Olivia Wilde joined Harry Styles for a ‘romantic vacation’ in Tuscany

Olivia Wilde attends the Vanity Fair Oscar Party at Wallis Annenberg Center for the Performing Arts...

Either Jason Sudeikis and Olivia Wilde have both moved on with new partners and everything is healthy and fine, or they’re engaged in some kind of ex-lover tit-for-tat in the press. You decide! I honestly haven’t figured it out yet. I think Olivia moved on quickly with Harry Styles and Jason was hurt, or his pride was wounded. But I also think he has plenty of options and he quickly began dating Keeley Hazell, his Ted Lasso costar and longtime friend. Jason and Keeley did their first pap stroll – in New York – several days ago. So… it honestly looks like Olivia saw those photos of Jason and Keeley, immediately booked a flight to Italy and bum-rushed Harry Styles on what was his quiet Italian holiday. Thankfully, someone went to Page Six to paint it as a romantic getaway:

Harry Styles and Olivia Wilde were spotted enjoying a romantic vacation together in Tuscany, Italy, on Wednesday. The pair were seen looking very much in love in photos taken by fans as they strolled with their arms around each other in the picturesque seaside town of Porto Ercole.

“Harry has been seen taking a break on the beach in Porto Ercole after he finished filming ‘My Policeman’ in London,” a source exclusively told Page Six. We’re also told Wilde added the Italian getaway to her schedule after spending time with her son, Otis, 7, and daughter, Daisy, 4, whom she shares with ex-fiancé Jason Sudeikis.

“Olivia has also been in London, spending time with her kids, who are there with Jason,” the source said. “Olivia stayed behind with her kids, then she flew into Porto Ercole to join Harry.”

The “Watermelon Sugar” singer had been spotted frolicking alone on a Venice beach on Friday ahead of Wilde’s visit.

[From Page Six]

Maybe Olivia has been in London, but she was in LA last week, and Jason has been in New York this week with his girlfriend Keeley. Where are the kids? In London, or in New York with Jason? Or in LA? I think Page Six got the cities wrong. But the Harry Styles-watchers knew that he was in Italy for several days before Olivia arrived. So… it is what it is. I find them to be an odd couple and I’m very curious about what Olivia will say about him once they do break up.

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30 Responses to “Olivia Wilde joined Harry Styles for a ‘romantic vacation’ in Tuscany”

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  1. Sean says:

    For some reason, I imagine this relationship ending similar to how Aldous Snow broke it off with Sarah Marshall.

  2. Xoxo says:

    Olivia was in LA last week while her kids were in NY with Jason. She then flew back to NY for three days then flew to Italy. Not to be that person but she barely spent time with her kids before ditching them to be with Harry. Couldn’t Harry fly to her like Keeley did for Jason? Like why is she doing all the work and making the effort with Harry?

    • LightPurple says:

      Because she is chasing hm.

    • girl_ninja says:

      Cause she’s chasing that DACK.

    • Erica says:

      Because she is way more into him than he is into her. She is chasing him and he enjoys the attention.

    • Cava24 says:

      The Italian coast is much nicer than NYC in the summer. Not that surprising that she would go there.

      • jo says:

        Yeah, I know old hags wanna be old hags about it, but this obsession with other people’s kids is weird.

    • Natters says:

      Well, wouldn’t you rather be in on a picturesque Italian coast with your boy lover than hot, sweaty, dirty, noisy NYC (I live here and looking forward to escaping the madness next week on vacation). I just can’t see leaving a man for a boy, but whose knows what brought her to this decision. I feel sorry for the kids.

      • AlpineWitch says:

        A 27-year-old man isn’t a boy!!
        Your take sounds ageist towards Olivia.

        My husband was that age when we got married and I was far older than Olivia. You wouldn’t blink twice if a 37-year-old man was dating a 27-year-old woman.

      • Xoxo says:

        Yeah but after 3 days with your kids who you were away from an entire week prior to that. It’s not the best look to leave so soon.

      • Cava24 says:

        The kids are supposedly on a toad trip with Jason.

  3. Stephanie says:

    Olivia has been with her kids over the past few months, while they were in London. There are stalker pictures of Olivia and Harry in London from the past few months too. Harry finished his movie The Policeman in Italy and stayed there. Olivia went onto NY with her kids, while she was promoting and doing interviews. I don’t like how this is making it seem like she is never with her children. It’s called co-parenting, which is what Jason and Olivia are doing. This is such an odd take. And the only reason I know all this information is because Harry has an extremely invasive fandom who is busy sending death threats to Olivia.

