10 Friendship Lessons from BFFs Oprah and Gayle

Perfete Blogger / Monday August 26, 2019

Dami D is a freelance writer and reading addict who likes to create stories out of even the most mundane things. Read ALL the things I talk about at whatdamidid.com

I cannot forget watching the Oprah Show when I was younger and Gayle would always be a permanent fixture on the show. Every one or so paragraphs was followed with a  “my best friend Gayle”. Sometimes it felt like her full name was MybestFriend Gayle. haha. Now so many years later, Oprah and Gayle cover O Magazine’s friendship issue as a celebration of their 43 years of friendship, and what an amazing friendship it has been: from matching bentleys, to hilarious wardrobe critique and even unfounded relationship rumors, here are some lessons we can learn from Oprah and “My best Friend” Gayle.

10 Friendship Lessons from BFFs Oprah and Gayle

  • Sometimes your presence is the best gift:

On Oprah’s 40th birthday, she was surprised on the Oprah Winfrey show by icons like Aretha Franklin and Patti Labelle, however, she wasn’t as overwhelmed as when Gayle walked into the studio- she immediately burst into tears! While other guests had shared profound words, Gayle only had a simple message, “I have no song to sing, I have no words of wisdom, I just wanted to be here with you today”. Another time, Oprah was expressing her pain after a betrayal on the phone and  Gayle hung up, asked the sitter to stay the night, and hopped on a flight to see Oprah. When Oprah opened the door, she said “I just wanted to see you”, had a glass of water and went back to the airport. Oprah has shown up too! When Gayle was spending her first holiday without the kids after her divorce, Oprah showed up on her doorstep with Stedman and spaghetti ingredients, and spent the holiday with her.

  • But sometimes thoughtful presents are nice too:

After the birth of her second child, Oprah said to Gayle, I have a surprise for you. It wasn’t a pushchair like Gayle expected, it was a nanny paid for as long as needed (which ended up being 7 or 8 years, lord Jesus! When?).

  • Friends are always honest:

Oprah and Gayle are never afraid to say things as they are, from ashy skin to wardrobe fails.

  • Friends can work together:

Gayle has worked as a tv and radio anchor on OWN and is currently the editor at large of O-magazine.  They met and became friends when working at the same TV station.

  • Love is in the details:

Oprah threw Gayle an epic surprise party for her 60th birthday. Everyone wore yellow (her favorite color)  and clogs (her favorite shoe), all her favorite foods and favorite people.

  • You can never talk too much -for 43 years of friendship:

Oprah and Gayle have talked multiple times a day and Oprah attributes her positive mental health to daily therapeutic conversations with Gayle.

  • Friendship endures big life changes:

When Gayle was getting married, Oprah apparently had reservations about the marriage but felt scared that it would change their relationship if she said something. It didn’t. Oprah hasalso said in no uncertain terms that her relationship with Stedman would not have progressed if he didn’t like Gayle.



  • Generosity of spirit is a big part of friendship:

“But let me just say this, too. The person who has the money has to have a generous spirit. Early on, when I started to make a lot of money and we’d go shopping, I’d say, “Look, the deal is this: If you see something you really want, I’ll get it. I don’t want to play this, ‘No, no, no, you don’t have to buy that for me,’ because I’m really willing to get it for you.” I do that now with all my friends.”

  • Friends support you completely:

When Oprah was taking a job at a new network, everyone told her she was too black and too fat and was bound to fail, except Gayle who believed in her completely. Now that they have both achieved amazing career successes, they take turns supporting each other with complete joy. When Gayle was renegotiating her CBS contract, Oprah called gayles lawyer to insist that he get her everything she wants, “what the f do you think i’m doing?” was his apt reply.

  • Friends talk about each other with love:


Female friendship is often layered and complex especially when you come from different worlds. For Oprah who grew up poor, and Gayle who grew up with staff and a swimming pool, they couldn’t have been more different except in all the ways that mattered. By focusing on the things that made them similar, they have managed to ignore the noise and maintain an inspiring 43 year old friendship!