Kendall Jenner stands out when it comes to high-profile celebrity relationships for keeping her romantic life hidden more discreetly than many of her famous relatives. Though linked with numerous athletes, musicians, and fellow celebs over time, Kendall rarely opens up publicly about any romances while leaving most details out of view.
Now, as reports continue to suggest Kendall Jenner may be dating an Oscar-nominated actor, many fans are once again taking an interest in Kendall’s past relationships – from NBA stars and chart-topping musicians all the way back through to music-video directors and models. Here is an in-depth look back into all Kendall’s most talked about relationships spanning from NBA stars and musicians all the way down the list!
Kendall Jenner Has an Achievable Dating History Over Time
Kendall stands apart from many reality TV stars by clearly distinguishing her professional life from personal relationships. Though her fashion campaigns and runway shows garner headlines, her dating life remains relatively low-key.
Here is a timeline showcasing her relationships with some of the more notable men she has been linked to.
Julian Brooks (2012-2013)
One of Kendall’s first known relationships was her high school sweetheart Julian Brooks; it reportedly took place while Kendall was building up her modeling career and appearing on Keeping Up With the Kardashians.
They eventually broke up quietly without much fanfare in 2013, both moving on without further public notice.
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Kendall began dating singer Harry Styles (2013-2016) soon after moving into Hollywood. Their romance quickly rose to become one of Hollywood’s fabled on and off relationships.
After being photographed together multiple times since 2013, dating speculation between these two was first rampant in late 2013. Over subsequent years, they were photographed vacationing, attending parties and engaging in private activities together – leading many people to speculate they may have reconciled several times over.
Though neither one ever confirmed their exact relationship status in interviews afterwards, both spoke positively of each other in later interviews and have remained friendly over time.
Kendall was linked with NBA player Jordan Clarkson during 2016.
Both were frequently seen together in Los Angeles attending birthday celebrations and spending time with mutual friends; although their romance never progressed further than casual dating before eventually parting ways. Multiple reports at the time claimed they dated casually before eventually going their separate ways.
Kendall had also been romantically linked with rapper A$AP Rocky during this same time period.
As they attended fashion events together and appeared at events like the Met Gala together, along with being regularly photographed having nights out together, their presence caused months of dating rumors; though both remained relatively silent about any potential romance between them.
Their relationship apparently ended in 2017 due to their hectic work lives and commitments.
Kendall began dating NBA star Blake Griffin during this period
Kendall made no secret of her connection with Griffin during interviews; both could often be seen attending sporting events together and attending dates together. Kendall even hinted at their romance during interviews without directly naming Griffin.
- By 2018, reports had confirmed their split due to time demands and distant commitments.
- Ben Simmons (2018-202020) Australian basketballer Ben Simmons became one of Kendall’s longest relationships.
- They first stirred up romance rumors in 2018 and continued their on/off romance for nearly two years.
Although they occasionally appeared together at family gatherings or public outings, Kendall always maintained an intentional distance in regards to her relationships, believing they work better away from public scrutiny. According to one interview she gave, Kendall explained she prefers keeping these intimate affairs between themselves because it allows the relationship to progress more naturally without constant public scrutiny.
In 2020, their relationship ultimately came to a conclusion.
Devin Booker (2022-2023).
Kendall had one of her closest and longest public relationships when dating NBA star Devin Booker.
These two began secretly dating in 2020 before making their romance public in early 2021 on Instagram. As their romance developed, the couple would often travel together, attend family functions together, and support one another professionally.
Although they appeared to have an intimate partnership, the couple experienced multiple separations and reconciliations over time.
At first, they reconciled later that year; however, by late 2023 multiple entertainment outlets confirmed they had once more parted ways due to busy schedules and different priorities.
Even after their split, sources indicated the two remain good friends.
Rumored Relationship with Bad Bunny
After her divorce from Devin Booker, Kendall made headlines after becoming linked with Puerto Rican superstar Bad Bunny.
These two were first seen together early 2023 and quickly appeared courtside at NBA games, attended fashion events together, and traveled together. Though neither publically acknowledged their romance, frequent public sightings of them strongly fuelled speculation of an ongoing romance between them.
Reports indicated they parted ways toward the end of 2023; however, later reports noted they spent time together again during 2024, which caused renewed reconciliation rumors to circulate.
Kendall nor Bad Bunny have publicly addressed the nature of their relationship.
Kendall Jenner Has Reported New Romance Plans
Recent entertainment reports reveal Kendall has been spending time with an Oscar-nominated actor, prompting new dating speculation in 2026.
As is typical for Kendall and most of her relationships, neither party has confirmed or disproved it publicly. Kendall tends to remain mum on matters related to love or relationships in public settings – preferring instead to keep the focus primarily on work.
So far, their relationship has only been confirmed through media reports rather than official confirmation by either party.
Why Kendall Does Not Share Details of Her Relationships
Kendall has often mentioned why she prefers not discussing much about her dating life.
Differing from some members of the Kardashian-Jenner clan, she believes relationships must develop organically in private. She has stated in past interviews that placing every aspect of romance under public scrutiny creates unnecessary pressure for all involved parties involved in any romantic encounters.
Since she first made headlines as one of entertainment’s premier families, she has retained this approach and become one of the more private celebrities within.
Kendall Jenner has amassed quite the dating history with some of entertainment and sports’s biggest stars, from Harry Styles and A$AP Rocky to NBA players Ben Simmons and Devin Booker – her dating life remains highly anticipated among public audiences but Kendall prefers keeping details private about it all.
With recent reports linking Kendall to an Oscar-nominated actor, fans are sure to closely follow any official confirmation or denial from either party. Kendall remains committed to maintaining one of the world’s leading modeling careers alongside maintaining a personal life which remains mostly out of public eye.
Mark is a staff writer at ScoopNit, covering celebrity news, social media creators, influencers, and internet culture. He focuses on delivering accurate, engaging, and timely stories by following trusted sources and the latest online trends.
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