Oprah's Friendship With Prince Harry & Meghan Markle Is Reportedly Soured

Meghan Markle and Prince Harry found the ally of a lifetime in Oprah Winfrey after they shed their senior royal status, left the U.K., and decided to find a new normal in 2020. Although the couple weren't besties with Winfrey before they sent her an invitation to their royal wedding in 2018, that soon changed. As The Times detailed, Winfrey and Markle were basically strangers before the highly-anticipated wedding, but they eventually struck up a friendship, with Winfrey at the helm as Markle's mentor. That foundation eventually led to the couple's 2021 bombshell Oprah interview, which pulled back the curtain on their increasingly difficult relationship with the royal family.

But it wasn't all business. Years before Markle, Harry, and Winfrey broke the internet, Winfrey took to her website and gave a first-hand account of attending the wedding. She described almost breaking the cardinal wedding rule (wearing off-white or cream), her love of seeing Windsor in person, and even her thoughts about the newlyweds. "We all want to feel as radiant, joyful, and alive as Meghan looked on her way down the aisle to meet Harry," wrote Winfrey. In 2023, the talk show mogul supported Prince Harry amid the speculation about whether he'd attend King Charles III's coronation. "I think they should do what they feel is best for them and their family," she said during "CBS Mornings." 

Unfortunately, their relationship with Oprah may not be what it once was, according to Princess Diana's former butler.

Once upon a time, Oprah Winfrey seemed to have a genuine friendship with Meghan Markle and Prince Harry. Although it appears that Winfrey skipped out on Markle's celeb-filled baby shower for Prince Archie in February 2019, as she wasn't one of the named A-list attendees, she honored their soon-to-be first born in another major way. In May of that year, Winfrey spoke with US Weekly, dishing on her super sweet gesture to the new parents: a gift to celebrate their new arrival. But she wouldn't spill the beans about exactly what she'd bought. "I'm not telling [what it is]," she said. "I haven't sent it yet."

Paul Burrell, who once worked as Princess Diana's butler, has implied the spouses aren't as close with Winfrey and some of their other celebrity friends anymore. "A-list stars are dropping like flies," shared Burrell with Closer! (via The U.S. Sun). "Some already have done — Oprah no longer seems involved with them and some other celebrities have also dropped them." He continued, "Back in the day, the A-listers were riding on the moment — Harry and Meghan were the most popular couple in the country at one time, when they got married, but there's since been a decline." According to Burrell, this decline is connected to American's love for the royal family, whom the Sussexes distanced themselves from.

This, of course, is the speculation of a single party.

Oprah Winfrey's relationship with Meghan Markle and Prince Harry may have become strained or they may just not be as public as they once were. However, Winfrey has addressed how she felt about the juicy interview she conducted with the royal spouses. "I was as surprised by the bombshell as everybody else," said Winfrey during "CBS Mornings" in September 2022. "I was doing an interview to offer them a platform to tell their story about why they left. That was my number one intention, was just clarity ... and so, some of the things that were revealed in that interview came as a surprise to me," she added before stressing once more that she hadn't intended to do a bombshell interview.

Later in the interview, Winfrey revealed that she didn't get involved in the familial business when asked about a possible reconciliation between Prince Harry and his brother, Prince William. However, she was slightly more open about sharing her opinion on the royal family's feud while speaking with Extra TV that same month. "When all families come together for a common ceremony, the ritual of, you know, burying your dead, there's an opportunity for peacemaking ... And hopefully, there will be that," said Winfrey, referencing Queen Elizabeth II's passing. Unfortunately, nearly two years onward, it doesn't appear as if Markle, Harry, and the royal family are any closer to getting back on the right path.