Who Has Kendall Jenner Dated? A Look at Her Romantic Journey

Kendall Jenner may be one of the world’s top supermodels, but when it comes to relationships, she has taken a more private approach compared to her famous sisters. While Kim, Khloé, and Kylie often share their love lives on social media and reality TV, Kendall has kept things low-key—though that hasn’t stopped fans from piecing together her dating history.

From high school sweethearts to NBA stars and chart-topping musicians, Kendall’s love life has evolved over the years. Here’s a chronological look at who Kendall Jenner has dated and how her relationships have shaped her journey.

2012-2013: The High School Sweetheart Era

Julian Brooks – The Teenage Romance

Before Kendall became a household name, she dated Julian Brooks, a football player from her high school, Sierra Canyon. Unlike her later relationships, this one was rooted in normal teenage life, away from the spotlight.

As Kendall’s modeling career began to take off, the couple drifted apart, with rumors of infidelity leading to their breakup. This was the last time Kendall dated someone outside the world of fame, marking the start of her high-profile romantic journey.

2013-2016: The Rockstar Phase

Harry Styles – The Mysterious Pop Star Connection

By late 2013, Kendall had moved on from high school romances and was linked to One Direction’s Harry Styles. Their relationship remained ambiguous and on-and-off, keeping fans guessing.

They were first spotted together in 2013, going on dinner dates.

By 2016, they rekindled their connection, vacationing in St. Barts.

Their undeniable chemistry led to ongoing speculation, though neither confirmed their romance.

Even after parting ways, the two remained friends, with Harry even playfully addressing their past on TV years later.

2016-2017: A$AP Rocky – The Fashionable Fling

Kendall’s next rumored romance came in the form of rapper A$AP Rocky, known for his bold fashion sense and music career.

The duo attended several high-profile events together, including the 2017 Met Gala.

Their relationship was more social than serious, and by the end of 2017, they had drifted apart.

2017-2019: The NBA Chapter Begins

Blake Griffin – The First NBA Love

Kendall’s dating history took a sporty turn in 2017, when she started dating NBA star Blake Griffin.

They were spotted frequently at games and events, marking one of Kendall’s more public relationships.

When Blake was traded from the LA Clippers to the Detroit Pistons in early 2018, the long-distance strain led to their eventual breakup.

Ben Simmons – The On-and-Off Relationship

Shortly after parting ways with Blake, Kendall began dating Australian NBA player Ben Simmons in mid-2018.

The couple kept their romance largely private, though they were frequently seen together.

Their relationship was on-again, off-again throughout 2019, before fizzling out completely.

2020-2023: The Longest Relationship

Devin Booker – The Love That Lasted

In early 2020, Kendall was linked to Phoenix Suns star Devin Booker. Unlike her previous flings, this was her longest and most serious relationship.

They became official in 2021, confirming their romance on Instagram.

Devin joined Jenner family gatherings, a rare move for Kendall’s boyfriends.

The couple traveled together, enjoying vacations and high-profile events.

After nearly three years together, they split in 2023, citing conflicting schedules.

2023-2024: The Unexpected Musician Romance

Bad Bunny – A Culture Clash Romance

Shortly after her split from Devin Booker, Kendall shocked fans by dating Puerto Rican reggaeton superstar Bad Bunny.

The relationship marked her first serious romance with someone outside the NBA world since her teenage years.

They attended Coachella together and were often spotted on dates.

Despite the initial chemistry, their romance quietly ended by early 2024.

2025: The Rekindled Love --Back with Devin Booker?

In March 2025, reports emerged that Kendall and Devin Booker had rekindled their relationship.

Sources close to the couple claim they have reconnected and are "very much together" again.

Whether this reunion will last remains to be seen, but it’s clear that Devin has been Kendall’s most significant relationship to date.

Conclusion: What’s Next for Kendall’s Love Life?

From pop stars to NBA champions, Kendall Jenner’s dating history has taken many turns over the years. Unlike her sisters, she avoids oversharing about her relationships, keeping much of her love life a mystery.

With her reunion with Devin Booker, fans are now wondering: Will this be the relationship that lasts? Or will Kendall’s love story continue to evolve? One thing is certain—her dating history remains just as fascinating as her career.