As the most secretive member of the Kardashians, the dating history of Kendall Jenner has long been a contested one. From rumours she briefly dated Justin Bieber thanks to a single Instagram photo (which was swiftly deleted) to leaving Anwar Hadid with love bites on her neck after a night out, the internet is rife with speculation on the model’s love life.

A source for Entertainment Tonight has now revealed that Jenner split from boyfriend of at least two years, Devin Booker. “Kendall feels like they’re on different paths,” they said. Another insider echoed this statement. “[The couple] have had discussions about their future but they are not on the same page.”

If the information is accurate, she is unlikely to ever address the break up publicly. In light of the news however we’ve reflected back on Jenner’s dating history from that brief stint with A$AP Rocky (who would later go on to share a child with Rihanna) to her on-again off-again relationship with Harry Styles. Ah, those were the days.

NICK JONAS

Back in 2015 when boho reigned supreme and Drake had released “Hotline Bling”, the star’s dating history began when Jenner was set up with Nick Jonas by close friend Gigi Hadid (who was dating Joe Jonas at the time). He had just split from Olivia Culpo but according to boy band star, he never dated the model. “We’re not dating,” he told E! News. “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.”

HARRY STYLES

The exact lineage of Harry Styles and Jenner is not clear but the couple had dated on and off between the years of 2013 and 2016. The singer is rumoured to have written a song about the model in his 2017 namesake album but has refused to discuss it.

JORDAN CLARKSON

Sometime around the end of her bond with Styles (a shame), Jenner very briefly dated NBA player, Jordan Clarkson from March 2016. The athlete who was playing with the Cleveland Cavaliers at the time was spotted with Jenner at Coachella and then again at a Fourth of July celebration in Malibu. In December 2016 they also shared a New Year’s Eve kiss. Neither Jenner or Clarkson addressed the relationship which soon fizzled out.

A$AP ROCKY

Kendell Jenner & ASAP Rocky / Credit: Raymond Hall/GC Images

In a crossover with Clarkson, Jenner was also believed to be dating A$AP Rocky across 2016 and 2017 with US Weekly reporting they were “full-on dating”. Whatever that means. They attended the 2017 Met Gala together where they were certainly cosy together. Just over a year later and the same publication revealed that they had part ways. The couple “weren’t seeing each other a lot. They weren’t really official but were obviously dating. Their schedules are really hard,” a source said.

BLAKE GRIFFIN

Between 2017 and 2018, Jenner controversially dated NBA player Blake Griffin after he filed for divorce from wife and mother to his children, Brynn Cameron. He later moved back to Detroit after a child support lawsuit was filed and ended his relationship with the reality star. Around the same time she was seen kissing Anwar Hadid at a party, but let us preface, a drunk smooch is probably not the equivalent of dating.

BEN SIMMONS

Kendall Jenner & Ben Simmons / Credit: Mitchell Leff/Getty Images

Jenner’s affinity with NBA players continued through the summer of 2018 when she was reported to be dating Australian basketball star, Ben Simmons. It was perhaps the most open Jenner had been about a relationship, and was often photographed on the side of the court or out to dinner with the athlete. We were shocked to learn that in May 2019, the pair had broken up.

A source told People that the relationship has simply “run its course”.

DEVIN BOOKER

Kendall Jenner & David Booker / Credit: NINO/GC Images

After nearly a year of secretly dating, Jenner debuted her relationship with Booker on Instagram stories shortly after Valentine’s Day last year. They kept details of their relationship somewhat secret on social media but had been photographed hand-in-hand many times, even attending Kourtney Kardashian and Travis Barker’s wedding in Portofino, Italy.

It was just a couple of months ago when Booker briefly commented on the relationship with the Wall Street Journal Magazine. Soon after on June 23, 2022 it was revealed they sadly called it quits.