As a new documentary delves into the life of Harry Styles, we take a look at his romances away from the stage, with the global megastar having dated some very famous women
As one of the most widely adored singers on Earth, Harry Styles’ colourful love life is of just as much interest to his legions of fans as his impressive musical repertoire.
The 29-year-old former One Direction band member has dated some incredibly famous women in his time, and is now reported to be in a relationship with actress Taylor Russell. The new couple were photographed together at various points over the summer, and in October, appeared to take things to the next level when Harry turned up to support Taylor, 29, on the opening night of her play, The Effect.
By November, fans were left in a frenzy after photos emerged of Harry and Taylor looking very cosy at a U2 concert, with Harry appearing quite content as he wrapped his arm around the Bones and All actor. As a new Channel 5 documentary delves into Harry’s rise to superstardom, we take a look at his various high-profile romances.
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2011: Caroline Flack
Caroline Flack met Harry Styles thanks to presenting The Xtra Factor with Olly Murs
The singer paid tribute to the late TV presenter when he walked the red carpet days after her death in 2020 ( Image: Getty)
Harry’s brief romance with original Love Island presenter Caroline Flack raised a few eyebrows back in 2011, thanks to the singer being 17-year-old 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,” the late TV presenter 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 after her suicide.
2012: Emily Atack
The actress admitted to a brief fling with the singer ( Image: INSTAGRAM)
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
The two singers collaborated on a romance for a year ( Image: GC Images)DON’T MISS
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 34-year-old megastar.
2013-2014: Kendall Jenner
Harry and the reality TV star at the British Fashion Awards in 2014 ( Image: Getty)
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
Harry’s longest relationship has been with film star Olivia ( Image: INSTAGRAM)
The pair found love on the set of thriller Don’t Worry Darling ( Image: Corbis via Getty Images)
Perhaps Harry’s most serious relationship, Harry sparked up a romance with one of his film colleagues, Olivia Wilde, back in 2021. 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. The two stars reportedly called it quits last year.
2013: Emily Ratajkowski
Harry and Emily were seen sharing a smooch ( Image: Jose Perez/INSTARimages)
Back in March, Harry was pictured smooching model Emily Ratajkowski in Japan, sparking plenty of gossip. Speaking with People at the time, a source claimed: “[Emily] hooked up with Harry, but they are not in touch every day. Emily is interested in seeing him again.”
