Kendall Jenner Relationship Timeline – Who Has Been Lucky Enough to Date the Most Graceful Kardashian
Kendall Jenner, the second youngest of the five Kardashian sisters, is perhaps the most different, for lack of a better word, branch of the Kardashian Family Tree.
While her parents and siblings for the most part are famous for finding themselves in scandals one way or another, the 27-year-old is a successful model, who attracts camera flashes for her graceful looks.
But there are two things that in certain ways connect her with the Kardashians: her appearance on the reality TV drama Keeping Up With the Kardashians and a long list of love interests. Let’s deep dive into every lucky individual who got to date Kendall!
Harry Styles – (2013-2016)
Harry Styles was one of Kendall Jenner‘s first partners that we know of. In 2013, he was still a part of the famous boy-band One Direction, who were touring around the world and making teenage girls crazy with their music.
Styles separated from One Direction in 2015, and a year later amicably put brakes on the romance with Jenner. The two remain friends to this day and she was even pictured enjoying his concert in Los Angeles in 2022.
Jordan Clarkson – (2016)
Let’s just say former Los Angeles Lakers star Jordan Clarkson kick-started Jenner’s love for the NBA which is still talked about on different platforms, mostly to roast the Kardashian family.
Us Weekly in March 2016 claimed the pair have been seeing each other for months and are “super into each other.” The couple’s image appeared on social media a month later, as they attended Coachella together.
A$AP Rocky – (2016-2017)
Jenner’s breakup with Clarkson didn’t get any spot in the newspapers. Rather, it only became clear that she has moved on when she was pictured attending Kanye’s Yeezy show with A$AP Rocky.
Later, the rapper and the supermodel were seen intimately hanging out at the 2017 Met Gala. But the relationship could only last for a year, and both got caught up in their respective commitments.
Blake Griffin – (2017-2018)
With Jenner coming out of her relationship with A$AP Rocky and Blake Griffin ending ties with Brynn Cameron, the duo found solace in each other in August 2017. The comfort with each other’s company, however, barely lasted six months.
But her relationship with the Basketball star got more limelight and laughs than most of her flings. At Alec Baldwin’s Comedy Central roast in 2019, Griffin thanked Caitlyn Jenner by jokingly stating: “On behalf of the entire NBA and half of the rappers on the Billboard charts, I want to thank you for giving your daughters their daddy issues.”
Ben Simmons – (2018-2019)
The summer of 2018 brought new links, with Jenner thought to be dating the Philadelphia 76ers star. Khloe Kardashian’s video on Snapchat confirmed their relationship as eagle-eyed users noticed Jenner cuddling with Ben Simmons.
Later, she went public with the romance suggestions on The Ellen DeGeneres Show in February 2019. But just a few months later PEOPLE confirmed their relationship “ran its course.”
Devin Booker – (2020-2022)
This might be Jenner’s longest relationship to date. And interestingly, it all started with a long getaway road trip to Arizona, where Devin Booker and Jenner were spotted at a rest stop in April of 2020.
Later in August, Booker appeared to make a spot for himself in the family, as he headed to dinner with Kendall and Kylie Jenner. In June, they celebrated their first anniversary.
However, by the next June, the romance had cooled down, and it was reported Jenner and Booker had called it quits. The next few months saw some hints (social media posts and public appearances) of the revival of the relationship. But in November, multiple outlets confirmed things between the two are over for good.
Bad Bunny – (2023–present)
Less than six months after Jenner’s purported break-up with Booker, Puerto Rican singer Bad Bunny dissed her ex in his track “Coco Chanel.”
The rumors of the two seeing each other started in February of this year, straight after Bad Bunny moved to Los Angeles. They went public with their relationship at Coachella.
Ever since, the Moscow Mule singer and the graceful model have been spotted enjoying each other’s company multiple times, including on the back of a horse in California.
