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The Real Story Behind Meghan Markle's Friendship With Oprah

Two of the most famous women in the world have benefited by their connection in a number of ways.

As the world now knows, Duchess Meghan was miserable during her short tenure as a senior member of the British royal family. In her emotional interview with ITV's Tom Bradby when she and Prince Harry were on an official royal tour of Africa in 2019, the duchess revealed just how unhappy she was living in the royal fishbowl. But since leaving royal life and returning to her home state of California in the spring of 2020, she hasn't done much speaking out directly about her experience. Before Meghan and Harry's surprise announcement on Feb. 19 that they would not be returning to royal life, the couple had decided it was time they spoke for themselves. Next month, Meghan will be spilling the royal tea to her new friend Oprah Winfrey in a CBS special. Two of the most famous women in the world—who had met only once before the Sussexes' wedding—have forged what appears to be a strong bond that has bolstered and benefited both of them in a number of ways over these last few years.

Meghan and Harry have chosen Oprah (or, perhaps, the media maven chose them) for their first post-Megxit television interview, which will air on CBS on Mar. 7 as a two-part special. According to a statement from the network, the interview will focus mainly on Meghan's experiences with the royal family, parenthood, and dealing with the scrutiny of the British media. Harry will join his wife for the latter part of the special for a conversation about their new life in California and their hopes for the future. CBS anchor and Oprah's best friend Gayle King (who reportedly introduced the two) has said "nothing is off limits" in Oprah's sitdown with the royal couple.

But how did Meghan and Oprah become such fast friends? Read on to find out more about the fascinating story behind their connection, and for more on the Sussexes' latest news, check out Why Meghan and Harry's Pregnancy Announcement Seems So Familiar.

It started when Meghan invited Oprah to Kensington Palace in 2018.

Oprah Winfrey arrives at St George's Chapel at Windsor Castle for the wedding of Meghan Markle and Prince Harry.
PA Images / Alamy Stock Photo

According to The Times, the two women first met in March 2018 when Oprah "found herself in London" and King reportedly arranged a phone call between her and Meghan. The duchess then invited Oprah to Kensington Palace, the Daily Mail reported. A month later, Oprah invited Meghan's mother, Doria Ragland, to lunch at her sprawling complex in Montecito, California. She revealed afterward that they did yoga in her garden and she sent Ragland home with a basket of her homegrown kumquats.

The behind-the-scenes contact between Meghan and Oprah increased over the next year as evidenced by the "Queen of All Media's" announcement in April of 2019 that she would be sending Baby Sussex a "welcome to the world" present. "I have a standard gift that I do for people that I really care about," Oprah told Access Hollywood at the time. "I don't know the baby's name or the baby's gender, but this baby will have enough books to last a lifetime!" Meghan was reportedly thrilled by the gesture. (The following year, in May 2020, Meghan read one of Oprah's books for Archie in a video released in support of Save the Children's Save With Stories campaign.)

Also in the spring of 2019, Harry and Meghan announced the prince would be co-producing a docuseries on mental health with Oprah for Apple TV. And for more royals updates sent right to your inbox, sign up for our daily newsletter.

Meghan and Oprah were drawn to each other because of shared life experiences.

Meghan, Duchess of Sussex attends the Commonwealth Day Service 2020 at Westminster Abbey on March 9, 2020 in London, England; Oprah Winfrey attends the premiere of OWN's "David Makes Man" at NeueHouse Hollywood on August 06, 2019 in Los Angeles, California.
Max Mumby/Indigo/Getty Images; Rachel Luna/Getty Images

Before Meghan married Harry, she was a little known actor on cable television who was intent on building her own brand, including developing a following on her now shuttered website The Tig, and participating in charitable humanitarian and female empowerment projects. To have one of the world's biggest stars and respected humanitarians take such keen interest in her life was exciting and highly flattering to Meghan. With Oprah's approval, the duchess has entered the charmed circle of Oprah's celebrity friends, which undoubtedly aided in Meghan's arrival on the Hollywood A-list.

"I don't know if it's 'friendship' friendship, it could be a mutual admiration," psychotherapist and author Robi Ludwig, PsyD, told Best Life in an exclusive interview of the bond between Oprah and Meghan. She added that their shared experiences as "very ambitious" women who "beat the odds" could be the foundation for their connection. "Through their intellect, drive, and tenacity, they both got to achieve their own version of the American dream," she said. "On one level, it makes perfect sense they would be drawn to each other and serve each other's interests."

Oprah and Meghan have a mentor-mentee relationship.

