Kendell Jenner’s Ex-Boyfriends Have Opened Up About What It’s Like To Date Her

Kendall Jenner is one of the Kardashian-Jenner family’s most private members. Kendall prefers to be a bit conservative, particularly when it comes to her relationship status, consciously keeping her romances off media platforms and as out of the spotlight as she can. This contrasts with a few of her siblings who have been involved in heavily publicized affairs. In an interview with Harper’s Bazaar in 2017, Kendall discussed the value of keeping her love life a secret: “Why would I tell everyone else about someone with whom I’m not truly in love? Why would I tell the world something that I am not even sure about?”

She went on to say, “It seems to me to be a sacred thing. It’s a private matter between the two of them, and nobody else’s viewpoint should be considered. People would say all of these things to my partner if I had one, which would definitely lead to our breakup.” Although the supermodel rarely discusses her private life, she has been associated with several well-known figures over the years. Here, we hear from some of her alleged partners about what it’s truly like to date her.

Kendall Jenner and Harry Styles were allegedly dating back in 2014 after they were spotted having dinner and skiing in California at Mammoth Mountain. Following this, the couple wasn’t seen together for a long, leading some to believe that they had broken up. However, in December 2015, they were cuddling and snuggling on a yacht, sparking reunion rumors. Harry Styles acknowledged that Jenner served as a major inspiration for his self-titled solo album in a 2017 interview with Rolling Stone. He said: “She’s a big part of the song, sometimes you just want to tip the hat, and sometimes you simply wish to give them the entire hat and wish they were aware it’s just for them.”

Following a shared interview on The Late Late Show with James Corden in 2019, where the pair played the well-known game Fill Your Guts or Spill Your Guts, the couple got praise for their natural chemistry. They never publicly acknowledged their relationship, although Kris Jenner admitted that they were together on the Ellen Show in 2021. Despite the short duration of their relationship, they have remained close friends, with Jenner frequently attending his performances. In fact, on November 14, 2022, Kendall Jenner was captured on camera performing and grooving at the performance.

Us Weekly revealed that Nick Jonas and Kendall Jenner were dating in 2015, reporting that Gigi Hadid ( then dating Joe Jonas) had arranged their meeting. This happened before Nick Jonas was reportedly married to actress Priyanka Chopra. The insider said the two “had a playful chemistry from the start.” We’re not dating; Nick Jonas swiftly proclaimed in response to the rumors. Since Joe and Gigi are dating and Kendall is amazing, it just makes sense that we occasionally hang out together when we are all in the same place.

A$AP Rocky and Kendall Jenner were reportedly dating in the summer of 2016 before he began seeing Rihanna, according to Page Six. The two looked delighted in photos taken at the 2017 Met Gala. The couple was seen celebrating together when they were dating in several cities across the world, and in 2017 they even attended Paris and Milan Fashion Show together. Despite appearing to spend plenty of time together throughout their brief relationship, the two split up by September 2017. According to reports, the couple ended their romance peacefully. Their hectic schedules reportedly prevented them from continuing their romance.

There were speculations that NBA star Devin Booker and Kendall Jenner were dating when the two were pictured traveling together while under quarantine in April 2020. Kendall Jenner asked Devin Booker to attend her sister Kim Kardashian’s quarantine birthday celebration in October 2020, which was held on a secluded island with all of their family and friends. After almost a year of romance, Jenner announced their relationship on social media by sharing a picture of them holding hands on Valentine’s Day in 2021.

Although Kendall is notorious for keeping her romantic life very secret, her romance with Devin Booker appeared to be a break from this trend. The couple made their romance known on social media over the course of the subsequent two years by posting coordinating Insta pictures and overtly flirting in the comments. In 2021 Keeping Up With The Kardashians reunion special, Kendall even formally acknowledged their partnership, telling Andy Cohen: “He’s my boyfriend.” During an episode on The Tonight Show with Jimmy Fallon, Kendall Jenner spoke about her relationship with Devin Booker, saying: “Him and Stormi have an amazing bond, girl does have the massive crush on him, and I’m envious sometimes.”

Devin said, “Honestly, I’m living life to the fullest, and that fell off my tongue so effortlessly because I feel like I’m in a good place right now. Devin finally opened up about his relationship with WSJ magazine in March 2022. I cannot help but smile because I love my family, the people in my life, and the impact I have to make on this planet. Devin dropped some pictures of Kendell on her 26th birthday with the caption, “The most beautiful woman.” Kendall Jenner shared a sweet Instagram Story video in June 2022 to commemorate her first year with Devin Booker.

In 2017, there were rumors that Kendall Jenner and Blake Griffin, a player for the Detroit Pistons, were “hooking up.” Unlike Kendall Jenner, who is typically discreet, the pair made their relationship known to the public. At some of his basketball matches, Kendall was courtside, and he even had Kendall’s support during one of his standup gigs. I’m happy; he’s extremely sweet,” Kendall Jenner said in an interview with Vogue in March 2018. However, the two are said to have broken up the next month. Griffin poked fun at Kendall Jenner in the Comedy Central roast of Alec Baldwin the year after that, in 2019.

Ben Simmons, an NBA star, was reportedly dating Kendall Jenner, according to Page Six in May 2018. The couple was said to have rented a $25,000 per-month house in West Hollywood during the summer of that same year. They momentarily broke up in September following their romantic encounter, but they quickly got back together and remained so until they announced their separation in May 2019.

Also Read: Is Tom Cruise Concerned About His Deep Fake Videos Going Viral On TikTok?


Estelle J. Garrido

Estelle J. Garrido

I'm a full-time blogger who loves to write about relationships, self-help and technology. I receive a fair amount of marriage proposals, but I am happily married to myself ? I really enjoy helping others realize how easy it is to find the right person and how to sustain healthy relationship.

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  1. […] Kendall Jenner is one of the Kardashian-Jenner family's most private members. Kendall prefers to be a bit conservative, particularly when it comes to her  […]

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