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Harry Styles has been making girls swoon with his handsome looks, irresistible charm, and musical talent ever since he stepped onto The X Factor stage for a televised audition of Stevie Wonder‘s “Isn’t She Lovely” in 2010. So, it’s no wonder he’s led a steady romantic life over the years. Although the contestant-turned-superstar has many admirers from all over the world, only a few ladies have been lucky enough to be a part of his love life since he broke onto the music scene with his band One Direction and later started a successful solo career. From the late English television presenter, Caroline Flack, to his most recent ex, actress and director Olivia Wilde, we’re taking a look at all of the gals who’ve been romantically linked to the British superstar.
Harry Is Currently Dating Olivia Wilde
Harry Styles is seen visiting Olivia Wilde’s trailer on the set of her film ‘Don’t Worry, Darling’ in Nov. 2020. They were spotted holding hands at a wedding two months later. (Backgrid)Harry’s last love interest was actress and director Olivia Wilde, who he sparked a romance with after he was hired to star in her 2022 film, Don’t Worry, Darling. Their relationship caused some controversy, as the timeline of Olivia’s split from her fiancé of seven years, Jason Sudeikis, in late 2020 and the start of her relationship with Harry is a bit blurry. Olivia and Harry were first seen holding hands at Harry’s agent’s wedding on Jan. 3, 2021, and were photographed with luggage at his Los Angeles home the next day.
Over the next 19 months, they were seen cruising around Europe together, kissing in the streets of New York City, and hitting the gym together. Olivia was also spotted several times backstage at Harry’s Love on Tour shows in the fall of 2022. Articles Trending Now
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The viability of their relationship, however, was heavily speculated amid the chaotic promotion of Don’t Worry Darling and fans were convinced they broke up following the drama surrounding the movie and their relationship, which reportedly caused issues on set. However, a source close to the couple revealed to HollywoodLife that they were doing just fine at the time. “Despite rumors suggesting that there was trouble in their relationship, this entire experience has, in fact, made them stronger than ever,” the source divulged. “They both really wanted to keep their relationship out of the spotlight when they were promoting this film and they think that they did this. The love that they share this unbreakable bond, and they are both so supportive of each other’s careers and would never do anything to let that come in the way of their relationship.”
That’s why it was a shock to fans when it was reported that the pair went their separate ways by November of that year. “He’s still touring and is now going abroad,” an insider told PEOPLE. “She is focusing on her kids and her work in L.A. It’s a very amicable decision.” Another source added, “Right now, they have different priorities that are keeping them apart.” Related Link
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Caroline Flack
Harry Styles and Caroline Flack arrive at the Shoreditch House for a private party. (Backgrid)Harry and Caroline met when she was a presenter on The X Factor. Rumors started going around about Harry having a crush on the British beauty around 2011, and shortly after, they both made waves when reports claimed they were dating, specifically due to their age gap at the time. Harry was 17 and Caroline was 31 at the time.
Although neither confirmed nor denied a romance (Harry consistently said in interviews that they “just get on really well”), Caroline opened up about their connection years later in her autobiography, Storm in a C Cup, which was released in 2015. “I already knew that he had a crush on me, he’d made it pretty obvious,” she wrote in the book. “He’d said it in magazines and he’d said it to friends.”
“It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season,” she continued. “After that, anyone could say anything. In the street, people started shouting at me ‘pedophile’ and ‘pervert.’”
The two eventually split and moved on in their love lives, but sadly Caroline died by suicide at the age of 40 in Feb. 2020. Harry was spotted wearing a black ribbon as a “symbol of remembrance or mourning” to honor her at the 2020 BRIT Awards just a few days after her passing.
Emma Ostilly
Emma Ostilly, seen here at the 3rd annual amfAR Inspiration Gala New York at The New York Public Library in 2012, reportedly dated Harry in 2012. (MEGA)Harry was spotted kissing American model Emma Ostilly in New Zealand not too long after his split from Caroline in 2011. She later appeared in the One Direction music video for “Gotta Be You”, which premiered in November of that year.
Emily Atack
Emily Atack, seen here leaving The Palace Theatre in London, reportedly dated Harry in 2012. (Mega)Harry was rumored to be dating actress Emily Atack back in 2012 but she didn’t confirm it until 2014. “We were never boyfriend and girlfriend…We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions,” she told Reveal Magazine.
