In 2016 Prince Harry met Meghan. The pair began their relationship quietly, before it went public. Not long after that they were tying the knot and having children: Archie, five, and Lilibet, three. Two years after they got married, the couple decided to leave their royal duties and move to California, where they have been residing ever since.

Before Meghan, just like his brother Prince William, Harry had been tied to a string of women over the years – but he never seemed to settle down with any of them. Although, over the years there were a few relationships that lasted a while.

So from Cressida Bones to Chelsy Davy, let’s have a look at all of Prince Harry’s main ex-girlfriends over the years.

Prince Harry and Natalie Pinkham

Way back in 2003, Harry was rumoured to have been in a relationship with TV presenter Natalie Pinkham. However, neither of them ever publicly confirmed their relationship.

And it seems they have reportedly maintained a friendship over the years – and are now both happily married with kids!

Natalie even went to Mike and Zara Tindall’s wedding, so there definitely doesn’t seem to be any bad blood between the pair.

Prince Harry’s ‘steamy’ night with Cassie Sumner

While it seems Cassie Sumner and Prince Harry only shared one night together – it sounds like it was a wild night.

In 2004, Cassie detailed her “steamy” night with Prince Harry when they met at London’s Chinawhite nightclub. At the time, Harry was 19 and Cassie was 21.

As reported by the Mirror in 2004, Cassie allegedly said: “He made eye contact as I stood at the bar with my friends. And then he invited me to join his private table. It wasn’t long before he began cuddling up to me.”

She went on to give a very detailed summary of what went down between the pair, including his alleged “fascination” with her “breasts”. She also commented that Harry spent a lot of the night getting touchy and telling her “how sexy” she looked.

Prince Harry’s relationship with ex-girlfriend Chelsy Davy

It was Harry’s longest relationship that lasted from 2004 to 2010. The pair initially met in Cape Town during Harry’s gap year, and they continued to date on and off for years.

Despite the split, Chelsy attended William and Kate’s wedding in 2011.

Chels told me that paps had been following her to and from lectures.

Despite their final breakup, Chelsy admitted they will “always” be friends. And it seems the feeling is mutual, as Harry spoke fondly of her in his 2023 memoir, Spare. On top of that she even attended Harry and Meghan’s wedding in 2018.

He wrote that she wasn’t “bothered” by his prince status. But one thing that did get to her was the lack of privacy.

Harry penned: “Chels told me that paps had been following her to and from lectures. She asked me to do something about it. I told her I would try and how sorry I was. When she was back in Cape Town she phoned me and said people were tailing her everywhere. It was driving her crazy.”

Chelsy herself described the public attention as “crazy, scary, and uncomfortable”.

Duke of Sussex and Florence Brudenell-Bruce

It’s believed that Prince Harry had a brief “summer fling” with aristocratic model Florence Brudenell-Bruce after he and Chelsy broke up.

They were first spotted together at a music festival in London were they were seen hanging out backstage. But it seems the relationship didn’t last very long – as it was over in a few short months.

Prince Harry’s romance with ex-girlfriend Cressida Bonas

Harry’s next long-term relationship came in 2012, after Princess Eugenie introduced him to actress Cressida Bonas.

The pair stayed together for two years, before their relationship came to an end in 2014. They called time on it as Cressida reportedly struggled with the public scrutiny of being with the prince.

She opened up about feeling “pigeonholed” when a woman is constantly compared in comparison to the man she is with to BBC Radio.

Just four years later, Prince Harry found love with American actress Meghan Markle and the rest is history!