Kendall Jenner, the supermodel and reality TV star, has been in the public eye since she was a teenager. As one of the most famous members of the Kardashian-Jenner clan, her love life has been a constant topic of fascination for fans and media alike. From high-profile celebrity romances to low-key flings, Kendall’s dating history reads like a who’s who of Hollywood, sports, and music.
In this deep dive, we’re breaking down every confirmed ex-boyfriend Kendall Jenner has dated, along with the rumors, breakups, and relationship drama that followed. Whether you’re a longtime fan or just curious about her love life, this is the ultimate guide to Kendall’s romantic past.
---Early Relationships: Kendall’s Teenage Romances
Before she became a global supermodel, Kendall Jenner had a few low-key relationships as a teenager. These early romances were mostly kept out of the spotlight, but a few names have surfaced over the years.
1. Nick Jonas (2011) – Rumored Fling
One of Kendall’s earliest rumored romances was with Nick Jonas, the youngest member of the Jonas Brothers. The two were spotted together in 2011 when Kendall was just 15 years old and Nick was 18. While neither confirmed a relationship, fans speculated after they were seen at a movie premiere and hanging out in Los Angeles.
Why it didn’t last: The age difference (though small) and Kendall’s young age likely made this a short-lived fling. Nick later dated other celebrities, including Miley Cyrus and Priyanka Chopra (whom he married).
2. Julian Brooks (2012) – High School Boyfriend
Kendall’s first confirmed boyfriend was Julian Brooks, a fellow student at Sierra Canyon School in Los Angeles. The two dated briefly in 2012 when Kendall was 16. Not much is known about Julian, as the relationship was kept private, but he was one of the few non-celebrity boyfriends Kendall has had.
Why it didn’t last: Like many high school romances, this one fizzled out quickly. Kendall’s rising fame likely made it difficult to maintain a normal relationship.
---Rising Fame & High-Profile Romances
As Kendall’s modeling career took off, so did her love life. By her late teens and early 20s, she was linked to some of the biggest names in music, sports, and entertainment.
3. Harry Styles (2013–2014) – The One Direction Heartthrob
Kendall’s first major celebrity romance was with Harry Styles, the former One Direction singer. The two were first spotted together in November 2013 and dated on-and-off for nearly a year. Their relationship was highly publicized, with paparazzi capturing their PDA-filled outings in Los Angeles, New York, and even the Caribbean.
Key moments:
- Spotted kissing on a yacht in St. Barts (December 2013).
- Attended the 2014 Grammy Awards together (though not officially as a couple).
- Harry reportedly wrote songs about her, including "She" from his self-titled album.
Why it didn’t last: Their busy schedules and Kendall’s reluctance to be in a serious relationship at the time led to their split in early 2014. Harry later dated Taylor Swift and Olivia Wilde, while Kendall moved on to other high-profile flings.
4. Jordan Clarkson (2014–2015) – NBA Player Fling
After her split from Harry Styles, Kendall was linked to Jordan Clarkson, an NBA player for the Los Angeles Lakers. The two were spotted together in 2014–2015, with rumors suggesting they had a casual relationship.
Why it didn’t last: This appeared to be a short-lived fling, as Kendall was also seeing other people (including ASAP Rocky) around the same time. Clarkson later married a non-celebrity and kept his personal life private.
5. ASAP Rocky (2015–2016) – The Rapper Romance
Kendall’s relationship with ASAP Rocky (real name: Rakim Mayers) was one of her most talked-about flings. The rapper and model were first spotted together in 2015, and their on-again, off-again romance lasted nearly a year.
Key moments:
- Spotted at Coachella 2015 together.
- Kendall walked in Rocky’s 2016 Yeezy Season 3 fashion show (though they were already broken up by then).
- Rocky later referenced her in his song "Everyday" with the line, "I’m with my bitch, she Kardashian."
Why it didn’t last: Their relationship was plagued by cheating rumors (Rocky was linked to other women, including Rihanna) and Kendall’s growing disinterest in serious commitments. They officially split in 2016.
---The Supermodel Era: Serious Relationships & Public Scrutiny
By the mid-2010s, Kendall had become one of the highest-paid models in the world. With fame came more intense media scrutiny—and more high-profile boyfriends.
6. Blake Griffin (2017–2018) – The NBA Star Relationship
Kendall’s relationship with Blake Griffin, then a star player for the Los Angeles Clippers, was one of her most serious. The two dated from 2017 to 2018 and were frequently seen together at NBA games, red carpets, and vacations.
Key moments:
- First spotted at a Clippers game in April 2017.
- Celebrated New Year’s Eve 2018 together in Aspen.
- Blake was reportedly very serious about Kendall, even discussing marriage.
Why it didn’t last: Despite Blake’s hopes for a long-term relationship, Kendall was not ready to settle down. They broke up in mid-2018, with sources claiming Kendall felt "suffocated" by his intensity.
7. Ben Simmons (2018–2020) – The Australian NBA Player
Just months after her split from Blake Griffin, Kendall began dating Ben Simmons, an Australian NBA player for the Philadelphia 76ers. Their relationship lasted nearly two years, making it one of her longest.
Key moments:
- First spotted together in May 2018 in Los Angeles.
- Spent Christmas 2018 together in Australia with Ben’s family.
- Kendall supported Ben at multiple NBA games.
- Rumors of an engagement circulated in 2019, but nothing was confirmed.
