The Jenners and Kardashians are fairly open about their personal and romantic lives, seeing as they’re reality TV stars. But model Kendall Jenner is on the more private side. She told Vogue Australia in 2019 that she wants her love life to have more mystery than other aspects of her life.
“For me, a lot of things are very special and very sacred, like my friends and relationships,” she said. “I personally think that bringing things into the public makes everything so much messier.”
That being said, Jenner’s dating history is pretty well-documented because she tends to date other celebs, especially athletes. Here’s what we know about who Jenner has dated so far.
Harry Styles: 2013 and 2016
In November 2013, shortly after splitting up with Taylor Swift, Harry Styles was seen out with Jenner. However, they denied they were seeing one another romantically, maintaining that they were “just friends.”
By early January, the pair was traveling together, taking a New Year’s ski trip with some other celeb friends. The singer and The Kardashians star seemed to share a friendship and an on-and-off romantic relationship for several years. They were seen on another New Year’s trip to ring in 2016, this time in St. Barts on a private yacht.
“There has been a lot of flirting, touching and snuggling going on. They have acted like a couple. They look very cozy and happy,” a source told People at the time.
With interest in their connection renewed, Jenner’s older sister Khloé Kardashian weighed in on the seriousness of their romance.
“They were hanging out together. Do I think they’re dating? Yes. I don’t know if they’re like boyfriend-girlfriend. Nowadays, I don’t know, people are weird with stuff. So I don’t know their ‘title,’” Kardashian told Entertainment Tonight. “But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.”
She added, “I don’t know if they’ve had that talk yet.”
In November 2016, Styles was at Jenner’s birthday party, as was NBA star Jordan Clarkson, whom she had been rumored to be dating since March of that year. Years later, she and Styles seem to still be friends, but both have moved on.
“Harry was her first real relationship, so there is a lot of history there,” a source told People. “But they’re just friends.”
In 2017, Styles released his debut album. Fans believed he was talking about Jenner in a Rolling Stone interview when he spoke about a past partner inspiring his music.
“She’s a huge part of the album,” he said of the mystery muse. “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.”
In 2019, the pair seemed to be on good terms when they met on The Late Late Show and played “Fill Your Guts or Spill Your Guts.”
After reading one of the questions to herself, Jenner said, “I’m dying to know this: Which songs on your last album were about me?”
Rather than answer, Styles ate cod sperm.
In 2022, Jenner was seen at one of his concerts, enjoying some of the music that may be about her with sister Kylie Jenner and friend Hailey Bieber.
Nick Jonas: 2015
During the years she was on-off with Styles, it was rumored Jenner was casually seeing singer Nick Jonas as well. She met the Jonas Brothers star in August 2015 through his brother Joe Jonas, who was then dating model Gigi Hadid.
“Gigi wants Kendall around all the time,” a source told Us Weekly at the time. “She thinks it would be fun for all of them to hang out.”
Nick had recently split with girlfriend Olivia Culpo, and the insider claimed his texting with Jenner “had a flirty chemistry from the start.”
“Nick was single and looking to date, and there was an obvious attraction. He absolutely thinks she’s hot,” they continued. “When they’re ready, and it turns official, we’ll start seeing photos.”
That day did not come. He soon denied his connection with Jenner was romantic.
“We’re not dating,” he told E!. “Kendall is great, and naturally, 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.”
Jordan Clarkson: 2016
In March 2016, Jenner was seen with Cleveland Cavaliers star Jordan Clarkson, sparking rumors she was dating the basketball player. They made appearances all around Hollywood and eventually attended Coachella together.
“They keep things low-key when they’re in public, but in private, they’re very much together and affectionate,” a source said in April 2016. “He’s really into her.”
A few months later, another insider said, “He’s become really close friends with her group, and they’re still seeing each other, but it’s not a serious situation. Jordan’s been seeing other girls too.”
Like Styles, he was at Jenner’s 21st birthday in November of that year, but things fizzled out soon after.
A$AP Rocky: 2016-2017
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Before A$AP Rocky started dating Rihanna and welcomed two sons with her, Riot and RZA, he and Jenner were rumored to be a couple. The pair had been friends for some time and were first connected romantically in June 2016 when they were seen enjoying dinner in Paris at L’Avenue. That October, they both arrived at a hotel in Los Angeles together.
In December 2016, they attended Art Basel in Miami. In March 2017, things were seemingly getting more serious, and a friend of Jenner told People that they had been “spending more time” together, and she was “open to seeing where it goes.”
That year at Coachella, Jenner was in the audience of Rocky’s show. They were allegedly “all over each other” afterward, an eyewitness told People. In May that year, they were standing cheek-to-cheek in Jenner’s famous bathroom photo taken at the Met Gala. But they grew apart. Eventually, a source claimed to Us Weekly that they “weren’t seeing each other a lot. They weren’t really official but were obviously dating. Their schedules are really hard.”
Blake Griffin: 2017-2018
A few months after her Met Gala night with the rapper, Jenner was seen with another NBA player: Blake Griffin. They went on dates throughout the summer.
Things seemed a little more serious in the fall as cuffing season came into full effect. A source told Us Weekly in October 2017 that they had defined their relationship.
