Princess Eugenie and the Duchess of Sussex have forged one of the most unexpected friendships to emerge from the turbulent Sussex story.
Eugenie, 36, and Meghan, 45, have long appeared to share a close bond—one that has endured several notably awkward moments.
One of the most talked-about incidents came in 2018, when Meghan and Prince Harry announced they were expecting their first child just days after Eugenie married Jack Brooksbank at St George’s Chapel in Windsor. The couple’s eighth wedding anniversary falls next week.
There was also the story that Meghan allegedly mistook Andrew, now a former prince, for one of the Queen’s advisers. Whether accurate or not, the tale has become part of the mythology surrounding Meghan’s first meetings with the Royal Family.
Harry later criticised Eugenie’s father in his memoir, Spare, questioning why Andrew retained his security detail while he and Meghan lost theirs after stepping back as working royals.
Despite those tensions, Eugenie and Meghan have continued to appear to enjoy a warm relationship.
Eugenie holds a particularly significant place in the Sussex story. She was close to Harry long before Meghan entered his life and was even present at the Halloween party in Toronto in 2016, where Harry and Meghan spent what they described as their final night of freedom before their relationship became public.
In Finding Freedom, Omid Scobie and Carolyn Durand wrote: ‘Eugenie had always been more than just a cousin to Harry. They were also the closest of friends.’
Princess Eugenie attended the Halloween party in Toronto in 2016, where Prince Harry and Meghan Markle spent their last night together before their relationship was publicly revealed
The authors of Finding Freedom claimed Eugenie believed the couple should have waited until the excitement surrounding her wedding had faded before announcing their pregnancy
The Sussexes’ pregnancy announcement quickly became the biggest royal story of the day—an outcome that reportedly did not please the bride
The authors described Harry and Eugenie as sharing ‘one of the most natural connections’ among the Queen’s grandchildren, noting that they had enjoyed ‘many nights out together in London’.
Eugenie was also seemingly among the few members of the Royal Family to maintain close ties with the Sussexes after their move away from Britain, widely dubbed ‘Megxit’, in 2020. She and Jack have visited Harry and Meghan in California, preserving a personal relationship despite the deepening divisions elsewhere within the family.
However, their friendship faced an early test in the aftermath of Eugenie’s wedding.
According to Finding Freedom, Harry and Meghan told family and friends about Meghan’s pregnancy at the wedding reception. Eugenie reportedly felt they should have waited before making the announcement.
The timing was undeniably striking. While the newlyweds’ celebrations were still taking place, the Sussexes’ news suddenly became the day’s leading royal story.
‘It did not go down particularly well with Eugenie, who felt the couple should have waited to share their news,’ the authors of Finding Freedom wrote.
Several days later, Eugenie’s mother, Sarah Ferguson, posted a photograph of her daughter leaving St George’s Chapel alongside the words: ‘So proud of Eugenie and Jack.’ The timing prompted speculation that she wanted to keep attention focused on the newlyweds.
Another uncomfortable episode followed, this time involving Andrew.
Harry claimed that Meghan mistook Prince Andrew for an assistant when they first met, after seeing him carry the Queen’s handbag to the door
In his book, Spare, Prince Harry expressed his anger that Andrew had retained his security detail while he and Meghan had lost theirs
In Spare, Harry recalled Meghan’s first meeting with the late Queen at Royal Lodge in October 2016. According to his account, Meghan asked about ‘the Queen’s assistant’, referring to a man she had seen carrying a handbag and walking the monarch to the door.
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Harry explained that the man was not an assistant but his uncle, Andrew.
‘That was her second son. Andrew,’ he recalled telling her.
The anecdote has since become one of the enduring tales about Meghan’s early introduction to the Royal Family.
And Harry certainly did not spare his uncle in Spare.
He expressed anger that Andrew had retained his security detail while he and Meghan had lost theirs after moving to the US, pointing to the contrast between Andrew’s position following his scandal and the treatment of the Sussexes.
‘Meg asked me one night: “You don’t think they’d ever pull our security, do you?” Never. Not in this climate of hate. And not after what happened to my mother,’ he wrote.
‘Also, not in the wake of my Uncle Andrew. He was embroiled in a shameful scandal, accused of the sexual assault of a young woman, and no one had so much as suggested that he lose his security.’
Whatever Eugenie’s own feelings about her father, it can hardly have been comfortable to see a close relative publicly attack him in such terms.
Meghan previously revealed that her inspiration for her children’s book, The Bench, was a sweet poem that she wrote for her husband on his first Father’s Day
Another curious episode has entered Meghan and Eugenie’s colourful history with a personalised copy of The Bench landing on Ebay, the listing has since disappeared
And now another curious episode has entered the friendship’s colourful history.
A first-edition copy of Meghan’s 2021 picture book The Bench, apparently inscribed to ‘Eug and Jack’, was recently listed on eBay for the princely sum of £20,000.
The listing has since disappeared, with no explanation from either party.
Whatever the circumstances, it provides a suitably curious postscript to a friendship that has repeatedly found itself at the centre of royal awkwardness.
Perhaps the key to their enduring connection is that both women have occupied an unusual position within the royal machine.
Eugenie has had to navigate the fallout from the disgrace of her parents, while she and her sister Princess Beatrice have remained outside the core group of working royals.
Meghan, meanwhile, is the wife of the prince who stepped back from royal duties, following his increasingly strained relationship with senior members of the Royal Family – tensions that intensified after the couple left Britain.
In their shared position as royal outsiders, perhaps Eugenie and Meghan have found common ground, maintaining a friendship largely untouched by the public recriminations that have characterised so much of the wider family drama.
And this is precisely what makes Eugenie such a fascinating figure in Sussexworld.
She has managed the careful balancing act of remaining close to Harry and Meghan without cutting ties with the rest of her family – a remarkable position in a Royal Family where loyalties have been scrutinised more closely than ever.
As Eugenie celebrates her eighth wedding anniversary with Jack, her friendship with Meghan is a reminder that, even amid the most intense royal dramas, some friendships simply refuse to die.
Not even an ill-timed pregnancy announcement, a controversial memoir, a family feud and now a very expensive eBay listing can apparently finish them off.