For the longest time, Prince Harry was the world’s most eligible royal bachelor. He was seen jet setting around the world, going to parties, and getting friendly with a ton of women.
WATCH BELOW: Chelsy Davy watches on as Prince Harry marries Meghan Markle
This earned him a ‘party boy’ reputation – a reputation which couldn’t be farther from his current family man image.
These days, Prince Harry is laying low in LA with his beloved wife Meghan, their son Archie and will soon be joined by their baby girl.
Ready for a blast from the past? Let’s learn more about the women Prince Harry has dated over the years! We’ve included the prince’s girlfriends, short flings, and even speculated-yet-never-confirmed romances.
Who is Prince Harry?
Prince Harry (born Henry Charles Albert David) is the Duke of Sussex, grandson of Queen Elizabeth II, and sixth in the line of succession to the throne. His brother is Prince William, and his mother is the late Princess Diana.
Who is Meghan Markle?
Meghan Markle is the current Duchess of Sussex and Prince Harry’s wife. Prior to marrying Prince Harry, she was an American actress most known for her role as Rachel Zane on Suits. She is also the mother of Archie Mountbatten-Windsor, the seventh in line to the British throne.
How did Prince Harry and Meghan Markle meet?
Meghan and Prince Harry met in 2016 on a blind date. They were introduced by a mutual friend – allegedly it was socialite Violet Von Westenholz who gave Meghan’s number to Harry. The two had a drink and immediately clicked. Prince Harry later revealed that he knew Meghan was the one “the very first time we met.”
How long have they been together?
The pair’s first date was in July 2016. Within a month of meeting, Prince Harry had already invited the actress on a trip to Africa. The news about their relationship didn’t officially break until November 2016 – giving the famous couple a few precious months of privacy to get to know each other better.
When did Prince Harry get engaged?
The royal couple announced their engagement in November 2017, a year after their relationship was first confirmed to the public. Prince Harry proposed to Markle with a ring that contained a diamond from Africa (a reference to the trip that sparked their romance) and jewels from his mum Princess Diana’s own collection.
When did Prince Harry get married?
After the engagement, the royal wedding date was set for May 19, 2018. Prince Harry and Meghan Markle married at the St George’s Chapel in Windsor. Overall, the wedding cost around £32-million ($AUD 60-million).
However, in the explosive 2021 interview Oprah with Meghan and Harry, the former Suits star revealed that she and her husband tied the knot in secret three days before the royal wedding we all watched.
“No one knows that but we called the Archbishop [Justin Welby] and we just said ‘This thing, this spectacle is for the world but we want our union to be us.’ The vows that we have framed in our room are just the two of us in our backyard with the Archbishop of Canterbury.”
Do Prince Harry and Meghan have any children together?
Within a few months of marrying, Meghan and Harry announced that they were pregnant with their first baby. The due date was set for the end of April or beginning of May. True enough, Archie Mountbatten-Windsor was born on May 6, 2019.
Meghan is currently pregnant with their second child, a daughter, who is due “in the summertime.”
Prince Harry’s Girlfriends: Exes, Former Lovers, And Past Flings
Natalie Pinkham
Age: 43
Dated: 2003
British TV presenter Natalie Pinkham was rumoured to have dated Prince Harry. The two are friends today and have never confirmed their romance publicly.
She is now married to Owain Walbyoff, the Managing Director at Endemol Games and share two children – Wilfred and Willow.
Cassie Summer
Age: Unknown
Dated: 2004
The then 19-year-old shared details about a raunchy night with the prince in 2004, but the ‘affair’ was really just a one-night stand.
Chelsy Davy
Age: 35
Dated: 2004-2011
Prince Harry’s most famous relationship (before Meghan Markle, that is) was with Zimbabwean blonde beauty Chelsy Davy. The two dated on and off for seven years and Chelsy told The Times that she “couldn’t cope” with the intense scrutiny their romance received.
“It was so full-on: crazy and scary and uncomfortable. I found it very difficult when it was bad. I couldn’t cope… I was trying to be a normal kid, and it was horrible.”
The two however have remained friends and Davy even attended Harry’s wedding!
Natalie Imbruglia
Age: 46
Dated: 2009
The Australian singer was linked to the British royal after they were spotted at a concert together. Imbruglia has gone on to deny that their relationship was anything more than platonic, however.
Astrid Harbord
Age: 39
Dated: 2009
Socialite and party girl Astrid Harbord, who is also a friend of Kate Middleton’s, was rumoured to have dated Prince Harry briefly, especially after being seen out and about together.
They are still friends today.
Camilla Romestrand
Age: Unknown
Dated: 2010
Eddie The Gun lead singer Camille Romestrand revealed that she and Prince Harry were a ‘thing’ briefly, although Harry has never addressed these claims.
Caroline Flack
Age: 39
The late Love Island host was actually introduced to Prince Harry by rumoured ex-fling Natalie Pinkham in 2009.
However when the press discovered her link to the royal, they had to stop seeing each other.
Writing in her book Storm in a C Cup, Caroline revealed: “To meet a prince is so unlikely, it would be weird not to acknowledge it. However, once the story got out, that was it. We had to stop seeing each other. I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry’s bit of rough.”
Florence Brudenell
Age: 35
Dated: 2011
The model is now happily married, but she spent a summer with Prince Harry in 2011.
Cressida Bonas
Age: 32
Dated: 2012-2014
Another one of Prince Harry’s high-profile exes, actress Cressida Bonas was with Harry for a couple of years after being introduced by the royal’s cousin Princess Eugenie.
They called it quits due to the constant media scrutiny and criticism. Cressida also attended Harry and Meghan’s wedding and married her own Harry (Wentworth-Stanley) in 2020.
Mollie King
Age: 34
Dated: 2012
The pair met in July 2010 at the Asprey World Class Cup at Surrey’s Hurtwood Polo Club but in contrast to his previous girlfriends, singer King took to the spotlight rather well.
Maybe too well – Harry broke up with her because she was too open to the press about their relationship.
“Guys, I’m getting a lot of tweets about Prince Harry but…I’m not dating him and we’re not in a relationship. We’re just friends,” Mollie clarified via Twitter.
Ellie Goulding
Age: 34
Dated: 2015
Although it was never confirmed that the famous singer and prince were ever together, it was reported that the two were seen kissing and canoodling (no photos of this exist).
Goulding is now married to husband Caspar Jopling and the two are expecting their first child.
