The Six-Year Mystery: How Long Did Kendall Jenner And Harry Styles Really Date?

The question of "How long did Kendall and Harry date?" is far more complicated than a simple number, largely because their relationship was a masterclass in Hollywood's most elusive on-again, off-again romance. The truth is, the A-list duo were romantically linked and spotted together intermittently for approximately six years, from late 2013 until their final public interactions in 2019, though their actual exclusive dating periods were much shorter and intensely private. As of , both stars have recently emerged from high-profile relationships—Kendall from her time with NBA player Devin Booker and Harry from his romance with actress Olivia Wilde—leading to a fresh wave of speculation about a potential reconnection, a testament to their enduring and mysterious bond.

The relationship between the supermodel and the former One Direction heartthrob—dubbed "Hendall" by fans—was characterized by private yacht trips, secretive dinners, and a consistent public narrative of being "just friends," despite overwhelming evidence to the contrary. This enduring ambiguity is precisely what has kept the public and media fascinated with their dynamic for over a decade.

The Complete Biography and Profile of Kendall Jenner and Harry Styles

To fully appreciate the dynamic of their relationship, it is essential to understand the individual profiles of these two global superstars.

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Kendall Jenner: Model, Mogul, and Media Personality

• Full Name: Kendall Nicole Jenner
• Date of Birth: November 3, 1995
• Place of Birth: Los Angeles, California, U.S.
• Occupation: Model, Media Personality, Businesswoman
• Known For: Starring on Keeping Up with the Kardashians, being one of the world's highest-paid models, and founding the 818 Tequila brand.
• Notable Relationships: A$AP Rocky, Ben Simmons, Blake Griffin, Devin Booker (longest public relationship).
• Current Status: Continues to be one of the most in-demand figures in the fashion industry, walking for major designers and appearing in global campaigns.

Harry Styles: Musician, Actor, and Fashion Icon

• Full Name: Harry Edward Styles
• Date of Birth: February 1, 1994
• Place of Birth: Redditch, Worcestershire, England
• Occupation: Singer, Songwriter, Actor
• Known For: Member of the globally successful boy band One Direction, and a highly acclaimed solo career with hits like "Watermelon Sugar" and "As It Was."
• Notable Relationships: Taylor Swift, Camille Rowe, Olivia Wilde.
• Current Status: Continues his record-breaking solo music career and has taken on roles in films like Dunkirk and Don't Worry Darling.

The Intermittent Timeline: Breaking Down the Six-Year "Hendall" Romance

The relationship between Kendall Jenner and Harry Styles was less of a traditional dating period and more a series of intense, private hookups and public appearances spread across six years. Here is a breakdown of their key interactions.

Phase 1: The Initial Spark (Late 2013 – Early 2014)

The first rumors of a romance between the two young stars began in November 2013 when they were spotted leaving a dinner date in West Hollywood. This was Kendall’s first major public romance. They were later seen together on a ski trip in Mammoth, California. The most definitive sighting from this initial phase came in January 2014 when they were photographed on a yacht in St. Barts, a highly publicized trip that cemented the dating rumors, despite both denying an exclusive relationship. This initial dating period was short-lived, reportedly lasting only a few months.

Phase 2: The Extended Break and Reunion Rumors (2014 – 2015)

Following their initial spark, Kendall and Harry were not publicly linked for a significant period. However, they were often seen in the same social circles, leading to constant speculation. In late 2015, the rumors reignited when they were spotted having dinner together in Anguilla, followed by another highly photographed yacht trip. This second romantic getaway, again in St. Barts, was perhaps the most convincing evidence of their relationship, featuring intimate photos that left little doubt about their status.

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Phase 3: The Late-Night Confirmation (2016 – 2019)

While they continued to deny being a couple, their interactions became more infrequent but more telling. In 2016, they were seen together in Los Angeles, sparking another round of dating news. The most significant "confirmation" of their long-standing, complicated history came in December 2019 when Kendall Jenner appeared on The Late Late Show with James Corden. Harry Styles was serving as the guest host, and during a game of "Spill Your Guts or Fill Your Guts," Kendall was forced to rank her siblings’ parenting skills or eat a thousand-year-old egg. Instead, Harry asked her to rank his solo albums, a moment that fans interpreted as a playful, intimate exchange between two people who know each other very well.

In a separate segment during the same show, Kendall was asked to name the best song Harry had ever written about her, a question she expertly dodged, but one that further solidified the public's belief in their romantic past.

Why Their Relationship Endures: From Lovers to Close Friends

The primary reason the "How long did they date?" question is so hard to answer is that their relationship transitioned from romantic to platonic, but their bond never truly broke. The total duration of their on-off romantic involvement is best summarized as six intermittent years, with the longest continuous stretch likely being only a few months at a time.

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The Power of Privacy

Unlike many celebrity couples who use their relationship for publicity, both Kendall and Harry are notoriously private. They refused to confirm or deny the relationship, which allowed them to maintain a casual, no-pressure dynamic. This lack of public scrutiny likely helped them preserve their friendship after the romance fizzled out.

The Current Status: A Possible Reconnection?

The most recent and intriguing development, as of , is the speculation surrounding their current status. Both stars recently ended major relationships—Harry with Olivia Wilde and Kendall with Devin Booker. Following these breakups, sources reported that the pair had reconnected, suggesting that they remain a constant presence in each other's lives. Kendall was even spotted attending Harry's "Love On Tour" show, indicating their enduring support and close friendship.

This enduring connection, spanning over a decade, suggests that while the romantic chapter may be closed, the friendship between Kendall Jenner and Harry Styles is a deep and meaningful one. They represent a rare example of a celebrity couple who managed to successfully navigate the transition from secret lovers to supportive, lifelong friends in the public eye.

Key Entities and Topics Related to "Hendall"

• One Direction
• St. Barts Yacht Trip
• James Corden
• The Late Late Show
• Spill Your Guts or Fill Your Guts
• Devin Booker
• Olivia Wilde
• Taylor Swift
• Love On Tour
• Anguilla
• Keeping Up with the Kardashians
• Met Gala (where they were often seen together)
• Supermodel
• Solo Albums
• WeHo Dinner