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Prince Harry’s past relationships - from Chelsy Davy to Cressida Bonas and Caroline Flack

The Duke of Sussex is married to Meghan Markle

Prince Harry with exes Chelsy Davy and Cressida Bonas
Phoebe Tatham
Content Writer
Updated: 5 April 2024
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The Duke of Sussex is happily married to Suits actress Meghan Markle – and the loved-up couple share their luxurious Californian home with two adorable children.

After being introduced to one another by mutual friends, Meghan and Harry first started dating in 2016. Speaking to Vanity Fair at the time, Meghan, 41, gushed: "We're a couple. We're in love." The smitten couple announced their engagement in November 2017, before tying the knot in 2018 at St George's Chapel in Windsor.

However, when extracts of his leaked memoir, Spare, exposed his dalliance with an older woman, royal watchers were left intrigued. Ahead of its release in January 2023, it was rumoured to be Elizabeth Hurley, who has since refuted the sensational claims.

The British actress and model, now 58, addressed the speculation on an episode of Watch What Happens Live With Andy Cohen in April 2024.

Elizabeth said: "That was ludicrous. He said, 'She was English. She was older than me. It was in Gloucestershire.' And they were like, 'Ah, it's Elizabeth.' It was absurd. It was ridiculous."

She added that she had "never met" Harry in her life.

The older woman was later revealed to be former Highgrove groom Sasha Walpole, who was 19 at the time of her tryst with the 16-year-old Prince.

Prior to this and his marriage to Meghan, the flame-haired royal enjoyed a handful of relationships with the likes of Chelsy Davy and Cressida Bonas. We take a deep dive into what Harry's exes are up to now…

Chelsy Davy: 2004 to 2011

Harry and Chelsy Davy© Getty
Chelsy was Harry's first serious girlfriend

To date, Prince Harry's longest relationship remains with his ex-girlfriend Chelsy Davy whom he started dating in 2004. It was love at first sight for the young couple who first met during Prince Harry's gap year in Cape Town.

Their romance continued to blossom under the interest of the public, with Chelsy attending Prince Charles' 60th birthday and even meeting the late Queen at a society wedding. However, after an on-off romance, things sadly came to an end in 2011 after Chelsy struggled with being in the royal spotlight.

Chelsy has since found love with Oxford graduate Sam Cutmore-Scott. And in January 2022, the married couple welcomed their first child, a boy called Leo.

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It's not known how long Chelsy and Sam, who was a year above Harry at Eton College, have been dating, but in 2020,  the Zimbabwean businesswoman revealed that she was in a serious relationship, but didn't want to share who with.

She told Tatler: "There is someone, and I am quite taken by this one, but it's very new and I don't want to say too much.”

Caroline Flack: 2009

Caroline Flack smiling at Glamour Women Of The Year Awards© Getty
Harry dated the late TV star in 2009

Prince Harry and Caroline Flack enjoyed a romantic date back in 2009. Whilst their relationship didn't last long, the Duke of Sussex described the late TV star as "funny," "sweet" and "cool."

In his new memoir, Spare, Harry paid tribute to the presenter, who tragically died by suicide in 2020. Revealing that he didn't know who she was, Harry penned: "She wasn't taken aback that I didn't recognise her. She didn't have a big ego."

Despite "genuinely enjoying each other's company," Harry explained how the couple called it quits after the media refused to leave Caroline and her family alone. 

He added: "In time we realised it just wasn't worth the grief and harassment. Especially for her family. Goodbye, we said. Goodbye and good luck." 

Harry also touched on the impact of Caroline's heartbreaking death. Reflecting on the sad news, Harry said: "I felt so awful for her family. I remembered how they'd all suffered for her mortal sin of going out with me.

"She'd been so light and funny that night we met. The definition of carefree".

Mollie King: 2010

Mollie King attending The Fashion Awards© Getty
Mollie King enjoyed a date with Prince Harry

Harry and The Saturdays singer, Mollie, were first introduced at a polo match in Surrey's Hurtwood club in July 2010. The duo reportedly enjoyed a brief romance after spending an increasing amount of time together.

In an interview with Closer magazine, she said: "Yes, I have met Prince Harry, and we did go out for a drink. But a lot of the times I'm linked to men, I haven't even met them!". 

The singer is now loved-up with cricketer Stuart Broad. They started dating in 2018, and Stuart got down on one knee in 2021 and presented Mollie with a beautiful diamond ring!

In November 2022, Mollie and Stuart welcomed their first child, a daughter called Arabella. 

Cressida Bonas: 2012 to 2014

Cressida Bonas and Prince Harry attend We Day UK,
Cressida and Harry pictured together in 2014

Prince Harry started dating actress Cressida Bonas in 2012 after allegedly being introduced by Princess Eugenie. The former couple shared a lust for life and they were often snapped holidaying together, appearing the perfect pair.

But as rumours of a royal engagement escalated, Cressida is said to have become increasingly overwhelmed by the public attention. While the pair split in 2014, they proved they are still on good terms, with Cressida attending Harry and Meghan's wedding in 2018.

Cressida Bonas in a pink striped dress at Windsor Castle for Prince Harry's wedding© Getty
Cressida at Harry and Meghan's wedding

Cressida has since found love with Harry Wentworth-Stanley. She announced her engagement to Harry in August 2018, four years after they rekindled their romance. The pair are believed to have met when they were both students at Leeds University; they briefly dated before the property developer left for a year abroad in Argentina.

The actress and her long-term love Harry were married in a private wedding ceremony in July 2020. The White House Farm star exchanged vows with estate agent Harry, the son of the Marchioness of Milford Haven, with only a handful of guests present.

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The duo welcomed their first child together,  Wilbur James Wentworth-Stanley, in late 2022. 

LISTEN: Inside King Charles' private lunch with Princess Kate


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