Harry Styles, Olivia Wilde's Relationship Timeline: Photos

Walk through fire for her! After Harry Styles joined the cast of Olivia Wilde’s Don’t Worry Darling in late 2020, the pair soon sparked romance speculation off the set.

Following the conclusion of filming, the Booksmart director was spotted alongside the former One Direction crooner while attending the wedding of his manager, Jeffrey Azoff, in Montecito, California.

“The pair held hands and looked very much like a loved-up couple,” a source exclusively told Life & Style in January 2021. “They seemed very comfortable with each other — almost like they’ve been dating for months, not just weeks.”

Since then, the pair’s relationship has continued to flourish with the New York native even supporting her beau during his “Love on Tour” concerts and praising his Don’t Worry Darling role.

“Little known fact: most male actors don’t want to play supporting roles in female-led films,” the Life Itself star praised the “Kiwi” singer’s talents in a February 2021 Instagram post after the project wrapped. “The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles, which is one of the reasons it’s so hard to get financing for movies focusing on female stories. No joke, it is harrrrrd to find actors who recognize why it might be worth it to allow for a woman to hold the spotlight. Enter: @harrystyles, our ‘Jack.’”

While the couple has kept their romance under wraps, another source revealed to Life & Style in November 2021 that her kids Otis and Daisy — whom she shares with ex-fiancé Jason Sudeikis — were “crazy” about the England native.

“He’s a big kid at heart and spends hours playing and entertaining Olivia’s kids,” the insider explained. “He enjoys taking them to the park, playing hide and seek and making sandcastles on the beach.”

Later that month, several fans noticed Otis and Daisy attended the “Watermelon Sugar” performer’s concert alongside Wilde and Styles’ mom, Anne Twist. According to fan videos via social media, the kids danced in the pit with Wilde and Twist while the Grammy winner performed on stage.

Days later, the O.C. alum subtly supported her beau’s beauty line launch, writing via Instagram Story, “I find this very pleasing,” alongside promotional footage of his Pleasing brand.

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News of the pair’s budding romance came less than two months after her split from Sudeikis made headlines. The Drinking Buddies actress and the Kansas native were previously engaged for seven years.

“Olivia and Jason really did grow apart. They still care for each other, and there are no hard feelings,” an insider exclusively noted in November 2020. “Their relationship was solid for a very long time, but there’s a reason why they never tied the knot and made it official. They’ve been separated for months now and there really is no drama. They’re handling this like adults. It’s all about coparenting their kids. That’s the priority for them.”

Scroll below to relive the couple’s relationship journey.