If you haven’t been living under a rock, you probably know that Booksmart director
Olivia Wilde and Ted Lasso creator Jason Sudeikis called it quits.
One of the most beautiful low-key Hollywood romances has come to an end.
It’s hard to believe the actors ended their seven-year engagement, but the length of their
relationship is proof that these two were very much committed to each other.
What happened to the couple we all were looking up to?
Who initiated the relationship in the first place?
And how’s Olivia Wilde and Harry Styles’ romance fit into all of this?
Keep watching the video to unfold the story.
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Remember when we thought 2020 was the worst?
Well, as it happens, perfection has no limits, as well as a relationship drama.
Jason Sudeikis and Olivia Wilde’s split in November 2020 caught us off-guard, to say
the least.
After nine years together, they decided to go their separate ways.
No more couple goals, sadly.
And if that wasn’t a shocking revelation, in January 2021, we learned that Wilde was
moving on with our charismatic singer Harry Styles.
Jason must have been crushed to hear the news.
Especially considering all the confusing details around their breakup.
Some say they ended their engagement in early 2020, while others insist it happened, quote,
“after she already had gotten close” to the enigmatic pop star.
Was the breakup completely mutual with no drama whatsoever?
Before we dive deeper into it, let’s roll back the tape a little bit and take a closer
look at how it all started.
House alum and Horrible Bosses star have a story they can tell their grandkids.
It was pretty much love at first sight.
They met and hit it off right away at a finale party for SNL in 2011.
She was into him from the start.
But Jason heard she was dating someone, so he was playing it cool.
Over the next six months, they kept running into each other.
Olivia was the one who made the first move.
One of her friends went over to Sudeikis one day and said, “This is Olivia’s number.
Use it.”
Straight to the point.
It appears that the two were madly in love for two years when Sudeikis proposed over
the holidays in 2013.
Soon they welcomed their firstborn, Otis (named after one of Wilde’s favorite musicians
Otis Redding, well known to be one of the most incredible soul and R&B singers in American
history) and then, two years later, another bundle of joy named Daisy was born.
“Ladies and gentlemen, Otis Alexander Sudeikis has LEFT the building!
(I’m the building)” They took another major step in their relationship
when Sudeikis joined Wilde’s jaw-dropping and critically acclaimed directorial debut,
Booksmart, an endearing, witty, and adventurous film.
Most importantly, it’s unbelievably fun to watch again and again.
In February 2019, they still prioritized each other, going on dates a few times a week.
Sadly, 2020 being, well, 2020, marked the end of Wilde and Sudeikis’ relationship.
The couple reportedly broke up at the beginning of the year, but the news didn’t surface
until November.
Did they just fell out of love romantically?
Or was there someone else, presumably the sexy singer that everyone’s obsessed with?
The couple met on the set of her upcoming movie Don’t Worry Darling, a psychological
thriller starring Florence Pugh as a lead and Harry Styles as her husband, with Chris
Pine, Gemma Chan, and Olivia herself.
Having appeared already in Dunkirk, the One Direction star wasn’t such an outside-the-box
choice.
Wilde described the excitement over casting the singer, “It’s pretty powerful and
kind of extraordinary to see someone in his position redefining what it can mean to be
a man with confidence.”
At the 63rd annual Grammy’s ceremony, Styles won his first Grammy for Best Pop Solo Performance
for his hit single, “Watermelon Sugar.”
Wilde appeared to subtly show her support for him via her Instagram Stories.
She uploaded photos of some other music legends, giving a shout-out to a Mick Jagger performance.
It’s worth mentioning that one of her most memorable childhood moments involves the man
himself.
She once snuck down to spy on her parents hosting Jagger in their home when the rock
star noticed her.
As Wilde later said, “How many girls were told to go to bed by Mick Jagger?”
It’s safe to say that you genuinely can’t always get what you want!
She also posted a picture of Paul McCartney biting into a watermelon slice, which fans
seemed to think was a pretty obvious nod to Styles.
Some say that their relationship is fake, that it’s just a publicity stunt, while
others believe that this blooming romance was written in the stars (sorry, Jason).
According to intuitive astrologer Rachel Lang, Olivia Wilde is the woman of Harry Styles’
dreams and she thinks what they have, quote, is a “spiritual connection that can feel
out of this world.”
No wonder she gushed about him in an Instagram post, applauding him for stepping into his
role with humility and grace, without hesitation or insecurity.
