Image via Complex Original
For someone who found initial fame on a reality show documenting her family’s complicated personal lives, Kendall Jenner is notoriously private about her dating life. The model, who surrounds herself with people who are notoriously public with their dating lives (Gigi Hadid, her entire family, etc.), has somehow been able to keep her romantic happenings under the radar. Maybe once has Kendall been photographed on what can be called and confirmed as a date, and she's never openly commented on any relationship of hers. And yet, she's been linked to nearly 20 people over the last three years. Of course, most of her rumored relationships are about as fake as her storylines on Keeping Up with the Kardashians and for every real relationship there are about five other fake ones reported. This is especially helpful to keep in mind as we battle the news that Kendall is possibly, maybe, but most likely dating rapper A$AP Rocky, even though there is no photographic evidence to prove they even know one another exist. So, while we deal with that current mystery, let’s go on a journey to outline who Kendall has dated though the years and which of those relationships were real, fake, or a literal joke. (Note: the below probabilities are somewhat subjective.)
Julian Brooks
Years Active: 2012-2013
Probability They Actually Dated: 100%
Julian was Kendall’s high school boyfriend, and our entry into the model’s dating life. At just 17, and without even a hint of a high school diploma, Kendall broke up with Julian after he was rumored to have been cheating on her while away at college in Nevada. Young love is so complicated!!
Young Jinsu
Years Active: Oct. 2013
Probability They Were Actually Dating: 40%
In October of 2013, Kendall was rumored to have licked her Julian wounds with rapper, Young Jinsu. While she was still 17 and Young Jinsu 21, sources and friends claimed the two had been dating “for months.” Kendall shut rumors down on Twitter saying that her spectators needed to “relax” because she was “still single.” As history has proven though, it’s not out of the question for an underage Jenner girl to date a grown man with a struggling rap career, so there could have been some truth to this relationship.
Harry Styles
Years Active: 2013-2014, and 2016
Probability They Were Actually Dating in 2013-2014: 100%
Probability They Were Actually Dating in 2016: 30%
Probability Kendall Will Revisit That D Again in 2016: 100%
Kendall’s most public relationship happened during the winter of 2013 and 2014 when she started dating One Directioner, Harry Styles. Their relationship only lasted three months, most likely due to the rampant torture one was required to endure when dating a One Direction member in their prime. Their story didn’t end in 2014, though, as they were linked to one another yet again in February of this year after being photographed on multiple occasions—most notably seen kissing on a yacht. Both of their mothers and Ellen Degeneres were all aboard, so you know there's some real support for Hendall 2.0 (and any future versions).
Ashton Irwin
Years Active: Aug. 2014
Probability They Were Actually Dating: 0%
In August 2014, Kendall Jenner was accused of dating 5 Seconds of Summer member and friend of Harry Styles, Ashton Irwin. The only evidence of their relationship was a grainy Instagram photo posted by a friend of Kendall’s. In the photo, Kendall is seen in the foreground and Ashton in the extreme background. So yeah, it was BS. Ashton himself went on to admit that the two had barely even exchanged “hellos.”
Chandler Parsons
Years Active: Aug. 2014
Probability They Were Actually Dating: 30%
Ashton Irwin wasn’t the only man linked to Kendall in the late summer of 2014. The then budding model was also linked to her first NBA player Chandler Parsons, who was 25 at the time to Kendall's 18. It was said that Kris Jenner set the two up after they were seen out at dinner. Presumably not wanting to jeopardize his $40 million dollar empire and speculated dating show, Chandler denied reports. He said that the two shared a personal trainer, and basically went out to eat with a group. Sure you did, Chandler. SURE YOU DID.
Cara Delevingne
Years Active: Winter 2014
Probability They Were Actually Dating: 50%
Probability They Were Just Trying Something New and Fun: 100%
Kendall and Cara, colloquially known as CaKe, had a very close relationship. They not only shared a profession and an ex (Harry Styles) but a penchant for posing ~*closely*~ with one another. What really kicked this dating rumor into high gear is the apparent dissolution of CaKe’s friendship once Cara and her current girlfriend, St. Vincent, became publicly serious.
Justin Bieber
Years Active: Late 2014 and April 2015 (it's also kinda ongoing)
Probability They Were Actually Dating: 0.5%
Probability They Were Fuckin': 100%
Justin Bieber will move mountains to leave his mark on the Kardashian/Jenner family. He and Kendall were first rumored to be dating in late 2014 and into 2015. Now, Bieber is a longtime family friend, but there have been about one too many cozy photos of him with Kendall to let this one slide, and his admission that their fling was “not serious” seemed to be a tell too. What makes this rumor bone-chillingly disgusting is the fact the Justin Bieber has almost definitely slept with Kendall’s oldest sister, Kourtney, too.
