Who Are Kendall Jenner’s Ex-Boyfriends Dating Now? The Men She Loved and Lost

It’s no secret that Kendall Jenner has a type, and that’s NBA players or musicians. She’s almost exclusively dated the tall pro-athletes or music artists during her love life, leaving a trail of exes in her wake. While she’s been in a happy year-long relationship with Phoenix Suns star Devin Booker, Kendall gave clout to whom she was once linked.

Prior to Devin, Kendall’s most recent NBA boyfriend was Philadelphia 76ers star Ben Simmons, whom she dated on and off between May 2018 and May 2019. He’s now dating British TV host Maya Jama. The pair were first spotted in July 2021 attending Wimbledon together.

The two were photographed kissing and cuddling in the stands and made for quite the good-looking couple. But their relationship could prove challenging, as Ben will have to report to 76ers training camp on September 28, 2021, while Maya has a busy career with the BBC. She’s also an ambassador for Adidas and has an extensive modeling resume.

Prior to Ben, Kendall was with current Brooklyn Nets star Blake Griffin for a just under a year while he played for the Los Angeles Lakers. The pair were first photographed together in August 2017 and later broke up in April 2018.

Since the split, the NBA hunk has been daring Frankie’s Bikinis founder Francesca Aiello. Blake and the stunning Los Angeles-based entrepreneur are still going strong, being photographed together throughout the summer of 2021.

Kendall was briefly associated with then-Los Angeles Laker Jordan Clarkson in the spring of 2016. They attended the Coachella Music Festival together and spent the Fourth of July partying at her rented Malibu beach house. But their romance fizzled out quickly. The current Utah Jazz player now dating Instagram model Ally Rossel.

Later in 2016, Kendall was linked with A$AP Rocky, as the pair were photographed out and about in Paris, New York and other locations looking cozy and fashionable together. There was even that infamous photo Kim Kardashian took of him grabbing her behind at the 2017 Met Gala, where the pair were glued at the hip. Rocky has now scored the woman nearly all men dream about: Rihanna! The two have been a couple since the spring of 2021.

In a June 2021 interview with GQ, he called RiRi “my lady” and “the love of my life.” While he acknowledged being quite a ladies man in the past, he gushed, “So much better when you got the One. She amounts to probably, like, a million of the other ones. I think when you know, you know. She’s the One,” about Rihanna.

Between 2013 and 2016, Kendall was linked on and off with singer Harry Styles, although their deep flirtation turned into a close friendship. The “Golden” singer is now dating his Don’t Worry Darling director, Olivia Wilde. It is one of the most serious relationships of Harry’s dating life, as he’s beyond smitten with his nine-years-senior girlfriend.

The two have been photographed holding hands, kissing and proving they’re jet-setters, spending time between Los Angeles, London and romantic vacations to Italy. They were first photographed on January 4, 2021, holding hands while attending his manager Jeff Azoff‘s wedding in Montecito, California, and are still going strong today.

Scroll down to see photos of Kendall’s exes and who they are dating now.