She’s a former actress who has moved away from a burgeoning career in TV drama to write, make podcasts and create content around her experience of raising two children with her husband Harry.
This might sound just like a quick summing up of the trajectory of Prince Harry‘s wife Meghan Markle, but in fact it’s a potted history of the royal’s ex-girlfriend Cressida Bonas – his last serious relationship before meeting his now wife.
The similarities, down to the women’s personal projects and Instagram content, are notable, but where they diverge is in their relationship with the Royal Family.
In his memoir Spare, Harry revealed how Cressida had the seal of approval of Wiliam and Kate, and to this day she is close with Beatrice and Eugenie – with the latter being the one to introduce the couple in the first place.
It certainly raises intriguing ‘what if’s’ about the future Harry may have had if he’d wed his last serious girlfriend before finding his ‘soulmate’ Meghan.
Much like Meghan, Cressida kicked off her career as a model, actress and dancer, and was championed as a rising star by Harvey Weinstein when she was given a part in his £19 million costume drama Tulip Fever – before the disgraced movie mogul’s downfall. She also had a leading role in the ITV true crime drama White House Farm.
In recent years however, the Hampshire-born ‘It-Girl’, who is expecting her second baby with husband Henry Wentworth-Stanley, 35, has moved into writing and podcasting, with her social media feed turning from chic, artsy selfies to wholesome sunny snaps with her two-year-old son.
It’s a similar trajectory to that of the Duchess, who burst into the spotlight after playing paralegal Rachel Zane in the 2011 drama Suits – but shifted her focus after marrying Harry in 2018.
Before Prince Harry found love with the Duchess of Sussex , he enjoyed a dating life which featured a number of famous romances, one of which was with charismatic socialite Cressida Bonas. Both pictured in 2014
The socialite, who is expecting her second baby, appears happier than ever as she recently shared a snap on a sunny day, in a canal boat with her husband – baby bump in sight
The As Ever founder has, since making an Instagram comeback in the New Year, also come out with a Netflix cooking show and launched a lifestyle brand – As Ever – where she sells the likes of raspberry ‘spread’, flower sprinkles, herbal teas and cookie mixes.
Meghan’s path is comparable to Cressida’s, with the British star going from wowing audiences as Daisy Buchanan in the Great Gatsby play to sharing heartfelt op-eds on motherhood in national magazines.
The pair have even released new podcasts within days of one another – with Meghan announcing Confessions of A Female founder just days before Cressida launched Lessons From Our Mothers, hosted with her half sister, Isabella Branson, for a ‘series of conversations that celebrate motherhood and mothering in all its forms’.
The series features cameos from a variety of A-listers, including the likes of Kate Winslet, Giovanna Fletcher and Mary Berry – who made the duo a tasty homemade cake and a cup of tea.
Cressida’s close friend Princess Eugenie, who was the brains behind her match with Harry, will also speak as a guest.
A sneak preview posted on the podcast’s Instagram account saw Eugenie, 34, speak touchingly about her own mother, Sarah Ferguson.
‘What is the most valuable thing you have learned from your mum?’ Cressida asked in an episode.
Eugenie said: ‘I think for me, it’s the fire inside, you know, the strength inside of you, and how to bring that out, and to pull it in when you most need it.’
In recent years however, the Hampshire-born ‘It-Girl’, who is expecting her second baby with husband Henry Wentworth-Stanley, 35, has forayed into writing and creating content around her experiences as a parent. Pictured at Glastonbury in 2014
She kicked off her career on the stage and in television roles – but Cressida has not starred in anything for five years, with her social media feed turning from chic, artsy selfies to wholesome sunny snaps with her two-year-old son in recent years. Pictured in White House Farm
Meghan’s path is comparable to Cressida’s, with the British star going from wowing audiences as Daisy Buchanan in the Great Gatsby play to sharing heartfelt op-eds on motherhood in national magazines
Though Lessons With Our Mothers is an exciting new career venture for Cressida, it’s not the actress’s first foray into podcast hosting.
In 2020, she also launched Fear Itself, featuring guests such as Sir Richard Branson.
Cressida encouraged her guests to share their personal stories around the nature of fear, to explore why it shows up, why people try to hide it, and what can be learned from it.
The podcast ran for 37 episodes until 2021, with Matt Haig, Elizabeth Day, Jamie Laing and Emma Barnett among the guests featured.
It’s not the first time Cressida has spoken openly about her experiences with growing a family, as she has penned candid reflections on the topic for several outlets.
Most recently, she opened up about her heartbreaking struggles to conceive in an extremely candid personal essay, where she also spoke of fears of losing her elderly mother and how she coped with her sister’s death from cancer.
