Keep it informal! Over the years, Kendall Jenner has maintained the secrecy of the majority of her relationships despite being linked to several well-known singers and sportsmen.
The Keeping Up With the Kardashians actress has dated a number of famous guys, including musicians Harry Styles and Nick Jonas and basketball players Ben Simmons and Devin Booker.
In a behind-the-scenes video for her Calvin Klein campaign in February 2020, the model stated, “I think you learn various lessons in every relationship. Therefore, I believe that I have gained knowledge through a wide variety of connections.
“Many of the relationships have taught me more about myself, which is the most significant lesson,” she continued. Also, what I’m looking for in a partner or a relationship.
The co-founder of Kendall + Kylie’s first known relationship was with Styles, to whom she was originally connected in 2013 before reigniting romance rumors two years later when traveling to Anguilla with the former One Direction member.
The two have maintained their closeness after parting ways, as Jenner has done with other of her ex-boyfriends.
In December 2019, a source exclusively revealed to Us Weekly that Harry and Kendall have always been close pals. It’s a simple, laid-back friendship.
Although the reality star seldom discusses her personal life, she has retaliated against detractors who have incorrectly remarked on her former relationships.
A social media user claimed in July 2019 that Kendall Jenner was linked to a full starting lineup by writing, “This is a playoff team lol,” next to a picture labeled, “Starting 5 of NBA Players Kendall Jenner Dated.”
D’Angelo Russell, Jordan Clarkson, Simmons, Kyle Kuzma, and Blake Griffin were the five sportsmen included in the meme.
Jenner responded, “2 out of 5 correct, thanks,” alluding to her relationships with Simmons (whom she dated intermittently from May 2018 to May 2019) and Griffin (whom she romanced from September 2017 to March 2018).
After she was photographed cuddling up to Booker in April 2020, Jenner once more corrected a troll who had made light of her love past with basketball stars.
“Nba players throwing around Kendall Jenner,” a social media user captioned a video showing three guys playfully tossing a tiny girl in a circle. Maybe she’s spreading them around, a second user retorted.
They act like I’m not fully in charge of where I toss my cooch, the E! personality retorted.
Look back at the model’s illustrious relationships through the years by scrolling down:
After having dinner together and going skiing at Mammoth Mountain in California in January 2014, Jenner and the ex-member of One Direction were initially connected. On boats in Anguilla and St. Bart’s in December 2015, they were seen cuddling up and kissing once again. Despite the briefness of their relationship, the two have remained close. Jenner even supported Styles in the crowd at one of his gigs at The Forum in Inglewood, California, in July 2018.
The “Jealous” singer and the star of Keeping Up With the Kardashians were set up by her pal Gigi Hadid and Joe Jonas, who were dating at the time. They had a brief relationship in the summer of 2015. There was an evident appeal, a source told Us Weekly at the time. Nick was single and wanted to date. He genuinely believes she is attractive.
In March 2016, Jenner began dating the Cleveland Cavaliers point guard. The next month, they went to the Coachella Valley Music and Arts Festival together, and the Fourth of July was subsequently celebrated at a party in Malibu. But soon after, their relationship ended.
In late July 2016, the reality star began spending time with the rapper of “F—kin’ Problems.” In April 2017, they went to a Coachella party, where a bystander told Us that the pair “were really intimate and super tight.” The next month, Jenner and Rocky went to the Met Gala together and once more displayed lots of PDA. Despite their hectic schedules, a source told Us in September 2017 that the two “weren’t exactly formal, but were plainly dating.”
In September 2017, Jenner and the point guard for the Detroit Pistons started dating. A month later, a source close to the model told Us that the two had formalized their relationship and were now a “full-on couple.” She backed him during one of his comedic performances and sat courtside at numerous of his basketball games. In March 2018, Jenner said to Vogue, “I’m happy. He’s quite pleasant. Later on in the month, they split up.
After a brief engagement with singer Tinashe, the E! celebrity began seeing the Philadelphia 76ers point guard in May 2018. The pair were “dating and exclusive, albeit not ‘formal,'” a source told Us in July. In spite of this, they spent the summer renting a $25,000 per month house in West Hollywood. Along with her sister Khloé Kardashian and Tristan Thompson, they also visited Puerto Vallarta in Mexico. But a source told Us in September that the summer romance had ended. But soon after, they got back in touch, and in November, a source told Us that “they’re still hooking up and having fun.” In May 2019, the pair once more called it quits.
After stoking romance rumors in April while on a road trip to Sedona, Arizona, Us reported in June 2020 that the reality star and the Phoenix Suns basketball player were “hooking up” informally. The couple “are still seeing each other, but it’s not extremely serious,” a second insider told Us in October 2020. On Valentine’s Day in February 2021, Jenner and Booker made their romance IG official.
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When he attended Kourtney Kardashian and Travis Barker’s wedding in May 2022, things seemed to be taking a serious turn for the couple, but, according to sources, the wedding “put things into perspective” and the couple called it quits.
One insider said that as they “take this time to focus on themselves,” the couple hopes to “determine if a future together is what’s meant to be.”