Who is Kendall Jenner dating? Model’s relationship timeline explained

Molly Byrne

Kendall Jenner has been in the spotlight since before she was even a teenager. As she grew into adulthood, she emerged as a supermodel who also balanced a colorful dating life. Here’s everything to know about the reality star’s dating history.

Model and reality TV star Kendall Jenner, 28, was only 12 years old when she began her career in television on E!’s Keeping Up With the Kardashians. 

By the time she was 14, Kendall was signed to Wilhelmina Models and hasn’t stopped since. Though her family is still in the reality TV biz, as Hulu’s The Kardashians is currently on Season 5, Kendall shared with Vogue that filming isn’t her “biggest cup of tea.”

Despite not fitting in with her family’s claim to fame, Kendall has still managed to gain millions of fans, with 294M followers on Instagram and over 6M on TikTok.

Though she’s more introverted than her family members, Kendall’s dating life has been a hot topic of conversation over the years, especially after her relationship with NBA player Devin Booker in 2020.

But who is Kendall dating now? Here is everything to know about her dating history and current relationship status.

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What is Kendall Jenner’s relationship status?

At the time of writing this article, Kendall and her ex-boyfriend Bad Bunny may have rekindled their relationship after breaking up in December 2023.

However, neither party has confirmed nor denied getting back together, despite cozying up at the 2024 Met Gala in May.

Kendall Jenner and Harry Styles date & breakup 

In 2013, Kendall and musician Harry Styles grew close, marking her first ‘real’ romance in the public eye. The two were initially spotted in November of that year and celebrated New Year’s together just months later.

In 2016, the pair spent their second New Year’s together in the Caribbean. Though they broke up some time that year, Harry hinted to Rolling Stone that Kendall was the muse of his 2017 studio album.

Kendall Jenner and Harry Styles in 2017.
Kendall Jenner and Harry Styles in 2017.

The exes then joined James Corden on The Late Late Show in November 2019 where Harry refused to confirm which songs of his were about the model. However, they seem to be on good terms, as she supported him during a 2022 concert in Los Angeles.

Kendall Jenner sparks relationship rumors with A$AP Rocky

After being close friends for years, Kendall and rapper A$AP Rocky sparked romance rumors when they were spotted together in Paris in June of 2016. 

Several months later, the two were seen arriving together at a hotel in Los Angeles. By March 2017, a source close to the model told People that she was “open to seeing where it goes” with the artist.

She then supported him during his Coachella performance during that same year, with sources saying they were ‘all over each other.’ Fast forward to May, and the two cozied up at the Met Gala.

Though their flame was surely lit, it soon went out during the summer of 2017 before her next fling.

Kendall Jenner and “nice” Blake Griffin become close

During the summer of 2017, Kendall and NBA player Blake Griffin were seen enjoying a multitude of outings before a source close to the model said she was seeing Blake “romantically.”

And when his basketball season came around during the fall of the same year, she joined her sister Kylie Jenner at one of his Clippers games.

Though she didn’t confirm they were dating during a 2018 interview with Vogue, she did say that she had “someone [Blake] being very nice to me.”

The two did drift apart, though, when Blake was traded to the Detroit Pistons in January 2018, as he was no longer local to the model’s home.

Kendall Jenner dates & breakups with Ben Simmons

During May 2018, Kendall and NBA player Ben Simmons were seen on a lunch date at the Beverly Hills Hotel. About one year later in February 2019, the reality star confirmed on The Ellen DeGeneres Show that the two were in fact an item and had been seeing each other “for a bit now.”

However, several days after confirming their relationship, the duo called it quits. Despite their breakup, the two remained friends and spent the 2020 New Year’s together in Philadelphia.

Kendall Jenner starts dating Devin Booker

After going on an Arizona road trip together in April 2020, Kendall and NBA player Devin Booker were rumored to be dating. During the summer of that year, the two joined friends Justin and Hailey Bieber for a getaway in Idaho.

By Valentine’s Day the following year, the model and NBA star went Instagram official, as both of them shared photos of each other to their accounts.

Kendall Jenner and Devin Booker in Capri, Italy in 2021.
Kendall Jenner and Devin Booker in Capri, Italy in 2021.

The two continued to document their relationship online, as they gushed about each other on their first anniversary via social media. Though their relationship was a source of comfort, as he spent plenty of time with the model’s friends and family, the two would briefly break up after their two-year anniversary in June of 2022.

However, just one month later, the duo were spotted on a tropical vacation together. And by September, they went PDA-heavy at the U.S. Open.

Despite their reconciliation, Kendall and Devin officially broke up in October due to prioritizing their busy schedules.

Kendall Jenner & Bad Bunny begin dating

Kendall’s very public relationship with rapper Bad Bunny began in February 2023 after she was seen leaving an L.A. restaurant with him.

Just one month after fans caught wind of their speculated relationship, the artist dissed the model’s ex-boyfriend Devin Booker in his song ‘Coco Chanel’ by saying, “Sun in Puerto Rico is hotter than in Phoenix,” as Devin plays for the Phoenix Suns.

Just weeks after the diss track, Kendall introduced the rapper to her horse, Arizona, and even allowed him to take the animal for a jaunt at the Hidden Hills Equestrian Center in California.

Though the two would continue to date for several months, they would eventually split in December 2022.

Kendall Jenner sparks reconciliation with Bad Bunny

Kendall Jenner and bad bunny Afterparty 2024 met gala
Kendall Jenner and Bad Bunny at a 2024 Met Gala afterparty.

Kendall and Bad Bunny sparked reconciliation rumors after they were seen cozying up together at an afterparty for the 2024 Met Gala, where the model and rapper smiled happily at each other.

Sources inside the Après Met 2 party reported to People that the exes “were sitting together, laughing and having the best time.”

Despite getting close once more, neither Kendall nor Bad Bunny have confirmed if they are together again. 

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About The Author

In recent years, Molly has interviewed musicians from all over the world, to then transition into writing for the movie and hiphop industry. Molly began her Entertainment and Reality TV coverage for Dexerto in 2023 where she exhibits her passion across a broad range of topics. To contact Molly, you may email her here: molly.byrne@dexerto.com.