Olivia Wilde’s dating history: Her ex-husband, boyfriends and flings
If you had Olivia Wilde and Harry Styles coupling up on your 2021 bingo card, take a bow.
In early January, Wilde, 36, and Styles, 26, took their romance public by holding hands at his agent’s wedding in Montecito, Calif.
Before getting cozy with the “Watermelon Sugar” crooner, Wilde was in a long-term relationship with “SNL” alum Jason Sudeikis. But she and Sudeikis, 45, called off their engagement last year after roughly a decade of dating.
From Sudeikis to Styles and beyond, take a look at Wilde’s relationship history.
Tao Ruspoli
Wilde was married to filmmaker Tao Ruspoli, now 45, from 2003 to 2011. In a 2013 interview with Marie Claire, the “Booksmart” director opened up about lessons learned from her heartbreak.
“I had grown up with Tao; we had just drifted. I felt I had something to prove. If you fall off a horse, you get back up. I am not a quitter. I hung on for as long as possible, until it was more hurtful to stay,” Wilde said at the time.
“I’m so grateful for the pain and the heartbreak. It gave me the courage to leave and brought me to the great love of my life,” she continued, referring to Sudeikis.
Ryan Gosling
In 2011, the same year Wilde split from Ruspoli, she was linked to Ryan Gosling. The two were spotted on a brunch date in February of that year, according to People, while Gosling, now 40, filmed “The Ides of March” in Cincinnati.
Justin Timberlake
Following her reported rendezvous with Gosling, Wilde was spotted at a Hollywood club in April 2011 with her “In Time” co-star Justin Timberlake, now 39. But a source told People at the time, “They’re just friends.”
Jason Sudeikis
First linked in November 2011, Wilde and Sudeikis got engaged in January 2013. They later became parents, welcoming son Otis in 2014 and daughter Daisy in 2016.
In late 2020, news emerged that Sudeikis and Wilde had ended their engagement. But the actors seem to have the best breakup in Hollywood, and have been photographed embracing numerous times since the split news became public.
Harry Styles
Wilde and Styles made a splash into the new year as they held hands at the California wedding of Jeff Azoff, Styles’ agent. Wilde is directing the former One Direction singer in the upcoming film “Don’t Worry Darling.”
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