Originally when Olivia Wilde was romantically linked to Harry Styles, she seemed to get along well with her ex Jason Sudeikis, but that dynamic changed over time. Following speculation that the director and singer were dating on the set of Don’t Worry Darling, the two confirmed their romance when they were spotted holding hands at a joint wedding in January 2021. Around that time, an insider confirmed that Wilde and the “Watermelon Sugar” artist tried to keep their tryst a secret during filming. “They were very careful and even smart at times,” the source told Us Weekly. During an interview later that year, Styles spoke about the importance of keeping his dating life out of the spotlight. “I’ve always tried to separate my personal life and my work life,” he told Dazed in November 2021.
A little over a year after Wilde and the ‘Dunkirk’ actor officially started dating, tensions between the director and Sudeikis were mounting. The exes – who share two children – reportedly disagreed on which city their children should live in. This led to the “Ted Lasso” star filling out custody papers, which Wilde was known to have been served during April’s CinemaCon. “Jason’s actions were clearly aimed at threatening me and catching me off guard. He could have served me discreetly,” she said in court documents released by the Daily Mail on Aug. 10. Although Sudeikis denied the timing was intentional. “I deeply regret what happened,” he said in the documents. Amid the drama between the former couple, Styles had reasons not to contact Sudeikis himself.
Why Harry Styles prefers to keep relationship drama private
Harry Styles and Olivia Wilde’s relationship seems serious, but it doesn’t mean the Sign Of The Times singer wants to get involved in the public custody battle between his girlfriend and Jason Sudeikis. “Harry never reached out to Jason,” a source told Us Weekly on Aug. 31. Speak to Sudeikis about the matter. Though the singer has chosen to remain on the sidelines for the custody battle, he still enjoys working with Wilde, both personally and professionally. “They’re a great team together,” he added insiders added.
The former One Direction singer has opened up about how revealing relationship information can spark a heated reaction from some fans. “It’s obviously a difficult feeling, feeling close to me means you’re at the ransom of a corner of Twitter,” he told Rolling Stone during a cover story published Aug. 22.
Meanwhile, Wilde didn’t mince words when she opened up about how she felt when she spoke at CinemaCon that they were served custody papers. “Trying to sabotage that was really vicious,” she told Variety on Aug. 24. “But, you know, unfortunately, it wasn’t something that completely surprised me. I mean, there’s a reason I left this relationship.” Ouch.