#8: Olivia Wilde and Jason Sudeikis
Duration of Relationship: 9 years (2011–2020)
The split between Olivia Wilde and Jason Sudeikis in 2020 shocked fans who saw the couple as one of Hollywood’s most stable duos. After nearly a decade together and two children, the couple quietly ended their engagement.
Reports initially suggested an amicable separation, but things grew complicated when Wilde began dating Harry Styles, sparking rumors that the timing overlapped with the end of her relationship with Sudeikis.