From a teenage heartthrob to an icon of Millennial and Gen-Z culture, Harry Styles has been front and centre of the limelight since 2010. So, it’s no wonder fans have always taken a keen interest in whether Harry Styles’ has a girlfriend at any point in time, particularly when names like Kendall Jenner, Taylor Swift and even Kiwi model Georgia Fowler are thrown in the mix.
And although rumours of a new romance appear to be be swirling following his split from actress and most recent ex – Taylor Russell – Styles is yet to curb our curiosity with a confirmation either way.
In the meantime, let’s take a look back through Harry Styles’ enviable dating history – from his One Direction days, to who he’s rumoured to be in a relationship with now.
Harry Styles’ Girlfriend Timeline: From 2011 to Now
Caroline Flack: 2011
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 they still appeared to give things a go.
Writing of Harry in a later autobiography, Caroline revealed: “I already knew that he had a crush on me, he’d made it pretty obvious.”
Tragically, Caroline passed away in February 2020. 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.”
Taylor Swift: 2012
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 (though you could say they never stopped). Brad and Jen, eat your heart out.
While the relationship reportedly lasted mere months, the legacy lives on in the songs they both went on to write about each other.
Kendall Jenner: 2013
Next on Harry’s A-list romance repertoire was Kardashian reality star and model Kendall Jenner.
The half sister of the infamous Kardashian trio was—and has remained to be—incredibly private about her life behind the cameras. Getting a glimpse of them together was tough to come by, but at the time, reports about their relationship were rife.
Nadine Leopold: 2015
Things with Kendall apparently didn’t last long in 2013. He 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, so on the Harry Styles girlfriend timeline she stays.
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.
There was no actual evidence of the pair being anything more than friends, just a suss YouTube video from Georgia and probably a whole bunch of fanfic.
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.
There were also reports they rekindled things again after the 2019 Met Gala. Whatever the confirmed truth, the pair are clearly good friends but can’t seem to hang out without sparking a million dating rumours.
Tess Ward: 2017
Harry was rumoured to be dating food blogger Tess Ward in 2017, but apparently broke up when Tess decided she still had feelings for her ex, per Cosmopolitan.
Camille Rowe: 2018
French model Camille Rowe was linked to Harry in 2017, but this relationship was different to others because it was publicly acknowledged by Harry himself.
They dated around 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: 2021
Olivia and Harry got to know each other on the set of Olivia’s film, Don’t Worry, Darling, which began filming in late 2020.
Around the same time, Olivia split from her fiancée, Jason Sudeikis, with whom she shares two kids.
Then in January 2021, pictures of Harry and Olivia holding hands at a wedding surfaced, sending the internet into overdrive. At the time, PEOPLE claimed they had been dating “for a few weeks”.
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.”
She then celebrated her rumoured boyfriend who starred alongside the formidable Florence Pugh: “Enter: @harrystyles, our ‘Jack’ . Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold center 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.”
With reports continuing to colour their sweet relationship, and those pictures of a steamy makeout sesh on a boat in July 2021, it does seem like the two were an item for a while.
Taylor Russell: 2023-2024
Never one to make major public splashes with new girlfriends, Taylor Russell and Harry Styles were very low-key about their relationship from the start, and it seems like they kept things low-key until the end.
The dating rumours started flying during the 2023 US summer when Taylor and Harry were spotted on a date in London. And by September 2023, they were pretty much telling the world they were a thing by holding hands and getting snapped by the paparazzi in London.
But overnight, PEOPLE magazine confirmed they split up after almost a year together.
Despite a recent sojourn to Japan in April, a source spilled the beans to The Sun, saying, “Harry and Taylor called it quits. They hit a rough patch after their Japan trip and decided to take a breather. Harry’s been in the States, and Taylor’s been hanging in London. They were cute together, and Taylor really put a smile on Harry’s face. But lately, things haven’t been so easy.”
Taylor even rocked up to the Met Gala solo, however PEOPLE mag heard from another source that things were still good between them. “They’re pretty serious and have done some traveling together,” the source said. “They even hang out in England quite a bit.” Despite Harry being a bit of a private guy, they apparently clicked because they’re into similar stuff.
But The Sun reported that Harry and Taylor broke up in May 2024, which may mean Olivia Dean is the romantic interest some people think she is.
Who Is Harry Styles Dating?
While Harry Styles hasn’t confirmed he has a new girlfriend, he has recently been linked to singer Olivia Dean. The two of them have been spotted out and about together, first at a burger joint in London, then at a music festival in Spain.
But whether or not Olivia is Harry’s girlfriend is up for debate, with some people speculating that they may simply be friends (and possible collaborators), while others think it’s more romantic. Especially since he was seen putting his head on her shoulder during Sam Smith’s performance.
But even an insider wouldn’t give much away, simply telling The Sun: “Harry loves festivals and enjoyed his time with Olivia in Madrid. It was the perfect weekend after Olivia put on a stunning performance, and they both loved watching their favourite artists together.”
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