When Did Harry Styles And Kendall Jenner Date? Inside The Exes' Close Friendship

29 April 2021, 15:59 | Updated: 30 April 2021, 15:47

Kendall Jenner on the phone to ‘Harry’ in Kylie’s YouTube video

Capital FM

By Capital FM

Are Harry Styles and Kendall Jenner dating? Here's what we know about their close bond.

Harry Styles and supermodel Kendall Jenner have been close friends for years, with their close friendship often sparking speculation they're dating.

And after seeing how well they got along when Haz guest-hosted The Late Late Show for James Corden in 2019, fans began questioning once again whether the duo were dating, or have ever dated.

The pair were rumoured to have been dating in 2014 but they never confirmed their relationship.

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Here’s what we know about their friendship and former fling…

How did Harry Styles and Kendall Jenner meet?

Harry and Kendall are thought to have met in 2013 when they were introduced by their managers.

Did Harry Styles and Kendall Jenner ever date?

Harry Styles and Kendall Jenner have remained friends since their split
Harry Styles and Kendall Jenner have remained friends since their split. Picture: Getty

Harry and Kendall are said to have begun dating in 2013 until 2014, after they were spotted on a string of outings over a short few months and even went skiing together in January that same year.

They're thought to have had an on-off relationship before reuniting in December when they were pictured on holiday with their families in the Caribbean.

Harry and Kendall re-ignited romance rumours two years on when they were seen having dinner together in LA in April 2016.

They seemed to confirm their fling on The Late Late Show when the Keeping Up With The Kardashians star asked the singer which songs on his last album were about her.

She said: “I’m dying to know this” during a game of Spill Your Guts Or Fill Your Guts.

Harry’s reaction was to quickly tuck into the plate of cod sperm instead of answering the question.

Whether they were together or not, there’s no denying these two are genuinely close friends as fans couldn’t help but comment on how relaxed they looked in each other’s company.

Kendall's mother and momager Kris Jenner pretty much confirmed that they used to be an item when playing a Never Have My Kids Ever segment on The Ellen Show earlier this year, when asked if any of her children had dated a member of a boyband.

She went on to say "yeah" when asked by Ellen if she meant Kendall and the former One Direction star.

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Fans think Kendall Jenner and Harry Styles met up in 2021

In April 2021, fans of the stars were sent into meltdown after Kendall shared a snap of her dinner on her Instagram Stories, with many freaking out after speculating about whether or not Harry had joined her for the meal.

All that was visible from her dinner guest was dark brown trousers, a checkered blazer and an assortment of rings and black nail polish - which obviously caught the attention of some eagle-eyed fans.

Since they remained good pals, it wouldn't be a surprise for the pair to meet for a friendly catch up, as Kendall is dating NBA star Devin Booker, while Harry is rumoured to be dating his Don't Worry, Darling co-star, Olivia Wilde.

Was Kendall Jenner a Directioner?

Kendall Jenner was a true Directioner – after sharing this picture
Kendall Jenner was a true Directioner – after sharing this picture. Picture: Kendall Jenner/Twitter

Kendall posted an Instagram photo of herself many years ago holding up a One Direction banner she’d made, convincing the world she was a true Directioner.

How it wasn’t until she met the boys and realised how much of a big deal they were that she became a genuine fan.

Explaining the picture on The Late Late Show when Harry stepped in to present, Kendall said: “I didn’t really know… Someone asked me to do this photo and I wasn’t really sure what it was for.”

She continued: “I said, ‘sure’ and I wasn’t necessarily too aware of what One Direction was at the time, and then I became aware after meeting you and became a real fan. I’m a real fan.”

Whether they dated or not, we stan this friendship.

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