Kendall Jenner Dating History - Who's Kendall Jenner's Boyfriend?
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), 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. FYI, she’s broken her silence a couple of times recently, and also FYI—it’s next-level hot.
NICK JONAS: 2015
Dang, remember this? Kendall and Nick were linked right after he broke up with Olivia Culpo, with Us Weekly reporting 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.”
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:
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JORDAN CLARKSON: 2016
Kendall was briefly linked to Lakers player Jordan Clarkson, with Us Weekly reporting in March 2016 that they’d been hooking up for “months.”
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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.”
ASAP ROCKY: 2016 to 2017
Back in August 2016, Us Weekly broke the news that Kendall was “full-on dating” rapper ASAP Rocky. They even attended one of Kanye’s shows together:
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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 ASAP Rocky and Rihanna are fully together and have two gorgeous bb's.
A Love Story on These Two
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.
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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.
ANWAR HADID: 2018
Okay, so right before Anwar Hadid began 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 sadly, you truly hate to see it!
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:
Bendall went on to have many public moments, including a canoodle while celebrating Ben’s birthday:
Chilling (fine, from a distance) at basketball games:
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.” Whomp!
KYLE KUZMA: 2019
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!
EVGA, SARA, GICA//BACKGRID
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: 2020-2024 (on and off!)
Who was Kendall's longest relationship, 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 Jenner//Instagram
Kendall and Devin were first linked in 2020, at which point Kendall dealt with some trolling and delivered the perfect response:
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:
People//Instagram
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 two have gone on to celebrate their first anni (it was in June, FYI 😭), their bdays (she’s 28, he’s 27), and New Year’s together. Devin’s name was even added to Kris Jenner’s gingerbread house for Kendall one year (OMG, AW), so we knew for a fact that he was family-approved, too. The model also showed out to support Devin at an October 2021 game—the Suns won, and they smooched after (!!):
Kevork Djansezian//Getty Images
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.
Kevin Mazur//Getty Images
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 in 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.”
Obvi, Kenny went on to date Bad Bunny for a while (more on that below!), which made the fact that Devin and the model were “slowly navigating a restart” in February 2024 that much more !!!!!!!
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BAD BUNNY: February 2023-December 2023
I truly still feel like this one is a fever dream, tbh. But alas, it all started out with a tip on Deux Moi 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, “So I'm revealing it was Kendall Jenner and Bad Bunny, I have witnesses on the scene who saw her in the club.” In-ter-est-ing!
Cue: Everyone on Twitter having an absolute meltdown only to be driven even more 🌀🌀🌀 after they were then caught on a double date with Hailey and Justin Bieber. After this second sighting, a source told Entertainment Tonight that, “Kendall and Bad Bunny are attracted to each other and definitely have a flirty vibe. It is still new, but they’re enjoying each other’s company and like each other. They have mutual friends and had dinner with Hailey, Justin and friends at Wally’s in Beverly Hills on Saturday night. It’s been fun for both of them so far.”
The insider then added, “Bad Bunny recently bought a new home in Los Angeles and has spent a lot more time there. Kendall met him through a mutual friend and they hit it off. As of now, it’s not serious and the two are having fun.”
The celebs had a buncha fun being rich and hot, and even shot an iconic Gucci collab together.
However, they ultimately ended their 'ship in December 2023 with insiders telling Us Weekly, “Friends aren’t surprised that Kendall and Bad Bunny have broken up. They never really saw their relationship going the distance anyway. Of course, they want the best for their friend, but they really didn’t feel like Kendall was as compatible with Bad Bunny as she was in past relationships with other people. At the same time, Kendall has had a few on-off relationships in the past, so they wouldn’t be totally surprised if she got back together with him at some point.”
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As always, we'll keep you updated with any and all intel as soon as we know!
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