Harry Styles and Kendall Jenner's Relationship Timeline: Revisiting The Famous Exes' Past Romance

Here’s a look back at the relationship timeline of the famous Hollywood exes, Kendall Jenner and Harry Styles. Read ahead to know more.

Published on Aug 16, 2024  |  08:02 PM IST |  206.6K
Harry Styles (CC: YouTube) and Kendall Jenner (CC: Instagram)
Harry Styles (CC: YouTube) and Kendall Jenner (CC: Instagram)

Both Harry Styles and Kendall Jenner are two of the most successful figures in their respective lines of work. Both have followed a similar pattern in the sense that after the break up of One Direction band, Harry successfully created a name for himself.

On the other hand, Jenner, who initially rose to fame via Keeping Up With The Kardashians, is now mostly known for her modeling work more than the reality show. 

These two individuals have dated notable celebrities, but when they first got together, they instantly grabbed all the headlines as their fans always wanted to be updated about what was happening with the couple. 

Harry and Kendall never really confirmed their relationship but they were linked romantically from 2013 to 2919. If you are unaware of this Hollywood pair’s relationship, you are in the right place. Here’s a relationship timeline of  Harry Styles and Kendall Jenner.

November 2013: The pair was photographed in West Hollywood

Back in 2013, after the end of Harry's relationship with Taylor Swift, he was photographed with Kendall when they were leaving a restaurant and getting into Harry’s car in West Hollywood. This quickly sparked speculations.

As per People, an insider revealed to the publication at that time, “They're just friends,” along with Kendall assuring her fans that she was single on X. 

Harry Styles, Kendall Jenner and Cara Delevingne (CC: Getty Images)

They sparked rumors again the following month as they were spotted with Cara Delevingne at the British Fashion Awards at the London Coliseum. 

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January 2014:  Harry and Kendall are spotted during a skiing trip

Amid the rumors about the two at that time, both were seen skiing and snowboarding in Mammoth, California on New Year’s Day in 2014, per the outlet.

A source told the publication, “Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on." The insider added, "Harry was a gentleman and even offered to carry Kendall's snowboard to the ski lift."

January 2015: Harry and Kendall go on a vacation


They were seen vacationing in January 2016 as they boarded Portia de Rossi and Ellen DeGeneres’s Yacht. As per People, an insider revealed, “Things never got serious" between the two, and the singer thought that the model was, “hot and was sort of just waiting for a chance to spend more time with her again."

The insider elaborated on their trip saying, “New Year's worked out perfect, and (Harry) loved it." 

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January 2016: Khloe Kardashian reveals that Harry and Kendall were seeing each other

Khloe Kardashian (CC: Instagram)

Kendall's elder sister, Khloe made the revelation to Entertainment Tonight that she thought that both individuals were dating. She said, “They were hanging out together. Do I think they're dating? Yes. I don't know if they're like boyfriend-girlfriend.”

The Good American founder expressed that she did not know what their “title” was at that point as people were “weird” with this sort of stuff. She added that they spent time at St. Barts so for her that's “dating.” The reality star continued that she was not aware if they had had that talk yet.

In April of that same year, People confirmed the model’s relationship with Jordan Clarkson. But soon a fan on X claimed they saw both Harry and Kendall shopping together in LA. 

September 2016: Both give their romance another try

During this time, the musician and The Kardashians star were speculated to be giving their romance another chance but they were reportedly taking things slow.

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Per the publication, an insider said that they were not back with each other officially but were continuing to converse and see where things went.

The source added, "He's not going to settle down, and she understands that's just the way he is," adding that Kendall really liked the singer but her heart was not invested. 

November 2016: Harry shows up for Kendall’s 21st birthday


At that time, three people whose names were linked with Kendall, Harry, Clarkson, and Travis Scott (months later he and Kylie began their relationship) were present during the celebration of her 21st birthday in LA. 

An insider revealed to the outlet that during that time she was not with any particular individual and spent the same amount of time with all of them. 

April 2017: Harry's debut album was allegedly inspired by Kendall


When the vocalist released his debut album, Harry Styles, rumors about this album being about the model were making rounds online, especially after his interview with Rolling Stone.

He stated that the woman who inspired him was an enormous part of the album. He added, "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." 

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May 2019: Harry and Kendall attend the Met Gala


Both the celebrities attended the Met Gala separately. However, they were both spotted having a conversation during the event, per the outlet.

Both of them with their other friends partied and were seen leaving the afterparty at 6 am. A source told the publication that they were not dating and Kendall was seeing her then-boyfriend, Ben Simmons at that time. 

December 2019: Harry and Kendall appear on The Late Late Show

They surprised everyone as they appeared on James Cordon’s The Late Late Show and played the infamous game, Fill Your Guts Or Spill Your Guts. The game got a lot spicy when the model asked him which song in his last album was about her. Instead of answering that he chose to consume cod sperm.

ALSO READ: How Did John Krasinski Get Ryan Reynolds, George Clooney And Others Onboard For IF? Find Out

FAQ

How long did Harry and Kendall date?
Harry Styles and Kendall Jenner’s name was linked with each other on and off from 2013 to 2019.

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Journalist. Perennially hungry for entertainment. Carefully listens to everything that start with "so, last night...". Currently making web more

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Credits: People
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