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Jennifer Aniston And Justin Theroux
Length of Engagement: 3 years

The two met on the set of Tropic Thunder in 2007, which Theroux co-wrote, but the two didn't start dating until 2011. A year later he proposes on his birthday with an 8-carat diamond worth an estimated $500,000. But the Hollywood couple waited three years before having a private ceremony in the backyard of their Bel-Air home in 2015. 

Unfortunately the two announced their split three years later, on the day after Valentine's Day in 2018.