Kendall Jenner’s Dating History: From Harry Styles to Bad Bunny

While most of the Kardashians and Jenners are open books, Kendall Jenner prefers to keep her love life private.

“Kendall always had this rule — she felt like she had to be with someone for at least a year before she’d let them be on the show because she doesn’t always know what people’s intentions are,” Keeping up with the Kardashians executive producer Farnaz Farjam said in 2021, “So that’s why we kept her personal life out of it, just because she had a rule.”

In 2019, Jenner spoke candidly with Vogue Australia on her decision to keep her love life out of the spotlight.

“A lot of things are very special and very sacred to me, like my friends and relationships. Personally, I think putting things out in public makes everything a lot messier,” she said.

Still, the supermodel has been linked to several famous names over the years, from her teenage romance with Harry Styles to her two-year relationship with NBA player Devin Booker. Jenner’s most recent romance involved rapper Bad Bunny, though a source told PEOPLE that the couple has decided to call it quits in late 2023.

Jenner is known for dating athletes – like her older sisters. So it was especially comical when Kim Kardashian wore a T-shirt that read “Kendall Starting Five” and featured pictures of the five NBA players the model was previously linked to. She wore the shirt in a TikTok video, but also appeared during Season 3 The Kardashians.

Timeline of Kendall Jenner and Devin Booker’s relationship

Here’s a look at Kendall Jenner’s dating history from 2013 to present.

Harry Styles

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After splitting from Taylor Swift in 2013, Harry Styles was seen on his first date with Jenner in November. “They’re just friends,” a source told PEOPLE at the time, but by January 2014, the pair appeared to be a little more romantic on a New Year’s Eve ski trip with friends. “Kendall was snowboarding and Harry was skiing,” a source told PEOPLE. “They were very cute together. There was a lot of flirting and smiling.”

Two years later, they spent the New Year’s holidays together again in St. Barths where they were seen getting close on a private yacht. “There was a lot of flirting and touching and cuddling. They were acting like a couple. They look very cozy and happy,” an insider told PEOPLE.

Days later, older sister Khloé Kardashian said she thinks Jenner and Styles’ relationship is romantic. “They were hanging out together. Do I think they’re dating? Yes. I don’t know if they’re like boyfriend and girlfriend,” she told Party tonight. “Nowadays, I don’t know, people are weird about things. So I don’t know their ‘title.’ But I mean, they were in St. Barts together and hanging out, so that’s a date for me. I’d call it a date.”

The duo were seen together a few times in 2016, but in September PEOPLE learned that the pair “are not officially back together” but are “continuing to talk and see where things go.” He attended her birthday bash in November 2016 – but so did Jordan Clarkson, another of Jenner’s loves.

Terence Patrick/CBS

In December 2019, Styles was a guest host on Late, late show and Jenner appeared as a guest. During a game of “Spill Your Guts or Fill Your Guts,” she asked him which songs on his latest album were about her.

Styles was eating cod sperm to avoid answering questions, but the pair seemed comfortable with each other. “Harry was her first real relationship, so there’s a lot of history there,” a source told PEOPLE. “But they’re just friends.”

Nick Jonas

Arturo Holmes/FilmMagic; Matt Winkelmeyer/FilmMagic

In August 2015, Jenner was introduced to singer Nick Jonas through his brother Joe Jonas and Joe’s then-girlfriend Gigi Hadid. “They were totally set up by Joe and Gigi,” a source close to Jonas told PEOPLE. “They met recently, went to dinner and corresponded.”

But Jonas quickly dismissed all romance rumors. “We’re not dating,” he told E! News later that month. “Kendall is great, and naturally, since she’s good friends with Gigi and Joe and Gigi are dating, sometimes we’ll be in the same place and we’ll all hang out.”

Jordan Clarkson

Matt Winkelmeyer/MG18/Getty; David Livingston/Getty

Jenner and NBA player Jordan Clarkson were first spotted together in March 2016. Soon after, they were seen partying around SoCal — from Coachella to Hollywood nightclubs.

“When they’re out in public, they keep it quiet, but in private they’re very close and affectionate,” a source told PEOPLE in April 2016. “He’s really into her.”

In June of that year, an 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 has been seeing other girls.”

He celebrated Jenner’s 21st birthday in November, and the duo also attended Drake’s American Music Awards afterparty, where the two “definitely had a flirty vibe,” according to the source. Although their romance seemingly ended not long after that.

A$AP Rocky

Pierre Suu/GC Images

A$AP Rocky and Jenner have been friends for a long time and have never confirmed that they are anything more, but that hasn’t stopped fans from speculating. They were first spotted together in Paris in June 2016, walking to one of Jenner’s favorite restaurants, L’Avenue. A few months later, in October, they were seen arriving together at a hotel in Los Angeles.

In December, they enjoyed a whirlwind trip to Art Basel in Miami, where a source told PEOPLE they looked “very flirty.” By March 2017, a friend of the model told PEOPLE that Jenner was “spending more time” with the rapper and that she was “open to seeing where it goes.” The following month, she supported A$AP at his Coachella performance, and onlookers said they were “all over each other” at the after party.

