1
Harry Styles and Kendall Jenner separated in Feb 2014 after dating for 2 years...
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2
Harry Styles and Caroline Flack separated in Jan 2012 after dating for 3 months...
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3
Caroline Flack and Prince Harry separated in Jun 2009 after dating for 2 months...
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5
Michael Essien and Cassie Sumner separated in 2007 after dating for 1 year...
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