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Olivia Wilde Is Moving On From Jason Sudeikis With... Harry Styles?

Harry Styles driving a car with cool lighting.

Now and again, word of a new celebrity couple leaks and everyone collectively says ohhh, that makes sense. Now and again, word of a different celebrity couple leaks and everyone collectively says, wait, how did that happen? Well, you can go ahead and file this one in the the how did that happen category. Olivia Wilde, fresh off an amicable separation from former SNL cast member and current star of the much praised Ted Lasso Jason Sudeikis, was apparently spotted hanging out with One Direction star Harry Styles.

A picture of the alleged couple holding hands ran in Page Six today. It was reportedly taken at his agent’s wedding, and not surprisingly, the pair are looking quite stylish (and masked up, of course). Not a ton is known about the budding romance, but a source reportedly told People they’ve been dating for a few weeks and were openly affectionate during the wedding which took place in Montecito, California.

The connection between the 36-year-old Olivia Wilde and the 26-year-old Harry Styles might seem random at first, but the how did they meet is actually pretty direct. Wilde spent the fall making the film Don’t Worry Darling with Florence Pugh. It’s the first full length feature she’s directed since the critically acclaimed Booksmart, and there’s a lot of excitement for it. The film follows a suburban housewife who discovered a dark secret. Styles will play Pugh’s husband, though it’s unclear at this point whether he’s mixed up in the dirty secret she discovers. The role was originally earmarked for Shia LaBeouf, but conflicts and differences in opinion reportedly led to Wilde moving on and choosing Styles.

Both Wilde and Styles’ dating histories have been well covered in the media. She was previously with Jason Sudeikis from 2011 to 2020. The two reportedly broke up at the beginning of the year, though no one knew about it for months because it’s way easier to keep secrets in 2020. He, on the other hand, was previously with model Camille Rowe, but the two broke up back in 2018.

At this point, it’s way too early to tell whether this is the start of something serious or just beautiful and talented people having a good time together, but either way, good for them. These might not be the first two names we would have guessed to put together, but there’s always something fun about seeing famous people get together that don’t occupy the same spaces in your mind. Besides, some of those unlikely romances really thrive and work in their own quirky ways.

I can’t imagine either Wilde nor Styles is itching to comment and offer a bunch of details into what’s going on, but if we hear anything, we’ll make sure to pass it along. Until then, all we can do is cross our fingers and hope Jason Sudeikis moves on with someone equally as random.

P.S. I know it’s probably weird that I used a picture from Tron for this article, but that movie rules and should have started a franchise. So, I’m going to keep fighting the good fight and not letting it die.

Mack Rawden
Editor In Chief

Enthusiastic about Clue, case-of-the-week mysteries, the NBA and cookies at Disney World. Less enthusiastic about the pricing structure of cable, loud noises and Tuesdays.