Hot on the market! Kendall Jenner has dated some of the sexiest men in Hollywood and a few of the most skilled players on the basketball court.
The brunette beauty went Instagram official with pro baller Devin Booker on Valentine’s Day 2021 after months of speculation. They were first spotted on a road trip together in April 2020, and just one month later, Kendall was seen giving Devin a lift from Van Nuys Airport in Los Angeles.
They were then photographed enjoying dinner at Nobu in Malibu on August 15 and were joined by Kendall’s sister Kylie Jenner in photos obtained by TMZ. Their casual dinner came shortly after Kendall and Devin got flirty via Instagram in August 2020. The NBA star also gushed over her steamy bikini pic in January 2021.
An insider told Life & Style in March 2021 Kendall and Devin “are getting serious” and the model “definitely sees a future together.” However, the pair faced breakup speculation in June 2022 after reports surfaced that they called it quits.
Kendall and Devin reconciled that August and attended public events like the U.S. Open tennis tournament in September. Sadly, the former couple split the following month, Life & Style confirmed.
“Both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority,” a source told People, who was the first to report on their breakup.
While Kendall is clearly living her best life as she hangs out with the hottest bachelors, the Keeping Up With the Kardashians star has faced backlash for her dating life in the past. In a viral TikTok video of three men playfully tossing around a young girl, the caption read, “NBA players passing around Kendall Jenner.” Addressing the clip on Twitter, the starlet wrote, “They act like I’m not in full control of where I throw this cooch.”
The fashion icon was praised for her epic clapback by fans and friends alike. Even Kylie gave her seal of approval, writing, “Lmfao tweet of the year.” Kim and Khloé Kardashian also recognized their sister and praised her for being an independent woman.
When it comes to dating, Kendall definitely looks up to her older sisters for guidance. “I got a glimpse of how my sisters dealt with [the attention] and it’s cool to learn from that,” she told Vogue Australia in May 2019.
“For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier.”
Scroll through the gallery below to see Kendall Jenner’s dating history.
JULIAN BROOKS
Kendall’s dating history dates back to her high school days. Before graduating, the brunette beauty was in a relationship with Julian Brooks. He was a football player and she was a cheerleader, making them the perfect match on paper. The two dated for roughly a year before calling it quits in August 2013.
JUSTIN BIEBER
As Kendall became more high-profile, so did her boyfriends. The supermodel was linked to Justin Bieber from late 2014 to early 2015. The two sparked rumors when Justin shared photos with her in which he was getting a little too cozy. However, Kendall denied dating Justin. “No, he’s a longtime friend of our family,” she told Nightline at the time. “Everybody loves to assume things, but no. I’m truly focusing on my career. If it comes, it comes.”
HARRY STYLES
Kendall rang in 2016 with Harry Styles on a yacht St. Barts, and during their trip, they were photographed seemingly making out. Prior to that, she and the “Sign of the Times” singer were spotted having dinner a number of times. Their fling was short-lived, but it doesn’t seem like it ended badly. ~ Hendall ~ reunited at the 2019 Met Gala and based on a photo, they were having a friendly conversation.
JORDAN CLARKSON
Kendall and Jordan casually dated back in 2016. They were spotted at Drake’s 2016 American Music Awards afterparty together and seemed to be having a blast. “She was laughing the whole time! She was super giddy and loving every minute of it. It was obvious that they have a very playful, fun relationship,” an eyewitness told E! News at the time. “They were extremely affectionate and sweet towards one another. It’s obvious he makes her so happy!”
A$AP ROCKY
In July 2016, Kendall was linked to A$AP Rocky, but they weren’t exclusive, mainly because of their busy lives. “Kendall and A$AP weren’t seeing each other a lot. They weren’t really official but were obviously dating,” a source revealed to Us Weekly at the time.
BLAKE GRIFFIN
Like her sister Khloé Kardashian, Kenny sure seems to have a thing for athletes. In 2017, she was linked to basketball player Blake Griffin. They called it quits in April 2018 after seven months of dating.
ANWAR HADID
It wasn’t long until Kendall moved on with someone new. Photos of her making out with Gigi and Bella Hadid’s younger brother, Anwar, surfaced causing lots of speculation on whether or not they were an item. Regardless, it didn’t seem to be super serious because she began dating Ben Simmons shortly after.
BEN SIMMONS
Kendall and Ben first began dating in May 2018 but they split after a year of dating. “It wasn’t working out. They were long-distance too much of time, and it just fizzled,” a source told In Touch in May 2019. In February, the exes sparked reconciliation rumors after being seen together at Super LIV.
“Kendall and Ben are not officially back together,” another source told Us Weekly about their status at the time. “They both like having a no-strings-attached type of relationship with each other, for the most part. They both work and travel frequently and don’t find it very realistic to be in an exclusive relationship with one another.”
KYLE KUZMA
The model and the L.A. Laker linked up shortly after she split from Ben. Many speculated they were dating after being spotted on a boat together for the Fourth of July. “The two were hanging out over the holiday as friends,” a source told Entertainment Tonight at the time. “They’ve run in the same circle for a while and there’s no romantic relationship between them. Kendall is enjoying being single after ending things with Ben.”
DEVIN BOOKER
Kendall and Devin sparked dating rumors in April 2020 after the two were spotted on a road trip together to Sedona, Arizona, but kept their relationship on the down-low until Valentine’s Day 2021, when they made things Instagram official.
Later that year, after spending the holiday season today, a source exclusively told Life & Style that “they’re so in love,” adding that it’s “only a matter of time” before he pops the question.
However, in June 2022, rumors began swirling that the pair had split after they failed to acknowledge their two-year anniversary.
Life & Style confirmed their breakup the same month after an insider revealed they were “taking space to work on their own lives at the moment.”
The duo reconciled in August 2022, before breaking up once again that October.
BAD BUNNY
Kendall and the Grammy winning singer were spotted on what appeared to be a double date with her BFF Hailey Bieber and her husband, Justin Bieber. The foursome dined together at a Beverly Hills restaurant February 18, 2023, four months after Kendall’s split from Devin. Amid the possible new romance, eagle-eyed social media fans noticed the NBA star no longer follows his ex-girlfriend on Instagram, despite their amicable split, and Kendall has stopped following Devin.
The model and Bad Bunny continued to spark dating rumors when they were spotted hugging after enjoying dinner together in Los Angeles on March 7, 2023.
