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Kendall Jenner has historically been one of the most private members of the Kardashian-Jenner family. Unlike some of her sisters who have been in highly publicized relationships, Kendall tends to be more reserved, especially when it comes to her love life, choosing to keep her relationships off social media and as out of the limelight as possible.
Speaking to Harper’s Bazaar in 2017, Kendall shared her thoughts on the importance of keeping her love life private, saying: “If I’m not fully in it with someone, why would I make it public to everyone else? If I don’t even know what it is, why would I let the world know?”
She continued, “I think it’s something sacred. It’s something between two people, and nobody else’s opinion needs to be involved in it. If I had a boyfriend, people are going to say all this stuff that’s probably going to cause us to break up.” While the supermodel rarely speaks out about her personal life, she has been linked to several famous faces over the years, here’s what her alleged boyfriends have said about what it’s really like to date her…
7 Kendall Jenner And Harry Styles Had Effortless Chemistry Together
Kendall Jenner and former One Direction member Harry Styles were first linked back in January 2014 after having dinner and skiing together at Mammoth Mountain in California. After this, they weren’t spotted together for a while and people believed that the duo had called it quits, however, they sparked reconciliation rumors after the pair were spotted getting cozy and kissing on a yacht in December 2015.
In a 2017 interview with Rolling Stone, Harry Styles revealed that Jenner was a direct source of inspiration for his self-entitled debut album, saying: “She’s a huge part of the album, 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.”
The pair received compliments for their effortless chemistry in 2019 after a joint appearance on The Late Late Show with James Corden, during which the two played the popular game Fill Your Guts or Spill Your Guts. Although the duo never confirmed their relationship, Kris Jenner revealed that they were in fact dating on an Ellen Show appearance in 2021.
Though their romance didn’t last long, they have maintained a close friendship, with Jenner often attending his concerts. In fact, Kendall Jenner was photographed singing and dancing at the star’s concert on November 14, 2022.
6 Nick Jonas And Kendall Jenner Were Set Up By Gigi Hadid
Before Nick Jonas was happily married to Actress Priyanka Chopra, Us Weekly reported in 2015 that Nick Jonas and Kendall Jenner were dating, claiming that Gigi Hadid (who was dating Joe Jonas at the time) had set them up. The source claimed that the pair “had a flirty chemistry from the start.”
Nick Jonas quickly denied the reports, saying: “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.”
5 Kendall Jenner And Jordan Clarkson Had A Brief Fling In 2016
Kendall Jenner was rumored to be dating Cleveland Cavaliers player Jordan Clarkson in 2016. Us Weekly claimed that the duo had been hooking up for “months”, adding that: “they are super into each other. He is super sweet and a total gentleman and Kendall loves that.”
The pair reportedly attended Coachella Valley Music and Arts Festival together, and later celebrated the Fourth of July together at a party in Malibu. However, their romance fizzled out in the same year.
4 Kendal Jenner And Rapper A$AP Rocky Were A Loved Up Pair At The MET Gala
Before his longtime relationship to Rihanna, Page Six reported that Kendall Jenner and A$AP Rocky were dating in the summer of 2016, the two appeared enamored with each other when photographed at the 2017 Met Gala.
At the time of their relationship, the couple were photographed partying together in different locations worldwide and even attended the Paris and Milan Fashion Week together in 2017.
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Although the two appeared to spend a lot of time with one another during the brief time they dated, their rumored romance ended by September 2017. It was reported that the relationship ended amicably, they allegedly broke up due to their busy schedules that got in the way of them pursuing anything further.
3 Kendall Jenner Gave A Rare Insight Into Her Relationship With Blake Griffin
Kendall Jenner was linked to Detroit Pistons player Blake Griffin in 2017, with rumors circulating that the two were “hooking up”. In a rare moment for the usually private Kendall Jenner, the couple publicly confirmed their relationship.
Kendall sat court-side at several of his basketball games and even supported him at one of his comedy shows. In a Vogue interview in March 2018, Kendall Jenner gave a rare insight into their relationship, saying: “I’m happy, he’s very nice,” the two reportedly broke up the following month.
The following year in 2019, Griffin took a playful jab at Kendall Jenner during the Comedy Central roast for Alec Baldwin. The New York Post reported that he threw shade at Caitlyn Jenner, saying, “On behalf of the entire NBA and half the rappers on the Billboard charts, I want to thank you for giving your daughters their daddy issues.”
2 Kendall Jenner And Ben Simmons Were On And Off For A Year Before Breaking Up
Page Six reported in May 2018 that Kendall Jenner was dating NBA player Ben Simmons. In the summer of the same year, it was reported that the pair rented a $25,000-a-month home in West Hollywood. Their summer fling came to an end briefly in September, however, they reconnected their romance shortly after their split, staying together until they officially called it quits in May 2019.
Prior to their split, she told Vogue Australia that she was “maybe” considering marriage with the NBA star, saying: “Definitely not now, but maybe one day”
1 Devin Booker Was Kendall Jenner’s Longest And Most Public Boyfriend
Rumors that Kendall Jenner and NBA star Devin Booker were dating started circulating in April 2020 when the pair were photographed on a road trip together during quarantine. On October 2020, Kendall Jenner invited Devin Booker to sister Kim Kardashian’s now controversial quarantine birthday party that took place on a private island with all her closest friends and family. The supermodel confirmed their relationship after almost a year of dating on social media, by posting a photo of the duo cuddling on Valentine’s Day in 2021.
While Kendall is known for being very private with her love life, her relationship with Devin Booker seemed to be an exception to this rule. In the next two years that followed, the duo made their relationship public on social media by sharing matching Instagram photos and openly flirting in the comments. Kendall even confirmed their relationship to Andy Cohen in the 2021 Keeping Up With The Kardashians Reunion episode, saying: “He’s my boyfriend”
Kendall Jenner discussed her relationship with the NBA star during an appearance on the Tonight Show Starring Jimmy Fallon, saying: “Him and Stormi have an amazing relationship, she has the biggest crush on him, and I’m jealous sometimes.’”
In March 2022, Devin opened up about his relationship to WSJ magazine, saying: “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, So, like, I can’t stop smiling.” For Kendall’s 26th birthday, he shared photos of the supermodel, with the caption: “The most beautiful woman.”
In June 2022, Kendall Jenner posted a romantic Instagram Story message to mark her one-year anniversary with Devin Booker, she shared a collection of rare photos of the pair and captioned the photos: “365.”
They were an on and off again pair, reportedly calling it quits in June 2022, before shortly reconnecting and then calling it off again in November 2022.
