Kendall Jenner, the effortlessly cool and stunningly mysterious member of the Kardashian-Jenner clan, has mastered the art of keeping her relationships under wraps.
Unlike her sisters, who are more open about their romantic escapades, Kendall Jenner prefers a more subtle approach to her relationships, giving just enough to keep the public intrigued but never enough to fully confirm anything. Over the years, she has been linked to some of the biggest names in sports, music, and entertainment, yet her relationships remain as elusive as she is. Let’s take a deep dive into Kendall Jenner’s dating history, the rumors that swirled around her, and how she’s managed to remain one of Hollywood’s most desirable yet unattainable women.
The NBA Connection: Kendall and Basketball’s Elite
If there’s one pattern in Kendall Jenner’s love life, it’s her undeniable attraction to NBA players. She’s been linked to several high-profile ballers, earning herself a reputation as a “NBA girlfriend” (though she has cheekily denied the label).
Ben Simmons: A Love on the Move
Back in 2018, Kendall was frequently spotted with Australian basketball star Ben Simmons. The two had an on-again, off-again relationship that lasted until 2019, with Kendall even attending several of his games. While the couple never made any grand declarations of love, their chemistry was evident. They were often seen out on casual dates, jet-setting between Los Angeles and Philadelphia, and celebrating New Year’s Eve together. However, between Ben’s demanding basketball schedule and Kendall’s globe-trotting modeling career, things eventually fizzled out.
Devin Booker: A Relationship That Felt Different
Among all of Kendall’s NBA romances, her relationship with Devin Booker seemed the most serious. The two sparked dating rumors in 2020 when they were spotted on a road trip together. While sources initially claimed they were just friends, it became clear there was something more. Unlike her previous relationships, Kendall and Devin actually went Instagram official, sharing cute couple moments and posting flirty comments on each other’s pictures. They even made a rare public appearance together at Kourtney Kardashian’s wedding in Italy.
But by late 2022, reports surfaced that the couple had split due to their demanding schedules. Fans were heartbroken, believing that Devin might be “the one.” However, in early 2024, whispers of a rekindled romance started circulating. Could Kendall and Devin be giving love another shot? Time will tell.
The Music Men: A$AP Rocky and Bad Bunny
Kendall isn’t just drawn to athletes, she’s had her fair share of rumored romances with some of the biggest names in music.
A$AP Rocky: A Stylish Fling?
In 2016, rumors swirled that Kendall was dating rapper A$AP Rocky. The two were seen at various events together, from Paris Fashion Week to star-studded parties. While neither confirmed the relationship, insiders claimed they had a fun, casual fling. However, Rocky eventually moved on to a more high-profile relationship with Rihanna, leaving fans wondering what could have been between him and Kendall.
Bad Bunny: The Unexpected Pairing
2023 brought a surprising romance for Kendall, Puerto Rican superstar Bad Bunny. The unexpected pairing had fans buzzing, especially when the two were spotted on multiple dates. From horseback riding to sneaky getaways, Kendall and Bad Bunny seemed to be enjoying their time together.
However, by the end of the year, rumors of a breakup started circulating. Some fans speculated that their different lifestyles and cultural backgrounds might have played a role in the split. Others believed it was simply a fun fling that had run its course. Whatever the case, Kendall and Bad Bunny certainly had everyone talking.
Harry Styles: The Relationship That Keeps Coming Back
If there’s one relationship in Kendall Jenner’s history that remains a mystery, it’s her connection with Harry Styles. The two were first linked in 2013, and over the years, their chemistry has only grown stronger. Whether they were vacationing on yachts or engaging in flirty banter on late-night talk shows, Kendall and Harry have always had an undeniable spark.
Despite the romance rumors, neither has ever confirmed their relationship. Could they just be incredibly close friends, or is there something more? Fans continue to ship the duo, hoping that one day, they might make it official.
Keeping It Private: Kendall’s Unique Approach to Love
One of the most fascinating things about Kendall Jenner is how she handles her love life compared to her famous family. While Kim, Khloé, and Kylie have all been open about their relationships, sharing their highs and lows with the public, Kendall has taken a different route.
She rarely posts about her relationships, avoids discussing her love life in interviews, and keeps her breakups out of the spotlight. This level of secrecy only adds to the intrigue. Fans are constantly trying to piece together clues from paparazzi shots and social media breadcrumbs, making her dating life a never-ending mystery.
Kendall has also addressed her preference for privacy, stating in interviews that she believes relationships are more special when they’re kept between the two people involved. She doesn’t like the pressure of public scrutiny and prefers to keep her romances as normal as possible, something that’s understandably difficult when you’re one of the most recognizable faces in the world.
The Public Fascination with Kendall’s Love Life
So why is the world so obsessed with Kendall Jenner’s dating history? Part of it has to do with her aura of mystery, she’s one of the most private members of her family, making any glimpse into her personal life feel like a rare treasure.
There’s also the fact that she’s been linked to some of the most eligible bachelors in Hollywood and sports. From NBA stars to music icons, Kendall’s romantic roster is impressive, to say the least. Fans love to speculate about who she’s dating, who she might be rekindling things with, and who could be her next love interest.
And then there’s the sheer curiosity, how does someone as famous as Kendall manage to keep her relationships so low-key? In an age where social media oversharing is the norm, Kendall’s ability to maintain privacy is almost unheard of. It keeps people guessing, keeps them interested, and ultimately, keeps her one of the most intriguing figures in pop culture.
Final Thoughts: Will Kendall Ever Settle Down?
With a love life as fascinating as hers, the million-dollar question remains: Will Kendall Jenner ever settle down? While she seems to enjoy her independence and prioritizes her career, fans can’t help but wonder if one of her former flames, perhaps Devin Booker or Harry Styles, might be her happily ever after.
For now, Kendall seems content keeping the world on its toes. And honestly, we wouldn’t have it any other way. After all, a little mystery makes everything more exciting.
Whether she’s courtside at an NBA game, stepping out with a new flame, or dodging romance rumors, one thing’s for sure – Kendall Jenner’s relationships will always be a topic of fascination.
- Emma Watson Turns 35: Here’s What Her Net Worth Looks Like Now - April 15, 2025
- Ben Affleck Gets Real About Dating After J.Lo Split - April 15, 2025
- Carrie Underwood Ends Las Vegas Residency in Tears - April 15, 2025
