Taylor Swift, Kendall Jenner, More

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 then 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.”

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