Original Air Date: Aug 28, 2019

In a live conversation, Oprah sits down with New York Times best-selling author Cheryl Strayed. As a part of her “Path Made Clear” book tour, Oprah is joined on stage in front of a live audience by this special guest for a unique one-on-one conversation. Oprah and Cheryl discuss the meaning of forgiveness, the importance of vulnerability and the meaning of regret. Cheryl also talks about turning 50 and why she now puts herself first. Cheryl’s best-selling memoir “Wild,” which recounted her spiritual journey hiking the Pacific Crest Trail, was chosen as an Oprah’s Book Club selection and went on to become a critically acclaimed film starring Reese Witherspoon.

Original Airdate: September 11, 2019

Oprah talks to Cybill Shepherd, Ali MacGraw, Beverly Johnson, Jamie Lee Curtis and Bo Derek about what it's like to age in the spotlight. In a candid conversation, Cybill Shepherd reveals that her model looks opened doors for her and also discusses the moment she realized that heads were no longer turning her way. Oprah also sits down with ‘70s icon Ali MacGraw to talk about how she's learned to embrace getting older, as well as what it was like for her to realize she was not the "it girl" any more. Supermodel Beverly Johnson shares the moment she realized she should stop trying to look like a younger woman and Jamie Lee Curtis discusses why aging has finally given her freedom. Bo Derek reveals why getting older makes her better.

Original Airdate: October 23, 2019

Buddhist nun, author and pioneer of the mindfulness movement Pema Chödrön discusses her new book, Welcoming the Unwelcome. Pema reminds us how to connect to our basic goodness. She shares the first things we should do when moments show up for us that are uncomfortable, stressful or hopeless. Pema also addresses the sexual abuse allegations that rocked the Buddhist community.