Harry Styles Dating History

Harry Styles Dating History: Your Complete Guide To Harry Styles’ Previous Relationships

Celebrity

Ladies’ man! Since he became famous, Harry Styles has done a lot, and he’s had some very famous people by his side along the way.

In 2009, Styles was in the band One Direction, which competed on The X Factor U.K. The next year, he had a short relationship with Caroline Flack, who went on to host the singing competition. Then he started dating one of the most famous people in the world, Taylor Swift, but their relationship didn’t last long either.

“I think relationships are hard enough on their own, so I think you have to ignore everything from the outside,” the former boy bander told Us Weekly after he and the Grammy winner broke up in 2013. “When you’re just getting to know someone at the beginning of a relationship, you still feel like you need to know everything about them. It’s weird when a lot of people who don’t know you tell you what your relationship is, even though they don’t know you. So I think you have to sort of ignoring it.”

Swift, on the other hand, made art out of her life. For her 2014 album, 1989, she cowrote several songs that fans thought were about Styles, like “Out of the Woods” and “Style,” which didn’t bother the Englishman.

“I don’t know if they’re about me or not… “The problem is that she’s so good that they’re all over the place,” he told Rolling Stone years later. “Everyone writes about what they’ve been through. If everything we went through helped make those songs, I’ll count myself lucky. That’s what makes you feel something. That’s the stuff I find hard to talk about, so I don’t talk about it much. That’s the part where the two people are talked about. I’ll never tell everyone everything.”

Styles dated Kendall Jenner, who is still one of his best friends today. He also dated models Nadine Leopold, Sara Sampaio, and Georgia Fowler for a short time. Then he went out with French beauty Camille Rowe, whose voice is on the song “Cherry” on his 2019 album Fine Line.

The singer said of Rowe’s voicemail, “When we listened to the album again, I asked her to add it in.” “I wanted “Cherry” to show how I felt at that time. I didn’t feel very good. It’s all about not doing very well. Because, when things don’t go the way you want, you become petty.”

Scroll down to see who Styles has been with in the past:

Caroline Flack

Caroline Flack
Caroline Flack

The Brits were together from 2011 to 2012. They were 14 years apart in age. Styles tweeted at the time that they had decided to break up together and that Flack was “one of the kindest and sweetest people I know.” The Love Island host took her own life in 2019. She was 40 years old.

Emma Ostilly

Emma Ostilly
Emma Ostilly

In April 2012, Styles was seen kissing the model, but their relationship never went anywhere.

Taylor Swift

Taylor Swift
Taylor Swift

On their second date, in December 2012, the two famous people were seen walking through Central Park in New York City. A month later, Swift and Styles broke up because of a fight they had while on vacation in the Caribbean. The 1D member “said something he shouldn’t have,” a source told Us at the time.

Kendall Jenner

Kendall Jenner
Kendall Jenner

Styles and the Keeping Up With the Kardashians star were first linked in 2013. Two years later, when they got close on a yacht in Anguilla, it led to rumours that they were back together. They saw each other again at the Met Gala in 2019 and on The Late Late Show With James Corden a few months later. A source told Us at the time, “Harry and Kendall have always been great friends.”

Nadine Leopold

Nadine Leopold
Nadine Leopold

From 2014 to 2015, Styles and the Australian model were seen together in Los Angeles more than once, but they never confirmed that they were dating in public.

Sara Sampaio

Sara Sampaio
Sara Sampaio

In June 2015, the singer of “Ever Since New York” was seen hugging and kissing the Portuguese model. It was said that they had spent the night together at a hotel in New York City.

Georgia Fowler

Georgia Fowler
Georgia Fowler

Fans thought they were dating after the New Zealand model posted a Snapchat video of her and Styles playing Scrabble together in October 2015. Some people even thought that the musician’s 2017 hit “Kiwi” was about Fowler, but she laughed it off. “I didn’t have a baby, that’s for sure. Since that’s what the song is about, I don’t think so,” she said on Australia’s The Morning Show.

Tess Ward

Tess Ward
Tess Ward

Us said in May 2017 that Styles and the London-based food blogger had met through mutual friends and were “casually seeing each other and had been on a few dates.” After a few weeks, they broke up.

Olivia Wilde

Olivia Wilde
Olivia Wilde

Styles was seen holding hands with the actress at the wedding of his manager Jeffrey Azoff in Montecito, California, in January 2021. The actress directed him in the upcoming movie Don’t Worry, Darling. Wilde and Jason Sudeikis had been engaged for seven years before they broke up. In April, they spent some time in Styles’ home city of London. In July of the same year, they took a trip to Italy.

After the couple was seen holding hands on a yacht off the coast of Italy, an insider told Us, “Olivia is really in love with Harry.” “He really makes her happy. He seems to have brought out a silly side in her. The fact that they don’t hide their relationship from the public is what makes it work. They don’t care who sees them putting on the PDA.

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