Inside Kendall Jenner’s Dating History: NBA Stars, Singers & More

 Introduction

Kendall Jenner, one of the most famous models in the world, is known for her striking runway presence, effortless style, and, of course, her connection to the Kardashian-Jenner dynasty. Unlike her sisters, who often share their relationships publicly, Kendall prefers to keep her love life relatively private. However, over the years, she has been linked to several high-profile celebrities, including NBA players, musicians, and fellow models.

In this article, we take an in-depth look at Kendall Jenner’s dating history, exploring each relationship, the rumors, and how her love life has evolved over the years.

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 Early Relationships and High School Love

Julian Brooks (2012-2013) – The High School Sweetheart

Before stepping into the world of high fashion, Kendall Jenner had a normal teenage romance with her high school sweetheart, Julian Brooks. Both attended Sierra Canyon School in Los Angeles, where Julian was a star football player. Their relationship seemed strong at first, with Kendall often seen cheering him on at games.

However, as Kendall's modeling career started taking off, she became busier, which created some distance between them. Reports later suggested that their breakup was due to trust issues, with rumors of Julian being unfaithful. After their split, Julian went on to play college football, while Kendall focused on her skyrocketing modeling career.

The Music Connection: Singers in Kendall's Love Life

Harry Styles (2013, 2016) – A Special Bond

Kendall and British pop star Harry Styles first sparked dating rumors in 2013 when they were spotted having dinner together in Los Angeles. Both denied the relationship, but their frequent appearances together kept the speculation alive.

In 2016, the two reignited romance rumors when they were seen vacationing together on a yacht in St. Barts. Paparazzi captured them laughing, cuddling, and enjoying each other’s company. Their chemistry was undeniable, but neither confirmed the nature of their relationship.

Although their romance never became official, they remained close friends. In 2019, when Harry hosted "The Late Late Show with James Corden," he playfully teased Kendall about their past, hinting at their deep connection. Kendall has also been spotted at several of Harry’s concerts over the years, proving that their bond has endured.

A$AP Rocky (2016-2017) – Fashion Meets Music

Kendall’s relationship with rapper A$AP Rocky was built on their mutual love for fashion and music. They were first seen together in 2016, attending high-profile events and private parties. Their relationship became more public when they attended the 2017 Met Gala together, where their chemistry was evident.

A$AP Rocky, known for his influence in streetwear fashion, and Kendall, a top model, made a stylish duo. Despite their compatibility, their busy schedules made it difficult to sustain the romance, and they eventually parted ways. However, they have remained on good terms, often crossing paths at events.

Bad Bunny (2023-2024) – A Latin Love Affair

One of Kendall’s most surprising relationships was with Puerto Rican reggaeton star Bad Bunny. They were first linked in early 2023 after being seen on multiple outings together. Their romance quickly became a major topic, especially since Bad Bunny had previously kept his relationships private.

The two were often spotted on dinner dates, attending Coachella together, and even showing subtle signs of affection in public. Despite their different backgrounds, they seemed to enjoy each other's company. However, by early 2024, reports surfaced that they had quietly split due to their busy careers.

Kendall’s NBA Love Story: A History of Basketball Romances

Blake Griffin (2017-2018) – Courtside Chemistry

In 2017, Kendall started dating NBA star Blake Griffin, who was then playing for the Los Angeles Clippers. Their relationship was highly publicized, with Kendall attending several of Blake’s games and the two being seen at various events together.

Things seemed serious between them, but their relationship hit a roadblock in early 2018 when Blake was traded to the Detroit Pistons. The long distance made things difficult, and they eventually broke up. Another factor that contributed to their split was Blake’s legal battle with his ex-fiancée, which reportedly put additional strain on their relationship.

Ben Simmons (2018-2019) – An On-and-Off Romance

Shortly after her breakup with Blake, Kendall started dating Australian NBA player Ben Simmons. They were frequently spotted together, and Kendall often attended Ben’s games for the Philadelphia 76ers. Their relationship was on-and-off, with reports of breakups and reconciliations throughout 2019.

Despite their ups and downs, Kendall and Ben had a strong connection. However, by mid-2019, they officially ended things, with sources citing their demanding schedules as the primary reason for the split.

Kyle Kuzma (2019 – Rumored) – A Brief Summer Fling?

In 2019, Kendall was linked to NBA player Kyle Kuzma after they were seen spending time together on a yacht over the Fourth of July holiday. However, sources later clarified that their relationship was nothing serious and that they were just friends. The rumors faded quickly, and neither Kyle nor Kendall ever confirmed a romance.

Devin Booker (2020-2023, 2025-Present) – Kendall’s Longest Relationship

Kendall’s most serious relationship to date has been with NBA star Devin Booker. They started dating in 2020, and for three years, their relationship was the most public one Kendall had ever had.

Unlike her past relationships, Kendall openly shared moments with Devin on social media, and the two were seen vacationing together multiple times. Devin even attended family events with Kendall, suggesting that their relationship was strong. However, in 2023, they decided to part ways, reportedly due to their conflicting schedules.

Reunion in 2025?

In March 2025, reports emerged that Kendall and Devin Booker had rekindled their romance. According to sources, the couple has been spending time together again, with sightings in Aspen and Los Angeles. An insider shared, “They’ve always had strong chemistry, and after some time apart, they realized they still have feelings for each other.”

Fans are eagerly watching to see if this reunion will last or if Kendall will once again move on to another high-profile romance.

Conclusion

Kendall Jenner’s dating history includes some of the biggest names in the worlds of sports and music. While she tends to keep her relationships private, her high-profile romances have always been of great interest to fans and media alike.

From NBA stars like Blake Griffin and Devin Booker to musicians like Harry Styles and Bad Bunny, Kendall’s love life has been filled with excitement, mystery, and glamour. With reports of her rekindled romance with Devin Booker, fans will be watching closely to see where her love life goes next!