2
Jessica Simpson and Jensen Ackles separated in Dec 1998 after dating for 4 months...
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3
John Mayer and Jessica Simpson separated in May 2007 after dating for 9 months...
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4
Taylor Swift and John Mayer separated in Mar 2010 after dating for 3 months...
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5
Harry Styles and Taylor Swift separated in 2014 after dating for 1 month...
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6
Harry Styles and Caroline Flack separated in Jan 2012 after dating for 3 months...
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7
Caroline Flack and Prince Harry separated in Jun 2009 after dating for 2 months...
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