Kendall Jenner’s Complete Dating History, from NBA Players to Gigi Hadid’s Brother

STYLECASTER | Kendall Jenner Dating History
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Kendall Jenner’s dating history is somewhat of a mystery. Unlike her sisters, who have been in longterm relationships for most of their lives, the 23-year-old model has never confirmed any of her boyfriends, which makes fans wonder even more about who she’s dating. And though the Keeping Up with the Kardashians star has never been insta-official with any of her beaus, there are countless news articles about who she may or may not be hooking up with.

The speculation around Jenner’s dating life has been so intense that in 2017, the E! personality shut down longtime rumors that she’s gay. “I think it’s because I’m not like all my other sisters, who are like, ‘Here’s me and my boyfriend!’” she said. “So it was a thing for a minute because no one ever saw me with a guy. I would always go that extra mile to be low-key with guys, sneaking around all the time. You don’t want to, like, look crazy.”

So, who has Jenner dated? There are a few NBA players and, of course, Gigi and Bella Hadid’s younger brother, Anwar Hadid, but who else has made it to her list of exes? We did the hard work and found out.

Julian Brooks (2012 – 2013)

Fans of Keeping Up with the Kardashians may recognize Brooks, Jenner’s high school boyfriend who she dated for a year when she was 17. The couple, who met at Los Angeles’s Sierra Canyon School, broke up in 2013 after Brooks moved away to college and Jenner suspected he was cheating. Brooks went on to become a wide receiver for the University of Nevada’s Nevada Wolf Pack. “He would disappear for days and not answer Kendall’s text messages,” a source told Star magazine. “[She] couldn’t live with the doubt.”

Young Jinsu (~October 2013)

Rumor has it that Jenner moved on to rapper Young Jinsu soon after her breakup with Brooks. The rumored relationship, which lasted a “few months,” was controversial because of Jenner and Jinsu’s age difference. Jenner was 17, while Jinsu was 21. Rumors started after Jinsu posted an Instagram of what fans believe to be his and Jenner’s hands making a heart. Jenner’s sister Kylie Jenner posted the same picture on her Instagram. “They have that spark right now—they’re just really feeling each other,” a source told People. “They’re not putting it out there yet.”

However, it looks like Jenner didn’t see the relationship as official. Soon after the news broke that she and Jinsu were dating, the E! personality took to her Twitter to deny that she was in a relationship with anyone. “Enough with the rumors! I’m single, people,” Jenner  tweeted.

Harry Styles (2013 – 2014; 2016)

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Boston, Live On Tour.

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Jenner and Styles were rumored to be in an on-again, off-again relationship, which started in winter of 2013. Rumors started when the two were seen leaving a restaurant together in November 2013. A couple months later, they were seen together again at California’s Mammoth Mountain, where they were spotted skiing and snowboarding. “Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on,” a source told People. “Harry was a gentleman and even offered to carry Kendall’s snowboard to the ski lift.” However, a few months into their relationship, the young romance seemed to fizzle out. (“Things never got serious,” a source told People.)

Rumors started again in December 2015 when the two were seen having dinner and kissing on a yacht in Anguilla—then St. Barts. Jenner’s sister Khloé Kardashian even confirmed that the two were casually seeing each other. “They were hanging out together. Do I think they’re dating? Yes. I don’t know if they’re like boyfriend-girlfriend. Nowadays, I don’t know, people are weird with stuff. So I don’t know their ‘title,’” she told Entertainment Tonight. But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.”

The two were seen together several times in 2017 before their romance ended again. It’s also rumored that Styles’s debut solo album, Harry Styles, which he released in 2017, is about his model ex. “Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap … and hope they know it’s just for them,” he told Rolling Stone.

Chandler Parsons (August 2014)

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let me fly

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In the time that Jenner and Styles were broken up, rumors circled that she was dating NBA player Chandler Parsons. Rumor has it that they dated in the summer of 2014 after Jenner’s mom, Kris Jenner, set the two up. “Mama Kris met Chandler a few weeks ago and was blown away by not only his good looks, but his promising B-ball future,” a source told the Daily Mail.

However, Parsons, a player for the Dallas Mavericks, denied the rumors, telling Chelsea Handler that the two simply share the same personal trainer and went to eat once with a group. “It’s kind of a long story. I train with Gunnar Peterson here in L.A. She works out before me, so I kind of just got to know her, and then we had dinner. And the next thing I know I was on TMZ,” Parsons said. “It was more of a group activity.” (Fun fact: Parsons was also rumored to have dated Jenner’s best friend, Hailey Baldwin.)

Lewis Hamilton (May – September 2015)

Jenner sparked rumors that she was dating British race car driver Lewis Hamilton in the summer of 2015 after she was seen wearing the driver’s chain in a group picture with Lewis at one of his races. Hamilton, who considers Jenner’s mom, Kris Jenner, a close friend, was seen again with the model later that year at New York Fashion Week—though he denies that they were dating. “Me and Kendall have been friends for a while, so we’re just friends,” Hamilton told E! News.

