Olivia Wilde and Jason Sudeikis

Olivia Wilde and Jason Sudeikis once defied the odds of having a May-December love affair when they started dating in 2011. At the time, the actress was only 27, while the comedian was 36. The two met at the finale party of Saturday Night Live, where Sudeikis used to be a writer and cast member. After seven years, he finally popped the question and Wilde answered with the sweetest yes.

However, after having been engaged for seven years, they have since called it off. Although the couple have broken up, there appears to be no bad blood between the two. They have a son named Otis born in April 2014, and a daughter named Daisy born in October 2016. This is likely for the sake of their two children, for whom they are making important investments—emotionally and financially, too.