It feels like Olivia Wilde and Jason Sudeikis announced their split two seconds ago, but it actually happened in mid-November. Plus, the split had the feel of something that had been happening for months and they only bothered to confirm it after they had already split up residences and everything. What I’m saying is that Olivia has likely been single for months. And a few weeks ago, she began dating… HARRY STYLES. Yes, that Harry Styles. The angel who loves nail polish, pearls and pussybow blouses.
A hot new couple may be kicking off 2021 in style. Olivia Wilde and Harry Styles were seen holding hands at a friend’s wedding over the weekend, sparking dating rumors for the pair who recently worked together on the film Don’t Worry Darling, which Styles starred in and Wilde directed.
“They were in Montecito, California this weekend for a wedding,” a source tells PEOPLE. “They were affectionate around their friends, held hands and looked very happy. They have dated for a few weeks.”
In photos obtained by Page Six, Wilde is seen wearing a floor-length floral gown for the wedding as she holds hands with Styles, who’s in an all-black fitted suit paired with a white button-up shirt. Both actors are also seen wearing masks. Wilde, 36, and Styles, 26, were later seen photographed at his L.A. home with luggage in tow.
A rep for Wilde could not be immediately reached for comment, and a rep for Styles has not commented.
Wilde and Styles spent time together over the fall as they filmed Don’t Worry Darling around Los Angeles. Wilde pulls double duty on the film, which she also co-stars in. The 1950s-set film stars Florence Pugh as a housewife who discovers a disturbing truth while living in an isolated community in California. Styles plays her character’s husband.
Yeah, there’s a ten year age difference but I don’t think that matters to either of them. Harry has always had a thing for ladies who are older than him, and it’s not like he’s currently some dumb kid who doesn’t know what he’s doing. I do feel sorry for the Styles fans who wanted to see him with other people, like Louis Tomlinson or Lizzo. (Lizzo and Harry are good friends and affectionate friends, but I don’t think anything happened there.) As for Jason Sudeikis… he’ll be fine.
As for the wedding, Olivia attended as Harry’s plus-one, the wedding was for his friend Jeff Azoff. Harry wore a robe, Hugh Hefner-style, at one point.
Harry Styles and Olivia Wilde twin in Gucci at Jeff Azoff's wedding https://t.co/TWvibon6J7 pic.twitter.com/VRjaZRKwxP
— Page Six (@PageSix) January 4, 2021
EXCLUSIVE PHOTOS: Olivia Wilde and Harry Styles are dating, seen holding hands at a wedding https://t.co/Fg3QOOZtSg pic.twitter.com/bOkMU7bLl2
— Page Six (@PageSix) January 4, 2021
Photos courtesy of Backgrid.
Just came here to say that I called this in comments to the post on November 15th about her breakup with Jason Sudeikis. It may not actually have been happening then but I still called it.
Also, I think he is channeling The Dude, not Hefner in the bathrobe.
Impressive! Lainey predicted it too, and I remember thinking “yeah right.” On further reflection, I totally get the attraction on both sides.
Me too. Makes all the sense in the world.
I adore Harry Styles. I think he is really talented, interesting, weird, and hot. And i quite like Olivia, both as a director but even more as an activist.
One shallow comment though, I hate her dress in the picture. It is awful and prairie like. Just no.
Lainey wants to take credit bc another gossip site got the jump on it and has been breaking other celeb gossip stories like crazy.
Thank you, not disgusting Hugh
Harry certainly has a type, doesn’t he?
Hmmmmm hmmmmm.
No on the robe hahah
I thought maybe he was wearing it because everyone jumped in a pool or something but then seeing him with the bride and groom still fully dressed up, eek. He is adorable, though. They make a cute couple.
They seem like such a random couple, never thought of them together.
They are not. Olivia directed Harry in a film, so they go back a while.
Timing, is indeed everything.
They look pretty damn hot together I must admit
There’s a pairing I never would have expected….
Well. Sure wasn’t expecting that. Have fun ya crazy kids!
Why are people still insisting on gatherings? Whoever couldn’t wait a year for the party part of the wedding?
