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Simon Cowell And Mezhgan Hussainy
Length of Engagement: 2 years

Simon Cowell went the romantic route when proposing to his girlfriend, former American Idol makeup artist Mezhgan Hussainy, by getting down on one knee on Valentine's Day in 2010.

The two eventually split in 2012 after Hussainy brought up concerns of Cowell's involvement with ex-girlfriends, but the breakup wasn't all bad. Hussainy was given an $8 million Beverly Hills mansion as a "parting gift."