“They’re legit. They’re a full-on couple,” a source close to Jenner said. “Kendall has been going to a lot of his games, and they have been enjoying time at home when Blake is in town. They’re good.”
She attended Halloween Horror Nights with Griffin, her sister Kylie, and Kylie’s then-boyfriend, Travis Scott. She was also seen in public cheering him on at a Clippers game.
“Kendall is very happy with Blake,” an insider told People at the time. “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. They are spending time getting to know him.”
In March 2018, she was interviewed by Vogue and seemed to deny they were dating. The original interview took place just after Valentine’s Day, and Jenner was coy on the phone, saying she was visiting “a friend.”
“I like my private life,” she added. “Yeah… no. I’m happy. He’s very nice. I have someone being very nice to me.”
But things didn’t last after Griffin moved teams from the L.A. Clippers to the Detroit Pistons. A source later told People, “He got traded and isn’t local anymore, so they’ve grown apart a bit just because of distance.”
Ben Simmons: 2018-2019
In May 2018, Jenner was dating a new NBA star, player Ben Simmons. They were seen on a lunch date together at the Beverly Hills Hotel and dated off-and-on throughout the year. Jenner finally made things public and official in February 2019 while on The Ellen DeGeneres Show.
“So obviously you’re dating this guy who’s on the 76ers. How long have you been dating him?” DeGeneres asked.
Jenner smiled and replied, “For a bit now.”
Talking to Vogue Australia in May 2019, Jenner sounded pretty serious about Simmons when she was asked about marriage.
“Definitely not now, but maybe one day,” she said. “I got a glimpse of how my sisters dealt with [the attention] and it’s cool to learn from that.”
However, later that same month the couple were “on a break,” according to a People source.
“The relationship ran its course,” said the insider. “She’s spending time with her friends and back to being in fun mode.”
Devin Booker: 2020-2022
In April 2020, Jenner was road tripping with Phoenix Suns player Devin Booker through Arizona. In September that year, they were on a lake trip with Jenner’s friends Justin and Hailey Bieber.
“Kendall seems very happy,” an insider told People. “Devin is very sweet to her. He spends a lot of time with Kendall’s family and friends too. They both seem to enjoy the quiet time together.”
In February 2021, Jenner went Instagram official in a rare move, posting about him for Valentine’s Day.
“What first seemed like a fun hookup is now a relationship,” a source told People. “They are exclusive, and Kendall is very happy with Devin.”
She posted more pics of him for their one-year anniversary in June 2021. They continued on for another year, before briefly splitting in summer 2022. At the time, Entertainment Tonight said, “Kendall feels like they’re on different paths,” adding that they “have had discussions about their future but they are not on the same page.”
Only a month later, she was celebrating him on Instagram again, and they were vacationing. In September, they attended the U.S. Open.
But in October 2022, they’d broken up again, with a source telling E!, “Their schedules weren’t lining up...and eventually the relationship really took its course.”
However, when Jenner and rapper Bad Bunny split in late 2023, it was rumored she might be spending quality time with Booker yet again. On May 30, 2024, a People source acknowledged Jenner’s brief flirtation with reconciling with Booker before ultimately getting back together with Bunny.
Bad Bunny: 2023 to present
Jenner and rapper Bad Bunny were seen leaving a restaurant in Los Angeles together in February 2023 after reportedly enjoying a double date with the Biebers at Wally’s. A source told Entertainment Tonight, “Kendall and Bad Bunny are attracted to each other and definitely have a flirty vibe. It is still new, but they’re enjoying each other’s company and like each other. They have mutual friends and had dinner with Hailey, Justin and friends at Wally’s in Beverly Hills on Saturday night. It’s been fun for both of them so far.”
The insider added, “Bad Bunny recently bought a new home in Los Angeles and has spent a lot more time there. Kendall met him through a mutual friend, and they hit it off. As of now, it’s not serious and the two are having fun.”
A month later, Bad Bunny was already singing about her, with some lyrics on his track “Coco Chanel” sounding like references to her ex, Booker. In one lyric he says that the “sun in Puerto Rico is hotter than in Phoenix,” and “she knows it.”
He also mentioned Scorpios, which is Jenner’s birth sign. The couple spent the summer together before going public in September and even starring in a Gucci luggage ad.
Then, in December 2023, they split. An insider told Us Weekly, “Friends aren’t surprised that Kendall and Bad Bunny have broken up. They never really saw their relationship going the distance anyway. Of course, they want the best for their friend, but they really didn’t feel like Kendall was as compatible with Bad Bunny as she was in past relationships with other people. At the same time, Kendall has had a few on-off relationships in the past, so they wouldn’t be totally surprised if she got back together with him at some point.”
As predicted, it doesn’t seem like things have entirely come to a close—the former couple spent the New Year together with friends and were seen getting cozy at a Met Gala after-party in May. She then attended his Orlando concert a few weeks later and was seen dancing to the music in the VIP section while wearing his merch.
At the end of May, People confirmed Bunny and Jenner were back together. “It’s going well, and they’re prioritizing spending time together as they figure it out,” a source said. “There wasn’t ever any drama in their breakup, and they missed each other.”
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