Kendall Jenner is one of the more reserved of The Kardashians bunch, and has previously opened up about why she likes to keep her relationships and private life, well, private.
"If I'm not fully, fully in it with someone, why would I make it public to everyone else?" she explained to Harper's Bazaar in 2017. "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. People want to start drama. If I had a boyfriend, people are going to say all this stuff that's probably going to cause us to break up."
Fair play Kendall, that makes a lot of sense. But that doesn't stop fans being a little curious about who the 27-year-old model has dated in the past. So, want to take a look back on Kendall's dating history? Starting with the most recent update...
2023 - Bad Bunny
February 2023 saw a new cool celebrity couple hit the rumour mill: Bad Bunny and Kendall Jenner. The pair were spotted in a Beverly Hills restaurant having dinner with Hailey and Justin Bieber, while a rather interesting blind item on gossip Instagram account @Deuxmoi claimed: "This single, famous model sister was seen playing tonsil hockey with Bad Bunny at a private LA club last night."
In March, fans speculated Bad Bunny was throwing shade at Kendall's ex-boyfriend Devin Booker in his song ‘Coco Chanel’, in Spanish lyrics which said, "I’m not bad baby, that’s a gimmick / But the Puerto Rico sun is warmer than the one in Phoenix.”
Could this be taking aim at Kendall’s ex-boyfriend Devin Booker, who is an NBA basketball player for the Phoenix Suns?
Kendall and Bad Bunny (real name Benito Antonio Martínez Ocasio) were then spotted at Coachella, where he was headlining. In videos and pics shared on 16th April, the pair were seen whispering and leaning in together in the crowd, while Kendall was seen in the audience for his performance.
Finally, after four months of rumours, Kendall *kind of* addressed their relationship in an interview with WSJ Magazine. "No comment," she said when asked about Benito. "I try [to] find the balance of keeping things private and keeping things sacred, [and] also not letting the unfortunate frustration and stress of everyone trying to get in on it stop me from enjoying my side. Does that make sense? I'll go out of my way to do things as privately as possible because I just think that that's the healthier way of dealing with relationships anyway."
Fair enough.
2015 - Nick Jonas
Way back before he married Priyanka Chopra, Nick Jonas and Kendall Jenner were linked when a Us Weekly report claimed Gigi Hadid set them up (Gigi was dating Nick's brother Joe Jonas at the time). The source claimed, "They are all going to end up hanging out regardless, so it seems like a simple situation, which could be a lot of fun. They said Kendall and Nick had “a flirty chemistry from the start.”
But Nick quickly dampened reports, telling E! "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."
2013 - 2016 Harry Styles
The pair were first linked in 2013 when they shared a dinner date, before going skiing together over New Year into 2014.
They were then linked again when *those* photos of Harry and Kendall on Ellen DeGeneres' boat came out in early 2016. Khloé Kardashian confirmed they were a thing, telling Entertainment Tonight "Do I think they're dating? Yes. I don't know if they're like boyfriend-girlfriend."
Kendall's sister added, "Nowadays, I don't know. People are weird with stuff. So, I don't know their title. But I mean, they were in St. Barts together hanging out, so to me that's dating."
It's not clear when they split, but Harry opened up to Rolling Stone in 2017 about how his debut album was inspired by a special ex, "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."
Since then, the pair have been super friendly, with Kendall recently being photographed at Harry's Love On Tour gig in November 2022, while they also surprised fans with a joint appearance on The Late Late Show with James Corden in 2021.
2016 - Jordan Clarkson
When Kendall and Harry's relationship reportedly came to an end, Kendall was briefly linked to Lakers player Jordan Clarkson. Us Weekly said in March 2016 that they’d been hooking up for "months", adding, "they are super into each other. He is super sweet and a total gentleman and Kendall loves that."
The pair were never photographed together, mind.
2016 - 2017 - ASAP Rocky
Now this is a cool couple. In August 2016, Us Weekly said the pair were "full-on dating", when they attended Kanye’s Yeezy show together and he was pictured touching her butt at the 2017 Met Gala.
