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Harry Styles is one of those rare cultural phenomena the world simply refuses to move on from—and honestly, why would we? From his boy band beginnings to his current status as a feminist icon and certified rock god, the 29-year-old has mastered the art of reinvention (all while wearing a feather boa).
But if there’s one thing that rivals his Grammy-winning career in terms of public fascination, it’s his love life. Harry Styles, ever the enigma, rarely spills on who he’s dating, making every sighting, lyric, and whisper of a relationship all the more compelling. From Kendall Jenner to Olivia Wilde and even a rumoured rendezvous with New Zealand’s own Georgia Fowler, his dating history reads like a who’s who of impossibly cool women.
Below, a deep dive into the romantic escapades of Mr. Styles—because, let’s be real, we’re all still invested.
Harry Styles Dating History: A Complete Timeline
Caroline Flack: 2011
Caroline Flack.
(Image: Getty) (Credit: Image: Getty)
Harry and X-Factor judge Caroline Flack were linked shortly after the singer competed in the UK talent show. They immediately faced intense media scrutiny for their age gap (Harry was 17 while Flack was 31 at the time), but despite it all, decided to give things a go anyway.
Looking back on the experience in a later autobiography, Caroline revealed: “I already knew that he had a crush on me, he’d made it pretty obvious.”
The world mourned when Caroline took her own life in February 2020 after struggling with mental health. Harry paid tribute to the late star by wearing a black ribbon to the Brit Awards that year. When he took to the stage to perform, he also wore a badge reading: “Treat people with kindness”—which is also the name of one of his singles.
Taylor Swift: 2012
Harry Styles and Taylor Swift.
(Image: Getty) (Credit: Image: Getty)
Music fans understandably lost the plot when pictures surfaced of Harry and Taylor Swift going on dates and hanging out together. Their relationship was something of a celebrity couple enigma—both were peaking in their careers and had become household names in their own right.
While the relationship didn’t last very long (we’re talking mere months), the legacy lives on in the songs they both went on to write about each other (read: Style by Taylor Swift and Two Ghosts by Harry Styles).
Kendall Jenner: 2013
Next on Harry’s A-list romance repertoire was reality star and model, Kendall Jenner.
Kendall is notoriously private about her life, particularly her romantic one, so getting a glimpse of them together was tough to come by. Despite her private nature, reports about their relationship were rife—you know the media loves nothing more than a good gossip.
Nadine Leopold: 2015
After his romantic escapades with Kendall trailed off, Harry was later linked to Austrian model Nadine Leopold. Neither ever confirmed their romance, but multiple sightings of them together throughout 2014 and 2015 led many to believe they were the real deal at one point or another.
Georgia Fowler: 2015
Of course, we can’t forget Fowler-gate, or perhaps more accurately Kiwi-gate. The New Zealand model was long believed to be the muse behind Harry’s hit song Kiwi, which was later released in 2017 after they were linked.
While there was no actual evidence of the pair being anything more than friends, everyone based the rumours off a YouTube video from Georgia and a lot of fanfiction.
Kendall Jenner… again: 2016
After reportedly splitting two years prior, Kendall and Harry rekindled things after a New Years Eve party, according to Page Six.
Several reports were also flying that they had rekindled a romance after the 2019 Met Gala, which didn’t seem that farfetched given Kendall’s pattern of returning to an ex. Whatever the confirmed truth, the pair are clearly good friends, they just couldn’t seem to hang out without sparking a million dating rumours.
Tess Ward: 2017
In 2017, Harry was rumoured to be dating food blogger Tess Ward.
According to E! News, the pair enjoyed a “string of dates” and had been spotted driving around north London together on the weekends. The duo were also reportedly spotted together at the Audi Polo in Ascot.
The reason for their break up? Rumours say the two split when Tess decided she still had feelings for her ex, per Cosmopolitan.
Camille Rowe: 2018
Image: Getty Camille Rowe.
French model Camille Rowe was also linked to Harry in 2017, but was a very different relationship as it was one of the few Harry publicly acknowledged himself.
They dated for about a year before parting ways, and Harry confirmed that his song Cherry was about Camille.
The song references the tougher realities of their relationship: “I wanted it to reflect how I felt then. I was feeling not great,” Harry explained. “It’s all about being not great. Because you get petty when things don’t go the way you want it. There’s parts that’s so pathetic.”
Olivia Wilde: 2020-2022
You might be wondering how exactly these two met, and the answer is, on set. The pair got to know each other during the production of Olivia’s film, Don’t Worry, Darling, which began filming in late 2020. Around the same time, Olivia split from her fiancé, Jason Sudeikis, with whom she shares two children.
In January 2021, the internet went into overdrive after pictures of Harry and Olivia holding hands at a wedding surfaced. PEOPLE went on to claim that the pair had actually been dating “for a few weeks” which caused even more of a stir.
In February 2021, Wilde penned a tribute to Harry for his part in her female-led film, writing to Instagram: “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.”
Her praise for Harry just kept coming, writing: “Enter: @harrystyles, our ‘Jack’. Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold centre stage as our ‘Alice’, but he infused every scene with a nuanced sense of humanity.”
She continued: “He didn’t have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards.”
The pair dated for around two years, however called it quits in November, 2022.
Taylor Russell: 2023
This brings us to the present day, where Canadian actress Taylor Russell is the latest woman to be linked to Harry.
At this stage, we don’t know if their romance is any more than rumours. So far, the pair have been spotted together on one occasion, while walking the streets of London in what looked to be a low-key hangout.
More recently, Taylor was spotted in the audience at Harry’s concert in Vienna, ramping up rumours that they might really be an item. And, while we can’t deny our hearts are breaking, if the rumours do turn out to be true, we’re just glad Harry is happy.
Olivia Dean: 2024
It’s safe to say the fans were sent into a frenzy in late last year when Styles was spotted out and about in London with singer Olivia Dean.
The first sighting of the pair was in August, just two months after Styles supposedly ended things with Taylor Russel. Photos revealed the 30-year-old former One Direction member and the 25-year-old neo-soul singer spotted at a local Five Guys in what seemed to be a very low-key outing.
“Harry and Olivia have known each other for a while,” a source reportedly told The Sun. “They have loads in common with their music taste and are enjoying getting to know each other out of the spotlight.”
Later, in September, the duo were spotted by fans side by side at Kalorama festival in Madrid. However, speculation about the budding relationship remain just that, with both Olivia and Harry yet to comment on the situation themselves. And from all available information online, the two do really seem to be just good friends, maybe even possible collaborators on new music.
So, Who Is Harry Styles Dating Now?
Styles has been keeping a pretty low profile of recent—other than that one marathon in Tokyo—so it’s not clear if he’s actually dating right now. And with no concrete information on his relationship with Dean, it’s likely the singer is just enjoying some alone time. That and hanging out with long-time pal, James Corden.
But that hasn’t stopped fans keeping a close eye on Styles’ recent activity. A number of TikTok sleuths have dug up some loose-ended theories, including a 46-year-old Italian yoga teacher, but there remains to be any official sighting of Harry and the mystery woman.
The post A Complete Timeline Of Harry Styles’ Dating History appeared first on ELLE.