Oprah Winfrey poses backstage at the hit musical based on the film "Tootsie" on Broadway at The Marquis Theater on May 14, 2019 in New York City; Meghan, Duchess of Sussex attends The Endeavour Fund Awards at Mansion House on March 5, 2020 in London, England.
Bruce Glikas/WireImage via Getty Images; Max Mumby/Indigo/Getty Images

Oprah has become somewhat of a mentor to Meghan, which is one of the reasons why she landed the upcoming CBS interview. "You know when Oprah is interested in someone—you can tell when she's pulling for someone. That may be what she wants to do [with the interview]," Ludwig said.

In April 2019, Oprah went on CBS This Morning and championed the duchess. "I think she's being portrayed unfairly," Oprah said. "I feel that if people really knew her, they would know that she is not only everything that you perceive her as being—graceful and dynamic in holding that position—but she just has a wonderful warm, giving, loving heart. I see all the crazy press around her, and I think it's really unfair."

After the seismic aftershocks of her ITV interview in Oct. 2019, Best Life exclusively reported the royal couple planned to spend time with Oprah on their holiday visit to California the next month, where they likely discussed the fallout from the interview. And for more infamous interviews with the queen of daytime, check out Oprah Says This Was the Worst Guest She Ever Had.

Oprah played a key public role in promoting stateside support for Meghan and Harry after their split with the royal family.

Prince Harry, Duke of Sussex and Meghan, Duchess of Sussex on October 2, 2019 in Johannesburg, South Africa.
Chris Jackson/Getty Images

There was next to no support for the royal couple from the British press after their Megxit plan was announced in Jan. 2020. Oprah, on the other hand, went out of her way to praise Meghan and Harry's decision to step down as senior royals. Shortly after the announcement and amid rumors she helped them strategize their exit, Oprah told People, "Meghan and Harry do not need my help figuring out what's best for them. I care about them both and support whatever decisions they make for their family." She also said in an interview with TMZ that she supported the Sussexes "1,000 percent," adding that Harry "did what he needed to do for his family."

A month later, King was among a small coterie of celebrities, including Amal Clooney, who attended Meghan's baby shower thrown by Serena Williams in Feb. 2020. Afterwards, King revealed details about the intimate gathering and sang Meghan's praises. "She's very kind. She's very generous, and a really, really sweet person," King said on air.

"What we saw is what goes on with a lot of famous people—networking," Ludwig said. "There's a lot to 'who you know' with very famous people."

Meghan and Oprah's newfound friendship also means big business for both of them.

Oprah opens Christmas gift from Meghan Markle
Oprah / Instagram

For Oprah, landing an interview with Harry and Meghan—the current moment's biggest "get"—proves she is still "hot," Ludwig said. Since ending her star-making talk show in 2011, and now that her print magazine has ceased publication, this interview makes her the hottest ticket in television without even having her own show. It's sure to garner blockbuster ratings and will put Oprah back on top of a very competitive list in television, which almost certainly means there are even bigger deals (and possibly business ventures with Meghan) in the future.

The friendship has also had its business perks for Meghan. In December, Oprah shared her enthusiasm for a Christmas gift from her neighbor "M" with her 19.3 Instagram followers. It reinforced the idea that Oprah is still one of the country's most influential tastemakers while subtly reminding everyone of her friendship with the duchess, an important currency in today's zeitgeist. The "basket of deliciousness" from Meghan to Oprah contained latte mixes from Clevr Brands. The following day, when it was revealed that Meghan was an investor in Clevr, it became very clear what she'd gained from Oprah's endorsement. And for more on Meghan's plans for the year ahead, check out The One Thing Meghan and Harry Are Really Looking Forward to in 2021.

They have a shared fascination with Princess Diana.

Princess Diana on Walkabout on 6 October 1987
Lionel Cherruault Royal Picture Library / Alamy Stock Photo

Interestingly, both Meghan and Oprah have always been captivated by Princess Diana. "Oprah is enamored by royalty and as an American, [Meghan] is as close to royalty as you can get," said Ludwig. Like every other interviewer on the planet, Oprah was relentless in trying to land an interview with Princess Diana. (She did have Sarah Ferguson on her talk show and later produced a docuseries on the disgraced duchess.) A childhood friend of Meghan's has said, "She was always fascinated by the royal family. She wants to be Princess Diana 2.0." The duchess also reportedly pored over every page of Diana: Her True Story, a tell-all written by Andrew Morton with the princess's cooperation.

While Oprah never landed the royal interview to end all interviews, she has achieved the next best thing by befriending the woman who is doing all she can to follow in Diana's iconic footsteps. And for more on what Meghan and her late mother-in-law have in common, check out 3 Things Princess Diana and Meghan Markle Did to Change the Royals Forever.

Diane Clehane is a New York-based journalist and author of Imagining Diana and Diana: The Secrets of Her Style.

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