Kendall Jenner’s Ex Boyfriends: Dating History Uncovered From Devin Booker To Bad Bunny

20 December 2023, 12:04

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 is no longer dating Bad Bunny, who she got with four months after her split from ex-boyfriend Devin Booker, but who has the usually low-key supermodel dated before? And who is her boyfriend now?

Kendall Jenner has been linked to many famous faces over the years, including good pal Harry Styles, Ben Simmons and even best friend Gigi Hadid's brother Anwar Hadid.

However, Kendall, the model of the Kardashian-Jenner family, is known for keeping her romantic life very private, meaning we're never entirely sure who is her boyfriend actually is.

Rumours emerged in March 2023 that Kendall was dating Bad Bunny following her split from Devin Booker, sparking everyone's interest in the supermodel's romantic history once more.

However, fast forward to December 2023 and Kendall and Bad Bunny, real name Benito Antonio Martínez Ocasio, have broken up after less than a year of dating – but we've got more on that below.

Here's a look at Kendall’s boyfriend history and dating past:

Kendall is no longer dating Bad Bunny
Kendall is no longer dating Bad Bunny. Picture: Getty

Kendall Jenner and Bad Bunny

Kendall and rapper Bad Bunny were first linked in February 2023 and their romance quickly hotted up, making a few low-key public appearances together here and there but mostly keeping their relationship out of the spotlight.

However, they broke up around November/December due to their busy schedules and knowing their relationship wasn't a 'forever' thing.

They were first spotted kissing in LA on a date night in February 2023 and gossip Instagram account Deux Moi reported showbiz's latest hottest couple. The Kardashian sister and rapper – whose real name is Benito – were apparently introduced through mutual friends.

Bad Bunny made headlines when he seemingly referenced Kendall's ex-boyfriend during his verse on Eladio Carrión’s song ‘Coco Chanel’. Listeners assumed he was making a dig at Devin's current basketball team, the Phoenix Suns.

He rapped on the track in Spanish: "I'm not bad, baby that's a gimmick / But the sun in Puerto Rico is hotter than in Phoenix / She knows it."

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

Kendall Jenner and Devin Booker

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

Kendall Jenner and Ben Simmons

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

Kendall Jenner and Anwar Hadid

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. Picture: Getty

Kendall Jenner and Blake Griffin

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

Kendall Jenner and A$AP Rocky

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.

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

Did Kendall Jenner date Harry Styles?

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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