In 1998 Los Angeles, Winona (Jessica Barden) struggles to cope with an anxiety disorder after dropping out of college and works for her father as his secretary. Her relationship with her family is strained, particularly with her parents Pamela (Marcia Gay Harden) and Richard (Michael McKean). As she navigates her personal life, Winona attends group therapy sessions led by Dr. Monroe (Mary J. Blige), who helps her confront her emotional struggles. With the support of new friends Addie (Rosa Salazar) and Stephanie (Odeya Rush), Winona begins to rebuild her life and find a sense of direction.
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