Kendall Jenner has been a television personality since the age of 11, spending a significant portion of her time on magazine covers, catwalks for upscale fashion brands, and socializing with her family and stylish companions.
However, she adheres to the principle that merely being well-known for over half of one’s life does not necessarily imply that everyone should be privy to every detail about them.
From a very tender age, I’ve often found myself feeling disconnected within my family circle. In an interview with WSJ. The Magazine back in 2023, I shared this sentiment. I find myself in this world that was handed to me at birth, but it’s not the one I personally picked out for myself.
Kendall hasn’t stopped watching The Kardashians, even after Keeping Up With the Kardashians ended in 2021. However, she stands out from her sisters as a full-time model who doesn’t have children yet, unlike them. She expressed excitement about becoming a mother someday but stated that it’s not going to happen right now, being the aunt of 23 nieces and nephews.
Just as with all members of her family, her personal life has sparked widespread curiosity, which is why people took note when she was spotted dining with her former boyfriend Devin Booker during the Valentine’s Day weekend in Aspen.
While she’s open to discussing a wide range of topics such as anxiety, therapy, fashion, and business, details about her personal relationships remain private.
As an ardent devotee, I strive to navigate the delicate equilibrium between preserving intimacy and maintaining privacy, all while not allowing the disheartening pressure and strain caused by intrusions to dampen my enthusiasm for my personal sphere. I firmly believe that this approach is the more balanced, healthier way to manage relationships.
It’s highly unlikely that she will express any thoughts about the possibility of rekindling their relationship with the NBA player.
Could there be more stories between her and the latest ex-boyfriend known as “Bad Bunny”, who was present at her runway appearance for Calvin Klein during New York Fashion Week last week, that we don’t know about?
As a committed admirer, I’ve observed that Kendall often discusses relationships and emotions in a general sense, rather than explicitly revealing who might be sparking those feelings at any particular moment.
In a 2023 article for Harper’s Bazaar, she openly declared, “I love deeply, without reservation.” She added, “I abhor farewells, and I am prepared to battle to avoid having to say goodbye. I am unwavering in my commitment to relationships. I have been this way since childhood, despite being timid and sometimes closed off at times. I never surrender on anything. Some people may not be willing to engage with me at that level. However, I would prefer to persevere rather than close myself off to something without giving it a fair shot.
Instead, she often refers to herself as “the most solitary individual,” as she finds it more alluring to stay at home rather than venture out and socialize with others.
And yet romance still finds her.
Regardless of her current relationship status, the internet frequently connects her with various individuals, a fact that even Kim Kardashian acknowledged when she wore a “Kendall’s Starting Five” T-shirt on an episode of The Kardashians, showcasing her sister alongside rumored and confirmed love interests such as Blake Griffin, Ben Simmons, Jordan Clarkson, Kyle Kuzma, and Devin.
Among the basketball players you mentioned, which one did Kendall genuinely pursue a relationship with? Additionally, who are the individuals she has dated beyond the sporting arena? Here’s a breakdown of her low-key romantic past:
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Which of those basketball players were actually pursued by Kendall? Furthermore, who have been her dates outside the sports environment? Below is an overview of her discreet love life:
Kendall Jenner expressed to Giuliana Rancic of TopMob in November 2013 that she and Harry Styles weren’t involved romantically, saying, “We aren’t telling a story, we’re just friends,” adding, “He’s a great guy.
However, further encounters in New York and London led Brody Jenner to ponder if, regarding their relationship, it seemed like his half-sister was calling the shots.
He informed the New York Daily News in December that “she’s certainly enjoying herself with him.” He added, “She’s quite wise for her age, very smart. However, they are both quite young.
18 and 20, Kendall and Harry managed to keep each other’s contact information, meeting up for surprising public appearances in 2016 (like a passionate display on a yacht), as well as in 2018 and 2020…
To put it simply, it’s clear that these two have a strong bond that could potentially endure, given that they’ve been generating rumors of a romantic nature since as late as 2022, after Harry parted ways with Olivia Wilde.
According to our source, she and Harry have always been good friends. They’ve managed to stay on friendly terms throughout the years and they still keep in contact with each other.
Kendall has never been romantically involved with Justin Bieber, although they had frequent encounters that led some individuals to assume they might have been.
Enough so that it was brought up during a Nightline interview Kendall gave in 2014.
As a devoted fan, I can’t help but share this personal tidbit: The “Baby” singer is not just an acquaintance, he’s a longtime friend of our family. Misconceptions may float around, but let me assure you, there’s nothing to those assumptions.
Indeed, I’ve been utterly smitten with the fact that Kendall Jenner and Hailey Bieber have been close friends for quite some time now. It’s not uncommon to see them double date with the lovely couple, especially when I find myself in need of a plus-one. On those occasions when I don’t, I still enjoy spending quality time with this dynamic duo all by my lonesome.
