The Duchess of Sussex and Oprah Winfrey share a close friendship, living as neighbours in Montecito and often expressing their affection for each other publicly. 

Their first meeting took place at Kensington Palace in March 2018 when Oprah approached Meghan on behalf of CBS. 

According to Robert Lacey in his book Battle of Brothers, the pair are said to have bonded immediately, with Oprah’s ‘ground-breaking brand of black empathy providing a charismatic role model for a mixed-race actress seeking the limelight’.

Their connection was strong enough for Oprah to secure a prime seat at Meghan and Harry’s wedding just two months later. 

Prior to meeting Harry, Meghan was a moderately successful actress best known for her role in legal drama Suits. 

But her association with British royalty catapulted her into an entirely different level of fame – one that opened doors, including a close friendship with Oprah. 

Mr Lacey notes that ‘celebrities had become Meghan’s new family – the allies to whom she could turn as her royal relationships turned toxic’.

In 2021, Harry and Meghan sat down with Oprah for their first major interview after stepping back as senior royals. 

In 2021, Harry and Meghan sat down with Oprah for their first major interview after stepping back as senior royals

Prior to this, sources in Los Angeles suggested that Meghan’s US team had explored the possibility of a tell-all interview as a last-resort negotiating tactic. 

The interview became a defining moment, allowing Harry and Meghan to speak publicly on their own terms, with Lacey suggesting they ‘jumped before they were pushed’.

Harry reportedly recorded his portion within 24 hours of losing his military titles in the final Megxit negotiations.

During the interview, he claimed his father and brother were ‘trapped’ within the Royal Family, while Meghan revealed she had experienced suicidal thoughts as a working royal. 

They also made accusations of racism within the monarchy. 

Interestingly, years before Meghan’s interview, Princess Diana was said to have felt ‘very uncomfortable’ around Oprah. 

Former royal chef Darren McGrady recalled that Oprah met with Diana at Kensington Palace to discuss a potential interview, which the TV host reportedly said would be the ‘highlight of her career’.

However, Diana’s close friend, Simone Simmons, shared with Lacey that the late princess felt Oprah was more focused on sensationalism than genuine storytelling.

Meghan and Oprah’s connection was strong enough for the TV host to secure a prime seat at Meghan and Harry’s wedding

Prince Harry married Meghan at St George’s Chapel in May 2018, but they left the Royal Family less than two years later

In September 2024, Meghan attended Oprah’s book club session at the new godmothers’ bookstore in Summerland, just a few miles from their neighbourhood

In 1996, Oprah interviewed Sarah Ferguson, but the conversation appeared to centre more on Princess Diana than Sarah’s book

Ultimately, Oprah lost out to Martin Bashir, who conducted Diana’s notorious 1995 Panorama interview

Diana reportedly felt this way after watching Oprah’s interview with Sarah Ferguson, which appeared to centre more on Diana than Sarah’s book. 

‘That laid bare for Diana the basic lack of respect that she felt Oprah had towards her subjects and how she was just manipulating her to garner higher ratings,’ Mr Lacey writes. 

Ultimately, Oprah lost out to Martin Bashir, who conducted Diana’s notorious 1995 Panorama interview.

Viewed by approximately 23million people, it became one of the most controversial interviews in television history. 

During the conversation, Diana spoke candidly about her struggles with depression, bulimia and self-harm, as well as her fears that the Royal Family was working against her.

She famously declared, ‘there were three of us in this marriage,’ referring to Prince Charles’s affair with the future Queen, Camilla. 

A later investigation revealed that Bashir had used fraudulent documents to secure the interview, leading to a formal apology from the BBC.