March 3, 2018 - Dia Dipasupil/Getty Images North America more pics like this »
Olivia Wilde And Jason Sudeikis
Length of Engagement: 5 years

Wilde and Sudeikis got engaged in 2013 and went on to have two kids together — daughter Daisy and son Otis. They waited five years before they got hitched.

“It’s funny, people tend to skip over the engagement thing. They think it’s like, ‘Oh, engaged,” Wilde told Vanity Fair. “And then you get there. I don’t think you should spend your entire engagement planning a wedding. Because it’s fun. It’s this great time. It’s like dating-plus.”