Prince Harry recalls ‘painfully awkward’ first date with Cressida Bonas

Written by on January 16, 2023

Cressida and Harry, pictured in 2017, dated in university before rekindling their romance after her split from Prince Harry

Cressida and Harry, pictured in 2017, dated in university before rekindling their romance after her split from Prince Harry

Harry Wentworth-Stanley, an associate director at estate agents Savills, is the son of Nick Wentworth-Stanley, a debonair Old Etonian, and Clare, now the Marchioness of Milford Haven, who acquired the title upon her second marriage to Harry’s stepfather, the Marquess of Milford Haven.  

Before his relationship with his now wife became official, Harry, who is dashingly handsome and 6ft 4in tall, was regarded as one of London’s most eligible bachelors.   

He inherited his looks from his mother, Clare, a beauty who remains stunning. There was a brother, James, four years his senior, and younger sister Louisa. When Harry was a child, his mother and father divorced. In 1997, Clare married George, Marquess of Milford Haven, a cousin of the Queen, himself divorced with two children.

The family settled at Great Trippetts, an estate set in 1,000 acres in the Sussex Downs. For a time, life was perfect. Clare stayed on good terms with her former husband, Nick Wentworth-Stanley, who went on to marry Dutch beauty Millie Brenninkmeyer, with whom he had three more children. 

Shortly before Christmas 2006, the Marquess and Marchioness and their children went to stay with Nick and his wife in Worcestershire. James, Harry’s elder brother, was recovering from a relatively minor procedure. The operation was a success, but James had become very anxious in the days that followed.

Harry Wentworth-Stanley, an associate director at estate agents Savills, is the son of Nick Wentworth-Stanley, a debonair Old Etonian, and Clare, now the Marchioness of Milford Haven, who acquired the title upon her second marriage to Harry¿s stepfather, the Marquess of Milford Haven. Pictured, the Marquess and Marchioness in 2017

Harry Wentworth-Stanley, an associate director at estate agents Savills, is the son of Nick Wentworth-Stanley, a debonair Old Etonian, and Clare, now the Marchioness of Milford Haven, who acquired the title upon her second marriage to Harry’s stepfather, the Marquess of Milford Haven. Pictured, the Marquess and Marchioness in 2017

One evening, the family discovered that James had taken his own life. They were shattered by the tragedy.

Clare was floored by her son’s suicide. Touchingly, it was Harry, then 17, who helped her through it. She said in an interview 18 months after James’ death: ‘For the sake of the other children, you have to set an example. If you are strong, it gives them permission to be strong. If you fall to bits, they will.

Harry's father is Nick Wentworth-Stanley, pictured, a debonair Old Etonian

Harry’s father is Nick Wentworth-Stanley, pictured, a debonair Old Etonian

‘The day after James died, his brother Harry said his biggest fear was that it would destroy me, and that would destroy everything else. It suddenly made me feel how important I was.’

The family set up James’ Place in his memory, a suicide prevention charity for men which now runs centres in London and Liverpool.

The couple had a serious relationship when they were both students at Leeds University. The couple were known to their crowd — for reasons that aren’t entirely clear — as ‘Water-Cress’. The romance petered out when he took off for a gap year to Argentina in 2011 after graduating.

Friends have previously said Cressida wasn’t quite over Harry when another Harry — Prince Harry himself — began pursuing her in the summer of 2012 and a romance began. There were concerts, rugby matches, skiing trips and cosy nights in at Kensington Palace.  

However the couple split in 2014 after three years together. 

The following year Harry Wentworth-Stanley and Cressida were photographed on a Valentine’s Day date, although their relationship became public and official in 2017. 

In August last year Harry proposed while on a trip to the US and the couple’s smiles in the Instagram announcement told followers all they needed to know about their love for each other. 

Harry as a young boy with his stepfather, Marquess of Milford Haven (left), sister Louise (front), mother Clare (centre), the Marquess' brother Lord Ivar Mouthbatten, his children Ella and Alix and then wife Penny (right) at Cowdray Park in 2001

Harry as a young boy with his stepfather, Marquess of Milford Haven (left), sister Louise (front), mother Clare (centre), the Marquess’ brother Lord Ivar Mouthbatten, his children Ella and Alix and then wife Penny (right) at Cowdray Park in 2001

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