The duo looked particularly cozy in their infamous bathroom photo from the Met Gala in May 2017, but have been seen less often together since then.

Blake Griffin

Kevork Djansezian/Getty

Jenner and NBA player Blake Griffin were first spotted together in the summer of 2017, enjoying concerts, afterparties and double dates with friends. “She is seeing Blake romantically,” a source told PEOPLE. “It’s nothing serious. She’s been in LA a lot lately and she’s having fun… That’s all that matters to her.”

By fall, she and Griffin joined sister Kylie Jenner and Travis Scott at Halloween Horror Nights and supported him at a Clippers game. “Kendall is very happy with Blake,” an insider told PEOPLE. “They started out more as friends, and it was very casual back then. But lately it seems to be more serious. When they’re not together, they keep in touch on the phone. Her family has taken Blake in. They spend time getting to know him.”

In March 2018, she refused to admit that she was in a relationship with Griffin, but said Vogue, “He is very nice. I have someone who is very nice to me.” A source later told PEOPLE that the couple had “chilled out.”

The source added: “He’s been traded and he’s not local anymore, so they’ve drifted apart a bit just because of the distance.”

Ben Simmons

James Devaney/GC Images

Jenner and basketball player Ben Simmons were first linked in May 2018 when they were spotted having lunch together at the Beverly Hills Hotel. Although the duo was on and off at first and it took a while for them to become exclusive, Jenner confirmed the relationship on The Ellen DeGeneres Show in February 2019.

“So apparently you’re dating this guy who’s on the 76ers. How long have you been dating him?” DeGeneres asked. Jenner couldn’t help but smile and said, “Just a little more now.”

She even opened up about the possibility of marriage in an interview with Vogue Australia in May 2019 “Definitely not now, but maybe one day,” she said. “I got an insight into how my sisters dealt with it [the attention] and it’s great to learn from it.”

But later that month, the couple broke up. “They are on a break,” a source close to the couple told PEOPLE. “The relationship has run its course. She’s spending time with her friends and going back to partying.”

Despite the breakup, the couple remained cordial. After the split, Jenner and Simmons were seen hanging out together on New Year’s Eve.

Devin Booker

Kendall Jenner and Devin Booker. Kendall Jenner/Instagram

Supermodel and Phoenix Suns player Devin Booker first sparked romance rumors in April 2020 when they were spotted on a trip to Arizona together. “Kendall seems really happy,” an insider told PEOPLE in September after the couple enjoyed a lake vacation with Justin and Hailey Bieber. “Devin is very fond of her. He also spends a lot of time with Kendall’s family and friends. They both seem to enjoy the quiet time they spend together.”

While Jenner isn’t one to flaunt her relationships, she broke with tradition and made her Instagram official with Booker in February 2021 for Valentine’s Day. “What first seemed like a fun relationship is now a relationship,” a source told PEOPLE. “They are exclusive and Kendall is very happy with Devin.”

Gotham/GC images

The couple hit their one-year milestone in June 2021 and celebrated with a series of PDA-laden Instagram posts. “She is crazy about him,” a source told PEOPLE. “She’s never looked happier. Her whole family loves Devin too.”

Shortly after their two-year anniversary in June 2022, the couple briefly split — though it wasn’t long before the duo were spotted together again. She shared his NBA 2K23 cover on Instagram in July 2022, and they went on a tropical vacation together that same month.

In September, the pair were apparently back together and showed off some rare PDA at the US Open.

However, Jenner and Booker quietly called it quits the following month. “They both have incredibly busy schedules with their careers right now and have decided to make it a priority,” a source told PEOPLE at the time, with another source adding, “They have a lot of love and respect for each other and only want the best.”

Bad Bunny

Kendall Jenner; Bad Bunny. Jerritt Clark/Getty Images; Johnny Nunez/Getty Images

In February 2023, Jenner was seen leaving a restaurant in LA with rapper Bad Bunny. The two reportedly went on a double date with the Biebers at Wally’s in Beverly Hills.

A source later told PEOPLE that the two were “spending time together.” Another source added: “Kendall recently started hanging out with him. They met through friends. He moved to LA a few weeks ago and bought a house.”

The insider continued: “She likes him and she’s having fun. He’s different from the guys she’s dated in the past. He’s very charming.”

In March 2023, Bad Bunny seemingly dissed Jenner’s ex-boyfriend Devin Booker, who plays basketball for the Phoenix Suns, in his new song “Coco Chanel.” He said that “the sun is hotter in Puerto Rico than in Phoenix” and “she knows it.” In a now-deleted Instagram comment, Booker replied, “Worried about another MAN again.”

A few weeks later, Jenner introduced Bad Bunny to her horse, Arizona, at the Hidden Hills Equestrian Center in California. The couple went on a romantic horseback ride around the property before the rapper rode Arizona around the training track.

In December 2023, a source confirmed to PEOPLE that Jenner and Bad Bunny had divorced. The news comes nearly two months after the pair were spotted in Saturday night live afterparty, after Bad Bunny’s performance as host and musical guest.

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Source: HIS Education