Kendall Jenner’s love life has moved through Hollywood’s biggest names—Harry Styles, Devin Booker, Bad Bunny, and now Jacob Elordi—often with on-and-off twists, quick headlines, and moments that never quite fit a neat timeline.
Kendall Jenner’s relationships don’t just make headlines—they become a running series. with familiar names returning at just the right (or wrong) moments. From her early days dating high-profile stars to the latest buzz around Jacob Elordi. her dating history reads like a tour through modern pop culture.
Long before “quarantine couple” became a phrase, Jenner was already linked to Nick Jonas. The former Disney Channel star was tied to the supermodel back in 2015. the same year Joe Jonas was dating Kendall’s pal Gigi Hadid. At the time, it was reported that Gigi set up the pair, but Nick shut that down. “We’re not dating. Kendall is great. and naturally. with 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. ” Nick told E!.
Then came Harry Styles—one of the connections that never fully stays in the past. Kendall and Harry were first linked after they were spotted having dinner together in Los Angeles in November 2013. Reports later said they split in early 2014, but the romance didn’t disappear. They rekindled in the following year, spending New Year’s together and canoodling on a yacht while on vacation. Kendall’s big sister Khloe Kardashian also weighed in, saying, “Do I think they’re dating?. Yes,” while adding, “I don’t know if they’re like boyfriend-girlfriend. Nowadays I don’t know. People are weird with stuff. So, I don’t know their title.”.
Their timeline stayed active after that, even when the public didn’t see much for a stretch. They reappeared shopping together in April 2016, but later that year the pair split again. Still, it didn’t end in bitterness: they showed up together on James Corden’s The Late Late Show in 2019.
As the NBA world started to pull Kendall into its orbit, Jordan Clarkson entered in July 2016. She began casually dating NBA player Jordan Clarkson, hanging out sporadically throughout the year. An eyewitness report in E!. said the pair were cozy at Drake’s 2016 American Music Awards after-party—plus. the source claimed Kendall was “laughing the whole time. ” “super giddy. ” and “loving every minute of it.” The same report described an affectionate. playful dynamic: “They were extremely affectionate and sweet towards one another. It’s obvious he makes her so happy!” Despite that, they split sometime in 2016.
Later that year, Kendall’s relationship energy shifted again—this time toward A$AP Rocky. Romance rumors flared when she attended Kanye West’s Yeezy fashion show together in August 2016. They were also spotted together at the 2017 Met Gala. But even after more than a year of being linked, nothing was officially confirmed. In September 2017, an Us Weekly source said, “Kendall and ASAP weren’t seeing each other a lot. They weren’t really official but were obviously dating. Their schedules are really hard.”.
By August 2017, Blake Griffin was on the list. Kendall reportedly began dating the NBA star then. and although the romance didn’t last. she did open up about him in a March 2018 Vogue interview. “I’m happy. He’s very nice,” she said. “I have someone being very nice to me.” The two were spotted together for around seven months before calling it quits in April 2018.
Next came Ben Simmons, who started the relationship in July 2018. Kendall and the Philadelphia 76ers star had an on-again, off-again situation for nearly two years. They broke up for the first time in May 2019, then rekindled. Kendall confirmed the dating connection on a February 2019 episode of The Ellen DeGeneres Show. saying she dated the athlete “for a bit.”.
The romance heated up again in early 2020. She spent time with his parents during and after a Feb. 11 Sixers game in Philadelphia. In an Instagram pic. Kendall appeared all smiles walking with the NBA star and his parents after the 76ers beat the L.A. Clippers. Shortly afterward, they called it quits as the coronavirus pandemic began.
If there was a relationship that felt tailor-made for the moment, it was Devin Booker. Kendall and Booker were first spotted on a road trip in Arizona in 2020. Booker even took the romance interstate—visiting pals Justin Bieber and Hailey Baldwin in Idaho on September 3. They dated on and off for two years until a brief split in early 2022. with a reunion that apparently made things feel good again—until they ended things later that year.
After her breakup from Bad Bunny, TMZ reported in February 2024 that Kendall started seeing Devin again, with the pair “taking things slow.” Then, in late 2025, Kendall and Devin were spotted out together again, sparking reconciliation rumors.
Bad Bunny entered the story after a short transition period from Devin. Months after splitting from Booker, Kendall was photographed kissing rapper Bad Bunny in early 2023. Even without public commentary. they showed up together publicly—sitting in the front row of Gucci’s fashion show during Milan Fashion Week in September that year. As their romance became more visible. they spent time together multiple times. but the relationship ended by the end of 2023. with multiple outlets reporting they had split. At the start of 2024. Bad Bunny and Kendall reportedly took a trip to Barbados with a group of mutual friends. though the reunion didn’t last.
And now, it’s Jacob Elordi.
Kendall’s connection to Elordi began with gossip and quick, telltale sightings. A celebrity gossip account, DeuxMoi, said Kendall was spotted kissing Jacob Elordi at a Coachella after-party in April 2026. Later that month. a source told People that the pair had “been hanging out and getting to know each other the last couple months.” In May. Kendall and Jacob were spotted spending time together in Hawaii.
What stays consistent through all of it is the cadence: high-profile connections, a public moment, then a pivot—either toward a rekindling or a clean break. Kendall’s dating life may change names and locations, but the pattern of sudden sightings and shifting status keeps the attention locked in.
Kendall Jenner dating history Harry Styles Devin Booker Bad Bunny Jacob Elordi Nick Jonas A$AP Rocky Blake Griffin Ben Simmons Jordan Clarkson Coachella after-party Hawaii