The Most Famous Women Harry Styles Has Ever Dated

Harry Styles' dating history is lengthy and includes an A-list singer, famous actors, and plenty of models. While the "Golden" singer consistently dates people in the spotlight, he is adamant about keeping his love life private. In fact, he has barely ever confirmed any of his relationships. Speaking to Rolling Stone in 2022, Styles admitted that it was difficult to date as a public figure because he had to awkwardly warn all his romantic partners early on of all the ways in which the media could twist their relationship.  

"I've never talked about my life away from work publicly and found that it's benefited me positively," Styles explained. He asserted that he had made his peace with the fact that the media wouldn't ever stop twisting the truth of his life and he had no desire to try and sway the public narrative in a more favorable direction. The "Adore You" singer also touched on the struggles of dating in the limelight during his 2020 appearance on "The Howard Stern Show," saying, "It's always kind of a balance thing, because you want to date normally but then, you also want to protect it so it can be normal." Ultimately, all he could do was hope that he had formed a strong enough relationship with someone before the media storm began. Although Styles had remained coy about his relationships, he still stopped a show once to offer a little bit of friendly advice to a fan about her dating life.

Harry Styles got into a controversial age-gap relationship with Caroline Flack when he was around 17 and she was 31. Their paths likely crossed when One Direction appeared on the "X-Factor" aftershow, "The Xtra Factor," which Flack hosted, in 2011. In the British TV personality's 2015 memoir "Storm in a C Cup: My Autobiography," she shared that she was well aware that the "As It Was" hitmaker had a bit of a crush on her. Further, Flack stated that she didn't pay much mind to their 14-year age gap because she neither truly felt like she was a woman in her 30s and didn't behave like it either. Still, the pair decided to keep their romance under wraps because they were both employed under Simon Cowell's company. 

Although Flack and Styles had an easy-going relationship in private, things went south after the media broke news of it. "It began to go wrong when he was pictured coming out of my house one morning. And that was that. In the street people started shouting 'pedophile' at me in the street and 'pervert,'" Flack wrote in her memoir, per The Independent. In January 2012, the Grammy winner took to X, formerly known as Twitter, to confirm the end of their relationship and dispel a major rumor, writing, "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."

Harry Styles and Taylor Swift's paths apparently crossed at the 2012 Kids Choice Awards in March. However, the A-listers only sparked relationship rumors in November of that year after insiders told People that they were packing on the PDA while One Direction rehearsed their performance for "The X Factor." The pop stars were spotted on a few dates in the following month and even rang in the New Year by sharing a kiss at "Dick Clark's New Year's Rockin' Eve with Ryan Seacrest." 

Shortly afterward, Styles and Swift happily jet-stetted off to the British Virgin Islands. Unfortunately, things went awry during the getaway because the "Blank Space" hitmaker left their romantic vacation by herself on a boat, while her beau stayed back and hung out with Richard Branson. Later, an insider told the Daily Mail that they had decided to part ways after getting into an explosive argument on their romantic holiday.

After Styles looked back on photos of their Central Park date during his Rolling Stone interview in 2017, he stated that it helped him realize that "relationships are hard, at any age." He later added, "I mean, you're a little bit awkward to begin with. You're on a date with someone you really like. It should be that simple, right? It was a learning experience for sure. But at the heart of it — I just wanted it to be a normal date." Although the two singer-songwriters chronicled their heartbreak in their music, they ultimately remained on friendly terms and even shared a hug at the 2024 Grammys.

After Harry Styles and Taylor Swift's relationship ended, he swiftly moved on to another A-lister, Kendall Jenner. The model and the "Golden" singer first sparked dating rumors in November 2013 after being spotted sharing a meal in Los Angeles. However, an insider informed People that their dinner was platonic, and Jenner shared an X post to confirm that she wasn't seeing anybody. However, things supposedly weren't all that platonic when they took a New Year's trip to Anguilla in December 2015. At the time, an onlooker told People that Styles and Jenner appeared to be dating because of all their PDA. 

Then, in January 2016, an insider set the record on their romance to People by explaining that they had remained casual through the years, adding, "He has thought all along that Kendall is hot and was sort of just waiting for a chance to spend more time with her again." However, when Styles and Jenner's rumored relationship came up in Khloe Kardashian's Entertainment Tonight interview that same month, she shared that she believed they were dating but was unsure if they had officially decided to be exclusive. 

Meanwhile, in the Grammy winner's chat with Rolling Stone in 2017, Styles confirmed that Jenner had inspired his songwriting on his self-titled debut, asserting, "Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap ... and hope they know it's just for them." While their relationship status remained a mystery, they continued to see each other on and off in the following years.

Harry Styles fell for Olivia Wilde when she directed him for her thriller "Don't Worry Darling." Although the "Booksmart" director gushed about the "Falling" singer's acting abilities several times in 2020, they only sparked dating rumors in January of the following year after being photographed holding hands at a wedding. The couple was spotted on several dates throughout the year, and Wilde even showed up to support her beau when he took the stage for his Love On Tour show in Las Vegas.  

Wilde similarly cheered the Grammy winner on after he launched his nail polish brand, Pleasing, by reposting the announcement video to her Instagram Story and writing, "I find this very pleasing," per People. When Wilde spoke to Vogue in 2022, she shared that she paid no mind to people who critiqued their 10-year age gap or those who incorrectly assumed that she had ended her long-standing relationship with Jason Sudeikis to be with Styles. 

"I'm happier than I've ever been. And I'm healthier than I've ever been, and it's just wonderful to feel that," she stated. It's safe to say that their romance got more serious in 2022, as "The Tron: Legacy" actor brought her two children to Styles' concert in November. However, just a few days after the show, insiders told People that the couple was "taking a break." Although the "Watermelon Sugar" hitmaker and Wilde were never spotted together again, he still had an "Olivia" tattoo on his thigh in July 2023.

A few months after Harry Styles and Olivia Wilde parted ways, the Daily Mail shared photos of him making out with Emily Ratajkowski in Tokyo. Shortly afterward, an insider informed People that they were not officially dating, saying, "She hooked up with Harry, but they are not in touch every day. Emily is interested in seeing him again though." Unfortunately, it doesn't seem like the model got her wish because they weren't seen together again. 

Then, in June 2023, a TikTok user spotted the "Sign of the Times" singer on a date with Taylor Russell at an art gallery in London. The relationship rumors seemed more plausible in August of that year after TMZ shared photos of the "Bones and All" star at Styles' concert in Vienna. The Grammy winner then supported his rumored partner by showing up to the opening night of her play, "The Effect," a few days later. Although the pair never officially confirmed their relationship, they were spotted together on several occasions throughout 2023. 

In fact, in October, a confidant told Us Weekly that their romance was heating up, stating, "Harry definitely sees a future with Taylor." However, in May 2024, a source told The Sun that Russell and Styles had called it quits, explaining, "They went through a rough patch after their trip to Japan and are taking some time apart." They continued, "He's been in America and she's been in London. They made a lovely couple, and it was obvious Taylor made Harry happy."