There are way too many seasons and hookups to focus on, but here are 12 of the most surprising hookups of all from the most recent seasons of .
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His bad-boy behavior - he told her in 2009 he'd hooked up with a Challenge castmate to spite her - didn't win him fans in Brown's family.
"They thought Diem could do better," says the friend.
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FILE - In this July 26, 2014 file photo, Diem Brown attends the 17th Annual Super Saturday Ovarian Cancer Research Fund Benefit, presented by QVC, at Nova's Ark Project in Water Mill, in New York. (Photo by Scott Roth/Invision/AP, File) with a ruby ring - and a Go Pro video camera.
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