Kendall Jenner’s Ex Boyfriends And Dating History Uncovered – From Harry Styles To Devin Booker

21 November 2022, 16:57 | Updated: 21 November 2022, 17:09

Kendall Jenner's ex boyfriends include Anwar Hadid and Harry Styles
Kendall Jenner's ex boyfriends include Anwar Hadid and Harry Styles. Picture: Getty / Kendall Jenner/Instagram
Capital FM

By Capital FM

Kendall Jenner has split from boyfriend Devin Booker, but who has the usually low-key supermodel dated before?

Kendall Jenner has been linked to many famous faces over the years, including good pal Harry Styles, but she chose to keep her latest relationship with Devin Booker out of the spotlight.

After splitting and reuniting earlier this year, it's reported the couple have split for good due to their respectively busy schedules.

The supermodel only confirmed their romance on Valentine’s Day 2021 after almost a year of dating, but almost another two years on and Kenny is single again. But who has Kenny dated before?

Why Did Kim Kardashian And Pete Davidson Split?

Let’s take a look at Kendall’s boyfriend history and dating past…

Kendall Jenner and Devin Booker

Kendall Jenner and boyfriend Devin Booker
Kendall Jenner and now-ex boyfriend Devin Booker. Picture: Kendall Jenner/Instagram

Kendall and Devin, who split in October 2022, went Instagram official on Valentine’s Day 2021, almost a whole year after they were seen meeting up in lockdown.

They start dating in the spring, which is when the Kardashians star shut down some savage trolling about dating basketball players. The couple went on to confirm their romance by leaving a bunch of flirty Instagram comments on each other’s uploads.

They broke up in June 2022 before reuniting weeks later, but in October they split again. A source told PEOPLE: "Both have incredibly busy schedules right now with their careers and they've decided to make that a priority."

Kendall Jenner and Ben Simmons

Kendall Jenner and ex-boyfriend Ben Simmons
Kendall Jenner and ex-boyfriend Ben Simmons. Picture: Getty

NBA player Ben and Kendall dated between 2018 and 2019, keeping things out of the spotlight until they were seen cuddling in the background of a Snapchat Khloé Kardashian uploaded.

They had an on-off relationship, even going on a double date with her now-ex boyfriend Devin and his then girlfriend and former Kardashian family friend Jordyn Woods.

Kendall Jenner and Anwar Hadid

Kendall Jenner is close friends with the Hadid family
Kendall Jenner is close friends with the Hadid family. Picture: Getty

Yep, Kenny broke one of the ultimate girl code rules and dated bestie Gigi Hadid's little brother.

To be fair, the Hadid siblings hung out with Kendall A LOT so they were obviously cool with it, but it’s believed they briefly dated after becoming more than friends in 2018.

Their romance only lasted a few months and mostly consisted of them leaving love bites on each other’s necks.

Kendall Jenner and Blake Griffin

Kendall Jenner and Blake Griffin
Kendall Jenner and Blake Griffin. Picture: Getty

After basketball player Blake broke up with his fiancée Brynn Cameron, who he shares two kids with, he was photographed with Kendall everywhere they went back in 2018.

They didn’t last long though, ending things when he moved to Detroit.

Kendall Jenner and A$AP Rocky

Kendall Jenner and A$AP Rocky briefly dated in 2017
Kendall Jenner and A$AP Rocky briefly dated in 2017. Picture: Kim Kardashian/Snapchat

In 2016, Kendall and A$AP cemented themselves as one of the hottest showbiz couples of the year.

Remember the bum grab snap at the 2017 MET Gala?

Things soon fizzled out due to their busy schedules however.

Did Kendall Jenner date Harry Styles?

Kendall Jenner and Harry Styles at the 2019 MET Gala
Kendall Jenner and Harry Styles at the 2019 MET Gala. Picture: Getty

Ok, maybe this was the hottest showbiz couple – Kendall and Harry reportedly dated on and off from 2013 to 2016 but they remain very good friends to this day.

Their most recent interaction was when Harry blew Kenny a kiss as she watched him sing 'Love of my Life' at his 'Love on Tour' concert in LA on 15th November.

In 2019 they hosted James Corden’s Late Late Show together, a stint which not only proved they remain close friends but provided the kinda content we watched on a loop.

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