How Meghan's relationship with Eugenie has survived some VERY awkward moments - as Princess' signed copy of The Bench mysteriously ends up on eBay

Theirs is one of the most unlikely and intriguing friendships to have survived the ups and downs of the Sussex soap opera.

Princess Eugenie, 36, and the Duchess of Sussex, 45, have long appeared to share a solid bond that has withstood some seriously awkward moments.

Who could forget the small matter of Meghan announcing that she and Prince Harry were expecting their first child – just days after Eugenie married Jack Brooksbank at St George’s Chapel, Windsor, in 2018, the very wedding whose eighth anniversary falls next week.

Then there was the claim that Meghan once mistook now former prince Andrew for one of the Queen’s advisers – a story that, whether true or not, has become part of the mythology surrounding Meghan's early encounters with the Royal Family.

As if that were not enough, Harry later poured scorn on Eugenie’s father in his memoir Spare, criticising the fact that Andrew retained his security detail while Harry and Meghan lost theirs after stepping down as working royals.

Yet through it all, Eugenie and Meghan have remained on seemingly warm terms.

Indeed, Eugenie occupies a unique place in the Sussex story. She was close to Harry long before Meghan arrived on the scene. She was even present at the famous Halloween party in Toronto in 2016, where Harry and Meghan enjoyed what they described as their last night of freedom before their relationship became public.

‘Eugenie had always been more than just a cousin to Harry,’ Omid Scobie and Carolyn Durand wrote in the book Finding Freedom. ‘They were also the closest of friends.’

Princess Eugenie was at the famous Halloween party in Toronto in 2016 where Prince Harry and Meghan Markle enjoyed their last night together before their relationship became public

The authors of Finding Freedom claim Princess Eugenie felt the couple should have waited to share that they were expecting a baby until the excitement around her wedding had died down

The Sussexes' pregnancy announcement became the biggest royal news of the day – which didn't go down too well with the bride

The authors described the pair as having ‘one of the most natural connections’ among the Queen’s grandchildren, adding that they had enjoyed ‘many nights out together in London’.

Eugenie was also seemingly one of the few members of the Royal Family to maintain warm relations with the Sussexes after their departure from Britain – known as 'Megxit' – in 2020. She and Jack have visited the Sussexes in California, maintaining a personal connection despite the increasingly icy divisions elsewhere in the family.

But their friendship was tested almost immediately after Eugenie’s wedding.

According to Finding Freedom, Harry and Meghan’s decision to announce Meghan’s pregnancy at the wedding reception did not go down well with Eugenie, who reportedly felt they should have waited.

The timing was certainly striking. As the newlyweds’ celebrations were still unfolding, the Sussexes’ pregnancy announcement to the family and friends at the occasion suddenly became the biggest royal news of the day.

‘It did not go down particularly with Eugenie, who felt the couple should have waited to share their news,’ the authors of Finding Freedom wrote.

A few days later, Eugenie’s mother, Sarah Ferguson, tweeted a photograph of her daughter leaving St George’s Chapel with the words: ‘So proud of Eugenie and Jack.’ The timing inevitably prompted speculation that she was keen to keep the spotlight on the newlyweds.

Then came another awkward episode – this time involving Andrew.

According to Harry, Meghan mistook Prince Andrew for an assistant when she first met him as he was carrying the Queen's handbag with her 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.

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.