Orlando Bloom (Summer 2015)

Jenner was also linked to the Pirates of the Caribbean star in summer 2015. Two years after his divorce from Miranda Kerr, Bloom moved onto another model after he and Jenner were seen on a string of dates, including movies and sushi, in Los Angeles. Jenner was 19 at the time, while Bloom was 38. “The age difference doesn’t seem to bother them although it’s far too early for either to tell if it’s going to develop into something serious,” a source told The Sun.

While accepting the Britannia Humanitarian Award in October 2015, Bloom addressed the rumors, denying that he has dated—or even knows—Jenner. “And I don’t know Kendall Jenner, but if anyone has her number I would love it,” he said.

Jordan Clarkson (~ April 2016)

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#TheLand #BeTheFight

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Before she rekindled her romance with Styles, Jenner was rumored to be dating NBA player Jordan Clarkson (who plays on the Cleveland Cavaliers with Khloé Kardashian’s boyfriend Tristan Thompson) in the spring of 2016. Rumors of the model and basketball player’s romance started in April 2016 when Jenner and Clarkson posted videos of each other at Coachella together on Snapchat. “They keep things low-key when they’re in public, but in private they’re very much together and affectionate,” a source told People. “He’s really into her.” Their romance ended after the summer, a few months before Jenner reunited with Styles.

A$ap Rocky (July 2016 – September 2017)

Jenner’s longest and most confirmed relationship was with rapper A$ap Rocky. The couple first started seeing each other in July 2016 when they were seen on a date in Paris, which involved them eating dinner, walking the City of Light’s streets and going out dancing. However, their romance didn’t become more serious until about a year later, when Jenner and Rocky were seen getting cozy at the 2017 Met Gala. Jenner’s sister Kim Kardashian even shared a Snapchat of Rocky grabbing Jenner’s butt as her younger sister Kylie Jenner laughed and watched.

Because of their busy schedules, couple stopped seeing each other in September 2017, though a source maintains that their relationship was never serious.. “Kendall and ASAP weren’t seeing each other a lot. They weren’t really official, but were obviously dating,” a source told Us Weekly. “Their schedules are really hard.”

Blake Griffin (August 2017 – February 2018)

Jenner and Griffin first started seeing each other in August 2017—around the same time that her flirtmance with Rocky was winding down—when they were seen leaving a Travis Scott concert together. A few weeks later, Jenner and Griffin were seen together again on a double date with Hailey Baldwin and Jenner’s rumored ex Chandler Parsons. In October, the couple went on another double date at Universal Studios’ Hollywood Horror Nights with Jenner’s sister Kylie Jenner and her boyfriend, Travis Scott.

At the end of November, around the time Jenner ended things with Rocky, she and Griffin made their relationship more serious. The couple’s relationship was trouble-free until February 2017 when Griffin was sued by his former girlfriend Brynn Cameron, whom he shares two young children with, for palimony. In the suit, Cameron alleged that Griffin “had no problem” trading her, “his former fiancée and mother of his two children, for reality television star Kendall Jenner.” She also claimed that Griffin “cared more about the glamour of dating a Hollywood celebrity than the day-to-day responsibilities of being a father and a family man.”

It was around this time that the two ended their relationship, though a source told People it was because their romance had run its course—not because of any particular drama. “They’ve definitely cooled off and are taking things at a slower pace, but not because of any particular drama,” the source said.

Anwar Hadid (June 2018 – November 2018)

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Rumors that Jenner and Hadid, the younger brother of Gigi and Bella Hadid, were dating started in June 2018 when they were caught making out by TMZ. Soon after, Jenner Instagrammed a photo of Hadid’s hands, which has the phrase, “I love you, my angel” on his hand. The two continued dating for several months, and in September, Anwar was even seen with a hickey on his neck. “They all hang out together and Gigi and Bella actually think they’re good together. Their friends think it’s a little weird, but it works,” a source told People.

Their relationship seemed to end in November when Jenner was seen with NBA player Ben Simmons. After the news that Jenner had moved on, Hadid took to his Instagram with a cryptic note about love: “I used to be afraid to feel things deeply cuz I felt as if the feeling of abundant happiness couldn’t be obtained forever, but openly feeling is now my only source of inspiration. And now that I’m not afraid to express my thoughts and feelings, I kinda feel like everything’s pretty mellow.”

Ben Simmons (November 2018 – Present)

In November 2018, People reported that Jenner was dating Philadelphia 76ers player Ben Simmons after her breakup with Anwar Hadid. “Kendall was spending time with Anwar [Hadid], but that ended and she started hanging out with Ben again. She hasn’t seen Anwar recently,” a source told People “When she’s not working, she’s been focusing her free time on Ben and flying to Philadelphia.” The source added, “They’re still not exclusive though.”

That same month, Simmons played against Tristan Thompson’s Cleveland Cavaliers, for which Khloé Kardashian’s boyfriend Tristan Thompson plays. After Jenner caught some heat for booing Thompson’s team, her sister took to Twitter to defend her behavior. “My sister was watching HER man Play against my man … So of course she’s going to heckle the opposing team,” Kardashian tweeted to a fan who questioned why she didn’t seem bothered by her sister’s actions.

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