Why it didn’t last: The couple called it quits in May 2020, with sources citing long-distance struggles (Ben was based in Philadelphia) and Kendall’s desire to focus on her career. Ben later dated model Maya Jama.
---Recent Years: Casual Flings & Relationship Rumors
In the past few years, Kendall has taken a step back from serious relationships, opting for more casual flings and keeping her love life relatively private.
8. Devin Booker (2020–2022) – The Phoenix Suns Star
Kendall’s most recent confirmed relationship was with Devin Booker, the NBA player for the Phoenix Suns. The two were first linked in April 2020 and dated on-and-off for nearly two years.
Key moments:
- Spotted on a road trip together in Arizona (2020).
- Celebrated Valentine’s Day 2021 together.
- Kendall attended multiple Phoenix Suns games to support Devin.
- Rumors of a breakup surfaced in June 2022, but they were seen together again months later.
Why it didn’t last: Their relationship officially ended in late 2022, with sources claiming they had different priorities—Kendall wanted to focus on her career and personal growth, while Devin was deeply invested in basketball. Devin has since been linked to model Irina Shayk.
9. Bad Bunny (2023) – The Short-Lived Fling
In February 2023, Kendall was spotted getting cozy with Bad Bunny (real name: Benito Antonio Martínez Ocasio) at a Super Bowl afterparty. The two were seen kissing, sparking rumors of a new romance.
Why it didn’t last: Their fling was extremely short-lived, lasting only a few weeks. Bad Bunny was also linked to other women around the same time, and Kendall seemed to move on quickly.
10. Justin Bieber (Rumored, 2023) – The Controversial Link-Up
In October 2023, Kendall was spotted leaving a hotel with Justin Bieber in Los Angeles, sparking massive speculation. However, sources close to both stars denied any romantic involvement, claiming they were just friends.
Why it was likely nothing: Justin was (and still is) married to Hailey Bieber, making this rumor highly unlikely. The media frenzy was likely due to Kendall and Hailey’s public feud at the time.
---Kendall’s Dating Patterns: What Do Her Relationships Reveal?
Looking at Kendall’s dating history, a few clear patterns emerge:
- She prefers athletes and musicians. Nearly all of her confirmed boyfriends have been NBA players or singers/rappers.
- She avoids serious commitments in her 20s. Despite multiple long-term relationships, Kendall has never been engaged or married.
- She values privacy. Unlike her sisters (Kim, Khloé, and Kourtney), Kendall rarely discusses her love life publicly.
- She moves on quickly. Most of her relationships overlap or are followed by new flings within months.
- She’s attracted to confidence and talent. Her exes are all high achievers in their fields (NBA stars, Grammy-winning artists, etc.).
Kendall has also openly admitted that she struggles with trust issues due to her fame. In a 2021 interview with Vogue, she said:
"Dating is hard. I feel like people don’t really get to know the real me because of who I am and my last name. It’s hard to find someone who genuinely cares about me and not just the idea of me."---
Who Is Kendall Jenner Dating Now? (2024 Update)
As of 2024, Kendall Jenner is officially single. After her split from Devin Booker, she has been focusing on:
- Her tequila brand, 818 Tequila.
- Modeling campaigns (including Chanel, Versace, and Calvin Klein).
- Spending time with family (especially her niece North West and nephew Aire).
- Travel and self-care (she’s been spotted on solo trips to Italy and the Maldives).
While rumors occasionally surface (like a recent dinner with The Weeknd), nothing has been confirmed. Kendall seems to be enjoying her single life for now.
---Kendall Jenner’s Love Life: FAQs
Who was Kendall Jenner’s first boyfriend?
Kendall’s first confirmed boyfriend was Julian Brooks, a high school classmate, in 2012. Her first celebrity fling was with Nick Jonas in 2011 (though unconfirmed).
Has Kendall Jenner ever been engaged?
No, Kendall has never been engaged or married. Rumors about an engagement to Ben Simmons in 2019 were never confirmed.
Who is Kendall Jenner’s longest relationship?
Kendall’s longest confirmed relationship was with Ben Simmons (2018–2020), lasting nearly two years.
Does Kendall Jenner have any kids?
No, Kendall does not have any children. Unlike her sisters (Kim, Khloé, Kourtney, and Kylie), she has not expressed a desire to start a family yet.
Is Kendall Jenner dating anyone in 2024?
As of 2024, Kendall is single and not publicly dating anyone.
Who is Kendall Jenner’s most famous ex?
Kendall’s most famous exes are Harry Styles (One Direction), ASAP Rocky (rapper), and Devin Booker (NBA star).
---Conclusion: What’s Next for Kendall Jenner’s Love Life?
Kendall Jenner’s dating history is a mix of high-profile romances, casual flings, and short-lived relationships. From her teenage years to her current status as a supermodel and businesswoman, she has dated some of the biggest names in entertainment and sports—yet she remains one of the most private Kardashian-Jenners when it comes to love.
Unlike her sisters, who have had very public marriages and divorces, Kendall has avoided serious commitments, preferring to focus on her career and personal growth. While fans continue to speculate about her next romance, Kendall seems content taking her time and enjoying her independence.
Will she ever settle down? Only time will tell. For now, Kendall Jenner’s love life remains as mysterious and fascinating as ever.
What do you think? Who would you like to see Kendall date next? Drop your thoughts in the comments!
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