Olivia Wilde, 36, And Jason Sudekis, 44—9 year difference

In any case, Jason shared for an interview that it was at an SNL party that they met. They spoke to each other and apparently—and immediately—hit it off. According to Jason, he didn’t pursue Olivia after, and it took him a while to do so despite the initial electricity he felt for her. These two started dating in 2011 and announced their engagement in 2013.

They gave birth to a son and a daughter, but it seemed that completely overlooked tying the knot. Surprisingly, the pair separated after their 9-year relationship in the beginning of 2020. Someone who is really close to this family revealed that the couple’s separation was really peacefull and they have changed their relationship into another level. We believe Wilde and Sudeikis will definitely do things that is good for the whole family.