From April 27, 1999: Oprah dedicates a show to women who have a hard time expressing their true feelings when in difficult situations and conversations. Assertiveness coach, Jan Ferris, shares the importance of boundary setting and tips for learning how to say, “No.” New York Times Business Bestselling authors of Difficult Conversations, Doug Stone and Sheila Heen, discuss why some conversations are more difficult than others, teach what they call the doubling technique and give advice for tough scenarios.

From April 3, 1998: Oprah talks to people who have survived terrible tragedies. Dr. Paul Stoltz, keynote speaker and #1 New York Times best-selling author of The Adversity Quotient discusses how to turn obstacles into opportunities and how adversity leads to strength. Dr. Stoltz also explains what he calls the “constructive blame zone.” Holocaust survivor, psychologist and author Dr. Edith Eva Eger shares her traumatic experiences at the Auschwitz Birkenau concentration camp and explains how to overcome anything through the power of your mind.

From September 11, 1996: Oprah and Bob Greene, exercise physiologist and personal trainer, discuss their No. 1 New York Times best seller, Make the Connection, a book that outlines 10 steps to change your life, lose weight and keep it off. Oprah shares insights from her own weight loss journey, including how to gain discipline and will power, and why it’s important to care about yourself daily. She also talks to people who have successfully lost weight.

From October 10, 1995: Author and science journalist Dr. Daniel Goleman discusses his New York Times best-selling book, Emotional Intelligence. He explains how to handle our anger, how controlling impulses affect our lives and how we can increase our EQ at any point in our lives. Also, Dr. Martin Seligman—psychologist, educator and author of The Optimistic Child—explains the three aspects of optimism, how optimism increases emotional intelligence, and the correlation between pessimism and depression. 

From March 6, 1990: Oprah and Dr. Paul Pearsall, neuropsychologist and author of the New York Times best-seller, The Power of the Family, take the audience through a ‘rituals test’ to assess their family health. Dr. Pearsall discusses why families are failing, the importance of developing the “us” quotient and how just 15 minutes of spending time together as a family unit can make a difference. Dr. Paul Pearsall passed away in 2007.

From October 17, 1988: Do we have the ability to think ourselves well? A panel of doctors and patients debate mind over body cures and share their personal stories of healing through medical and non-medical means. Guests include Dr. Bernie Siegel, pediatric surgeon and author of New York Times #1 Bestseller, Love, Medicine and Miracles; Dr. Sherwin Nuland, author of Doctors: The Biography of Medicine and Orthodox Rabbi Benjamin Blech. Dr. Sherwin Nuland passed away in 2014 from prostate cancer.

From October 15, 2008: Oprah takes her audience through a test to determine if they are rude. Professor at John Hopkins University and author of Choosing Civility: Twenty-Five Rules of Considerate Conduct, P.M. Forni, discusses the principles of respectful people, the difference between being rude and mean and explains why our quality of life depends on the quality of our relationships. Steve Dublanica, author of the New York Times bestseller, Waiter Rant, shares restaurant etiquette that most people don’t know. P.M. Forni passed away in 2018.

From October 12, 1998: Television personality, author and former psychologist Dr. Phil McGraw helps guests dealing with devastating loss. JoAnn Compton Powell shares that she has been unable to move forward after the death of her daughter, Laurie, over a decade ago. Dr. Phil shares his five coping skills for grief, causing JoAnn to have one of the deepest aha! moments in Oprah show history. Oprah and Dr. Phil also speaks to Brian Janette, who stopped taking care of himself after losing his mother.

From March 28, 1989: Oprah talks to adults who share stories of the emotional abuse they suffered as children and how it still affects them today. Psychotherapist and author of How to Raise Your Self-Esteem, Dr. Nathaniel Branden explains the difference between conscious living and unconscious living, and how making small changes to be more conscious in your life can improve your self-esteem. He also explains why some people are able to transcend abusive circumstances when others cannot. Dr. Branden passed away in 2014 at age 84 from complications with Parkinson’s disease.

From October 9, 1997: Oprah talks with author and psychiatrist Elisabeth Kubler-Ross about her autobiography, Wheel of Life. A pioneer in death and dying studies, Elisabeth shares the greatest lessons she’s learned from those who are dying, how she is welcoming death at the end of her own life and how she’s able to never give up. Also, journalist, philanthropist and author Mitch Albom discusses his New York Times best-selling book Tuesdays with Morrie. He explains how death is an opportunity to teach, and shares why he believes the love we create in our lives continues after death. Elisabeth Kubler-Ross passed away in 2004 at a nursing home in Scottsdale, Arizona.