Princess Eugenie ‘sighed’ when Prince Harry told her about ‘awkward’ first date

Prince Harry has recalled telling his cousin Princess Eugenie that his first date with the model and actress Cressida Bonas was “awkward”. In his tell-all memoir Spare the Duke of Sussex recounts details of many romantic exploits including when he tried to woo the attractive blonde socialite between 2012 and 2014. Writing in his fast-selling book Harry talks about sharing with Princess Eugine how his first date went with Cressida, and how his cousin “sighed” when he told her.

Prince Harry is known to have a very close relationship with Prince Andrew and Sarah Ferguson’s daughter and he reveals how she set up his first date with Cressida, who was also her friend.

But despite the Duke going on to date the actress for two years in his book he recalls how things got off to a rocky start with a “painfully awkward” ending to their first date when Harry fluffed sealing a first kiss.

In an amusing twist the 38-year-old prince said when he phoned Eugenie to tell her about his embarrassment he discovered she had already spoken to Cressida about it.

The Mirror reports he wrote: “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.”

Cressida and Harry’s relationship did blossom despite the rocky start and in a moving entry in his book he recalls he first cried about his mother Princess Diana’s death in front of her during a skiing holiday in 2014.

Despite going their separate ways Cressida and Prince Harry remained friends and she attended his wedding to Meghan Markle in Windsor in May 2018.

In July 2020 Cressida had her own wedding when she married Harry Wentworth-Stanley. In July last year the actress confirmed her first pregnancy.

Writing about their break-up the Duke said the pressures of royal life and the scrutiny it brought were some of the reasons the pair decided to call it a day.

In his ghost-written book Spare Prince Harry is not shy about recalling his romantic life and even discusses losing his virginity aged 17 in a field behind a pub.

Harry describes how he had sex for the first time with an older woman who loved horses and treated the teenage prince like a “young stallion.” It was, he says, an “inglorious episode.”

In the book, the Duke of Sussex writes: “I mounted her quickly, after which she spanked my a*** and sent me away.

“One of my many mistakes was letting it happen in a field, just behind a very busy pub. No doubt someone had seen us.”

The Duke then recounted how a royal bodyguard had reportedly been sent by his father to “find out the truth” about what had happened.

However, the royal bodyguard, known as Marko, had not in fact been sent to investigate Harry’s sexual status but had reportedly been asked to investigate rumours that Harry had been taking illicit drugs.