Natalie Pinkham Back in 2003, the young royal was rumored to have dated drinking buddy, TV presenter Natalie Pinkham.  The two have never publicly confirmed a romantic relationship.  Pinkham is now married with two kids and is a reporter for Sky Sports F1.

Cassie Sumner (right) and Lauren Pope (left), Harry was 19 when he met the two at London's Chinawhite nightclub. His advances on both women, apparently lasted one night; the same night.

Chelsy Davy Harry's longest relationship to date remains his romance with Chelsy Davy, which lasted on-and-off from 2004 to 2011.  The two first got together during Prince Harry's gap year in Cape Town and continued to date on and off for years.  Davy was even Harry's date to the Duke and Duchess of Cambridge's wedding in 2011 after the two had rekindled following a 2009 breakup.  Despite breaking up for good, the two will according to Davy, "always remain friends."

Astrid Harbord In 2009, Harry was briefly linked to Kate Middleton's friend Astrid Harbord after the two were seen out in London together.

Caroline Flack Harry was also linked to X Factor host Caroline Flack in June of 2009.  Flack , revealing the two began dating after being set up by a mutual friend.  As soon as the relationship went public, however, they called it quits. "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," Flack revealed.

Camila Romestrand Following Harry's breakup with Chelsea Davy in 2010, he briefly dated Norwegian singer Camila Romestrand.  She told friends that she stayed over at the royal residence Clarence House, and was even served breakfast in bed by Harry.  Romestrand's account, was never confirmed by Prince Harry.

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