Iyanla travels to Chicago to work with two co-dependent sisters, Charese and Andrea. Charese increasingly finds herself torn between dedicating the time needed to be a mom and future wife to her fiancé, and caring for her irresponsible sister, Andrea. In a private sit-down, Iyanla discusses with Charese the situation with her sister. Charese reveals that she has felt responsible for Andrea since they were young, because they were neglected by their addict mother. Iyanla also works with Andrea and helps her to finally admit that she has a drinking problem. Andrea says it is hard for her to admit her issues with addiction, because she does not want to repeat the past mistakes of her mother. In an emotional episode, Iyanla must not only address the wounds of the sisters' past, but also persuade Andrea to take full responsibility for her future and to get help for her problems with alcohol, freeing her sister Charese to live her own life.

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