From Artists to Athletes, Kendall Jenner's Dating History Is Star-Studded

For about two years, Jenner and Harry Styles were in an on-and-off-again relationship. The celebrity couple first fuelled dating rumours after being spotted several times together in late 2013, followed by a Mammoth ski trip over the winter holidays, per Us Weekly.

The duo kept quiet about the status of their relationship until January 2016 when they were seen holidaying on a yacht together in St. Barts. At the time, Jenner's sister Khloé Kardashian told Entertainment Tonight that she believed the two were dating, though she was unsure whether it was casual or serious.

Naturally, it was momager Kris Jenner who confirmed that her daughter had dated the former One Direction singer. While playing "Never Have My Kids Ever" on "The Ellen DeGeneres Show" in 2021, Jenner showed the "They have" card after being asked, "Never have my kids ever dated someone from a boy band." Host DeGeneres quipped back, "Well, of course, Kendall, right? And Harry?," to which Jenner smiled and responded, "Yeah."

While they're no longer together, the two are amicable. Back in 2019, Jenner and Styles played "Spill Your Guts or Fill Your Guts" on "The Late Late Show With James Corden," in which they asked each other an array of personal and funny questions.

According to The Sun, Jenner and A$AP Rocky allegedly took their friendship to new heights in 2016 when they were photographed together in Paris. They never publicly spoke about their rumoured romance but were spotted getting cosy with one another on a number of occasions, including at the 2017 Met Gala, per People. The same The Sun report said the two split in 2017 "due to difficult schedules."

According to People, Jenner and NBA player Blake Griffin first sparked dating rumours in 2017 when they were seen leaving a club together in Los Angeles after attending a concert. Despite the gossip, Jenner and Griffin's relationship is left largely in the dark.

A very private person, Jenner only once (and very briefly) acknowledged being in a relationship around the same time the dating rumours started. "I'm happy. He's very nice. I have someone being very nice to me," she said during a 2018 interview with Vogue. However, according to a report from People, things started to fizzle out that same year shortly after Griffin was traded to the Detroit Pistons.

Jenner and Simmons's relationship was a rollercoaster, to say the least, as the couple took many breaks during their two-year relationship. According to E! News, the two began dating in 2018, but almost a year in, they went on their first break.

This was short-lived, though, as Jenner confirmed she was seeing the 76ers basketball player during an appearance on "The Ellen DeGeneres Show." According to Elle, the pair hit the pause button again in May 2019, just shortly after Jenner had spoken highly of Simmons in an interview with Australian Vogue, saying "maybe one day" she could envision them married.

However, the couple rekindled the flame just in time for the 2019 holiday season. "They've been on and off and there are periods where they definitely lost touch, but they've always had their eye on one another," an anonymous source told People. "Their breakup always seemed more like a break because of careers and distance."

Despite this, the couple likely called it quits in early 2020, right before Jenner started seeing Devin Booker.

Jenner also had an on-again-off-again relationship with her ex-boyfriend Devin Booker. In a 2020 report from TMZ, Jenner and Booker were first spotted together back in April of that year when they took a road trip together. In 2021, according to Bustle, the two went public and IG official on Valentine's Day and later celebrated their one-year anniversary that June with a slew of cute behind-the-scenes photos of their relationship.

While together, the two kept details about their romance relatively private, but every now and again, we'd hear from the former couple. In a March 2022 interview with WSJ Magazine, the Phoenix Stars player hinted at his relationship, saying, "I'm enjoying life to the fullest, and that came off my tongue so easily because it wasn't always this way, but I feel like I'm in a good place right now." He added, "I love the people around me."

However, three months later, the pair reportedly split after two years together. Though they seemingly reconciled shortly after, Jenner and Booker called it quits for good in October 2022, with a source telling People it was because of their "incredibly busy schedules." "They have a lot of love and respect for each other and wish only the best," the insider added.