Who Is Harry Styles Dating Now? From Taylor Swift To Kendall Jenner, A Look At His Most Popular GFs

Harry Swift had left many teenage hearts fluttering with his boyish charms and cute smile as part of the boy band, One Direction. After years, though his fans have grown up and the boy band parted ways long ago, Harry is still a heart-throb. However, despite his numerous love songs, Harry seems to have a complicated love life. But is there a new leading lady in the singer’s life? Here’s a look at Harry Styles’ dating history and his current relationship status.

Harry Styles’ controversial relationship with Caroline Flack in 2011

Harry Styles and Caroline Flack met each other when the former was competing in The X Factor and she was presenting the show. The two of them were linked in 2011, when Harry was 17 years old and Caroline was in her 30s. However, following a lot of trolling and criticism for their age gap, the two broke up. Sadly, Caroline Flack died by suicide in February 2020. In her autobiography, Storm in a C Cup, Caroline had revealed that things were going good between them before their romance became public. She had penned down:

“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 anyone could say anything. In the street people started shouting at me ‘p*dophile’ and ‘pervert’.”

Harry Styles and Taylor Swift’s brief romance

Taylor Swift and Harry Styles grabbed many headlines as their respective fandoms started speculating that romance was blooming between the two. They also took vacations together, and Harry met Taylor’s family. However, after a ‘swift’ romance, the duo broke up. In her music album 1989, Taylor has reportedly made subtle hints about her relationship with Harry Styles in the songs ‘Style‘ and ‘Out of the Woods‘. Currently, the two exes maintain a cordial acquaintance. In an interview with Rolling Stones in 2017, Harry had opened up about the relationship and shared:

“When I see photos from that day I think: Relationships are hard, at any age. 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. 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.”

Harry Styles and Kendall Jenner dated for a while

Harry Styles and Kendall Jenner have been linked since 2013. However, both of them denied the rumours and maintained the fact that they were just friends. However, in 2015, the pair was seen getting cosy on a trip and even shared a kiss. Kendall’s sister, Khloe, confirmed the relationship in an interview with Entertainment Weekly. The exact date timeline of when they broke up isn’t known, but they weren’t spotted together after 2018. However, now Harry and Kendall are on good terms with each other and were also seen on The Late Late Show, where their segment of Fill Your Guts or Spill Your Guts’ went viral.

Harry Styles included Camille Rowe’s voicemail in his song

After many linkups with several models, Harry Styles was rumoured to be dating Victoria’s Secret model, Camille Rowe. The two were spotted together several times during the time, and the model also attended a lot of Harry’s concerts. It’s unclear when the two broke up, but Harry Styles included a voicemail of Camille at the end of his song ‘Cherry‘. In an interview with Zane Lowe, Harry shared:

“It got added in later on, and it felt so part of the song. It just felt like it needed it. We’re friends and stuff, so I asked her if it was OK. And she was OK with it.”

Harry Styles and Olivia Wilde’s relationship and the negative attention it got

Olivia Wilde and Harry Styles met on the sets of her film, Don’t Worry Darling. A few months later, she split up from her long-time fiance. As Olivia and Harry were spotted together after this, many people accused her of leaving her partner. Additionally, the age gap between the two became a subject of trolling. However, Olivia once said that she doesn’t pay any heed to the negative attention. After a publicised and high-profile relationship, the two broke up to pursue their busy schedules. A source confirmed their break-up to People and shared:

“He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A. It’s a very amicable decision. They’re still very close friends. Right now, they have different priorities that are keeping them apart.”