason discovers by accident that Emily is suffering from leukemia, and sees this family as a chance to develop a strong bond with someone. Indeed, the emergence of his "true" self is the key theme of the film.

From that point onwards he tries as best he can to help Emily have a great life while it lasts. Emily also engineers and encourages a romance between Jason and her mother. Also, as Jason works through the twelve gifts in twelve months, he comes to see his grandfather as more than a dead billionaire who he believes disliked him. After Jason has completed his twelve tasks, he is given a sum of $100,000,000 to do with whatever he pleases and all of his property is returned to him. His former girlfriend, knowing that he has regained his wealth, makes an attempt to win him back merely with the offer of sex, but he disgustedly walks out on her.

With his inheritance, Jason chooses to build a hospital, called Emily's Home (named after Emily), for patients with deadly diseases and their families, which also includes a church (knowing that Emily was often in the hospital chapel). But then before the building begins Emily dies. Alexia and Jason pray for her at the chapel. After the groundbreaking for Emily's Home, he is brought back to the law firm for one more meeting. He had exceeded the expectations of his dead grandfather and receives one final "gift" of $2,000,000,000, rewarding Jason not only for his completing the tasks, but for using everything he gained to give to the unfortunate ones. That night, Jason is seen sitting on a bench in the park, when Alexia joins him. He thanks her for the help that she and her daughter gave him. Then they kiss and a butterfly, representing Emily, is shown flying around them.