“Little known fact: most male actors don’t want to play supporting roles in female-led
films.
The industry has raised them to believe it lessens their power (i.e., financial value)
to accept these roles, which is one of the reasons it’s so hard to get financing for
movies focusing on women,” she wrote.
Whatever it is, fate or no fate, it seems to be working for them.
What about her other romances?
Is she just drawn to charming and charismatic rebels?
Both Styles and Sudeikis fit that description perfectly.
It might be so, considering her marriage to a filmmaker and Italian prince (no kidding!)
Tao Ruspoli in 2003.
Wilde, born Olivia Jane Cockburn (yep, she based her stage name on one of the most famous
writers in Irish history), eloped when she was just 19 years old.
“There was this wave of romantic excitement, and we were very open to the idea that if
it didn’t work, we would let it go its course.
No pressure.”
The lovebirds parted ways after eight years of marriage.
Sadly, it seems like marriage didn’t work for Jason Sudeikis as well.
He divorced Pitch Perfect writer Kay Cannon in 2010 after 11 years of relationship.
Since then, he was linked to a string of actors, including Scarlett Johansson, Eva Mendes,
Jennifer Aniston, and January Jones.
When he was asked in a Vanity Fair interview why he broke Jennifer Aniston’s heart, he
said, “I don’t know, I don’t know.
Bad manners, maybe?”
Sudeikis went on to say that, “You know the worst part?
Even joking about it gets taken out of context.”
Still, men usually aren’t condemned for their relationships, even with younger women.
And the fact that they are fathers plays no part in it.
Unfortunately, that’s exactly what’s happened to Olivia Wilde.
“If she has two kids at home but is out running around with a dude ten years younger
during a pandemic, she belongs to the streets,” tweeted one person.
Wilde, wrote another, “should be taking care of her two kids instead of dating one”.
How can we still be here?
And somehow, there wasn’t much talking about the 9-year difference between her and Sudeikis.
What do you think?
Maybe we should stop judging and start appreciating each other more?
As for how things are going for former lovers and current co-parents, Jason has been in
London for the last couple of months filming a new season of his award-winning Apple TV+
show Ted Lasso, which is loosely based on him and now actually resembles his life a
little bit.
Eerie, isn’t it?
In any case, he’s trying to live minute by minute and stay optimistic.
When the show won at the 2021 Critics’ Choice Awards, he thanked Wilde and their children
for the show’s inspiration as she was the one who suggested it in the first place, proving
just what good terms he and Olivia are on.
Wilde later congratulated Sudeikis and his team on the wins.
“So happy for you guys,” she tweeted.
“I hope this means we all keep wearing hoodies when the ceremonies are in person next year.
Yes, our lovable and handsome comedian recently has been making headlines at the 2021 Golden
Globes and CCA by sporting hoodies while accepting his wins.
Sudeikis said he was fully aware of the blowback he might receive — and was actually looking
for it.
“That’s me.
I’m a rebel rouser,” he said.
At the Globes, the actor wore a tie-dye hoodie from his sister’s dance studio, Forward
Space.
And at the CCA, he gave the nod to ex-fiancée Olivia Wilde by wearing a Crockett High sweatshirt,
representing the fictional school from Wilde’s directorial debut, Booksmart.
He isn’t adhering to black-tie style rules this awards season, but no one can say he
doesn’t know how to handle statement dressing.
At SAG Awards, Sudeikis continued to eschew formal wear, choosing to go with a navy wool
sweater decorated with “My Body My Choice,” designed for Gucci.
When explaining how he feels about accessing painful things from the past, talking about
him leaving Saturday Night Live, Sudeikis said he doesn’t want to close off.
Especially as an artist.
He wants to access the things that broke his heart, even if it may hurt to see or feel
them again, but he’d rather have that than feel numb and checked out.
Even though he doesn’t have closure, Jason believes he’s lucky and that from a distance
everything looks better.
“This is spectacular.
May we all maintain the bravery to try to ask the girl out or write a screenplay or
whatever it may be.”
Let’s hope he feels the same way about moving on from his love of ten years and the woman
who stole our hearts as an actor, director and simply human being.
Despite their split, Olivia Wilde and Jason Sudeikis are on such friendly terms that she
has stayed in the UK to spend more time with her two kids after her new love Harry Styles
flew back to the US.
What can we say?
Sometimes things just don’t work out.
Even when we really want them to.
They may no longer be together, but Wilde and Sudeikis made one beautiful couple, don’t
you agree?