Harry Styles and Olivia Wilde – Together for 4 Months

Olivia Wilde broke up with Jason Sudeikis after their nine years together, and for seven of those years, they were engaged. Their relationship resulted in the birth of their son Otis and daughter Daisy. In September 2020, Wilde brought together a star-studded cast including Chris Pine, KiKi Layne, and Harry Styles for her upcoming psychological film Don’t Worry Darling.

In January 2021, photos of Wilde and Styles holding hands surfaced while attending his agent’s big day in Montecito, California. They have a ten-year age gap, with Wilde being older, but only time will tell if theirs is a romance meant to last.