Financial planner has long helped households struggling with mounting debt try to get out of their financial messes on (2005). Gail now turns her attention to spoiled young women - princesses - whose reckless spending has not only created financial problems for themselves, but for family and friends who have enabled that behavior. In the same vein as "Til Debt...", Gail issues a series of challenges to these princesses which helps them deal with their financial problems directly, with root causes or subsequent consequences of their reckless behavior, or with the relationships with these family and friends that have been negatively affected by this spending. With weekly status checks over the course of a month, Gail will provide these princesses with up to $5,000 to help them pay off their debt, the amount based on how successfully Gail believes they have embraced and completed the challenges.