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

“Kendall’s always had this rule — she felt like she had to be with someone for at least a year before she let them be a part of 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 kind of kept her personal life out of it, just because she had a rule.”

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

“For me, a lot of things are very special and very sacred, like my friends and relationships. I personally think that bringing things into the public makes everything so much messier,” she said.

Still, the supermodel has been linked to a few 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 decided to call it quits in late 2023.

Jenner is notorious for dating athletes — not unlike her older sisters. So, it was especially comical when Kim Kardashian wore a T-shirt that said, “Kendall Starting Five,” and featured images of five NBA players the model has been formerly linked to. She wore the shirt in a TikTok video but it also made an appearance during season 3 of The Kardashians.

Kendall Jenner and Devin Booker’s Relationship Timeline

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

Harry Styles

After splitting from Taylor Swift in 2013, Harry Styles was spotted 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 seemed to be a bit more romantic on a New Year’s ski trip with friends. “Kendall snowboarded and Harry skied,” a source told PEOPLE. “They were very cute together. There was a lot of flirting and smiling going on.”

Two years later, they spent the New Year’s holiday together again in St. Barths where they were seen getting close 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,” an insider told PEOPLE.

Days later, big sister Khloé Kardashian said she thought Jenner and Styles’ relationship was romantic. “They were hanging out together. Do I think they’re dating? Yes. I don’t know if they’re like boyfriend-girlfriend,” she told Entertainment Tonight. “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. I would call that dating.”

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

In December 2019, Styles was a guest host on The 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 last album were about her.

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

Nick Jonas

In August 2015, Jenner was introduced to crooner 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 out to dinner and have been texting.”

Jonas quickly shut down any rumors of romance, however. “We’re not dating,” he told E! News later that month. “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

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

“They keep things low-key when they’re in public, but in private they’re very much together and affectionate,” a source told PEOPLE in April 2016. “He’s really into her.”

In June of that year, an insider shared, “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.”

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 going on,” according to a source. Although their romance seemingly ended shortly after.

A$AP Rocky

A$AP Rocky and Jenner were friends for a long time and never confirmed that they were anything more, but that didn’t stop fans from speculating. They were first seen together in Paris in June 2016, walking to one of Jenner’s favorite restaurants, L’Avenue. A few months later, in October, they were spotted 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 had been “spending more time” with the rapper and 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 an afterparty.

The duo looked extra cozy in their infamous Met Gala bathroom photo in May 2017 but were seen together less frequently after that.

Blake Griffin

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

By the 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 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 refused to admit she was in a relationship with Griffin, but she told Vogue, “He’s very nice. I have someone being very nice to me.” A source later told PEOPLE that the couple had “cooled off.”

The source added, “He got traded and isn’t local anymore, so they’ve grown apart a bit just because of distance.”

Ben Simmons

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

“So obviously you’re dating this guy who’s on the 76ers. How long have you been dating him?” DeGeneres asked. Jenner couldn’t contain her smile, and said, “For a bit 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 a glimpse of how my sisters dealt with [the attention] and it’s cool to learn from that.”

But later that month, the couple called it quits. “They’re on a break,” a source close to the pair told PEOPLE. “The relationship ran its course. She’s spending time with her friends and back to being in fun mode.”

Despite breaking up, the pair stayed cordial. After their split, Jenner and Simmons were spotted hanging out together on New Year’s Eve.

Devin Booker

The supermodel and Phoenix Suns player Devin Booker first sparked romance rumors in April 2020 when they were spotted on a road trip together to Arizona. “Kendall seems very happy,” an insider told PEOPLE in September after the pair enjoyed a lake getaway with Justin and Hailey Bieber. “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.”

While Jenner isn’t one to flaunt her relationships, she broke with tradition and went Instagram official with Booker in February 2021 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.”

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

Soon after their two-year anniversary in June 2022, the couple briefly split — although it didn’t take long for the duo to be spotted together again. She shared his NBA 2K23 cover on Instagram in July 2022, and they took a tropical vacation together that same month.

By September, the couple were clearly back together and showed some rare PDA at the U.S. Open.

However, Jenner and Booker quietly broke up the following month. “Both have incredibly busy schedules right now with their careers and they’ve decided to make that 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 wish only the best.”

Bad Bunny

In February 2023, Jenner was seen leaving an L.A. restaurant 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 “are spending time together.” Another source added: “Kendall recently started hanging out with him. They were introduced by friends. He moved to L.A. a few weeks ago and bought a house.”

The insider continued, “She likes him and is having fun. He is different from guys that she dated in the past. He is 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 track “Coco Chanel.” He rapped that the “sun in Puerto Rico is hotter than in Phoenix” and “she knows it.” In a now-deleted Instagram comment, Booker responded: “He 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 took a romantic horseback ride around the property before the rapper rode Arizona around the training ring.

In December 2023, a source confirmed to PEOPLE that Jenner and Bad Bunny had split. The news came nearly two months after the couple were spotted at a Saturday Night Live afterparty, following Bad Bunny’s performance as both the show’s host and musical guest.