Chelsy Davy
Poor Chelsy. She surely thought she was in for good when she accompanied Harry to his brother's national holiday of a wedding back in 2011, but alas, things did not work out. The Zimbabwe-born blonde still remains Harry's longest relationship, as the two were on-again, off-again from 2004 to 2011. Nevertheless, Davy seems to be doing just fine, hanging out with exotic animals in her native Africa and heading up a jewelry company called Aya.
[Photo via Getty]
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