Kendall Is Reportedly Seeing Bad Bunny Again A Month After Breakup

Kendall Jenner is extremely private about her personal life. Unlike the rest of her family, the model typically keeps the details of her romances so under wraps, the world might not know she’s dating someone until after they’ve called it quits. Since her love life is so secretive, you may not even know who Kendall Jenner has dated — or has reportedly dated — over the years, though the list includes a lot of famous faces. From models and musicians to basketball players, Kenny has been connected with some pretty fascinating people during her time in the spotlight, and at the moment, her love life is more in flux than ever.

Jenner’s most recent rumored boyfriend was the hit-making superstar Bad Bunny. The two were first spotted out on a date together in February 2023, and they went on to spend almost all of the year together, although they kept their romance largely hidden from the public. For instance, when they both went to the Met Gala, they walked the carpet separately but then reunited at an after-party.

However, Jenner and Bad Bunny’s relationship has been a big question mark recently. They reportedly ended things in December 2023, but some sus pics and reports seem to imply they’re not as over as they seemed. Before we get to the latest drama, let’s look back at all the people she’s dated in the past.

Julian Brooks: 2012-2013

Even supermodels like Jenner had a high school sweetheart. Hers was Julian Brooks, apparently. The two reportedly dated for just about a year before calling it quits in August 2013. There isn’t much known about Brooks (because he’s not a celebrity), but in a February 2016 interview with Hello, Jenner gave some insight into what their relationship was like.

“When I got to high school I used to pretend that I had work, and I would go and tell the head of school that I really needed to leave,” Kendall said. “I would just leave school and go hang out with my boyfriend and get food and do absolutely nothing."

Harry Styles: 2013-2014 & 2015-2016

Jenner reportedly had a thing with Styles on-and-off for a few years, though the two never put a label on their mysterious relationship. Their romance reportedly kicked off when they grabbed dinner together in November 2013, and they’ve hung out sporadically in the years since — from vacationing together in Anguilla in 2015 to getting flirty during Jenner’s December 2019 appearance on the Late Late Show when Styles was guest-hosting.

The closest thing fans of the pair got to a confirmation they were dating was in a 2016 interview with Entertainment Tonight, when Jenner’s older sister Khloé Kardashian teased a few details about the relationship.

“Do I think they’re dating? Yes,” Kardashian told ET. “But I don’t know if they’re like boyfriend-girlfriend. You know, 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.” Fans may never know what the deal was with these two.

Justin Bieber: 2014-2015

In late 2014, dating rumors began circulating about Jenner and Justin Bieber, though she denied them at the time. "No, he’s a longtime friend of our family," she told ABC News in November 2014 when asked about the nature of their relationship. "Everybody loves to assume things, but no. I'm truly focusing on my career. If it comes, it comes." Dating rumors ramped up after Bieber shared a series of couple-y photos on Instagram in April 2015, but it’s still a mystery whether these two were ever more than friends.

Jordan Clarkson: 2016

Back in July 2016, Jenner reportedly began dating NBA player Jordan Clarkson. By November 2016, photos of the couple made it seem like the relationship was getting a bit more serious. At the time, an eyewitness told E! that Jenner and Clarkson were really into each other at Drake’s 2016 American Music Awards after-party. “She was laughing the whole time! She was super giddy and loving every minute of it. It was obvious that they have a very playful, fun relationship," the source said. "They were extremely affectionate and sweet towards one another. It's obvious he makes her so happy!" However, little else was heard about the maybe-couple after that.

A$AP Rocky: 2016-2017

Though Jenner and A$AP Rocky were romantically linked for over a year, the two stars were never quite official... at least according to US Weekly. Back in September 2017, an inside source told the magazine Jenner and A$AP Rocky didn’t really spend that much time together. “Kendall and ASAP weren’t seeing each other a lot. They weren’t really official, but were obviously dating,” the source claimed. “Their schedules are really hard.”

Blake Griffin: 2017-2018

Jenner reportedly began dating basketball star Blake Griffin in August 2017, following his split from his ex-fiancée, Brynn Cameron. By the following March, Jenner even opened up about the new romance. “I’m happy. He’s very nice,” she gushed to Vogue during an interview. “I have someone being very nice to me.” The two were photographed out and about together for about seven months before they reportedly called it quits in April 2018.

Anwar Hadid: 2018

In June 2018, not long after her relationship with Griffin reportedly ended, Jenner was reportedly spotted kissing Anwar Hadid, Gigi and Bella Hadid’s younger brother. Later that September, Jenner and Hadid were reportedly seen hanging out with friends at the Malibu Chili Cookoff. Their public interactions fizzled out after that, and there’s been no official word they were ever anything more than friends.

Ben Simmons: 2018-2019

Jenner’s relationship with Ben Simmons reportedly kicked off in July 2018, when Us Weekly published a story saying Jenner and the Philadelphia 76ers player were inseparable. By February 2019, Jenner confirmed the relationship during an appearance on The Ellen DeGeneres Show. Unfortunately, the two couldn’t make things last, and they reportedly split in May 2019 after about a year of on-and-off dating.

Jenner and Simmons have been spotted hanging out after their 2019 breakup, but it’s reportedly not been anything serious. “They both like having a no-strings-attached type of relationship with each other, for the most part,” a source told Us Weekly in February, shortly after the pair were seen together at the 2020 Super Bowl in Miami. “They both work and travel frequently and don’t find it very realistic to be in an exclusive relationship with one another. They do really like each other though and love spending time together.”

Kyle Kuzma: 2019

In July 2019, shortly after Jenner reportedly broke up with Simmons, the model was linked with Kyle Kuzma, the L.A. Lakers power forward. The two sparked dating rumors when they were spotted on a boat together on the Fourth of July; however, the spark seemingly fizzled out pretty quickly. "The two were hanging out over the holiday as friends," a source told Entertainment Tonight at the time. "They’ve run in the same circle for a while and there’s no romantic relationship between them. Kendall is enjoying being single after ending things with Ben."

Fai Khadra: 2019

After Fai Khadra, a model who is part of Jenner’s social circle, served as Jenner’s date to Hailey Baldwin and Justin Bieber's wedding in September 2019, she and Khadra were spotted together at a restaurant in Santa Monica in October, and that was enough to convince fans they were dating. Still, the caption of Jenner’s photo with Khadra from Jailey’s wedding (“We don’t date he’s just my date”) says differently.

Devin Booker: 2020-2021

The model was first linked to Phoenix Suns player Devin Booker in April 2020 when TMZ reported they went on a road trip together to Arizona. After that, they kept the rumor mill turning with rumored hangouts and flirty social media interactions, and in February 2021, Jenner seemingly confirmed their relationship by posting a loved-up photo with Booker on her Story.

But after a couple years together, Jenner and Booker reportedly broke up in November 2022.

Bad Bunny: 2023-Present

Jenner reportedly began dating Bad Bunny at the start of 2023, and although they mostly kept their romance out of the public eye, they did offer a few peeks into their love life. Bad Bunny subtly hinted at his sex life with Jenner during a Vanity Fair profile in September. Later that month, the couple helmed a Gucci campaign together.

But the relationship hit a hurdle not long after that. In December 2023, Jenner and Bad Bunny reportedly ended things. But fans noticed they didn’t physically split up. The exes still rang in 2024 together at a New Year’s party with friends.

Then, later in January, Us Weekly reported that the couple was on the road to rekindling things. “She’s seeing Bad Bunny again,” a source told the outlet. “It’s not the type of situation where they’re fully back together, but they have hung out a few times since breaking up last month.”