Prince Harry’s ‘painfully awkward’ blunder with ex caused tense call with Princess Eugenie

Prince Harry has opened up about a “painfully awkward” dating blunder that led to a ‘discouraging’ phone call with his cousin Princess Eugenie.

The Duke of Sussex, 39, dated actress and model Cressida Bonas between 2012 and 2014. Cressida, now 34, is close friends with 33 year old Eugenie, who was said to have played matchmaker between the pair.

But Harry, writing in his memoir Spare, discussed how – although sparks flew between them initially – their second date led to a very awkward encounter that left his cousin Eugenie ‘sighing’ in dismay. The Duke described how he dropped Cressida home after the date and she did not invite him inside – so he decided to go in for a kiss.

Unfortunately though, Harry said his ‘aim was off’.

He added: “She turned, I tried again on the return trip, and we managed something like a graze. Painfully awkward."

The following day, Harry called his cousin Eugenie – daughter of Prince Andrew and Sarah Ferguson – to tell her about the date and to fill her in on the awkward ending – but Cressida had beaten him to it.

The Duke added: "Discouraged, I told her the date had gone well but the ending had left something to be desired. She didn’t disagree. She'd already spoken to Cressida. She sighed. Awkward."


The incident can not have been too discouraging, however, as Harry and Cressida ended up dating for two years. They broke up because Cressida reportedly found the attention that came with dating a Royal to be too overwhelming.

Prince Harry, of course, went on to marry former Suits actress Meghan Markle and the pair share two children – Prince Archie and Princess Lilibet. Eugenie, meanwhile, is now married to husband Jack Brooksbank and they also have two children – sons August and Ernest.

Relations between Harry and the Royal Family continue to be strained following the publication of the Duke’s bombshell memoir and the release of the Sussexes’ controversial Netflix documentary. Harry’s book brought a fresh round of attacks against the Royal Family just weeks after the Netflix series levelled a fresh round of damning claims against the monarchy.


But Harry’s bond with Eugenie appears to have remained strong. She was one of the only royals to have appeared in the Netflix docuseries after visiting the Sussexes at their home in Montecito, California.

And, according to a source, his relationship with Eugenie and her big sister, Princess Beatrice, remains a good one.

The insider told PEOPLE: "They're still the best of friends and talk constantly. This whole drama between him and Meghan and the rift with the rest of the family has been really stressful for the girls. It’s hard to watch because they see both sides of it."

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