Prince Harry’s ex-girlfriend, 36, who is the daughter of Lady Mary-Gaye Curzon, 78, and Jeffrey Bonas, 81, is currently expecting her second child with her property investor husband Harry Wentworth-Stanley.
In an article written for the Telegraph, Cressida admitted that being a mother ‘is unpredictable and frightening’ and said she has ‘elements of her childhood she would like to leave in the past’.
The actress added that her late sister Pandora Cooper-Key, who died in July aged 51, always ‘played a maternal role’ and was ‘protecting her even in her final days’.
Cressida married 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
In a further candid confession, she revealed that she and her siblings feared they were going to ‘lose their mother’ when she was rushed into intensive care last year.
‘My husband and I struggled to conceive, and our son is a product of IVF. Fortunately, after the successful transfer of another of our embryos, I am pregnant with our second child.
‘Even though I remind myself how fortunate we are to have been able to have children, being a mum is the most challenging thing I’ve ever done. It is unpredictable, frightening and it tests me every day,’ she wrote.
The socialite has also previously spoken about how she conceived her first child through IVF.
Cressida revealed that she was pregnant with her second child in January of this year.
‘I am now well into my second pregnancy,’ she wrote in The Spectator magazine. ‘Having conceived through IVF the first time, we were fortunate to have another embryo stored away in a freezer.’
Cressida added that it had been difficult pregnancy. ‘I’ve been battling morning sickness,’ she said. ‘I’ve never had it before, and now feel like I’ve been swaying on a boat for months.’
The writings offer yet another similarity between Cressida and the Duchess, who has also numerous times spoken about parenting and how motherhood has shaped her.
Cressida launched Lessons From Our Mothers, hosted with her half sister, Isabella Branson, for a ‘series of conversations that celebrate motherhood and mothering in all its forms’
It’s not the first time Cressida has spoken openly about her experiences with growing a family, as she has penned candid reflections on the topic for several outlets
During her Harry’s trip to Nigeria last year, Meghan spoke poignantly about fulfilling her dream of becoming a parent as she opened up about her ‘very chatty, sweet children’ Archie, five and Lilibet, two at a Women in Leadership event she was co-hosting with Dr Ngozi Okonjo-Iweala, Director General of the World Trade Organization.
Meghan told the audience how much she loves being a mother but admitted that balancing her family and her career posed its own set of challenges.
During the talk, Meghan was asked how she juggled her duties with her career. She replied: ‘I love being a mum.’
Despite being told more than ten years ago by her friend and mentor that she would never be able to balance both, the 42-year-old said her priorities are constantly changing.
During the panel discussion, Meghan said that ‘balance’ in her life has changed over the years and looks different to ten years ago before she was married and had Prince Archie and Princess Lilibet.
She said: ‘What I think that to mean now is that that balance will always change for you. That balance, what seems balanced ten years ago is going to shift.’
Harry’s relationship with Cressida – from 2012 to 2014 – was marked however, in contrast, a very unglitzy affair compared to his star-studded romance with Meghan, who he met in 2016.
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 and aristocrats.
Meghan – much like Cressida – has come out with a podcast where she speaks to female business founders
The As Ever founder has, since making an Instagram comeback in the New Year, also come out with a Netflix cooking show and launched a lifestyle brand – As Ever – where she sells the likes of raspberry ‘spread’, flower sprinkles, herbal teas and cookie mixes
During her Harry’s trip to Nigeria last year, Meghan spoke poignantly about fulfilling her dream of becoming a parent as she opened up about her ‘very chatty, sweet children’ Archie, five and Lilibet, two
Meghan told the audience how much she loves being a mother but admitted that balancing her family and her career posed its own set of challenges
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.
It 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.
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.
Prince Harry and Cressida pictured leaving the Prince of Wales Theatre after seeing The Book Of Mormon in October 2013
Cressida Bonas (pictured in 2014) was Harry’s last serious relationship before Meghan and was a big hit with the Royal Family
Cressida, known as Cressie, dated Prince Harry between 2012 and 2014. Pictured with his cousin Princess Beatrice at Annabel’s Club in London in May, 2014
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.
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’.
Cressida was introduced to Harry by his close cousin Princess Eugenie at a music festival in Hampshire. Pictured at Glastonbury in June 2013
Cressida remains good friends with Princess Eugenie (pictured together in June 2013 at a wedding)
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.
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.
Cressida also reportedly 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’.
According to Brown, it was Cressie who first persuaded him to see a therapist. In Spare, Harry revealed how the couple broke up after a skiing trip to Kazakhstan in March 2014.
He recalled 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.
The Duke had 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 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.
The socialite, who is expecting her second baby, appears happier than ever as she recently shared a snap on a sunny day, in a canal boat – baby bump in sight.
