Harry was reportedly “absolutely infatuated” with Natalie Pinkham, a journalist and TV personality. Though their 2003 relationship was short-lived, the two have remained close friends since.
Before Meghan, it looked like Prince Harry was going to settle down with Chelsy Davy, a businesswoman who he dated for six years (2004-2010). But celebrity life took its toll on their relationship. She went back to her home country of Zimbabwe to step out of the ‘intense” spotlight. Though an unexpected 2015 reunion in Africa sparked romance rumors, nothing became of it.
While things were cooling down with Chelsy in 2009, the Prince made headlines when he began hanging out with Kate Middleton’s pal, Astrid Harbord. Though their flame didn’t last long, they raised eyebrows when they were caught leaving an illegal rave in East London a month later.
That same year Prince Harry began dating X Factor host Caroline Flack, to whom he was introduced by none other than Natalie Pinkam. But the two were forced to call it quits once their relationship made headlines, with Caroline stating "I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry's bit of rough.”
In 2010, Prince Harry got back into his first real relationship after Chelsy when he began dating Florence Brudenell-Bruce. But similar to Chelsy, the lingerie model and socialite reportedly couldn’t handle the media attention and they later broke up.
Harry was also seen partying with singer Mollie King in 2012. However, the pop star has remained mum about the details of their relationship.
Apparently that reunion was also short-lived as Doctor Who star Jenna Coleman caught the Prince’s attention back in 2015, when the pair was snapped with his hand on her knee in a number of photos. The actress caused quite a controversy among the royals having appeared topless in a sex scene for the BBC series, A Room at the Top.
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