Caggie Dunlop
Caggie Dunlop, seen here attending Fran Cutlers Halloween party at The Berners Tavern in 2019, reportedly dated Harry in 2013. (MEGA)In 2012, Harry also reportedly dated actress Caggie Dunlop, who starred in the reality show, Made in Chelsea, for a brief time.
Taylor Swift
Harry Styles and Taylor Swift, seen here during a Dec. 2012 outing, dated in the later part of 2012 into the first few days of 2013. (Backgrid)Who can forget Harry’s romance with fellow singer Taylor Swift? The two apparently met and clicked at the 2012 Kids Choice Awards before they were later spotted on numerous outings together (often hand-in-hand) during the latter part of 2012, and even shared a kiss in New York’s Times Square on New Year’s Eve during the first minute of 2013. They apparently split just a few days into the new year, however, but Taylor put the memories of the relationship to good use in songs on her highly successful album 1989, which was released in 2014.
Many of the tracks on the musical masterpiece are reportedly about Harry, including “Style”, “Out of the Woods”, and “I Wish You Would”. It was also rumored that Harry’s song “Two Ghosts” from his self-titled debut solo album, which was released in 2017, was about their relationship.
Nicole Scherzinger
Nicole Scherzinger, seen here leaving Hakkasan restaurant in Mayfair in 2014, reportedly briefly dated Harry in 2013. (MEGA)The Sun reported that Harry and lead singer of the Pussycat Dolls, Nicole Scherzinger, briefly hooked up in 2013. She was a judge on The X Factor when Harry appeared on it in 2010.
Kendall Jenner
Harry Styles and Kendall Jenner, who reportedly dated on and off until 2016, are seen leaving Craig’s Restaurant. (Backgrid)Harry was first spotted having dinner in Los Angeles with Kendall Jenner in Nov. 2013. They were rumored to be dating until a split in Feb. 2014, but they seemed to be on again by 2015 and were seen canoodling on a yacht during the first days of 2016. Although they never confirmed their relationship, Kendall’s sister, Khloe Kardashian, admitted she thought they were “dating” in a 2016 interview with ET Online.
“Do I think they’re dating? Yes,” she told the outlet. “I don’t know if they’re like boyfriend-girlfriend. Nowadays I don’t know. People are weird with stuff. So, I don’t know their title.”
Erin Foster
Erin Foster, seen here at the 2017 Baby2Baby Gala, reportedly dated in 2014. (MEGA)Harry and writer Erin Foster were first spotted getting pumpkins at a pumpkin patch in 2014 and dating rumors started swirling right away. The blonde beauty was known for being Gigi and Bella Hadid‘s (now ex) stepsister and her romance with Harry seemed to be short-lived.
Nadine Leopold
Nadine Leopold, seen here at the CFDA Fashion Awards in 2019, reportedly dated Harry in 2014. (MEGA)Nadine Leopold was reportedly the first Victoria’s Secret model Harry ever dated. They were first seen together in Nov. 2014 and followed that outing up with some frozen yogurt dates, but by March 2015, things seemed to be over.
Sara Sampaio
Sara Sampaio, seen here at the 2020 Vanity Fair Oscars party, reportedly dated Harry in 2015. (MEGA)Harry was seen kissing another Victoria’s Secret model, Sara Sampaio, in New York in 2015. The Portuguese pretty lady was also spotted leaving Harry’s hotel the following day.
Georgia Fowler
Georgia Fowler, seen here during a 2019 outing, reportedly dated Harry in 2015. (MEGA)Harry and model Georgia Fowler, who is from New Zealand, reportedly dated for a brief time in Oct. 2015. He was seen playing the board game Scrabble with her in a Snapchat video she posted around the same time.
Tess Ward
Tess Ward, seen here at the an event at the Australia House at The Strand in London in 2018, reportedly dated Harry in 2018. (MEGA)Harry reportedly had a brief relationship with chef and flood-blogger Tess Ward in the spring of 2017, but by June of the same year, things ended and she was soon seen back with her ex.
Camilla Rowe
Harry Styles and Camille Rowe, seen here after enjoying a dinner together in Hollywood in 2018, dated for a year. (MEGA)The third Victoria’s Secret supermodel Harry was romantically linked to was Camille Rowe in 2017 and 2018. Fans first started speculating they were dating when a voice that sounded like Harry’s could be heard in one of the French-American beauty’s Instagram stories. They were seen together on multiple occasions but split up after a year. One of Camille’s voicemails can be heard in Harry’s heartbreaking song “Cherry” from his 2019 sophomore album, Fine Line.
