Kendall Jenner’s Dating History Is Genuinely Impressive

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, Kylie and Timmy, Kim and Lewis…), 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 ’ship with Bad Bunny and her romance with Devin Booker to her previous on-again, off-again thing with Harry Styles and her current…entanglement with Jacob Elordi.

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:

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

“They are all going to end up hanging out regardless, so it seems like a simple situation, which could be a lot of fun,” a source said, adding that Kendall and Nick had “a flirty chemistry from the start.”

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.”

Kendall was briefly linked to Lakers player Jordan Clarkson, withUs 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 (via Elle), “They are super into each other. He is super sweet and a total gentleman and Kendall loves that.”

Back in August 2016, Us Weeklybroke the news that Kendall was “full-on dating” rapper A$AP Rocky. They even attended one of Kanye’s shows 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 Rocky and Rihanna are fully together and have three gorgeous babies.

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 began dating Dua Lipa (remember that??), 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, sadly—you truly hate to see it!

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:

View full post on Instagram

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

View full post on Instagram

And also 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, “The relationship ran its course.” Whomp!

Later in 2019, news broke that Kendall was maaaybe dating Lakers forward Kyle Kuzma. Well, technically, the Daily Mailclaimed 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.

Who was Kendall’s longest relationship with, 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:

View full post on Instagram

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 with 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 model also showed out to support Devin at an October 2021 game—the Suns won, and they smooched after (!!):

And the two were 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 2022, 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.”

However, all good things must come to an end, and the couple took their first break back in June 2022. At the time, Entertainment Tonight reported that Kendall and Devin were taking some time apart. As a source put it, “Kendall feels like they’re on different paths” and she and Devin “have had discussions about their future but they are not on the same page.”

And after getting back together shortly thereafter, they finally called it quits for good in the fall of that year, with a source reporting to E!that, “Their schedules weren't lining up...and eventually the relationship really took its course.”

Since then, the two have sparked reconciliation rumors on several occasions (like when it was reported that Devin and Kenny were “slowly navigating a restart” in February 2024…or when it was reported in February 2025 that Kendall and Devin were “very much together” again…) but at the moment, it seems like they’re dunzo.

I truly still feel like this one is a fever dream, tbh. But alas, it all started out with a tip on DeuxMoi revealing that Kenny and Bad Bunny had been spotted making out in a club, which the person behind the famous account confirmed when they said, “This single famous model sister was seen playing tonsil hockey with Bad Bunny at a private L.A. club last night. Word is he is in an open relationship.” In-ter-est-ing!

View full post on TikTok

Eventually, chatty sources revealed the two had indeed been “spending time together.” “Kendall recently started hanging out with him,” a source forPeoplesaid before revealing, “They were introduced by friends. He moved to L.A. a few weeks ago and bought a house. She likes him and is having fun. He is different from guys that she dated in the past. He is very charming.”

We all got to see the ’ship in action for ourselves with the two being spotted on everything from casual date nights to after-parties for the freakin’ Met Gala!

But by December 2023, multiple sources claimed the two had split, with an insider for Entertainment Tonight offering additional details: “Kendall and Bad Bunny have been doing their own things lately and things slowly started to fizzle out between them. They both knew going into this that it likely wouldn’t be a forever type of relationship and that was mutually understood from the get-go.”

The two briefly gave their ’ship another chance in May 2024, when People reported that Kendall and Bad Bunny were officially back together, but by September of that year, an Us Weekly insider claimed the two stars were “still friendly but have taken a step back and aren’t dating.”

It all started with a DeuxMoi post, alleging that Jacob and Kendall were “making out at Justin Bieber’s party” and “all over each other” following the first weekend of Coachella.

Soon after, The Sun reported that they actually hung out again the next day, with an insider saying, “Kendall is 100 percent Jacob’s type. I heard they’re having fun and he hung out with her Sunday, too…Him and Olivia are so done.”

The latest update? A Daily Mail source just claimed that Kendall and Jacob have actually “been together for a couple of months already, and it's going well. They were an item as far back as early February, so it's been a while. It helps that they have both been in Los Angeles a lot for the past couple of months, it has really given them time to bond.”

As always, we’ll keep you updated with any and all intel as soon as we know!