Harry Styles has always been notoriously private regarding his love life. Since rising to fame in One Direction, Styles has been in his fair share of high-profile relationships. Even early into his career, he made headlines for his romance with the late Caroline Flack. Less than a year later, his paparazzi photos with Taylor Swift went viral after the rumored couple was spotted on a date in Central Park. Styles has also been linked to several Victoria’s Secret models, including Kendall Jenner and Camille Rowe. The “As It Was” singer dated his Don’t Worry Darling costar Olivia Wilde for nearly two years after her very public split from Jason Sudeikis. Despite the controversy surrounding their relationship, Styles maintained his stance on keeping his romances private. “I’ve never talked about my life away from work publicly and found that it’s benefited me positively. There’s always going to be a version of a narrative, and I think I just decided I wasn’t going to spend the time trying to correct it or redirect it in some way,” Styles previously told Rolling Stone. After his split from Wilde, the pop star was seen in June 2023 hanging out with actress Taylor Russell before they split the following May. Then, in August 2025, he was romantically linked to actress Zoë Kravitz when the two were spotted on a stroll in Rome; they’ve been spotted together in New York City in recent days ahead of his Saturday Night Live appearance on March 14. Here’s a look back at Harry Styles’ dating history. Felicity Skinner Before Styles was a megastar, he met one of his first girlfriends, Felicity Skinner, through a mutual friend. The two teenagers began dating, despite living in different cities. The couple remained together for almost a year before drifting apart. Looking back on the relationship, Skinner says Styles was a great boyfriend. “He was a really good boyfriend, very romantic and, yes, shy. He was good looking and obviously I found him very attractive. We were together for just under a year … We just clicked straight away and got on really well. He has a really cute smile. We started seeing each other when we were both about 15. He was really sweet. It was puppy love and we were definitely each other’s first loves,” Felicity shared in an interview. Caroline Flack Karwai Tang/WireImage In 2011, Styles was linked with television personality Caroline Flack. At the time, One Direction had recently wrapped their run on The X Factor, and Flack had just begun hosting a spin-off show, The Xtra Factor. The couple, who had a 14-year age gap, went on to date for several months. They split in early 2012, with Styles tweeting that it had been a “mutual decision.” “Please know I didn’t ‘dump’ caroline. This was a mutual decision. She is one of the kindest, sweetest people I know. Please respect that,” Styles posted. Flack looked back on the brief relationship in her 2015 autobiography Storm in a C Cup, where she explained that things had been going well until their romance was made public. It wasn’t long before the public’s scrutiny of their age gap led to the relationship’s demise. ”We were both single, we got on well and we had a laugh. It was only when it became public knowledge that things turned sour. At the beginning it was all very playful. He joked about being attracted to older women. 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. After that
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