Top News

Kendall Jenner has never been one to broadcast her love life. She's said before that relationships feel too personal to hand over to the public, and that oversharing tends to complicate things rather than help.

Even so, more than a decade in the spotlight means her romances have played out, at least partly, in front of an audience, from a teenage fling with Harry Styles to her most recent split from Bad Bunny.

Jenner has also learned to laugh at the narrative that's followed her: the so-called "curse" that suggests every athlete she dates hits a slump.

She leaned into the joke herself in a Super Bowl 2026 ad for Fanatics Sportsbook, turning the internet's running gag into a punchline about how she's funded her lifestyle, and reminding everyone that the "Kardashian curse" isn't even her last name.

Here's a look back at the men who've been part of her story.

Harry StylesJenner and Styles were first linked in late 2013, not long after his split from Taylor Swift, though early reports insisted they were just friends.

That changed by a New Year's ski trip with friends in 2014, where the flirting was obvious to everyone around them.

The two drifted in and out of each other's orbit for years, reuniting over New Year's in St. Barths in 2016 and again at the 2019 Met Gala, where insiders of People described their bond as more nostalgic than romantic. Styles is widely considered her first serious relationship.

Nick JonasA 2015 setup by Joe Jonas and Gigi Hadid sparked brief dating chatter around Jenner and Nick Jonas.

"They were totally set up by Joe and Gigi," a source close to Jonas told People. "They met recently, went out to dinner and have been texting.”

But Jonas shut it down almost immediately, chalking their time together up to mutual friends and overlapping social circles.

Jordan ClarksonJenner and the NBA guard were spotted together starting in the spring of 2016, hitting Coachella and L.A. nightlife together.

Soon the couple was seen partying around SoCal; from Coachella to Hollywood nightclubs.

Sources described the relationship as affectionate but never especially serious, and it fizzled out by early 2017.

A$AP RockyRocky and Jenner spent years being photographed together, Paris dinners, Art Basel trips, a viral Met Gala bathroom photo in 2017, without either side ever confirming a real relationship.

Their first meeting happened in June 2016 at L’ Avenue, one of Jenner’s favourite restaurants.

Friends said she was open to exploring things with him, but it never evolved into anything official.

Blake GriffinThe pair connected in mid-2017 enjoying concerts, afterparties and grew closer through the fall, with Jenner's family reportedly warming up to him.

But after Griffin was traded, distance took its toll, and the relationship quietly cooled by 2018.

Ben SimmonsJenner and Simon’s dating life started out in 2018 and became her first relationship which she directly confirmed, telling Ellen DeGeneres in 2019 that they'd been together "for a bit."

She even floated the idea of marriage down the line. They split later that year but stayed on good terms.

Devin BookerJenner's romance with the Phoenix Suns guard began in 2020 after the couple was captured on a road-trip together to Arizona and became her most public and longest-lasting, going Instagram official in 2021 for Valentine's Day.

The couple encountered a brief 2022 breakup before reconciling, ultimately splitting for good in October 2022 after prioritizing their careers.

Bad BunnyJenner and the Puerto Rican superstar were first spotted together in the early 2023 at a L.A restaurant.

Their relationship included a diss-track moment aimed at Booker, a horseback ride at Jenner's equestrian ranch, and multiple breakups and reconciliations through 2024. The two have since split again.

Through it all, Jenner has kept the details close letting the headlines write themselves while she stays mostly silent.