Kendall Jenner's Boyfriends: A Deep Dive Into Her Dating History

Gunnar Borer Jr. 22 Jun 2025

When it comes to the highly scrutinized world of celebrity romances, few figures capture public attention quite like Kendall Jenner. As one of the most recognizable supermodels globally and a prominent member of the Kardashian-Jenner dynasty, her personal life, especially her romantic relationships, has consistently been a topic of intense fascination. From red carpets to social media whispers, the question of "Does Kendall Jenner have a boyfriend?" is one that frequently surfaces, prompting countless headlines and fan discussions.

Her dating history is as dynamic and talked about as her career, often involving high-profile athletes and fellow celebrities. Unlike some of her siblings who have had very public long-term relationships, Kendall has often maintained a more private stance, though the nature of her fame means little remains truly hidden. This article will take a comprehensive look at the various individuals Kendall Jenner has been linked to, focusing on the most significant relationships that have played out in the public eye, particularly her enduring connection with NBA star Devin Booker.

Unraveling Kendall Jenner's Dating History

Kendall Jenner has had several known boyfriends since entering the public eye, navigating the complexities of fame while trying to maintain some semblance of a private life. Her romantic journey has been a subject of continuous speculation, with every public sighting or social media hint sparking new rumors. From music sensations to professional athletes, the list of individuals she's been associated with reflects her diverse social circle.

While the media often links her to various personalities, a few relationships have stood out due to their duration, public acknowledgment, or the sheer volume of attention they garnered. For instance, Kendall Jenner has dated Harry Styles, Devin Booker, and Bad Bunny, each relationship offering a unique glimpse into her personal life and the challenges of dating under constant scrutiny. This section will provide a general overview before delving deeper into specific connections, offering a comprehensive look back at the model's dating history.

Who is Kendall Jenner? A Brief Biography

Before diving into her romantic entanglements, it's essential to understand the person at the center of it all. Kendall Nicole Jenner, born on November 3, 1995, in Los Angeles, California, is an American model, socialite, and television personality. She first rose to fame through the reality television series "Keeping Up with the Kardashians," which documented the lives of her extended family. However, Kendall quickly carved out her own path, distinguishing herself in the high-fashion world.

Beginning her modeling career at the age of 14, she soon became a fixture on international runways for designers like Chanel, Marc Jacobs, and Givenchy. By 2017, Forbes named her the world's highest-paid model, a testament to her widespread influence and success. Beyond the catwalk, Kendall has leveraged her massive social media presence to launch various ventures, including her tequila brand, 818 Tequila. Her status as a global icon, combined with her family's fame, ensures that her life, including who Kendall Jenner's boyfriend might be, remains a constant subject of public interest.

Attribute	Detail
Full Name	Kendall Nicole Jenner
Date of Birth	November 3, 1995
Age (as of 2024)	28 years old
Place of Birth	Los Angeles, California, U.S.
Occupation	Model, Socialite, Television Personality, Businesswoman
Height	5 ft 10 in (1.78 m)
Parents	Kris Jenner, Caitlyn Jenner (formerly Bruce Jenner)
Siblings	Kylie Jenner (full sister), Kourtney Kardashian, Kim Kardashian, Khloé Kardashian, Rob Kardashian (half-siblings)
Known For	"Keeping Up with the Kardashians," High-fashion modeling, 818 Tequila

The Public Eye and Private Lives: Navigating Celebrity Relationships

Dating in the public eye is an entirely different ballgame than a typical relationship. For someone like Kendall Jenner, whose every move is documented and dissected, maintaining a sense of normalcy in her romantic life presents unique challenges. The constant media scrutiny, the pressure from fans, and the inevitable rumors can strain even the strongest connections. Celebrities often face the dilemma of how much to share versus how much to protect, and Kendall has historically leaned towards keeping her relationships relatively private compared to her sisters.

This desire for privacy, however, often fuels more speculation. A simple lunch date can be blown into a full-blown romance, and a lack of public appearances can be interpreted as a breakup. The narrative around Kendall Jenner's boyfriend is often shaped by paparazzi photos, anonymous "sources," and social media sleuthing, making it difficult for the public to discern what's truly happening behind the scenes. This constant battle between public interest and personal boundaries defines much of her dating experience.

The Devin Booker Chapter: An On-Again, Off-Again Romance

Among all the individuals Kendall Jenner has been linked to, her relationship with NBA player Devin Booker has arguably been the most significant and enduring. Their connection has spanned several years, characterized by periods of intense togetherness, public displays of affection, and multiple splits and reconciliations. For the last five years, Jenner and Booker have been on again and off again, dating other people in between and now are back, making their story a captivating saga for fans and media alike.

