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Megan Fox And Brian Austin Green
Length of Engagement: 4 years

The Hollywood couple hasn't had an easy relationship, which is why they took it slow with their engagement. The two dated for two years before getting engaged in 2006, but three years later they split and went their separate ways. Their love story wasn't over, though, when a year later in 2010 Green proposed again and they got married a quick few weeks later. 

Five years later, Fox filed for divorce in 2015, but in 2016 they reconciled and welcomed their third son together.