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A complete timeline of Oprah Winfrey and Meghan Markle's friendship

Debanjali Bose   

A complete timeline of Oprah Winfrey and Meghan Markle's friendship
Prince Harry, Meghan Markle, and Oprah Winfrey sat down for a televised conversation that aired on March 7, 2021.Harpo Productions/Joe Pugliese via Getty Images
  • Years before interviewing them, Oprah attended Meghan Markle and Prince Harry's wedding in 2018.
  • In December 2020, Winfrey posted a video of a gift from Markle, who she called her "neighbor."
  • Take a look at Oprah and Markle's friendship over the years.

May 2018: Oprah Winfrey attends Prince Harry and Meghan Markle's wedding at Windsor Castle.

May 2018: Oprah Winfrey attends Prince Harry and Meghan Markle
Oprah Winfrey arrives at St George's Chapel at Windsor Castle for the wedding of Meghan Markle and Prince Harry on May 19, 2018.      Ian West/Pool via REUTERS

Harry and Markle got married at St. George's Chapel, Windsor Castle, surrounded by 600 of their closest friends and family members.

The guest list included the British royal family as well, as celebrity royalty like Serena Williams, David Beckham, James Corden, and of course, Winfrey.

While Winfrey was included in the star-studded guest list, according to The Independent, Winfrey had only met Markle once before attending her and Harry's wedding.

Winfrey told Entertainment Tonight in June 2018 that the event was "transformative."

"It was more than a wedding, I thought," she said. "It was a cultural moment."

June 2018: Winfrey tells Entertainment Tonight that she and Markle's mother, Doria Ragland, have bonded over yoga and fruits.

June 2018: Winfrey tells Entertainment Tonight that she and Markle
Markle with her mother, Doria Ragland.      WPA Pool/Getty Images

Shortly before Harry and Markle's wedding in 2018, Ragland and Winfrey were spotted together, leading to some speculation of a televised conversation between the two.

A month later, Winfrey clarified in a conversation with Entertainment Tonight that while the two weren't planning an interview, the TV host had invited Ragland over to her home.

"The story was that Meghan's mom had come to my house and she left laden with gifts," Winfrey told the publication. "You know what the gifts were? First of all, she's great at yoga, so I said, 'Bring your yoga mat and your sneaks in case we just want to do yoga on the lawn.' So one of the bags was a yoga mat and the other was lunch."

Winfrey added that Ragland did leave her house with one unexpected gift: kumquats from Winfrey's garden.

"She said, 'I love kumquats,' and I said, 'I have a kumquat tree! You want some kumquats?' So it was a basket of kumquats, people," Winfrey told Entertainment Tonight. "For all of the people who said I am getting her gifts and I'm trying to bribe her for an interview, they were kumquats. If kumquats can get you an interview, I'm all for it!"

April 2019: Winfrey tells Access Hollywood, just days before Archie was born, that she has a "standard gift" that she planned to send the newborn and his parents.

April 2019: Winfrey tells Access Hollywood, just days before Archie was born, that she has a "standard gift" that she planned to send the newborn and his parents.
Harry and Markle pose with their newborn son Archie Harrison Mountbatten-Windsor during a photocall on May 8, 2019.      Dominic Lipinski/WPA Pool/Getty Images

While chatting with Access Hollywood's Scott Evans, Winfrey said that while she might not know too many details about Markle and Harry's baby, she already had a gift in mind.

"I have a standard gift that I do for people that I really care about," Winfrey said. "I don't know the baby's name or the baby's gender, but this baby will have enough books to last a lifetime."

January 2020: Winfrey says she supports Harry and Markle's decision to step back from royal duties.

January 2020: Winfrey says she supports Harry and Markle
Harry and Markle at the Commonwealth Service in March 2020, one of their last engagements as working members of the royal family.      Phil Harris/WPA Pool/Getty Images

"I support them 1,000%," Winfrey said in a video clip published by TMZ.

Winfrey added in the video that she didn't believe Harry and Markle's choice to "step back" from the royal family was an impulsive decision.

Referencing Buckingham Palace's statement that mentioned "many months of conversations and more recent discussions" between the couple and Queen Elizabeth II, Winfrey said in the video clip that she didn't think the Queen was blindsided by the couple's choice.

"He did what he needed to do for his family," Winfrey added, commenting on Harry.

May 2020: Markle read a story to Archie from Winfrey's book collection in an Instagram video to celebrate his 1st birthday.

May 2020: Markle read a story to Archie from Winfrey
Archie and Markle read a book from "Archie's Book Club."      Save The Children/Instagram

In May 2020, the nonprofit Save the Children UK posted an Instagram video showing Archie sitting on Markle's lap as they read the book "Duck! Rabbit!"

The caption said that the video was a fundraising effort for coronavirus relief.

The book had a small white sticker on it that said "Archie's book club," possibly modeled after the label for Winfrey's popular book club.

Oprah Magazine confirmed that it was a part of the collection of books Winfrey had gifted the toddler and that all books that come from Winfrey have the same white sticker.

Winfrey gave a similar literary-leaning gift to Mindy Kaling when her daughter, Katherine, was born in 2017. Winfrey sent Kaling a bookcase filled with classic children's books, Kaling told USA Today.

December 2020: Winfrey shares an Instagram video with a basket of goodies that she says is a gift from Markle. She also reveals that they are "neighbors."

A post shared by Oprah (@oprah)

"On the first day of Christmas my neighbor 'M' sent to me...a basket of deliciousness!" Winfrey wrote in the caption to the post. 

"Yes that M," she added, in brackets, heavily implying that Markle was behind the Christmas goodies. Oprah Magazine later reported that it was indeed Markle who had sent Oprah the gift.

The basket had a number of pouches of latte blends from Clevr, a California-based oat milk latte startup that Markle invested in.  

March 2021: Markle and Harry sit down with Winfrey for an explosive two-hour, tell-all interview.

March 2021: Markle and Harry sit down with Winfrey for an explosive two-hour, tell-all interview.
Harry, Markle, and Winfrey during their chat.      Getty Images

Markle and Harry's interview with Winfrey aired on CBS in the US and the following day in the UK.

In the interview, Markle told Winfrey that she had suicidal thoughts during her pregnancy but received no help from the palace, and that there had been "concerns and conversations" about Archie's skin tone before he was born.

Buckingham Palace released a statement on Tuesday following the couple's interview with Winfrey, saying that "the whole family is saddened to learn the full extent of how challenging the last few years have been for Harry and Meghan."

"The issues raised, particularly that of race, are concerning. While some recollections may vary, they are taken very seriously and will be addressed by the family privately. Harry, Meghan and Archie will always be much loved family members," the statement said.

If you or someone you know is struggling with depression or has had thoughts of harming themselves or taking their own life, get help. The National Suicide Prevention Lifeline (1-800-273-8255) provides 24/7, free, confidential support for people in distress, as well as best practices for professionals and resources to aid in prevention and crisis situations.

Winfrey's representatives did not immediately respond to Insider's request for comment for this story. Markle's representatives declined to comment.

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