Harry’s VERY unstarry relationship before Meghan: Cressida Bonas, who was loved by the royals, had glum date nights with the Prince eating takeaways and watching Netflix

Before Harry met Meghan Markle in 2016 at the age of 32 he was worried he would be single forever.

Despite his status as the most eligible bachelor in the country, the prince’s love life involved a series of failed relationships with an array of heiresses, airheads and aristocrats.

His on-off relationship with Chelsy Davy petered out after seven years, his fling with the late Love Island host Caroline Flack bombed and his romance with The Saturdays pop star Mollie King fizzled.

Following the repeated failures, one expert claimed he started to feel like the ‘royal Bridget Jones’.

But his last serious relationship before Meghan was with someone who turned out to be an almighty hit with the entire Royal Family – Cressida Bonas.

The relationship between the pair lasted for two years, in which Cressida and the Prince spent un-glamorous date nights glumly holed up inside his small bachelor pad eating takeaways and watching Netflix, a book by royal expert Tina Brown claimed.

But their relationship also had a more serious side, and in Harry’s tell-all memoir Spare he wrote how he cried to Cressida about his mother for the first time since she died when he was 12.

The Royal Family were so sad to see her walk away that Charles labelled her the ‘one that got away’, a source told Brown.

Here MailOnline looks back at Harry’s relationship with Cressida Bonas and reveals why she decided to turn her back on a gilded royal life.

Cressida, known as Cressie, dated Prince Harry between 2012 and 2014 after being introduced to him by his cousin Princess Eugenie at a music festival in Hampshire.

She drank rum straight up, a magazine approvingly reported, and when embarrassed she was heard to exclaim ‘Cringe de la cringe!’, according to Brown.

Blonde Cressida is the daughter of 1960s It girl Lady Mary-Gaye Curzon – who once famously posed apparently topless, smeared in motor oil – and Old Harrovian Jeffrey Bonas (her mother’s third husband) who owns a fabric company called MacCulloch & Wallis.

She was also athletic, winning a sports scholarship to Prior Park College in Bath before attending the co-ed boarding school Stowe.

After school she studied dance at Leeds University and later pursued acting as well as modelling for Mulberry. 

Throughout her relationship with Harry, the couple went on trips together to Switzerland, attended concerts, and were even spotted on date nights at burger joints.

Brown wrote she was Harry’s guest at Sandringham for shooting weekends, and she blended easily with his friends. 

Cressida also passed the Africa test on a successful holiday together with the prince in Okavango Delta in Botswana.

The budding actress was encircled by her discreet but entertaining extended aristocratic family and it seemed like she was perfectly suited for palace life.

She also seemed to be understanding of the prince’s shortcomings. 

Just before he deployed to Afghanistan in late 2012, he was photographed naked while playing ‘strip billiards’ in his Las Vegas hotel suite.

Following the incident he apologised to her for ’embarrassing her’.

Tina Brown wrote in her book The Palace Papers: Inside The House Of Windsor – The Truth And The Turmoil, ‘Cressie was amused and forgiving’ after the antics.

With one royal source telling Brown, who was a confidante of Diana’s, following the incident Harry appeared with ‘his tail between his legs, looking like a puppy who had peed on the carpet’.

Harry also wrote about the incident in Spare: ‘After hearing my careful and abashed explanation, she came to the same conclusion. I’d been a dummy, not a debaucher. I apologised for embarrassing her.’

But eventually it is claimed Cressida got tired of his frat-boy antics and wanted him to be less laddish.

She also reportedly found him stingy when it came to money. Brown reported that when the pair were invited to Harry’s friend Guy Pelly’s Tennessee wedding to Holiday Inn heiress Lizzy Wilson, she was told by the prince to buy her own ticket.

The episode reportedly left her feeling not only that the prince was cheap, but disrespectful as he would be off for half the weekend at his pal’s bachelor booze up.

While media reports talked of her romantic and glamorous love affair with the prince, Brown writes the ‘bizarre reality of date nights was glumly eating takeaway and watching Netflix at Nottingham Cottage, Harry’s none-too-tidy two-bedroom grace-and-favour bachelor pad in the grounds of Kensington Palace’. 