But sadly, their busy lives got in the way - Us Weekly later said "weren’t seeing each other a lot. They weren’t really official but were obviously dating. Their schedules are really hard."
2017 - 2018 - Blake Griffin
Kendall and Blake were linked multiple times over the course of two years. In August 2017, Jenner was spotted leaving a Travis Scott concert with Griffin, with a source later telling People, "Kendall is very happy with Blake. They started out more like friends, and then it was very casual. But it seems more serious lately. When they are not together, they keep in touch over the phone. Her family has accepted Blake."
By winter 2018, after they were spotted on multiple dates and were very much A Thing, another source said they'd called it quits. "They’ve definitely cooled off and are taking things at a slower pace, but not because of any particular drama," an insider told PEOPLE.
"He got traded and isn’t local anymore, so they’ve grown apart a bit just because of distance."
2018 - Anwar Hadid
Now this was a curveball. In photos obtained by TMZ, Kendall and BFF Gigi and Bella's brother Anwar were pictured all over each other, before sporting matching love bites a few days later. A source told E! at the time it was 'nothing serious', adding, "Kendall and Anwar have known each other for years and have always been flirtatious and this is just another sign of that. The two enjoy one another's company and things could change, but for now, it's nothing serious."
2018 - 2019 Ben Simmons
Now this got pretty serious. Reports that Kendall and basketball player Ben were an item hit the news cycle in summer 2018, and were later accidentally confirmed by Khloe Kardashian on 4th July, when she shared a video of them cuddling:
They spent Ben's birthday together, and went on multiple dates over the course of the year. By May 2019, though, Page Six reported the romance "ran its course", and Kendall and Ben decided to call it a day. PEOPLE added that the pair are "on a break", and that Kendall was enjoying "spending time with her friends and back to being in fun mode".
But wait! They were also pictured by TMZ on New Year's Eve in January 2020 at a rooftop bar and restaurant in Philadelphia, which Ben had rented out for a party. Were they back on? Or just friends?
Ben was later linked to Maya Jama in 2019, before taking their relationship public at Wimbledon in July 2021. Later, they went Instagram official to celebrate his birthday, with Maya sharing a sweet post with the caption, "Happy birthday to youuu," and tagging the basketball player. They then got engaged over Christmas 2021, before calling off their engagement due to distance in September 2022.
2020 - 2022 Devin Booker
Rumours surrounding Kendall Jenner and basketball star Devin Booker first started when they went on a road trip during quarantine to Arizona in April 2020. They shared matching Instagram photos (though not of each other), before flirting in the comments.
By September 2020, they were also reported to be on holiday together with Justin and Hailey Bieber. "Kendall and Devin have spent the past few weeks together," a source told People. "They have mostly enjoyed Malibu, but over the weekend, they were vacationing with Justin and Hailey in Idaho. They were all enjoying the lake life and also played golf." Exciting!
As of October 2020, it looks like Kendall and Devin are still very much an item as she invited him to sister Kim Kardashian's birthday celebrations on a private island with all her closest friends and family. Fans spotted the basketball player lurking in the back of a family photo which showed Scott Disick hugging son Mason.
"Kendall and Devin are hooking up and dating," a source confirmed to Us Weekly. "She invited him to Kim’s birthday and knew it would be easy for him to hang out with her family and friends.”
The source added, "Kendall likes Devin, and he doesn’t want her dating anyone else, but she wants to keep her options open. He makes her laugh, and they are so cute together."
In the two years that followed, Devin and Kendall *finally* went Instagram official, while also being papped together, with Kendall confirming their relationship at the final Keeping Up With The Kardashians Reunion episode. "He's my boyfriend," she told Andy Cohen in June 2021.
In June 2022, they reportedly called it quits for a bit, with a source at E! News claiming: "Kendall and Devin hit a rough patch recently and have been split for about a week and a half", though the pair were later photographed together looking loved up.
It wasn't until November 2022 that another report broke, suggesting they had split again. According to PEOPLE the pair quietly went their separate ways in October, with an insider claiming, "Both have incredibly busy schedules right now with their careers and they've decided to make that a priority.
"They have a lot of love and respect for each other and wish only the best."
