Kendall Jenner's romantic journey: From Harry Styles to Bad Bunny

In contrast to the openness of most Kardashians and Jenners, Kendall Jenner opts to maintain privacy around her dating life. Despite her life being portrayed on a reality show, Jenner has established guidelines regarding when a romantic partner can make an appearance alongside her. 

"Kendall has always adhered to this rule — she believed it necessary to be with someone for at least a year before involving them in the show, as she is cautious about understanding people's intentions," Executive producer Farnaz Farjam of Keeping Up with the Kardashians stated this in 2021.

Also Read: Kendall Jenner and Bad Bunny call It quits after short-lived romance 

Navigating Fame and Love

Nevertheless, the supermodel has been associated with several well-known figures over the years, ranging from her teenage fling with Harry Styles to her two-year involvement with NBA player Devin Booker. In the most recent development, Jenner has been casually spending time with rapper Bad Bunny.

Harry Styles

After parting ways with Taylor Swift in 2013, Harry Styles was first seen on a date with Jenner in November. Initially dismissed as just friends, their dynamic took a more romantic turn by January 2014 during a New Year's ski trip with friends. Two years later, they welcomed the New Year together on a private yacht in St. Barths, displaying closeness.

 Although spotted together a few times in 2016, by September, sources revealed to that they were "not officially back together" but were "continuing to talk and see where things go." Styles attended Jenner's birthday bash in November 2016, where another flame of hers, Jordan Clarkson, was also present.

Nick Jonas

In August 2015, Jenner crossed paths with crooner Nick Jonas through his brother Joe Jonas. Despite any speculation of romance, Jonas promptly dispelled the rumors. "We're not dating," he clarified to E! News later that month. He added, "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."

Blake Griffin

Jenner and NBA player Blake Griffin were initially seen together in the summer of 2017, sharing experiences like concerts, afterparties, and double dates with friends. A source informed PEOPLE, "She's seeing Blake romantically. It's nothing serious. She has been in L.A. a lot lately and is having fun... That's all that matters to her."

In March 2018, she declined to confirm her relationship with Griffin, but she did acknowledge to Vogue, "He's very nice. I have someone being very nice to me." A source later informed PEOPLE that the couple had "cooled off."

Also Read: Meet Bad Bunny: Quick facts about Kendall Jenner's Ex 

Ben Simmons

Jenner and basketball player Ben Simmons were initially connected in May 2018 when they were seen on a lunch date at the Beverly Hills Hotel. Despite an on-and-off beginning and some time before becoming exclusive, Jenner officially confirmed the relationship on The Ellen DeGeneres Show in February 2019. In May 2019, the couple decided to part ways. A source close to the pair informed PEOPLE, "They're on a break. The relationship ran its course. She's spending time with her friends and back to being in fun mode."

Devin Booker

The supermodel and Phoenix Suns player Devin Booker initially ignited romance rumors in April 2020 when they were seen on a road trip together to Arizona. The couple marked their one-year anniversary in June 2021, commemorating the milestone with a series of affectionate and PDA-filled posts on Instagram.

Shortly following their two-year anniversary in June 2022, the couple experienced a brief split—however, it wasn't long before they were spotted together again. By September, the couple had evidently reconciled and showcased some rare public displays of affection at the U.S. Open.

Nevertheless, Jenner and Booker discreetly ended their relationship the next month. A source conveyed to PEOPLE at the time, "Both have incredibly busy schedules right now with their careers, and they've decided to make that a priority."