Their journey together highlights the complexities of modern celebrity relationships, where careers, travel schedules, and public pressure constantly test the bond. Despite the frequent ups and downs, the recurring nature of their relationship suggests a deep connection that keeps drawing them back to each other.

The Early Days: Going Instagram Official

The initial whispers of a romance between Kendall Jenner and Phoenix Suns basketball player Devin Booker began in 2020, but it wasn't until Valentine's Day 2021 that they went Instagram official. This move, a significant step for the usually private Kendall, confirmed what many had suspected. Sharing a cozy photo of the two snuggled up on a countertop, Kendall simply captioned it with a white heart emoji, signaling a new, more public phase of their relationship.

Their "Instagram official" status was a clear indication that their relationship was serious enough for them to acknowledge it publicly, a rarity for Kendall. This public declaration came after months of subtle hints and paparazzi sightings, solidifying their status as one of Hollywood's most talked-about couples. Fans eagerly followed their journey, from courtside appearances to intimate vacation photos, as their bond seemed to grow stronger.

The First Split and Reconciliation

Like many relationships under the glare of the spotlight, Kendall and Devin's journey hasn't been without its bumps. Jenner and Booker split for the first time in June 2022. An insider exclusively told us at the time that they were “taking this time to focus on themselves and their careers.” This initial breakup, though disappointing to fans, seemed to be a mutual decision to prioritize individual growth.

However, the separation proved to be temporary. Within a few months, reports surfaced of their reconciliation, indicating that the time apart had perhaps allowed them to reassess their priorities and reaffirm their feelings for each other. This pattern of splitting and reuniting would become a recurring theme in their relationship, underscoring the deep-rooted connection that continuously drew them back together, even after periods of distance.

Public Displays of Affection and Support

Despite Kendall's general preference for privacy, both she and Devin occasionally offered glimpses into their affectionate dynamic. Devin, in particular, was often seen as a proud boyfriend. The athlete makes it known that he’s a proud boyfriend when he reposts one of Kendall’s cheeky bikini photos to his Instagram story, adding a simple yet expressive, “whew,” alongside a sweating emoji. These small, public gestures, though rare, spoke volumes about their comfort and affection for each other.

Kendall, too, would often be seen courtside at Devin's games, quietly showing her support. These instances, whether a quick repost or a discreet presence at a game, provided fans with authentic moments of their relationship, demonstrating a genuine connection beyond the rumors and speculation. Their ability to maintain a strong bond, even with the demands of their respective high-profile careers, was often highlighted by these subtle yet meaningful public interactions.

Kendall Jenner and Devin Booker: A Detailed Relationship Timeline

To truly understand the dynamic between Kendall Jenner and Devin Booker, it's helpful to revisit their complete relationship timeline, from their apparent reconciliation in 2024 to their multiple splits and all the way back to when they first sparked rumors. Their journey has been a testament to an on-again, off-again romance that has captivated public interest for years.

Here's a breakdown of the key moments in the Kendall Jenner and Devin Booker relationship timeline:

April 2020: Kendall and Devin are first spotted together on a road trip from Los Angeles to Arizona, sparking initial dating rumors. At this point, sources suggest they are just friends.
August 2020: They are seen dining together in Malibu and later at a beach, fueling more speculation. Photos surface of them looking cozy.
Valentine's Day 2021: Kendall Jenner and Phoenix Suns basketball player Devin Booker went Instagram official, sharing a sweet photo on her story, confirming their romance to the world. This was a significant step for the notoriously private model.
June 2021: They celebrate their one-year anniversary, with Kendall sharing a rare photo of them together on her Instagram story.
February 2022: Devin Booker publicly celebrates Kendall's 818 Tequila, reposting one of her bikini photos with a "whew" and sweating emoji, showcasing his proud boyfriend status.
June 2022: Kendall Jenner and Devin Booker split for the first time. An insider exclusively told us at the time that they were “taking this time to focus on themselves and their careers.”
August 2022: Reports surface that they have reconciled and are back together, seen attending events and vacations together.
November 2022: Kendall Jenner was in a relationship with NBA player Devin Booker for two years before they reportedly broke up again. A source told People, they “both have incredibly demanding schedules and careers that are not conducive to a long-distance relationship.” This marks their second major split.
Early 2023: Both are rumored to be dating other people. Kendall is linked to Bad Bunny, and Devin is seen with other individuals.
Late 2023 - Early 2024: Rumors of Kendall and Devin reconnecting begin to circulate. They are spotted together more frequently, albeit discreetly.
Spring 2024: Sources confirm that Kendall and Devin are "very much together." For the last five years, Jenner and Booker have been on again and off again, dating other people in between and now are back, seemingly stronger than ever.