    • Cava24 says:

      According a couple of reports from yesterday (all copying each other) Jason is going on a / is on a road trip with their kids, they aren’t in NY. Olivia only has 50% custody.

      • Stephanie says:

        Co-Parenting. I watch close friends handle this on a daily basis. To see people wonder “why isn’t she with her kids?” leaves a bad taste in my mouth.

        Every woman Harry gets involved with goes through this type of scrutiny with the fanbase on social media. His last gf, went through the exact same thing. When she joined him on tour, she was “chasing” him.

      • Cava24 says:

        Right. I was agreeing with you. she couldn’t be with her kids right now anyway. And no one complained that he was taking time away from his kids to squire Keeley around and get papped and massively overdress for the current weather in NYC.

      • KNy says:

        @ Stephanie, I agree. The kids’ parents are no longer together, and since they seem to have an involved father, that means that Olivia is going to not be with her children for chunks of time. This is life. To so many parents, going from having your kids 100% of the time to 50% of the time is a huge adjustment and not easy, and their kids are still little so when they are there, there are THERE and in your face. If I were her, I’d rather be in Tuscany with Harry Styles instead of home constantly passing by my kids’ empty rooms. Same for Jason. Neither of them seem like parents who completely depend on nannies to do all the work (a la Alec and Hilaria).

      • Xoxo says:

        Jason has always been in the same city as his kids, girlfriend or no girlfriend….Olivia on the other hand has not. This isn’t the first time.

        You can’t criticize a woman nowadays without people going on some feminism rant. Questioning a woman’s shady love life choices isn’t misogynistic.

      • Cava24 says:

        The film she directed got pushed back because of a positive Covid test on set and pushed back again because LA County wouldn’t let film sets reopen after the holidays, she also had to do some reshoots. The original plan was for her to go with Jason to London with the kids but because of COVID and the film she was directing, she couldn’t do that. was she supposed to quit her film in the middle of filming? Seems to me she was generous in letting him take the kids to London since she could have insisted they stay in LA where she was and where they had been living for a year.

    • Tiffany :) says:

      I agree, Stephanie, this is an odd take. People are trying really hard to force this narrative that Olivia is doing something wrong, either bad mother or bad wife. There’s a hint of sexism about it.

      • Stephanie says:

        This is a take I’ve seen in Harry’s fandom, by people who are 15-23 years of age. Seeing this take by older women, is a bit ?????? for me. Her kids are now with their dad on a trip, what is she supposed to do? Stay home and stare at her walls or join her boyfriend, the one she’s been with for several months, in Italy? I sure know what I would do. Italy, here I come!!!!

      • tealily says:

        I get what you’re all saying, but I was reading this as more of a genuine question since we were also getting pap photos of Jason in NYC this week. I don’t see why that means he can’t have his kids with him though.

  4. Holland S says:

    I find them boring, both separately and especially together. There’s no burning passion or anything to keep me nosy, just two people dating. Meh.

  5. Mrs. Smith says:

    It’ll be over the second his tour starts.

    • BothSidesNow says:

      Yes, I am afraid to say that I agree as well. He’s 27 and IMO, men need much more time to grow up, and some never do. Styles isn’t one to stay with someone for long periods of time. I think his longest relationship lasted close to a year. But he’s young and should have fun. The 20’s are your years to grow and become who you want to be and travel, travel, travel!!

    • LaurenMichelle says:

      I hope not. In Olivia’s defense, Jason has been rumoured to be a world class Dog. Cheated on Olivia repeatedly. She has looked sad the past 2 years, until she met Harry. Not gonna judge her. She is a good mother, and has a career. I too am concerned that Harry will break her heart.

  6. TJ says:

    She was COVID tested in New York last weekend (otherwise she couldn’t enter Italy) so it was a planned visit. Also she & Stlyes were not paped in Italy, a stranger made that picture (& later another girl a video where they were seen spending some time together in a restaurant), Page Six saw that picture & wrote a story which we doesn’t know for sure how accurate is. So it’s not exactly what her ex did earlier this week. I know, I know don’t botch a good narrative with facts…

  7. Lena says:

    I can’t imagine how heartbreaking it would be to have your 4 and 6 year olds only half the time. It’s bad enough to understand why people stay together for the kids’ sake. I’m sure they didn’t separate just because of Harry (or other women for that matter).

  8. wow says:

    I cannot stand him, but f*ck it. I’m rooting for them. I love seeing “older” women with younger men (above 25 pls) and living their best life. The time of the DILF is over. This is the MILF century.