Back in August 2015, finding myself newly single, I was whispered to be romantically linked with the stunning Kendall. It all started when my brother, Joe Jonas, and his girlfriend at the time, the fabulous Gigi Hadid, brought her into my orbit.
But they weren’t on the level of dating, according to Nick.
Kendall is fantastic, he shared with TopMob News. Given that she’s close pals with Gigi, and considering Joe and Gigi’s relationship, it happens occasionally that we find ourselves at the same spot, and then we all socialize together.
In the summer of 2016, there were reports of a heated argument between Jordan Clarkson (who was on the Los Angeles Lakers at the time) and Kendall over the Fourth of July—yet by November, it appeared that they had patched things up amicably, as basketball season commenced.
In that same month, Jordan attended Kendall’s high-profile 21st birthday gathering alongside many celebrities; however, their relationship remained informal.
Also on Kendall’s radar at the time, at least as a cool guy to hang out with, was A$AP Rocky.
Despite waiting seemingly patiently until Rihanna was prepared to start dating him, he and Kendall enjoyed spending time together in 2016 and 2017, attending dinners, partying in Miami and New York, showing up at Coachella, and getting close for Kylie Jenner’s iconic Met Gala selfie.
In August 2017, Los Angeles Clippers player Blake Griffin was spotted taking out Kendall on several occasions around the city, and she attended a few games from the sidelines.
However, it turned out to be more about casual companionship and enjoyment rather than the start of a deep romantic relationship. Then, in 2018, Blake got traded to the Detroit Pistons, effectively ending that chapter.
Ben Simmons initially pursued Kendall, with their first encounter happening in the spring of 2018. They made an effort to meet whenever they could, despite Simmons being stationed in Philadelphia at the time. Interestingly enough, as of 2025, Simmons now plays for the Clippers.
In the vibrant season of 2019’s spring, I had a unique opportunity to model for Australian Vogue while simultaneously streaming a thrilling 76ers game. As fate would have it, this event was chronicled in the subsequent cover story. Later on, I made a call to the Melbourne-born icon, eager to share my pride over his recent GQ Australia cover gracing my possession.
The individual shared with Australian Vogue that they hold many aspects of life, such as friendships and connections, in high regard and consider them extremely significant. They believe that exposing these matters to the public can lead to unnecessary complications. Moreover, they expressed their youthfulness and the current uncertainty they feel about relationships.
By the time of the Met Gala on the first Monday in May 2019, they had parted ways in a friendly manner, with Kendall anticipating that her busy schedule might create numerous difficulties.
According to her, everyone takes a unique journey, and we each have our individual methods of navigating life’s twists and turns. Your twenties, she suggests, are primarily about making mistakes and discovering your own way forward.
In the meantime, the Internet seemed to notice a recurring trend. Back in 2019, a fan posted a meme on Twitter titled “NBA Starting Five of Players Dated by Kendall Jenner.” The meme included pictures of Jordan, Ben, Blake, Kyle Kuzma (who was then with the Lakers), and D’Angelo Russell.
“This is a playoff team lmao,” the fan wrote.
Then it was Kendall with the dunk: She reposted, adding, “2 out of 5 accurate, thanks.”
Kendall started dating Devin Booker around 2020 and their relationship lasted nearly two years. In fact, she invited the Phoenix Suns’ shooting guard as her date to her sister Kourtney Kardashian’s wedding in Italy, which took place in May 2022.
However, within the next month, they found themselves spending time separately. A source shared with TopMob News that upon their return from their trip, they began to sense a lack of compatibility and recognized their lifestyles were vastly different.
Come July, it was back to the game for me, but come November, we were drifting apart, our schedules still clashing. (Though I replaced D’Angelo from my “Kendall’s Starting Five” by the time Kim Kardashian got her hands on a T-shirt version of that meme.)
In 2025, a Valentine’s Day weekend encounter of the couple wearing snow goggles at a restaurant in Aspen indicated that one’s twenties are indeed a time for going with the flow and sorting things out as they come.
In the year 2023, Bad Bunny made his entry into Kendall’s world, and their first public appearance together was reportedly a double date with Justin Bieber and Hailey Bieber in February.
Later on, Kendall attended the Puerto Rican artist’s performance at Coachella in April. The two of them were spotted attending a Met Gala afterparty the following month, and they both matched their outfits at a Lakers game.
Over time, they had many romantic evenings together, and they attended the Gucci fashion show during Milan Fashion Week in September. However, by the end of the year, their relationship had come to an end.
On the other hand, since they could remain friends, it’s not surprising that they have reconnected multiple times in various parts of the globe, given their common circle of friends.
During New York Fashion Week in February, Bad Bunny chose not to miss out on a front-row view, attending the Calvin Klein Collection’s Autumn/Winter 2025 show where Kendall strutted her stuff on the runway.
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2025-02-22 16:18