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Love History of Harry Styles from Emily Atack, Olivia Wilde to Emily Ratajkowski

Love History of Harry Styles from Emily Atack, Olivia Wilde to Emily Ratajkowski
Published 11 months ago on Mar 27, 2023

Harry Styles is one of the most popular bachelors in the the world but he could possibly be off the market once again!

The former One Direction singer, 29, only broke up with Don't Worry Darling director Olivia Wilde, 39, last year but the Watermelon Sugar hitmaker appears to have already moved on.

As the one-time boyband heartthrob is pictured passionately making out with in Tokyo, we take a look back at Harry's most famous romances since he rose to fame as a teenager on The X Factor in 2010. 

From his infamous relationship with the late Caroline Flack to his attempt to keep up with a Kardashian during his fling with Kendall Jenner, Harry has a string of famous exes.

Harry's brief romance with original Love Island presenter Caroline Flack that did not last long raised a few eyebrows back in 2011, thanks to the singer being 17-year-olds while the late TV star was in her early thirties.

In August 2011, Harry told the official X Factor website: "If Caroline Flack is ­reading this, say ‘Hi’ from me. She is gorgeous!"

It was soon revealed the two stars had been dating, with Caroline subjected to a slew of online abuse from One Direction fans due to their age-gap romance.

"It began to go wrong when Harry was pictured coming out of my house one morning," Caroline explained in her autobiography. "And once that was out, it was open season – anyone could say anything. In the street people started shouting at me 'paedophile' and 'pervert'."

The pair, who met thanks to The X Factor, parted ways on good terms after a few months together and remained friendly.

Following Caroline's tragic death in February 2020, Harry paid tribute to the former Xtra Factor host by wearing a subtle black pin as he walked a red carpet just days on from her suicide.

2012: Emily Atack

In May 2012, a year on from his high-profile union with Caroline, it was rumoured Harry and The Inbetweeners actress Emily Atack had struck up a romance, although the pair did not confirm it at the time.

Then, the following year, Emily admitted to Hello!:  "Yeah, we had a short-lived thing. But we were never boyfriend and girlfriend.

"Harry and I had fun, then went in opposite directions. We haven’t spoken in a while."

2012-2013: Taylor Swift

Two of the biggest pop stars in the world once made up a much-loved romantic pairing.

Taylor Swift and Harry dated for roughly a year and were snapped several times together, but the singers eventually called time on their relationship and went their separate ways in 2013.

The pair remained on good terms but music fans suspect the songwriters have referenced their time together in their respective songs - with Taylor's bop Ready For It said to be about Harry, while some believe his Two Ghosts track is about the 33-year-old megastar.

2013-2014: Kendall Jenner

Away from dating British TV stars and fellow singers, Harry can also count a reality TV star as one of his ex-girlfriends.

In an interview with Rolling Stone, Harry admitted his now-ex Kendall Jenner was a big inspiration for his May 2017 debut studio album.

"She's a huge part of the album," he told the magazine, while sweetly adding, "Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap … and hope they know it's just for them."

The pair never confirmed their romance but stayed on good terms and even enjoyed a cosy chat at the 2019 Met Gala. 

2021-2022: Olivia Wilde

Perhaps Harry's most serious relationship began back in 2021 when he sparked up a romance with one of his movie co-stars, Olivia Wilde.

The Sign of the Times singer met his now-ex-girlfriend on the set of her film Don’t Worry Darling in late 2020, in which Olivia directed Harry who appears as Jack in the thriller.

Their meeting came just months after the actress and director split from her long-term partner and fiance, Ted Lasso creator Jason Sudeikis.

"Harry and Olivia had chemistry almost instantaneously on set," an insider told US Weekly in 2021. "It was only a matter of time before they got together."

The rumour mill went into overdrive in January 2021, when the couple were snapped holding hands at the singer's manager’s wedding and the pair eventually went on to be snapped several times looking loved-up.

Engagement speculation began over the summer last year, as Olivia was pictured cheering and dancing in the crowd as her boyfriend Harry headlined the 2022 Coachella Valley Music and Arts Festival in Indio.

But the two stars reportedly called it quits last year, with Harry going on to be pictured smooching model Emily over the weekend.

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