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

Reflecting upon the intricate dance of love and friendship between Kendall Jenner and Harry Styles, I find myself utterly fascinated by their enigmatic relationship. As someone who has never had the privilege to mingle with the glitterati, it’s captivating to observe the twists and turns in these two lives that seem as unpredictable as a rollercoaster ride at an amusement park.


Harry Styles and Kendall Jenner are both highly accomplished in their individual fields. After the disbandment of One Direction, Harry has managed to establish a strong personal brand for himself, similarly to how Kendall has thrived in her career following certain events.

Instead, it’s worth noting that while Jenner first gained notoriety through “Keeping Up with the Kardashians,” she is currently recognized more for her modeling endeavors rather than her role in the reality series.

These two people have previously been romantically linked to famous personalities, but when they initially became a pair, they swiftly caught everyone’s attention, with followers eager for constant updates on their relationship.

From 2013 to 2019, there was speculation about the romantic connection between Harry Styles and Kendall Jenner, although they never officially confirmed it. If you’re not familiar with this famous duo’s relationship, here’s a brief overview of their romantic history: The Harry Styles and Kendall Jenner Relationship Timeline.

November 2013: The pair was photographed in West Hollywood

In 2013, following the conclusion of his relationship with Taylor Swift, images emerged of him exiting a restaurant and entering Harry’s vehicle with Kendall in West Hollywood. This incident fueled rumors almost immediately.

According to People, a source shared with the magazine at the time that they were “just friends”, and Kendall herself confirmed to her followers that she was unattached around X.

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

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

In the midst of speculations surrounding them back then, they were spotted enjoying winter sports like skiing and snowboarding in Mammoth, California on New Year’s Day 2014, according to reports from that media outlet.

According to a source, Kendall enjoyed snowboarding while Harry opted for skiing. They made a charming pair, with plenty of friendly banter and smiles exchanged between them. Notably, Harry demonstrated chivalry by helping Kendall carry her snowboard to the ski lift.

January 2015: Harry and Kendall go on a vacation

Back in January 2016, I found myself embarking on a tropical getaway aboard the luxurious yacht owned by the dynamic duo, Portia de Rossi and Ellen DeGeneres. As reported by People magazine, an inside source disclosed that while our paths crossed, no serious relationship ensued between us. The singer in question, captivated by the model’s allure, admitted to viewing her as “a tempting sight, eagerly anticipating another opportunity to spend more quality time together.”

The informant discussed their vacation, mentioning, “The New Year’s celebration was just right, and Harry really enjoyed it.”

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

Khloe, Kendall’s older sibling, confided to Entertainment Tonight that she believed both of them were seeing each other. She stated, “They were spending time together. To me, are they dating? Yes. I’m not sure if they’ve labeled it as a boyfriend-girlfriend relationship.”

In simpler terms, the founder of Good American said she wasn’t sure about their relationship status because people found such matters peculiar. She mentioned they were vacationing in St. Barts, which for her meant they were dating. Furthermore, she admitted she wasn’t certain if they had discussed their relationship officially yet.

That very April, People made public the model’s connection with Jordan Clarkson. Yet, whispers started circulating amongst us fans when someone on X alleged they spotted both Harry and Kendall out shopping in Los Angeles. I couldn’t help but wonder if there was a grain of truth to those rumors!

September 2016: Both give their romance another try

During this period, there were rumors that the musician and the famous Kardashian family member might rekindle their relationship. However, it was said that they were moving cautiously.

According to the report, it’s been indicated that they haven’t formally reconciled yet, but they’ve been keeping in touch and exploring how their relationship might develop further.

I affirm that the information shared indicates, “I realize he won’t commit, and I accept that’s simply his nature.” Furthermore, it’s important to mention that I admire the singer deeply, but my emotions towards him haven’t quite taken root yet.

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

During her 21st birthday celebration in Los Angeles, there were three individuals – Kendall, Harry, Clarkson, and Travis Scott (it was later revealed that Kendall and he started dating) – who were all present at the event.

A source close to the situation disclosed to the media outlet that during that period, she didn’t have a specific partner and evenly distributed her time among all of them.

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

During the launch of his first studio album, it was widely speculated on the internet that Harry Styles’ record was inspired by a particular model, following his conversation with Rolling Stone magazine.

He expressed that the woman who significantly influenced him played a significant role in the creation of the album. Furthermore, he mentioned, “At times you wish to doff your hat as a token of respect, and at other times you want to offer the entire cap… and pray they understand it’s meant specifically for them.”

May 2019: Harry and Kendall attend the Met Gala

As an over-the-moon fan, I couldn’t believe my eyes when I saw my two favorite stars gracing the Met Gala red carpet, each in their own glamorous splendor. To my delightful surprise, even though they arrived separately, a glimpse through my binoculars revealed them engaged in a heartwarming conversation during the event, according to the latest reports.

1. It’s reported that both individuals, along with their groups of friends, celebrated by partying together. At six in the morning, they were spotted leaving the post-party event. However, a reliable source informed the media that they weren’t romantically involved during that period; Kendall was actually dating Ben Simmons at the time.

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

As I graced the stage on James Cordon’s Late Late Show, I left everyone buzzing with excitement as we dived into the fiery game of Fill Your Guts Or Spill Your Guts. The heat really turned up when a model questioned me about the track from my last album that held a special melody for her. Rather than revealing the truth, I opted to take a bite of cod sperm instead!

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2024-08-16 17:38