It sounds like it was a very small gathering and rule compliant.
one in five people in LA county are currently testing positive. hospital beds are full. It’s incredibly irresponsible to have any gathering at all at this point. I am passionately devoted to Harry, but I’m mad at him and Olivia both for attending this wedding when the local case numbers are devastatingly high. It’s a bad look.
‘People are dying, Snuffles”
Their people have been leaking that it was very COVID safe. It was kind of fun to watch them see how people were responding and then have sources plant rebuttals in real time.
So jealous of people still managing to have fun during a pandemic!
That floral dress appears to be at least one size too large. It also seems to be a rip off of basic Jessica McClintock Gunne Sax designs. Can’t Gucci copy its own designs instead of borrowing from other designers?
Enjoy the fling,, Olivia.
I try to keep an open mind about fashions recycling.But I wore almost the same dress back in the early 80s prairie style period. It looked like granny’s nightgown back then and still does.
Man, I thought Gunne Sax dresses were *the bomb* back in the day. My mom never bought them for me, but we had family friends who would give me hand-me-downs and there were always a couple in there.
A year ago, a friend did her wedding in vintage gunne sax dresses. She found a vintage Jessica McClintock wedding dress and vintage gunne sax dresses for the bridesmaids.
Good for them I’m happy to gawk at a new celeb couple, but I do hope that layered curtain doily dress style does off soon.
I honestly was kind of shocked that people were tripping so hard. Harry LOVES him an older woman and she’s not really THAT much older. Trust me, he was shagging middle aged women in his teens.
And I can’t blame Olivia one bit. Who knows if it’s serious but I bet she is having a LOT of fun. Harry seems like a great dude.
Exactly! If Harry was 36 dating a 26 year old no one would bat an eyelid.
Misogyny everywhere, take cover
Yep. He also seems older than his age so I get it.
I thought Olivia was older than 36. I was thinking she was early-mid 40s for some reason.
Could see this coming as soon as the announcement to of her and Jason came out. I’ve never really been on the Olivia Wilde hype train but I think this couple is cute.
I have an irrational dislike of her and I really don’t know why. Maybe because of her character on the OC? I really don’t know much about her, but my instant reaction is always ‘that woman with the smug punchable face’. I hope these two are happy – quite an attractive couple.
It’s weird, right? I have the same strong dislike for Robert Downey Jr. for example. Although that’s not quite as unfounded but I do sometimes dislike celebs for no reason whatsoever. She’s fine in my book although sometimes she tries a little too hard to be cool.
Anyway. This isn’t a surprise. Two attractive people working together.
She’s said some pretty small problematic things about her and Jason fu*king like Keyan runners and bitching pretty hard about her Prince ex husband but nothing major. I’ve still never warmed to her. I don’t dislike her but I’m not on the hype train either
@Cat — I forgot all about the Prince!
I suspect they have been friends a lot longer than a few weeks and maybe Olivia and Jason announced their split because one of them was starting to date. It seems that Oliva and Jason split a long time ago but did not announce it until they were about to be papped with other people. Either way good luck to them. Everybody seems fine with it
Pull your damn mask up, Harry!
That’s great for them but what the F are people doing gathering & having weddings ??
LA County has zero ICU beds & ambulances are having to ration oxygen. This was in Montecito so a little north of LA but it doesn’t matter, everywhere its advised to not do these events or gatherings even this small. It’s so exhausting seeing celebrities get away with this but tbh it’s not as heinous as the celebs that have been vacationing for months…
Back to them: I think they’re a hot couple & ive always had a girl crush on Olivia plus it’s cool she’s the older one, not Harry. I think her & Sudeikis split a long time ago before the announcement publicly. I love that they seem to be on good terms
They are both due back on set to finish the movie they are shooting. I read somewhere that there aren’t that many days of photography left but given that the Grammy’s just got pushed back (at which he is supposed to perform) because of COVID, I wonder if the rest of the film shoot will be pushed back as well.
I think he’s sexy as hell and I would too.
Get it
HOT! That’s all I’ve got. They’re both super attractive and I’m into it.
I didn’t have this on my 2021 bingo card but it’s an exciting pairing. They’re both beautiful! Best of luck to them.
Sure, yeah, I believe it. I guess. No… not really.
I like it. Harry seems like a fun guy. That floral dress is a hot NO from me though.
