Kendall Jenner’s dating history reads like a who’s who of entertainment and sports royalty.
But the supermodel has always kept her personal life fiercely private, rarely confirming relationships publicly.
From musicians to NBA stars, her romantic timeline spans over a decade of speculation, brief flings, and a few serious relationships.
Here’s everything we know about who Kendall has dated—and who she’s just been friends with all along.
Harry Styles: More Than Just Friends?
When Kendall and Harry Styles were spotted at dinner in West Hollywood back in 2013, rumors immediately swirled. But Kendall was quick to shut them down.
No story, we’re friends. He’s cool.
She told E!’s Giuliana Rancic during an interview in November that year. At just 18 and 20 years old respectively, both were navigating early fame.
Half-brother Brody Jenner weighed in that December, telling New York Daily News that Kendall had things under control. He noted they were both young but praised her level-headedness.
I’m sure she’s having a fun time with him. She has a very level head, great head on her shoulders. But they are both so young.
Their connection didn’t fade with time. The pair reunited for headline-making outings in 2016—including a PDA-packed yacht vacation—and were spotted together again in 2018 and 2020.
Romance rumors resurfaced as recently as 2022 following Harry’s split from Olivia Wilde. But sources insisted they remained just friends who’d kept in touch over the years.
Justin Bieber: Just Family Friends
Despite numerous public appearances together, Kendall never dated Justin Bieber. But that didn’t stop speculation from running wild.
During a 2014 Nightline interview, Kendall addressed the rumors head-on.
He’s a longtime friend of our family. Everybody loves to assume things, but no.
Kendall has been longtime besties with Hailey Bieber, who eventually married Justin. She’s been known to double date with the couple or hang out with them solo, proving their friendship transcends any unfounded dating gossip.
Nick Jonas: Brief Overlap Through Mutual Friends
In August 2015, freshly single Nick Jonas sparked dating rumors with Kendall after being introduced through brother Joe Jonas and his then-girlfriend Gigi Hadid.
But Nick quickly clarified they weren’t dating, telling E! News at the time:
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.
It was simply a case of overlapping friend groups, not romance.
Ben Simmons: Basketball Romance Takes Shape
Ben Simmons actually pursued Kendall, marking one of her first confirmed relationships with an NBA player. They met in spring 2018 and made efforts to see each other despite his Philadelphia base.
During a 2019 Australian Vogue cover shoot, Kendall streamed a 76ers game and FaceTimed Ben to show off his GQ Australia cover. But she remained characteristically guarded about their relationship.
For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier. Also I’m very young and right now I feel like relationships aren’t always super-certain.
By May 2019—Met Gala time—they had amicably split. Kendall anticipated her packed schedule would create complications.
She reflected philosophically to Australian Vogue:
Everyone has their own path and their own way of letting the cards fall. Your 20s are for messing up and figuring it out.
“Kendall’s Starting Five” NBA Meme Gets Her Response
In 2019, a fan tweeted a meme titled “Starting 5 of NBA Players Kendall Jenner Dated,” featuring photos of Jordan Clarkson, Ben Simmons, Blake Griffin, Kyle Kuzma, and D’Angelo Russell.
The fan quipped that this lineup was “a playoff team.” Kendall had the perfect response.
She reposted with a correction: “2 out of 5 accurate, thanks.”
Her clapback became instant Twitter gold, proving she could laugh at herself while setting the record straight.
Devin Booker: Nearly Two Years Together
Kendall’s relationship with Phoenix Suns star Devin Booker lasted almost two years, starting in 2020. This became her most serious public relationship to date.
She even brought him as her date to sister Kourtney Kardashian’s Italian wedding in May 2022, a significant step for someone so private.
But by June, they were taking time apart. Sources told E! News that after returning from their trip, incompatible lifestyles became apparent—they realized they weren’t aligned despite their connection.
They briefly reunited that July before splitting again by November. Their demanding schedules remained incompatible.
Ironically, Devin earned his spot on an updated version of “Kendall’s Starting Five” T-shirt that Kim Kardashian wore, replacing D’Angelo Russell.
A Valentine’s Day weekend 2025 sighting in Aspen—where the pair sat side-by-side at a restaurant wearing snow goggles—suggested they might still be figuring things out.
Bad Bunny: Recent Romance That Keeps Rekindling
Puerto Rican music superstar Bad Bunny entered Kendall’s life in early 2023. They were first spotted in February on what appeared to be a double date with Justin and Hailey Bieber.
Kendall caught his Coachella set in April, and by May they were slipping into Met Gala afterparties together and twinning courtside at Lakers games.
Date nights multiplied throughout 2023. They sat together at Gucci’s Milan Fashion Week show that September, turning heads as a fashion power couple.
By year’s end, they were no longer together. But their mutual friend group kept them connected.
They’ve reunited numerous times since across different continents, proving exes can stay friendly when there’s genuine connection and shared social circles.
Bad Bunny showed up to support Kendall at Calvin Klein Collection’s Autumn/Winter 2025 show during New York Fashion Week in February, sitting runway-side to watch her walk.
Kendall’s Approach: Privacy Above All
Throughout her dating history, one theme remains consistent: Kendall values privacy fiercely.
Unlike some family members who share relationship details publicly, she’s kept romantic connections largely under wraps. Her philosophy about keeping things sacred has guided her through numerous relationships.
Whether with musicians, athletes, or other celebrities, Kendall has consistently prioritized protecting her personal life from public scrutiny—even while living in one of entertainment’s most visible families.
As she navigates her romantic life, she continues letting things unfold naturally, embracing that your twenties—and beyond—are for figuring it all out.