Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More

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Ladies’ man! Harry Styles has accomplished a great deal since he rose to stardom — and he’s had some very famous faces by his side along the way.

One year after competing on The X Factor U.K. as a member of One Direction in 2010, Styles had a brief relationship with Caroline Flack, who went on to host the singing competition in a twist of fate. Then, he started seeing one of the biggest stars in the world, Taylor Swift, but they, too, had a short-lived romance.

“I think relationships are hard enough, so I think you have to completely ignore everything from outside,” the former boy bander told Us Weekly exclusively after his 2013 split from the Grammy winner. “When you’re in the opening stages of a relationship as it is, you’re still under the pressure of getting to know everything about a person. If you have a lot of people from outside telling you what it is and they don’t even know you, telling you what your relationship is, that’s weird. So I think you sort of have to block it out.”

Swift, for her part, turned life into art. For her 2014 album, 1989, she cowrote multiple songs that fans speculated were about Styles, namely “Out of the Woods” and the not-so-subtly titled “Style,” which did not faze the England native.

“I mean, I don’t know if they’re about me or not … but the issue is, she’s so good, they’re bloody everywhere,” he told Rolling Stone years later. “I write from my experiences; everyone does that. I’m lucky if everything [we went through] helped create those songs. That’s what hits your heart. That’s the stuff that’s hardest to say, and it’s the stuff I talk least about. That’s the part that’s about the two people. I’m never going to tell anybody everything.”

After Swift, Styles romanced Kendall Jenner, who remains one of his close friends today, and was briefly linked to models including Nadine Leopold, Sara Sampaio and Georgia Fowler. He most recently dated French stunner Camille Rowe, who lent her voice to his 2019 album, Fine Line, for the song “Cherry.”

“When we listened back to the album, I asked her to add it in,” the singer said of Rowe’s voicemail. “I wanted [‘Cherry’] to reflect how I felt then. I was feeling not great. It’s all about being not great. Because, you get petty when things don’t go the way you want it.”

Scroll down to take a look back at Styles’ dating history!

 

Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More
Caroline Flack
The Brits, who had a 14-year age gap, were in a relationship from 2011 to 2012. Styles tweeted at the time that their breakup “was a mutual decision,” calling Flack “one of the kindest, sweetest people I know.” The Love Island host died by suicide in 2019 at age 40.

David Fisher/Shutterstock; Richard Young/Shutterstock

Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More
Emma Ostilly
Styles was spotted kissing the model in 2012, but their fling never amounted to much.

Picture Perfect/Shutterstock; David Fisher/Shutterstock

Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More
Taylor Swift
The entertainers were famously photographed walking through Central Park in New York City in 2012 on their second date. A month later, Swift broke up with Styles over an argument they had during a trip to the Caribbean. A source told Us at the time that the 1D member “said something he shouldn’t have.”

Humberto Carreno/Startraks

Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More
Kendall Jenner
Styles and the Keeping Up With the Kardashians star were first linked in 2013 and sparked reconciliation rumors two years later when they got cozy on a yacht in Anguilla. They reunited at the 2019 Met Gala and again months later on The Late Late Show With James Corden. “Harry and Kendall are great friends and always have been,” a source told Us at the time.

Nick Harvey/Shutterstock

Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More
Nadine Leopold
Styles and the Australian model were spotted together in Los Angeles several times in 2015, but they never publicly spoke about their rumored romance.

Javier Mateo/Startraks; Kristina Bumphrey/Starpix/Shutterstock

Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More
Sara Sampaio
The “Ever Since New York” crooner was seen hugging and kissing the Portuguese model in 2015 after reportedly spending the night together at an NYC hotel.

Gregory Pace/Shutterstock; Jordan Strauss/Invision/AP/Shutterstock

Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More
Georgia Fowler
After the New Zealand model shared a Snapchat video of her and Styles playing Scrabble together in 2015, they had fans convinced that they were dating. Some people even speculated that the musician’s 2017 hit “Kiwi” was about Fowler, which she laughed off. “[I] definitely didn’t have a baby. That’s what the song’s all about, so I think it’s highly unlikely,” she said on Australia’s The Morning Show.

Gregory Pace/Shutterstock; Shutterstock

Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More
Tess Ward
Us exclusively reported in 2017 that Styles and the London-based food blogger were “casually seeing each other and [had] been on several dates” after meeting through mutual friends. They split just weeks later.

Richard Young/Shutterstock; Beretta/Sims/Shutterstock

Harry Styles’ Dating History: Taylor Swift, Kendall Jenner and More
Camille Rowe
The Dunkirk star sparked dating rumors with the French model in 2017 while attending a Fleetwood Mac concert in NYC. An eyewitness told Us at the time, “They looked really cozy. They seemed like they were having a good time and were enjoying each other’s company.” The pair dated for a year before calling it quits. Styles’ collaborator Tom Hull told Rolling Stone in 2019 that the breakup “had a big impact on him.”

MEGA; Laurent VU/SIPA/Shutterstock

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