KUWTK: A Look At Kendall's Dating History Throughout The Years

Kendall Jenner is an aunt to 10 nieces and nephews and she's the only one of her famous siblings who don't have kids. Famously, in 2017, her sisters Kim and Khloe Kardashian as well as Kylie Jenner were all expecting children at the same time. When we do see Kendall, she's often flying solo, and usually on the runway.

When it comes to wanting kids and starting a family, Kendall told E! News in May 2019 that sometimes it depends on the day.

"I go in and out of phases," she said about getting baby fever. "Some days, I'll be there and I'll be like, 'OMG, I think it's happening. I think I have the fever.'" However, at times, she's happy to wait. "Most days, I'm like, 'This is too much. It's a lot to be able to play with them. I'll just be like, 'Go to your mom.'"

Before trying for a family though, Kendall is trying to find Mr. Right. Allow us to go through the contenders who had their chance.

Kendall Jenner and Harry Styles casually dated on and off

Kendall Jenner and Harry Styles were on and off from 2013 to 2016. Although the status of their relationship was never officially announced, Kendall's sister Khloe Kardashian indirectly answered the question for us in an interview with Entertainment Tonight in January 2016.

"Do I think they're dating? Yes," Khloe said. "I don't know if they're like boyfriend-girlfriend. Nowadays I don't know. People are weird with stuff. So, I don't know their title. But I mean, they were in St. Barts together hanging out, so to me that's dating."

A few weeks later, Hollywood Life reported that Kendall revealed to her friends that Harry was "just not that into" her.

However, the former couple seem to be on friendly terms and can even stand being in the same room or red carpet. The former couple even appeared on an episode of "The Late Late Show" in the game Spill Your Guts or Fill Your Guts. During the game, while there weren't direct questions about their relationship, Kendall asked, "I'm dying to know this. Which songs on your last album were about me?" Styles turned red and decided not to answer the question.

Although we may never know why they ended their relationship, it's nice that they're still friends.

Kendall Jenner also dated a few basketball players

Having an attraction for athletes seems to run in the Kardashian-Jenner family. First, it was Kim Kardashian and Reggie Bush, then Khloe Kardashian and Lamar Odom. And then it seemed Kendall Jenner fell into this trend when she started dating Lakers player Jordan Clarkson the same year it was reported that Kendall and Harry Styles had stopped dating.

In March 2016, Us Weekly reported via unnamed sources that she'd been dating the basketball player and according to another unnamed source, they'd been "hooking up for months." Kendall was seen out with him in West Hollywood after a winning game on March 30.

They didn't last long, however, because a month later, it was reported Kendall had moved on.

She also dated basketball player Blake Griffin in August 2017. After a few weeks, a source told People that Kendall and Griffin were keeping things casual. A couple months later, though, Griffin was traded from the L.A. Clippers to the Detroit Pistons, effectively cooling off their tryst.

Kendall also briefly dated Ben Simmons in 2018, but in May 2019, E! News reported that the couple had split before the Met Gala.

However, in June 2019, the history of Kendall and her track record for dating basketball players got blurry. She responded to a tweet with pictures of basketball players D'Angelo Russell, Jordan Clarkson, Ben Simmons, Kyle Kuzma, and Blake Griffin claiming she'd dated all of the above. However, Kendall's response indicated that only "2 out of 5 accurate, thanks." 

Kendall Jenner also had a thing with A$AP Rocky

In August 2016, Us Weekly reported that Kendall Jenner was "full-on dating" rapper A$AP Rocky. However, it was all speculation, until Kim Kardashian shared a photo on Snapchat of her sister being intimate with the rapper at the 2017 Met Gala seemingly confirming the relationship (per The Sun). Even after the Met Gala picture, the two had yet to go public. However, in June, a source told People that things were "getting more serious."

"They're definitely still hanging out and are progressively getting more serious," the source claimed. They also highlighted the couple's outings, which included Khloé Kardashian's birthday and trips to Paris the summer before.

While there was no public statement on the two going their separate ways, a source told People that Kendall didn't see him as good boyfriend material while dishing on details about her reported new beau at the time, basketball player Blake Griffin.

"She's still talking to Rocky as well," the source said. "But he isn't the type to settle down or be a good boyfriend, so she's playing the field too."

Although they were linked for over a year, Us Weekly reported in September 2017, that while they were dating, they were never really official.

Kendall Jenner romanced Anwar Hadid for a bit

By June 2018, Kendall Jenner shared to her Instagram Story a picture of her holding hands with Anwar Hadid (per TMZ), the younger brother of models Gigi and Bella Hadid.

In September, Hadid was pictured with a massive hickey on his neck, and a few days later, Kendall had a hickey in a similar spot (per Seventeen). While it may seem weird since Kendall and the Hadid sisters are friends and work together, in October, a source told People that things were working out for the two of them.

"They actually kind of like it," said the source. "They all hang out together and Gigi and Bella actually think they're good together. Their friends think it's a little weird, but it works."

However, it wasn't meant to last. In November, Hadid took to his Instagram Story to hint that the two were over. "I wonder if I could be loved as deeply as I love," followed by a photo of his hands featuring the words, "why are you still in my mind."

Hadid later added another text post to his Story. "I used to be afraid to feel things deeply cuz I felt as if the feeling of abundant happiness couldn't be obtained forever, but openly feeling is now my only source of inspiration. And now that I'm not afraid to express my thoughts and feelings, I kinda feel like everything's pretty mellow," (per Seventeen).

Kendall Jenner is currently dating Devin Booker

Currently, Kendall Jenner is dating basketball player Devin Booker. The two were spotted together back in April 2020, but it wasn't until Valentine's Day 2021 that they went Instagram official with both of them posting the same picture of Booker cuddling up to a smiley Kendall on their Stories (per Cosmopolitan).

Since then, their support for each other has been strong. He gets her attention by leaving flirty comments on her Instagram photos. In April, he commented on pictures she took on a golf course over Easter weekend, showcasing his funny side. "Very beautiful...course," he commented.

Even Kendall's famous family seems to approve. According to an Us Weekly source, the family likes him.

"The Kardashian clan is fond of him for sure ... they've gotten to spend a lot of time with him and find him very charming, respectful, and fun," the source said.

While Kendall has often remained private in her relationships, a source told E! that she's happy.

"This is the happiest Kendall has been in a relationship," the insider shared. The source also added that what Kendall likes most about Booker is his lack of interest in the spotlight. "They are really similar and love just being low-key and staying in and laughing together."

Only time will tell if Kendall has found Mr. Right, but for now, it seems like she's content.