Kendall Jenner’s Dating History Will Make You Thirsty, so Grab Water

You know your ex-boyfriends/ex-girlfriends? And how they fully suck? Same, same. We all relate. And by “we all,” I mean everyone but Kendall Jenner, whose exes are best described as hot/talented/cool/chill/💦.

Unlike some of her sisters who have been in highly publicized relationships (oh, just a few come to mind—Khloé and Tristan, Kim and Kanye, Kylie and Travis, Kourt and Scott, Kim and Pete, Kourt and Travis—ya know, not dramatic at all), Kenny seems to prefer that her love life stays out of the public eye. Which I totally respect. But I also respect ~your~ commitment to staying parched. So on that note, enjoy a somewhat thirsty trip through Kendall’s dating history, from her recent (ongoing!) romance with Devin Booker to her previous on-again, off-again thing with Harry Styles. FYI, she’s broken her silence a couple of times recently, and also FYI—it’s next-level hot.


Dang, remember this? Kendall and Nick were linked right after he broke up with Olivia Culpo, with Us Weekly reporting that Gigi Hadid set up Kendall and Nick (makes sense: Gigi was dating Joe at the time).

That said, Nick shut down the reports, telling E!, “We’re not dating. Kendall is great, and naturally, with her being good friends with Gigi and with Joe and Gigi dating, there are times we’ll be in the same place and we all hang out.”

HARRY STYLES: 2013 to 2016 (on and off!)

Remember when Harry Styles and Kendall Jenner were photographed hooking up on a boat? Classic. These two were dating on and off over the course of about three years—and most recently were spotted leaving the Met Gala together in 2019, which, 👀.

Here’s a pic of their cute vibes a few years back for reference:


Kendall was briefly linked to Lakers player Jordan Clarkson, with Us Weekly reporting in March 2016 that they’d been hooking up for “months.”

This fling was short-lived and no pics were snapped, but a source told People, “They are super into each other. He is super sweet and a total gentleman and Kendall loves that.”

A$AP ROCKY: 2016 to 2017

Back in August 2016, Us Weekly broke the news that Kendall was “full-on dating” rapper A$AP Rocky. They even attended Kanye’s show together:

And ah, yes, he grabbed her butt at the 2017 Met Gala:

The pair was linked for over a year, but eventually, Us Weekly reported that they “weren’t seeing each other a lot. They weren’t really official but were obviously dating. Their schedules are really hard.” Fast forward to 2022, and now A$AP Rocky and Rihanna are fully together.

BLAKE GRIFFIN: 2017 to 2018

In July 2017, NBA player Blake Griffin broke up with his fiancée (and the mother of his kids) Brynn Cameron and was seen with Kendall shortly after. Like, these two made sure to be photographed ev-er-y-where.

Around Valentine’s Day in 2018, Brynn filed a child support lawsuit against Blake, in which she partially blamed Kendall for their split. Per court docs: “Griffin had no problem trading Brynn Cameron, his former fiancée and the mother of his two children, for reality television star Kendall Jenner…Griffin cared more about the glamour of dating a Hollywood celebrity than the day-to-day responsibilities of being a father and family man.”

Truly, yikes. But it’s cool: A few months later, Blake moved to Detroit, effectively ending his relationship with Kenny.


Okay, so right before Anwar Hadid started dating Dua Lipa, Kendall was spotted—as TMZ delightedly put it—“sucking face” with Gigi and Bella’s little brother in early June 2018. She even Instagram Storied a picture of his hand on the night in question:

Apparently, Kendall and Anwar were “just having some fun while out with friends,” but PLOT TWIST: A few months later, she was seen making out with Anwar at a Fashion Week party. No photos were taken, but here’s a pic of Kendall hanging with the Hadids that same night:

A post shared by Kendall (@kendalljenner)

BEN SIMMONS: 2018 to 2019

Reports that Kendall and Ben Simmons were an item hit the news cycle in summer 2018, but the internet refused to believe anything until they had receipts. Luckily, they got ’em when the pair was (accidentally) caught cuddling in the background of Khloé Kardashian’s Fourth of July Instagram:

A post shared by Khloe Kardashian News (@khloesnapchats)

Bendall went on to have many public moments, including a canoodle while celebrating Ben’s birthday:

A post shared by The Shade Room (@theshaderoom)

Chilling (fine, from a distance) at basketball games:

A post shared by House of Highlights (@houseofhighlights)

And attending Drake’s party, which was awkward because Ben’s ex Tinashe was also there.

Sadly for those of you who were deeply invested in this narrative (anyone?), Kendall and Ben broke up in May 2019, with a source confirming to People that “the relationship ran its course.”


Later in 2019, news broke that Kendall was maaaybe dating Lakers forward Kyle Kuzma. Well, technically, the Daily Mail claimed Kendall and Kyle “took a romantic cruise” on a yacht during Fourth of July weekend before she headed to a party in Malibu and avoided her ex Ben Simmons. Here’s a blurry pic that proves approximately nothing!

Meanwhile, TMZ claimed the pair *wasn’t* dating, so who knows what was really going on. Hate it when tabloids can’t agree. Please, get it together, you guys.

DEVIN BOOKER: from 2020 onward

Who is Kendall dating now, you ask? That would be NBA star Devin Booker, who was snapped cuddling up to Kenny in 2021’s Valentine’s Day picture on her Insta Stories:

Kendall and Devin were first linked in 2020, at which point Kendall dealt with some trolling and delivered the perfect response:

A post shared by Comments By Celebs (@commentsbycelebs)

The couple then lowkey confirmed their relationship in August with this flirty moment:

And things quieted down in the winter, until Devin went ahead and reposted Kendall’s bikini pic in January:

In September 2021, Kendall actually opened up about the relationship to Jimmy Fallon, saying that he’s close to her nieces and nephews. “He loves them,” she said, adding, “Him and Stormi have an amazing relationship. She has the biggest crush on him, and I’m, like, jealous sometimes. I’m like, ‘Stop. Can you guys not?'”

The two have celebrated their first anni (it’s in June, FYI), their bdays (she’s 26, he’s 25), and New Year’s together. Devin’s name was added to Kris Jenner’s gingerbread house for Kendall (OMG AW), so he’s family-approved, too. Kendall even came to support Devin at an October 2021 game—the Suns won, and they smooched after(!!):

And the two were even spotted ~in public~ at the 2022 Super Bowl game with Hailey and Justin Bieber—the foursome apparently double date together a lot, casual. The guys were in sunglasses, the gals were snuggly in white tees—like, I want my life to look like that.

In March, Devin was asked about life in the spotlight (and his v public relationship) and said, “Honestly, I’m enjoying life to the fullest, and that came off my tongue so easily because it wasn’t always this way, but I feel like I’m in a good place right now…I love my family, I love the people around me, and I love the impact that I get to have on this world.” So, like, I can’t stop smiling?

Cool, that’s it, I’ll let you hop in the shower now. And we’ll keep ya updated (keep your eyes on their Instas, obv.)

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