This timeline illustrates the cyclical nature of their relationship, a pattern of separation and reunion that suggests a powerful, underlying connection.

Before Devin: Other Notable Relationships

While Devin Booker has been her most consistent and public relationship, Kendall Jenner's dating history includes other high-profile individuals who captured media attention. Before Devin, people reported in November 2018 that Jenner was dating Philadelphia 76ers player Ben Simmons after her breakup with Anwar Hadid.

Harry Styles: One of Kendall's earliest and most talked-about rumored relationships was with One Direction heartthrob Harry Styles. Their on-again, off-again romance spanned several years, with sightings on yachts and ski trips, though neither ever officially confirmed their relationship beyond a casual friendship. Their connection remained largely speculative, yet it fueled a significant amount of fan excitement.
Anwar Hadid: The younger brother of models Gigi and Bella Hadid, Anwar Hadid, was another brief but notable connection for Kendall. They were linked in 2018, seen kissing at various events. This relationship followed a pattern of Kendall being linked to individuals within her social and professional circles.
Ben Simmons: Following her breakup with Anwar Hadid, Kendall was reported to be dating NBA star Ben Simmons in November 2018. Their relationship was also on-again, off-again, characterized by public appearances at games and private dates. Like her relationship with Booker, her connection to Simmons highlighted her penchant for dating professional athletes.

These past relationships, though less enduring than her bond with Devin Booker, contributed to the narrative of Kendall Jenner's boyfriend choices, often linking her to figures who share her level of fame and lifestyle.

Does Kendall Jenner Have a Boyfriend Now? Current Status

Given the cyclical nature of her most prominent relationship, the question "Does Kendall Jenner have a boyfriend?" is perpetually relevant. As of recent reports, the answer points back to her long-time on-again, off-again partner, Devin Booker. After a period of being linked to Bad Bunny in 2023, and following their reported breakup in November 2022, Kendall and Devin appear to have found their way back to each other once more.

Sources close to the couple have indicated that the model and NBA player are “very much together.” This renewed connection suggests that despite their past splits and the challenges of their demanding careers, the bond between Kendall Jenner and Devin Booker remains strong. For the last five years, Jenner and Booker have been on again and off again, dating other people in between and now are back, reinforcing the idea that some relationships are simply meant to be, regardless of the detours. Their current status indicates a comfortable and committed phase, with both seemingly prioritizing their connection amidst their busy lives.

The Enduring Fascination with Celebrity Relationships

The public's unwavering interest in who Kendall Jenner's boyfriend is, or any celebrity's romantic life for that matter, speaks volumes about the human fascination with love, drama, and aspiration. Celebrities often represent idealized versions of life, and their relationships become a form of modern-day fairy tale or cautionary tale. We project our own hopes, fears, and curiosities onto their public personas.

For Kendall, her relatively private approach to dating, combined with her immense fame, only intensifies this curiosity. Each rumored sighting, each subtle social media post, becomes a piece of a larger puzzle that fans eagerly try to solve. This collective investment in her romantic narrative highlights how deeply intertwined celebrity culture is with our own desires for connection and understanding of human relationships, played out on a global stage.

Conclusion

Kendall Jenner's dating history is a compelling narrative, marked by high-profile relationships and a consistent effort to maintain privacy amidst relentless public scrutiny. From her early links to Harry Styles and Ben Simmons to her most significant and enduring connection with Devin Booker, her romantic journey reflects the unique challenges and complexities of celebrity life. The "on-again, off-again" nature of her relationship with Devin Booker, spanning five years and multiple reconciliations, stands out as a testament to a deep and recurring bond that continues to draw them back together.

As the question "Does Kendall Jenner have a boyfriend?" continues to surface, the answer, for now, points firmly to Devin Booker, with sources confirming they are "very much together." This comprehensive look back at her relationships offers a deeper understanding of the woman behind the supermodel persona and the intricate dance between public life and private love. What are your thoughts on Kendall's approach to relationships in the public eye? Share your comments below, and don't forget to explore more of our articles on celebrity lifestyles and relationships!

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