The digs were a far cry from the grandeur that might have been expected from dating Princess Diana’s son, as the ceilings were so low that when William lived there with Kate he had to stoop to avoid hitting his head.

But perhaps the biggest problem Cressida had in her relationship with Harry was his resentment towards the media.

As a normal 25-year-old, she ‘wanted to go out to dinner and touch knees under the table,’ a friend tells Brown.

‘Harry would walk four paces ahead of her, instead of holding her hand. When they went to the theatre, he left at the interval to get out without a hassle.

‘She was either being dragged through the streets being yelled at or ignored while he threw a hissy fit.’

A family friend told Brown she knew the relationship wouldn’t last when there was a Valentine’s Day fight because Harry cancelled dinner plans when he heard a photographer was waiting for them at the restaurant. 

Cressida also became increasingly concerned about Harry’s mental health.

She saw the stress of William and Kate’s royal tour on television and became overwhelmed with the thought of doing it herself, especially with Harry’s increasingly explosive temperament, claims Brown.

He took up boxing because, as he later said, he was always ‘on the verge of punching somebody’. 

Cressida understood the historical reasons why Harry hated journalists but believed that he should, like his brother William, come to terms with his royal fame.

According to Brown, it was Cressie who first persuaded him to see a therapist. To find the right person, he took advice from MI6.

‘There was a need for someone who would be incredibly discreet and who understood what it’s like to have a public version of your life and a private version of your life,’ Brown quotes a contact.

‘Therapists at MI6, that’s what they do.’ 

But the therapy came too late to save the relationship. 

In Spare, Harry writes that the couple broke up after a skiing trip to Kazakhstan in March 2014.

Harry recalls how Cressida was the one who he broke down in tears to when talking about the loss of his mother on a skiing trip to Switzerland the previous year.

Harry said this was the first time he cried since Princess Diana’s burial when he was 12. 

‘Wiping my tears, I thanked her. She was the first person to help me across that barrier, to help me unleash the teats. It was cathartic, it accelerated our bond, and added an element rare in past relationships: immense gratitude’, he wrote.

‘I was indebted to Cress, and that was the reason why, when we got home from Kazakhstan, I felt so miserable, because at some point during that ski trip I’d realised that we weren’t a match.

‘There was massive affection, deep and abiding loyalty – but not love everlasting,’ he shared. ‘I’ve learned so much from you, Cress’, he told her. 

‘She nodded. She looked at the floor, tears running down her cheeks. Damn, I thought. She helped me cry. And now I’m leaving her in tears.’

After their relationship broke down, Harry wrote her a sweet letter saying, ‘I admire you, I wish you well and above all thank you for helping me to address my demons and seek help’, Brown claimed a contact told her.

In Spare, Harry revealed how he considered marrying Cressida, and that his brother Prince William and sister-in-law Kate had ‘mentioned, pointedly, repeatedly, how much they liked Cressida’.

And according to one source Brown spoke to, Prince Charles expressed his regret at a Buckingham Palace function some time after the couple split, saying: ‘I don’t know what to do about Harry. We so miss Cressida.’ 

Nevertheless she remained close to her friend Eugenie, who remains Harry’s best friend in the Royal Family today. 

And she kept in touch with Harry, attending his and Meghan’s wedding in 2018. 

She also moved on herself in 2020, marrying another Harry, the son of the Marchioness of Milford Haven – Harry Wentworth-Stanley.

The dashingly handsome 6ft 4in partner in a property investment firm comes from a 1,000 acre estate in the Sussex Downs.

The couple initially struggled to conceive, and Cressida eventually fell pregnant through IVF before welcoming a boy, Wilbur, in 2022.

They chose his middle name in honour of her husband Harry’s brother James, who took his own life in 2006 at the age of 21.

In recent years, Cressida has been photographed on occasion walking around London in casual attire, sometimes with her baby in tow.

In May she was spotted smiling at the lavish wedding of a billionaire in Venice, seemingly completely at peace with not having married into the Royal Family.

But after the fallout of Megxit and Harry’s estrangement with The Firm, perhaps they are wishing she had.