I know, right. That dress is horrible. Well, Harry is delicious but that also means that you have to try harder in the style department because that guy will overshadow anyone, even with a good sense of style.
Why are so many people so ‘hell-bent’ over a ten-year difference couple? I don’t see a problem with partners who are 26-36 between them.
I know that when someone’s fanbase is mostly teenagers, the limits of what is appropriate are blurry and they feel entitled to the famous’ person life. But I find it so weird that their fans still insist on his “romance” with Louis Tomlinson, when Louis himself has said multiple times that it makes him uncomfortable.
I’m all for people having fun during these trying times but… is a wedding with guests during a pandemic a good idea?
Harry Styles loves older women, he even is rumored to have had a fling with Tracee Ellis Ross! Olivia Wilde seems like a cool chick and she is insanely gorgeous IRL.
I saw her at SXSW years ago and she was literally the most beautiful woman I’ve ever seen in real life. She looks pretty on film but in person she just glows. Loved Booksmart too! Get it Olivia!
I loved her in Drinking Buddies and she’s got a great future as a director… this is a pairing that I do not mind at all.
Harry is very talented and sweet. He is one of the few Hollywood men I actually find interesting. He did covers of Fleetwood Mac tracks a while back and was blown away by his talent. I still wonder why Jason didn’t marry Olivia, but I am happy for her. Jason seems very smug, and Harry is a sweetheart. No one says anything bad about him. Go Olivia!
I’m more jealous that they can attend a wedding and gather than anything else in this story.
Like good for both of them. Olivia seems cool, Harry seems cool, they’re both gorgeous. I’d get with either of them too if I had the chance.
My husband is 10 years younger than me. It’s not a huge deal. We’re both way into adulthood like these 2.
I’m a little jealous as I love Harry Styles! They kind of make sense to me, hope they are having (COVID safe) fun!
I’m old enough to be his mother and I still would.
Harry’s not aging well for only being 26. He looks at least in his mid-thirties.
WTEF???
🤢
I’ve always liked Harry Styles. He’s got an “other world” look, style, and self-assurance.
He seems like such a great person. I’ve heard good things about her too. So I’m all for this.
I’m just confused. Maybe I believed false gossip about his sexuality. (I know I know it’s not my business.) For the record, I was also confused by his friendship with Cindy Crawford and Rande Gerber. He’s too good for them. Always have distrusted them.
I do find his friendship with the Gerbers odd? Didn’t he date Kaia for a hot minute??
NO!!!! Sorry for the caps lockl, he’s known her since Kaia was a kid and views her as a kid. Kaia has even commented on how he is her parents’s friend.
@basi I 100% believe that he’s queer. Remember that the B in LGBT stands for “bisexual.” As in, people attracted to multiple genders. I’m a bisexual woman married to a man. He could be a bisexual man dating a woman. Bisexual people don’t lose and regain our queerness depending on our current partner, we’re queer all the time.
Good for them both. I just finished reading The Idea of You by Robinne Lee and just about died when this news came out lol. But seriously good for her. That Harry Styles is a SNACK.
So she is a director of a film and is having a relationship with an actor who is in the film and is 10 years younger than her. She is abusing her position and power in the workplace, not good at all unprofessional. Not appropriate for a man or a woman to do.
Sorry, but I just don’t get the appeal of Harry. The only One Direction member I ever found attractive was Zayn, even if his personality is meh.
I don’t actually care about the age difference, it’s mild and they’re both good people in my book, but I didn’t see it happen and it kinda shocked me lol.
Harry is lush, but WTF was with the dressing gown with the bride and groom?!? Looks like he assisted in the consummation and didn’t bother to dress again afterwards! Love the bride’s dress too, super simple.
Didn’t he also date the late Caroline Flack?
I’m willing to take one for the team and hook up with Jason Sudekis. You’re welcome.
Harry always struck me as mature and super respectful, especially of women, in interviews. Hopefully it’s true, because then lucky Olivia! He’s a catch!
Wow, I did not know Harry Styles was so loved. He’s ugly to me, and he’s got that British hairline, so he might as well have fun before he starts to shrivel.
She seems fine I guess.
I think Olivia and Harry make a really cool, fun couple. I would like to see Jason with Jennifer Aniston. I know there is nothing there but I think they would be cute together.