Olivia Wilde Spotted With Ex Jason Sudeikis Amid Harry Styles and Emily Ratajkowski Rumors

Chisom Ndianefo
Olivia Wilde and Jason Sudeikis
Getty | David Crotty

It's a case of two different worlds for Olivia Wilde and Harry Styles. The former couple had their hands full this weekend but with other people. While the former stole some time away with an old flame, the latter was spotted engaging in heavy PDA with a fellow celebrity.

Keep reading for all the scoop.

Olivia Wilde And Jason Sudeikis

Olivia Wilde and Jason Sudeikis
twitter | Gypsy Girl

The Booksmart director and her ex-fiance, Jason Sudeikis, put their fiery custody battle on temporary hold and showed up as a team to attend their son's soccer game in Los Angeles on Saturday.

Cheerleading All The Way

Olivia Wilde and Jason Sudeikis
twitter | Twitter

The parents of two watched and cheered from the bleachers as they kept it super casual with their fits. Wilde showed a bit of skin in a white crop top paired with a brown sweater over a pair of denim and white sneakers with a cream tote bag. She wore her dark brown tresses in a center part and rocked bold dark shades.

Sudeikis looked dapper in a zip-up sweater, face cap, denim, and white sneakers.

No Tension In Sight

Olivia Wilde
Giphy

Wilde and Sudeikis appeared cordial, as they smiled and even shared a hug before parting ways at the end of the game.

Inside Their Custody Battle

Olivia Wilde
Flickr | imdtopost

This rare sighting comes after a judge requested Sudeikis request to have their child custody case moved to New York. According to Wilde, they were scheduled to start working with a family therapist in California in mid-January as she thought the dust was finally settling, but she later discovered he had been plotting to have the case moved to New York behind her back.

The Surprise Serve At CinemaCon

Olivia Wilde
Giphy

It's been a rather daunting experience for Wilde since they parted ways. Last year, the Don't Worry Darling director was served legal documents from her ex during the Vegas screening of the film at CinemaCon.

According to sources, the document was marked "Personal and Confidential."

What's Up With Harry Styles

Harry Styles
Giphy | Recording Academy / GRAMMYs

As for Styles, who recently broke up with the actress, he was spotted in Tokyo sharing a passionate kiss with actress and model Emily Ratajkowski. The 29-year-old looked chic in a black suit and white shirt unbuttoned at the collar.

Ratajkowski kept it edgy in a black crop top paired with a matching black skirt and a black and red bumper jacket. The loved-up couple didn't give a care in the world as they fully expressed themselves in public glare.

When Did Harry Move On?

Emily Ratajkowski
Giphy

The news about Styles moving on surfaced last month as sources confirmed that the As It Was star was indeed seeing someone but wanted to keep it private, especially after his widely publicized romance with Wilde.

Emily Ratajkowski's Moves

Emily Ratajkowski
Giphy | The Tonight Show Starring Jimmy Fallon

The actress has had much going on in the dating world herself. Earlier this year, she was linked to a serial dater and comedian, Pete Davidson. The actress also filed for divorce from her producer ex-husband Sebastian Bear-McClard in September 2022 after splitting amid claims that he was a serial cheater.

Harry Styles And Olivia Wilde

Harry Styles
Giphy | Storyful

Styles and Olivia broke things off in November 2022. The split was amicable as sources claimed that they agreed they had different priorities and it just wouldn't work at that time.

One Last Time

Olivia Wilde
Giphy

Wilde was last spotted with Styles on November 15, 2022, when she attended his concert with her two children. The actress showed up to support her beau during their whirlwind romance.

How Harry And Olivia Met

Olivia Wilde
Flickr | imdtopost

The pair met on the set of Don't Worry Darling, where Styles starred as the lead character alongside Florence Pugh. The connection was instant and a friendship brewed.

Spotted At A Wedding

Olivia Wilde
Giphy | Don't Worry Darling

The couple was then spotted holding hands and enjoying each other's company at Styles agent's wedding in California. This sighting sparked dating rumors across the halls of Hollywood in 2011.

Did Harry Break Up An Engagement

Olivia Wilde
Flickr | imdtopost

News began to surface about Styles being responsible for Olivia and Jason's split. But sources close to the actress revealed that the relationship was already done when Styles and Wilde began dating.

Knowing The Kids

Harry Styles
Giphy | The Late Late Show with James Corden

Wilde and Styles took their relationship to the next level as the actress introduced her kids to the Sign Of The Times singer.

Promoting Harry's Album

Harry Styles
Giphy | Harry Styles

The director publicly supported her boyfriend by promoting his album Harry's House on its release day. She shared Styles's Music For A Sushi Restaurant track from the album by using it as a soundtrack to a black and white clip from the 2018 film Cold War.

Trouble In Paradise?

Harry Styles
Giphy

A little drama happened in their relationship at the Venice Film Festival after a viral video suggested the award-winning singer spat on co-star Chris Pine. Both parties, however, denied such happening, including Wilde herself.

'Don't Worry Darling' Release

Wilde also celebrated the release of her new project by posting a picture of herself, Styles, Florence Pugh, and Katie Silberman sitting around a table on the movie set.

Rare Sightings

Harry Styles
Giphy | Harry Styles

While their relationship was super public, Olivia and Harry kept things from the press as much as they could, and they also made rare outings that usually involved hiding from the paparazzi.

Disappointing Split

Olivia Wilde
Flickr | imdtopost

Sources close to Wilde spilled that the whole breaking up process was hard on her, as she thought they had a fighting chance, but they remain good friends.