Kendall Jenner, arguably the most stylish face in the fashion world, one of the biggest reality TV stars and her personal life, especially so, has always remained a shell, shrouded in secrecy. Notwithstanding her discretion, her relationships have often been news stories. However, as of February 2025, breakthroughs have resulted in the return of her dating involvement with an NBA star, Devin Booker.
Early Relationships and High-Profile Romances
Jenner's public dating life started in the early 2010s. She was associated with British pop idol Harry Styles in 2013. Their on-again-off-again affair lasted for more than a couple of years, and it received a considerable amount of media coverage. The duo was spotted together on multiple occasions, fueling speculation about their bond.
Having partnered with Styles, Jenner was also rumored to have been in a relationship with several other celebrities. In 2016, she was seen with rapper A$AP Rocky, and their relationship reportedly lasted into 2017. Roughly at the same time, she was also rumored to have slept with NBA pro-Jordan Clarkson, but the relationship was a short affair. Later in the year 2017, Jenner cohabited with an NBA player, Blake Griffin. Their relationship, however, concluded in early 2018.
Ben Simmons and the NBA Connection
Jenner's fandom included Australian sportsperson Ben Simmons also. They started dating in May 2018 and their relationship displayed a repeated pattern of on-and-off behavior. They were regularly seen together, and Jenner especially liked to attend Simmons' games. Although there are easily identifiable products of the chemistry of the pair, it broke up in early 2020.
Devin Booker: A Significant Chapter
Rumors began in April 2020 of Jenner's involvement with Phoenix Suns' shooting guard, Devin Booker. Their affair quickly evolved into having a stronger public presence as the couple shared pictures of their time together on social media. They marked birthdays and anniversaries together, and shared events together, displaying strong bonding. However, by November 2022, news broke that Jenner and Booker had quietly broken up and that they had conceded to be in disagreement about their professional career and how to live their life.
The Bad Bunny Interlude
Jenner was alleged to have been romantically linked with Puerto Rican rapper Bad Bunny in early 2023 following the breakdown of her relationship with Booker. The whirlwind dating lead them to multiple events such as modeling shows and musical festivals. Remembering the initial euphoria, the relationship has all the time been fraught with problems that ended with a separation in December 2023. They reunited in May 2024 but, alas, by September 2024, they actually split.
Rekindling with Devin Booker
New reports from February 2025 report that the pairing of Jenner and Booker has once again fallen in love. The couple was photographed enjoying a meal together during the Valentine's Day weekend in Aspen, Colorado, at a cozy and romantic restaurant and seemed to be having "fun together,". The reunion has opened the door for discussion on whether they should consider getting back together.
A Private Personal Life
With respect to all her relationships, Jenner has a strong sense of privacy in her private life. During interviews, she has emphasized her desire to keep her romantic life off the radar for personal reasons in lieu of a spectrum of publicly known relationships of her immediate family. And that discretion has enabled her to, in effect, give her dating relationships a "normal" veneer, even though unkind media notoriety.
The timeline of relationships in Kendall Jenner as shown early in her life history reveals a pattern of public affairs that has enabled her growth as an individual and in the public sphere. Until early 2025, her rekindled personal affair with Devin Booker seems to point to a new phase of their shared story. Although media clamor is intense, Jenner still maintains her private, discrete way of life in the private sphere.
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