In the series premiere, Oprah meets the ten contestants and hands each an envelope with only the name and picture of a stranger whose lives they must change. Each contestant must use resources awarded to them to drastically improve the life of their assigned person within five days, forcing them to deal with the stress of it all by using ultimate strategy and creativity. At the end of the episode, one contestant is eliminated from the competition.

The remaining nine contestants are taken to a major U.S. city where they must be creative with the distribution of their money, for which they only have two days. As the pressure mounts, the contestants discover that there is a surprise twist that leaves everyone in shock.

The eight contestants arrive in Houston, where they are challenged to make 1,000 children's dreams come true. They are split into two groups of four, "Field of Dreams" and "Forgotten Christmas". Andre Agassi and Tony Hawk guest star.

The contestants are taken to Miami, where they have 1 day to give away $100,000.

Oprah sends the contestants on a "Big Give Road Test" challenge. Guest star in this episode is the famous race-car driver Danica Patrick.

The four final contestants arrive in New York. Their task is to fulfill the last wishes of two parents. Guest stars in this episode are eight-time Grammy Award winner Natalie Cole, film star Jada Pinkett Smith and editor-at-large for O, The Oprah Magazine Gayle King.

Four days given the last three contestants head home to organize family reunions. They are given a budget of 10.000 $. Guest star this time is John Travolta.

For the finale episode of the first season the last contestants must create "Big Gives" with NO MONEY and very little time. Watch out for a last unexpected twist, that will make everyone talk about. Jennifer Aniston is special guest star in the season finale.