Harry Styles and Kendall Jenner's relationship history: A look back at the famous exes' past romance

Both Harry Styles and Kendall Jenner are among the most successful personalities in their respective industries. Both have followed a similar pattern in that Harry successfully made a name for himself after the band One Direction split up.

Jenner, on the other hand, who first became famous through “Keeping Up With The Kardashians,” is now better known for her work as a model than for the reality show.

These two have dated well-known personalities, but when they first got together, they immediately made headlines as their fans always wanted to stay updated on what was going on with the couple.

Harry and Kendall never actually confirmed their relationship, but they were romantically linked from 2013 to 2019. If you don't know the relationship of this Hollywood couple, you've come to the right place. Here is a timeline of Harry Styles and Kendall Jenner's relationship.

November 2013: The couple was photographed in West Hollywood

Back in 2013, after Harry's relationship with Taylor Swift ended, he was photographed with Kendall as they left a restaurant and got into Harry's car in West Hollywood, quickly sparking speculation.

According to People, an insider told the publication at the time, “They're just friends,” and Kendall assured her fans that she was single at X.

The following month, they sparked rumors again when they were spotted with Cara Delevingne at the British Fashion Awards at the London Coliseum.

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

Amid rumors about the pair at the time, both were spotted skiing and snowboarding in Mammoth, California on New Year's Day 2014, according to the outlet.

A source told the publication: “Kendall was snowboarding and Harry was skiing. They were very cute together. There was a lot of flirting and smiling.” 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 holiday

They were spotted on vacation in January 2016, boarding Portia de Rossi and Ellen DeGeneres' yacht. According to People, an insider revealed, “It never got serious” between the two, and the singer found the model “hot and was kind of just waiting for a chance to spend more time with her again.”

The insider elaborated on the trip, saying: “New Year's Eve worked out perfectly and (Harry) loved it.”

January 2016: Khloe Kardashian reveals that Harry and Kendall met

Kendall's older sister Khloe revealed to Entertainment Tonight that she thought the two were dating. She said, “They were hanging out together. Do I think they're dating? Yeah. I don't know if they're in, like, a committed relationship.”

The Good American founder stated that she didn't know what her “title” was at the time because people were “weird” about that kind of stuff. She added that they were spending time in St. Barts, so for them, that was “dating.” The reality star went on to say that she didn't know if they had had that conversation yet.

In April of the same year, People confirmed the model's relationship with Jordan Clarkson. However, shortly after, a fan on X claimed to have seen Harry and Kendall together while shopping in LA.

September 2016: Both give their romance another chance

During this time, there was speculation that the musician and the Kardashians star would give their romance another chance, but they reportedly took it slow.

According to the publication, an insider said that the two are not officially back together yet, but are continuing to talk to see how things develop.

The source added, “He's not settling down and she understands that's just the way he is,” adding that Kendall really liked the singer but her heart wasn't set on him.

November 2016: Harry appears at Kendall's 21st birthday

At that time, at her 21st birthday party in LA, there were three people whose names are associated with Kendall: Harry, Clarkson and Travis Scott (months later, he and Kylie began their relationship).

An insider revealed to the outlet that she wasn't dating anyone in particular during that time, but spent equal amounts of time with everyone.

April 2017: Harry's debut album is said to have been inspired by Kendall

When the singer released his debut album, Harry Styles, rumors circulated online that the album would be about the model, especially after his interview with Rolling Stone.

He explained that the woman who inspired him was a huge part of the album. He added, “Sometimes you want to tip your hat, and sometimes you just want to give them the whole hat… and hope they know it's just for them.”

May 2019: Harry and Kendall attend the Met Gala

Both celebrities attended the Met Gala separately. However, according to the source, they were both seen chatting during the event.

Both were partying with their other friends and were seen leaving the after-party at 6 a.m. A source told the publication that they were not together and Kendall was dating her then-boyfriend Ben Simmons at the time.

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

They surprised everyone when they appeared on James Cordon's The Late Late Show and played the infamous game of “Fill Your Guts Or Spill Your Guts.” The game got particularly tense when the model asked him which song on his latest album was about her. Instead of answering, he decided to eat cod sperm.

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