There was a time when people assumed the Ginger Prince would never walk down the aisle. In less than 2 weeks, Prince Harry will be settling down with Meghan Markle; thus crushing the dreams of anyone hoping to live a life of royalty.

Before the royal wedding takes place on 19th May, we thought it’d be interesting to take a trip down memory lane at Harry’s pre-Meghan romantic history. He’s clearly had his fair share of actresses, pop stars, TV personalities, and more…

1. Cassie Sumner (2004)

Source: Getty

Cassie Sumner once had a scandalous fling with Prince Harry in 2004. The duo met at Chinawhite nightclub in London when she and Harry were aged 21 and 19 respectively. However, their encounter only lasted one night.


He made eye contact as I stood at the bar with friends and he invited me to join his private table. … I thought, ‘What the hell.’ I plonked myself down next to him and it wasn’t long before he began cuddling up to me,” the model told UK’s Mirror Online. She has since married Portuguese soccer star José Fonte.

2. Catherine Ommanney (2006)

Before she shot to fame for being in “Real Housewives of Washington D.C.”, Catherine Ommanney claimed she hooked up with the prince in July 2006. “We had a great time and a fun evening. We started talking and that was it for the rest of the evening. I was quite taken aback by him!” she told Daily Mail.

3. Chelsy Davy (2004 – 2011)

Source: Daily Express

Chelsy Davy was Harry’s first serious relationship and remains his longest one to date. This college sweethearts dated off-and-on again for 7 years, between 2004 to 2011. She even attended Prince William and Kate Middleton in April 2011. Rumour has it that Davy may have received an invitation to Harry and Meghan’s big day since the former flames have “remained friends long after ending their relationship”.

4. Caroline Flack (2009)

Source: Glamour UK

You may remember this lady as the former host of “X Factor U.K.”, but in the 2015 autobiography “Storm in a C Cup”, Caroline Flack wrote about her 2009 fling with Harry. They were introduced through a mutual friend. “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,” the TV presenter wrote in her book.

5. Astrid Harbord (2009)

Source: Hello

When Harry and Davy were separated for awhile, the prince was rumoured to be briefly dating Astrid Harbord in 2009. Interestingly, Harbord also happens to be one of Duchess Kate’s friends.


6. Camilla Romestrand (2010)

Before Harry rekindled his relationship with Davy, he reportedly dated Camilla Romestrand for a couple of months. For the uninitiated, the Norwegian singer is also the frontwoman for the band Eddie the Gun. According to CBS, the pop star once spend the night at Clarence House where she was treated with breakfast in bed by the prince.

7. Florence Brudenell-Bruce (2011)

Source: Getty

Florence had a brief fling with Harry in 2011. The pair kept their romance hush-hush but were spotted at London’s Hard Rock Calling music festival. However, they broke up around the time when Harry started his helicopter training with the Army Air Corps. The model later got married to banker Henry St. George and welcomed a daughter in 2014.

8. Cressida Bonas (2012 – 2014)

Source: ABC

Princess Eugenie allegedly introduced Prince Harry to Cressida Bonas before they started dating in 2012. However, the public scrutiny proved to be too overwhelming as they split up in 2014. During an interview in 2017, the model/actress shared how frustrating it is to be known as Harry’s ex.

I think it’s that thing of being pigeonholed. Especially in this country, I feel people are very quick to put you in a box or put you in a corner and think, ‘Oh, well, you’re that so you must be that’,” she was quoted as saying.

9. Ellie Goulding (2016)

Source: Getty

This coupling has never been confirmed but rumours started circling when an onlooker claimed they kissed under a blanket at the Audi Polo Challenge in June 2016. Ellie Goulding even performed Elton John’s “Your Song” as William and Kate’s first dance during their wedding.

Sources: US Magazine, Cosmopolitan.

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