Untangling Harry Styles’ Star-Studded Dating History

But before Miley swoops in and makes it official with Harry, let’s take a look back at his incredibly star-studded dating history. Shall we?

Styles and the late X Factor host dated in 2011. Flack, who is about 15 years older than him, wrote in her 2015 memoir, Storm in a C Cup, “At the beginning it was all very playful. He joked about being attracted to older women. There was 12 years between us…no one seemed to be bothered then about the age difference.”

She said “it began to go wrong” after there was an unflattering tabloid story about her romance with him, in which she was dubbed a “classic me-first cougar” and “predatory older woman.” She said strangers called her “pedophile” and “pervert” to her face and that One Direction fans harassed and mocked her.

The U.S. model appeared in One Direction’s music video for “Gotta Be You” in 2011. A year later, the two sparked romance rumors after they were spotted kissing while out in Auckland, New Zealand.

He very briefly romanced the Made in Chelsea star back in 2012.

In 2012, Styles was romantically linked to the Inbetweeners actress. A year later, she told Reveal magazine, “We were never boyfriend and girlfriend. I think that’s the first time I’ve ever admitted to what it was, because I’ve always just shrugged it off before. But I think it’s best to clear it up. So, yeah, we had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions.”

Ah, they Haylor days. The superstar duo dated from the fall of 2012 to winter 2013. During that time, the two were famously photographed walking together in Central Park. “When I see photos from that day, I think: Relationships are hard, at any age,” Styles told Rolling Stone in 2017. “And adding in that you don’t really understand exactly how it works when you’re 18, trying to navigate all that stuff didn’t make it easier.”

“I mean, you’re a little bit awkward to begin with,” he added. “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.”

Since going their separate ways, they have both seemed to pen songs about one another: “I Knew You Were Trouble,” “Style” and “Perfect.”

In 2013, Styles and Rod Stewart‘s daughter were set up by a mutual friend, an insider revealed to E!. “Kim is very strong willed, she goes for what she wants and Harry appreciates that,” the source said. “She is exactly his type.”

The twe have occasionally sparked dating rumors on and off since 2013 and remain friendly. In December 2019, they showcased great chemistry as they reunited on The Late Late Show for a funny and pretty gross segment.

Styles and the Pussycat Dolls singer had a fling in late 2013 when he was 19 and she was 35, according to The Sun. Though the duo never confirmed the report, Scherzinger did raise eyebrows when she wore a T-shirt bearing the name “Harry Styles” while out in London in 2017.

Styles and the TV and Instagram star and David Foster‘s daughter dated for a bit in the fall of 2014. At the time, a source told E! News that the twosome had a romantic relationship going on right, but noted it was “nothing serious.”

Styles and the Austrian model first sparked romance rumors when they stepped out together in November 2014. Set up through her agent Jeff Azoff, they went on to date for several months before calling it quits in early 2015.

Nick Jonas‘ ex was linked to the boy bander in 2015 after she shared a snap of him playing Scrabble with her. And while many fans believe his 2017 hit “Kiwi” is about her, the New Zealand model isn’t sold. “Ah, don’t really know anything about it,” Georgia, who called Styles her friend, said in an interview.  “I think it’s highly unlikely.”

The pair and sparked romance rumors when they were spotted looking cozy while out together in NYC in June 2015. “She came over to his hotel and they grabbed dinner,” an eyewitness told E! at the time, noting they “hugged and kissed goodbye.”

During her romance with Styles in the summer of 2017, the chef and food blogger received an almost unbearable amount of online hate. “It’s been so weird, the hate messages…very bizarre,” she told The Times that year. “I’m not the kind of person who’s interested in fame, and if you’re put in an environment which you don’t understand and you can’t control and you don’t want, it’s horrible.”

Styles and the French-American Victoria’s Secret model dated for a year until summer 2018. And while he hasn’t outright said it’s her voicemail that plays at the end of his song Cherry, he did confirm those vocals were provided by an ex. “We’re friends and stuff, so I asked her if it was OK,” he teased, “And she was OK with it.”

This story was originally published on Friday, December 13, 2019 at 10:31 a.m. PT.