Kendall Jenner dating history: from A$AP Rocky to Devin Booker

Kendall is known for her supermodel status, as well as her families famous reality show – but what do we know about the star’s love life?

Despite being quieter about her love life than her Kardashian-Jenner sisters, Kendall has been rumoured to have had a few boyfriends over the years.

Here’s all we know about the model’s love life.

1. Devin Booker: 2020 – presentThe model shared a picture of her, her boyfriend and her dog. Picture: InstagramKendall and boyfriend of two years Devin Booker are going strong despite a blip in July 2022.Jenner previously “wanted space and time apart,” a source told E! News, adding that “they have been in touch since and do care about one another.”They have now been spotted together at a friend’s wedding and Kendall even posted an Instagram story of her and Booker together, indicating that the pair were back on.Booker towers over 5″10 Kendall. Picture: InstagramThe picture did not have Devin’s face in it, however it has seemed to confirm that the couple are back together. Since then, the two holidayed together in Idaho in a couples getaway.Despite usually being private about her relationships, Kendall frequently shares snaps of her basketball player beau.Talking to Andy Cohen during the ‘Keeping Up With The Kardashians’ reunion episode, Kendall confirmed she was dating the NBA star, claiming: “He’s my boyfriend”.The model also shut down claims that she only dates basketball players, saying: “No, I actually don’t only date basketball players, if anyone’s ever done their research.”.The two are pictured cuddled up. Picture: InstagramTheir relationship also made it to Instagram official, as the model and the Phoenix Suns player took to Instagram to commemorate their one year anniversary in June 2021.Jenner posted some cute pictures to her story, where the pair look adorably cosy.Before this, Jenner had previously been spotted on the sideline of his games and a fan even shared a pic of the star sitting alone. The pair have also been seen together on continuous outings.In September 2021, the model shared some cosy snaps from her Italian vacation with Booker on Instagram.Kendall Jenner cosied up to boyfriend Devin Booker on their Italian vacation. Picture: Instagram/@kendalljenner
2. Kyle Kumza: 2019 – 2020Kyle Kumza. Picture: GettyFollowing the Hadid brother, Kendall was said to be dating LA Lakers player Kyle Kumza.Rumours were fuelled when the pair were pictured together as they spent the 4th of July together on a yacht. However, despite rumours of their romance – neither of the pair confirmed if they were dating.
3. Ben Simmons: 2018 – 2019Kendall wore her boyfriends basketball jersey. Picture: GettyIn November 2018, People reported that Jenner was dating Philadelphia 76ers player Ben Simmons after her breakup with Anwar Hadid.The ‘818 Tequila’ owner was pictured at the players games and according to Elle, the two first dated in May 2018 and broke up in August 2018.However, dating rumors emerged again in November 2018 when Jenner started going to Simmons’ games again. The model was even seen wearing Simmons’ jersey.
4. Anwar Hadid: 2018Kendall dated Gigi and Bella’s brother. Picture: Getty
5. Jenner was also linked to her friends Gigi and Bella Hadid’s brother, when the pair were spotted kissing by tmz.A source speaking to People said that the two were “very, very together” and added that the Kendall’s two model friends even approved.Saying: “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.”.
6. Blake Griffin: 2017 – 2018The couple were spotted out together. Picture: Getty
7. In August 2017 dating rumours began between Brooklyn Nets player Blake Griffin and Kendall Jenner, when they were seen leaving a Travis Scott concert together.Following this, the two were seen together again on a double date with Hailey Baldwin and her then boyfriend.The couple went on another double date to Universal Studios, with Jenner’s sister Kylie Jenner and her boyfriend, Travis Scott.However, their relationship ended months later. A source told People their relationship came to a natural end and the break-up wasn’t because of any “particular drama”.However, their relationship ended months later. A source told People their relationship came to a natural end and the break-up wasn’t because of any “particular drama”.
8. A$AP Rocky: 2016 – 2017The pair were originally spotted together in Paris. Picture: Getty
9. Kendall was rumoured to have dated rapper A$AP Rocky after they were spotted on a date in Paris in July 2016.However, the pair were said to be serious about a year later, when Jenner and Rocky were seen getting cozy at the 2017 Met Gala.Kendall’s older sister Kim Kardashian even shared a cheeky picture on snapchat of the rapper grabbing the models bum.
10. Jordan Clarkson: 2016Clarkson played on the same basketball team as Kendalls sisters boyfriend, Tristan. Picture: Getty
11. The reality star was rumoured to have dated Cleveland Cavaliers player Jordan Clarkson, who plays alongside her sister Khloé Kardashian’s boyfriend, Tristan Thompson.Rumors of the model and basketball player’s romance began when the two posted videos of each other at together Coachella.Despite neither of them confirming the rumours, a source told People that Clarkson was “really into her”, saying: “In private they’re very much together and affectionate”.
12. Orlando Bloom: 2015the actor joked about Kendall whilst accepting his Britannia Humanitarian Award. Picture: Getty
13. Kendall was rumoured to be dating legendary actor Orlando Bloom during the summer of 2015. Rumours began after the pair were spotted together going on a string of dates.Some fans were concerned about the age gap, as Jenner was 19 at the time, while Bloom was 38 – but a source told the Sun that the pair weren’t concerned about it.The actor was also reported to have made a joke about the Jenner sister whilst accepting his Britannia Humanitarian Award in October 2015, saying: “And I don’t know Kendall Jenner, but if anyone has her number I would love it”.
14. Lewis Hamilton: 2015The model was rumoured to be dating the Formula One racer. Picture: Getty
15. Kendall was rumored to be 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 at one of Hamiltons races.The pair were then seen again at New York Fashion Week, although he has quoted telling E! News –  “Me and Kendall have been friends for a while, so we’re just friends”.
16. Chandler Parsons: 2014Chandler Parsons. Picture: Getty
17. Following Harry, Kendall was rumoured to have dated NBA player Chandler Parsons and according to the Daily Mail, even met her mum – Kris Jenner.However – the basketball star shut down the rumours, saying: “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”.Kendall didn’t speak on the rumours.
18. Harry Styles 2013: 2014, 2015, 2016The two have been rumoured to be dating on multiple occasions. Picture: Getty
19. The model and One Direction heart throb, Harry Styles, were rumoured to have dated when in 2013 until 2014, they were spotted together on multiple occasions and even went skiing together.Khloe Kardashian was also said to have confirmed that the pair were dating when they were spotted kissing on a yacht in Anguilla in 2015.Romance rumours were refuelled two years on when they were seen having dinner together in LA in April 2016.