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Out of all the Kardashian-Jenner sisters, Kendall Jenner is the most low-key when it comes to her relationships.
In fact, the highest-paid supermodel has never had a beau appear on Keeping Up With the Kardashians or Hulu’s The Kardashians. She’s talked several times about the importance of keeping her personal life separate from work. “A relationship is only meant to be between two people, and the second you make it the world’s business is when it starts messing with the two people mentally,” she told Vogue in May 2019. “Like, once everyone is let in, you’re letting all these opinions into your relationships, and I don’t think that’s fair.”
Despite her best efforts to keep her dating life under wraps, Jenner has been spotted with a few A-list celebrities over the years. The most notable names include the likes of singer Harry Styles, and basketball stars Ben Simmons and Devin Booker. The latter was her most recent relationship, which lasted, on and off, for two years.
Before calling it quits in November 2022 due to conflicting schedules, Jenner gave fans Easter eggs pertaining to Booker. She shared an IG Stories photo of them together on their anniversary and also attended Kourtney Kardashian and Travis Barker’s wedding with the NBA star. Even with the hints and headlines in the media, fans felt like they knew everything about the former couple and yet nothing at all, which has become the formula for the model’s love life.
But in February, Jenner appeared to be back on the dating scene. The 818 Tequila founder was spotted leaving an L.A. restaurant with Bad Bunny, just two days after the two were rumored to be making out in a club. While neither party has confirmed or denied the relationship, the internet is currently in a frenzy about the possible union.
While the reality star’s dating history dates back to 2014, we’ve kept track of it all. Here’s a full timeline of Kendall Jenner’s public yet low-key relationships.
Harry Styles
When: January 2014
Jenner and Styles were romantically linked in January 2014 after the two were spotted on a dinner date, and went skiing together at Mammoth Mountain in California. From there, they enjoyed several outings together, including yacht trips and traveling to St. Barts. The two had an on-and-off relationship, before appearing to end things in 2016. The former couple remained friendly after their breakup. They appeared on the Late Late Show with James Corden in 2019 for a segment of “Spill Your Guts.” During the game, Jenner asked the former One Direction member what songs he had previously written about her, to which Styles refused to answer with a smile.
Nick Jonas
When: Summer 2015
There’s nothing like a summer fling. Jenner and Jonas dated briefly in 2015. They were brought together through their mutual friend Gigi Hadid, who was dating his brother Joe Jonas at the time. “Nick was single and looking to date, and there was an obvious attraction,” a source told Us Weekly at the time. “He absolutely thinks she’s hot.” The reason for their split is unknown.
ASAP Rocky
When: July 2016
The supermodel and the rapper began dating in July 2016. They attended a Coachella party in April 2017, where they were spotted being “super cozy and super close,” according to a source. The next month, the two attended fashion’s biggest night of the year, the Met Gala. In several photos, the couple didn’t shy away from showing plenty of PDA. By the time fall rolled around, Us Weekly reported that the two “weren’t really official but were obviously dating.” Jenner and Rocky’s busy schedules appeared to play a part in their romance not standing the test of time.
Blake Griffin
When: September 2017
Before Jenner and the Boston Celtics center became an official couple, it was reported that the two were hooking up in September 2017. Jenner offered her support toward Griffin on several occasions, including attending many of his games. In March 2018, Jenner spoke candidly about being in a good place with Griffin. “I’m happy. He’s very nice,” she told Vogue. One year later, they called it quits. Naija News reported that Griffin’s move to Detroit played a part, and long-distance became an issue for her.
Ben Simmons
When: 2018
Simmons and Jenner allegedly had a rocky start. Prior to getting with Jenner in 2018, the NBA star was dating singer Tinashe. The singer claimed that she found out that the former 76ers player was spending time with the reality star the same month that they called it quits.
It didn’t take long before Jenner and Simmons began vacationing together. They even traveled to Puerto Vallarta, Mexico, with her sister Khloé Kardashian and her then-boyfriend Tristan Thompson. In May 2019, People confirmed that the supermodel and Simmons went their separate ways. “The relationship ran its course,” the source explained. “She’s spending time with her friends and back to being in fun mode.”
This came after Jenner opened up to Vogue about the difficulties of having a relationship in the public eye. She also revealed in that interview that she was open to marriage one day but was hesitant based on seeing her family’s past experiences with tying the knot.
Devin Booker
When: 2020
Jenner remained off of the dating scene for two years before she became romantically involved with Devin Booker. They were spotted hanging out many times in 2020, without confirming their relationship status. The pair cozied up at Jenner’s 25th birthday party, but still, no confirmation came regarding their romance. It wasn’t until Valentine’s Day 2021 that they became Instagram official.
Jenner opened up about the relationship on an appearance on Jimmy Kimmel Live in April 2022. She gushed that she never misses her boyfriend’s games even if she’s out and about. "I watch every game unless I have—last night, I had a dinner, but all my friends and family know that I, like, sit with my phone wherever I am with the game on,” she explained.
The following month, after attending Travis Barker and Kourtney Kardashian’s wedding in Italy, the vows “put things into perspective” for the couple, per an Us Weekly source. They called it quits shortly after. However, their time apart was short-lived, and they were back together by August 2022. The same issues appeared to come up again, with Jenner and Booker wanting different things in life. They quietly called it quits around November, noting that the breakup was final and amicable.
Bad Bunny
When: February 2023
On Feb. 16, gossip account DeuxMoi suggested that a “single, famous model sister was seen playing tonsil hockey with Bad Bunny at a private L.A. club.” Then, the internet assumed that the famous model was none other than the reality star. Two days later, the two were spotted leaving the same restaurant after a double date with Hailey and Justin Bieber at Wally’s in Beverly Hills.
A source told People that Jenner and the singer were “spending time together.” The source said the two are enjoying each other’s company at the moment. “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. She likes him and is having fun,” the insider explained. “He is different from guys that she dated in the past. He is very charming.”
On March 7, Jenner and Bad Bunny were spotted hanging out together again. TMZ reported that the two went out for dinner at Sushi Park in Los Angeles. They were joined by Kylie Jenner and longtime friend Taco Bennett. As the evening came to a close, Bad Bunny and Jenner indulged in PDA, fueling dating rumors once again.
Just a few days later, TMZ reported that the two were still going strong with their new romance. Jenner and Bunny were spotted leaving Jay-Z and Beyoncé’s Oscars after-party on March 13 in Los Angeles. They both got into the same car at the end of the night, although it’s unclear whether they arrived together.
It appears as though they are still trying to keep their relationship on the down low. In several photos, Jenner covered her face as the town car drove off.