Jason Sudeikis' First Major Relationship After Olivia Wilde Might Be on Shaky Ground

Jason Sudeikis’ love life has been under quite a bit of scrutiny since he was first spotted with actress Elsie Hewitt, 28, in January. This is the Ted Lasso star’s first major relationship since his 2020 split with ex-fiancée Olivia Wilde, but the two-decade age gap sure did raise a few eyebrows. The couple are still going strong six months later, but sources are whispering that the 48-year-old star is reportedly weighing his options.

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“The good news for Jason is that he’s finally living for himself a little bit and after a lot of false starts, he’s finally opening himself up to a new relationship after being in the Ted Lasso bubble for the last five years and having almost no time to devote to anything else, personally or even with his career,” a Life & Style source revealed. While his relationship with Hewitt is “going well,” Sudeikis doesn’t seem to think that this is a long-term situation for him — he might be looking to play the field a bit.

“Jason has finally come to understand that he has a lot of options and that women do like him for more than just his incredible success,” they added. Because he’s feeling “more confident,” he’s “trying to figure out what he really needs” in his life. Sudeikis opened up to GQ in 2021 to share how much the split from Wilde affected him. “I’ll have a better understanding of why in a year, in two, and an even greater one in five, and it’ll go from being, you know, a book of my life to becoming a chapter to a paragraph to a line to a word to a doodle,” he explained. “That’s an experience that you either learn from or make excuses about. You take some responsibility for it , hold yourself accountable for what you do, but then also endeavor to learn something beyond the obvious from it.”

From a fans’ point of view, it looked like Wilde had an affair with Don’t Worry Darling co-star Harry Styles, but behind the scenes, the breakup timeline was much different. It didn’t matter because the media frenzy from the celebrity love triangle took over the headlines without any of the players getting their side of the story out. Sudeikis laid low in the U.K. while filming the remaining seasons of his Apple TV+ show while Wilde’s relationship with the pop star eventually fizzled out. Sudeikis’ love life didn’t seem like much of a priority until this year, but it doesn’t seem like Hewitt is endgame for him.

“Everybody’s rooting for Jason and Elsie to make things work, but Jason has proved in the past that even the best relationship can slip through his fingers if he isn’t giving it everything he has,” the Life & Style source added. “He deserves a personal life as successful as his acting career but it’s been a major struggle for him to make that a reality.”

Before you go, click here to see famous men who routinely date women half their age.