Lewis Hamilton
Years Active: May and Sept. 2015
Probability They Were Actually Dating: 40%
Kendall Jenner was linked to Marques Houston Lewis Hamilton, British race car driver, twice in 2015. In May of 2015, Kendall was photographed wearing Lewis’ chain in a group photo with Lewis while at one of his races. Lewis also, per an Instagram caption, admitted that he considered Kris Jenner a friend, so there's that. Then in September, Lewis and Kendall were seen walking with other people in broad daylight during New York Fashion Week. Overwhelming evidence, right?
Chris Brown
Years Active: Winter 2014 and Spring 2016
Probability They Were Actually Dating: 35%
Sadly, Kendall has been rumored to have dated Chris Brown twice, which is two times too many. For reasons that my poor brain can’t comprehend, Chris Brown has been a Kardashian/Jenner family friend who has gotten too close to the youngest set of Jenners during their most formative years. In 2014, rumors included details that Kendall was interested in Chris for his looks and the probable exposure she’d get from dating him. In 2016, the details include sheer lunacy and lack of guidance. It's also worth notiong that Chris is one of Tyga’s near and dear friends, which may add to the validity of these reports.
Alfredo Flores
Years Active: Feb. 2015
Probability They Were Actually Dating: 30%
Kendall Jenner kicked off 2015 with rumors surrounding her relationship with Justin Bieber friend and photographer, Alfredo Flores. Their relationship apparently blossomed due to Alfredo’s help in “perfecting” Kendall’s modeling poses. Even if this creepy factoid is true, the two can only cite Instagram when asked for photographic evidence of their friendship.
Michael B. Jordan
Years Active: May 2015
Probability They Were Actually Dating: 10%
Probability Kendall's Actually Met Michael B. Jordan: 70%
After the Met Ball in 2015, Michael B. Jordan was photographed walking behind Kendall Jenner as they both left an after party. In GQ later that year, Michael laid the rumors to complete rest by admitting that Kendall is a “friend” and that he doesn’t know her “that well.”
Nick Jonas
Years Active: Summer 2015
Probability They Were Actually Dating: 10%
While Nick Jonas’ older Brother Joe Jonas was dating Kendall’s BFF, Gigi Hadid, Nick and Kendall were rumored to have a romance. It’s no secret that both Gigi and Joe wanted to set up their Kendall and Nick, but this one definitely never took off. Shame.
Orlando Bloom
Years Active: Summer 2015
Probability They Were Actually Dating: 70%
Another reported Summer 2015 romance, Kendall was connected to Orlando Bloom, a 38-year-old recently divorced father. Kendall is just Orlando’s type (dark hair, way younger), so this really isn’t that shocking a duo. Plus, they were spotted on a few dates, according to sources. If Orlando hadn’t claimed he doesn’t even have Kendall Jenner’s number while accepting a Humanitarian Award that fall, this could have possibly been a sure thing.
D'Angelo Russell
Years Active: Nov. 2015
Probability They Were Actually Dating: 10%
Kendall was linked to LA Laker D’Angelo Russell, but the story lasted for about half of a news day, and presumably only came about because he was a warm body who plays her family's favorite sport.
Drake
Years Active: Jan. and Dec. 2015
Probability They Were Actually Dating: 0%
At both the beginning and end of 2015, Kendall was linked to Drake. Drake is a legitimate friend of the family, but I remain highly skeptical of this pairing. Despite his fuckboy mentality, I highly doubt Drake would jeopardize Kris’ confidence by engaging in a relationship with Kendall. But, if they ever decide to change their minds, I would be here for it 100%.
Scott Disick
Years Active: EVERY YEAR
Probability They Were Actually Dating: -100%
Because society is obsessed with finding the next best thing to incest, this rumor has been unsurprisingly pervasive. Yes, Scott has dated a Kendall look-alike, but bet money he’s yet to find romantic solace in the real deal.
Lauren Perez
Years Active: Winter 2016
Probability They Were Actually Dating: 90%
This one is my favorite. If you ask me, it’s very possible that this entire list is a cover-up for Kendall’s relationship with her BFF/close pal/possible girlfriend, Lauren Perez. The rumors around these two reached their peak in Winter 2016, and continue to thrive on Tumblr and in Instagram comments. Just food for thought—food that is so, so yummy.
Jordan Clarkson
Years Active: 2016
Probability They Were Actually Dating: 80%
There have been rumors about these two since spring 2016, and they flared up again this past Fourth of July weekend. Everything about this makes sense. Kendall skews towards the athletic type and Jordan towards the models (a recent ex of his was Chanel Iman). However, like many of Kendall’s “suitors,” there have only been rare sightings of the two, but in the few we’ve seen, they've seemed pretty cozy. This probably happened, but it probably isn’t that serious.
A$AP Rocky
Years Active: Right here, right now
Probability They're Actually Dating: a painful 100%
As recently as this Saturday, Kendall and A$AP Rocky were seen reportedly gallivanting all around New York City with little regard for the heat dome or our emotions. Rocky apparently even took Kendall to Harlem for the first time. That means it's serious. Help us, Jesus.