Kendall Jenner, known for keeping much of her personal life discreet, has experienced several high-profile romances over the years, including a notable relationship with NBA star Devin Booker from 2020 to 2022. Her dating history also includes connections with musicians and athletes, underscoring her ties to the entertainment and sports worlds.
Jenner has openly joked about her rumored “curse” on athlete boyfriends in a 2026 Fanatics Sportsbook Super Bowl commercial, highlighting the public fascination with her love life. This openness contrasts with her usual privacy regarding relationships.
Haven’t you heard? The internet says I’m cursed,
she quipped.
Any basketball player who dates me kind of hits a rough patch.
Embracing the humor surrounding this, Jenner added,
While the world’s been talking about it, I’ve been betting on it. How else do you think I could afford all of this? Modeling?
She then credited her exes for her luxuries before delivering a punchline:
Kardashian curse — it’s not even my last name.
Despite her candid remarks, Jenner emphasizes the sacredness of her close bonds and relationships.
For me, a lot of things are very special and very sacred, like my friends and relationships. I personally think that bringing things into the public makes everything so much messier,
she told Vogue Australia in 2019.
The Beginning: Teenage Romance with Harry Styles
One of Jenner’s earliest public relationships was with Harry Styles, the former One Direction member. Their connection gained attention following Styles’ split from Taylor Swift in 2013. Initially perceived as friends, their relationship appeared to progress to something more intimate by early 2014.
During a New Year’s ski trip, sources described their interaction as flirtatious and affectionate.
They were very cute together. There was a lot of flirting and smiling going on.
In 2016, the pair reunited for New Year’s in St. Barths, where they were observed acting like a couple, prompting insiders to describe their cozy behavior.
There has been a lot of flirting, touching and snuggling going on. They have acted like a couple. They look very cozy and happy,
shared a source.
Jenner’s sister Khloé Kardashian later suggested the pair were indeed dating, although perhaps without labeling their status traditionally.
They were hanging out together. Do I think they’re dating? Yes. I don’t know if they’re like boyfriend-girlfriend,
Khloé said.
I would call that dating.
Though they saw each other occasionally after 2016, their connection was described as undefined.
Continuing to talk and see where things go,
a source reported in September 2016. The two reunited publicly at the 2019 Met Gala, with sources labeling Styles as Jenner’s first serious relationship but framing them as friends at that point.
During a 2019 episode of The Late, Late Show, Jenner teased Styles about songs inspired by her, to which he humorously avoided answering by eating cod sperm during the game
“Spill Your Guts or Fill Your Guts.”
Short-Lived Connection with Nick Jonas
In 2015, Jenner was introduced to Nick Jonas through his brother Joe Jonas and Joe’s then-girlfriend Gigi Hadid. This setup led to a brief period of dating rumors, but Jonas quickly dismissed any romantic involvement.
They were totally set up by Joe and Gigi,
a source revealed. Jonas later clarified,
We’re not dating. Kendall is great, and naturally, her being good friends with Gigi and with Joe and Gigi dating, there are times we’ll be in the same place and we all hang out.
Relationship with NBA Player Jordan Clarkson
Jenner’s association with basketball extended to Jordan Clarkson starting in March 2016. Their appearances together at major events like Coachella and Hollywood nightlife attracted media attention.
A source described their dynamic as affectionate yet discreet in public.
They keep things low-key when they’re in public, but in private they’re very much together and affectionate,
the insider said. He’s really into her.
Despite growing close to Jenner’s social circle, their relationship was characterized as casual.
He’s become really close friends with her group and they’re still seeing each other, but it’s not a serious situation. Jordan’s been seeing other girls too,
a source revealed. Their romance appeared to conclude after late 2016.
Speculated Link with Rapper A$AP Rocky
Although A$AP Rocky and Jenner never confirmed a romantic involvement, the two were often seen together, fueling speculation. Their friendship was public during various outings from mid-2016 to early 2017.
Following appearances in Paris and Los Angeles, they were spotted at the Miami Art Basel event acting flirtatiously.
Very flirty,
a source noted. Jenner’s friends indicated she was
open to seeing where it goes
in early 2017.
The pair’s closeness was also highlighted at Coachella and a Met Gala bathroom photo in 2017; after this, sightings together became less frequent.
Casual Relationship with Blake Griffin
Summer 2017 saw Jenner romantically linked with NBA player Blake Griffin. They were photographed attending concerts and social events together, though the relationship was described as lighthearted at first.
She’s seeing Blake romantically. It’s nothing serious. She has been in L.A. a lot lately, and is having fun … That’s all that matters to her,
a source said.
By fall, their bond appeared to deepen, with Jenner’s family reportedly accepting Griffin.
Kendall is very happy with Blake,
an insider shared.
They started out more like friends, and then it was very casual. But it seems more serious lately. When they are not together, they keep in touch over the phone. Her family has accepted Blake. They are spending time getting to know him.
Jenner, however, did not publicly acknowledge the relationship in early 2018, stating,
He’s very nice. I have someone being very nice to me.
Sources later confirmed that distance caused the couple to drift apart after Griffin was traded out of Los Angeles.
Brief Period with Ben Simmons
Jenner’s romantic involvement with NBA player Ben Simmons began publicly in May 2018, when they were seen sharing lunch in Beverly Hills. Their exclusivity was officially confirmed by Jenner during a 2019 appearance on The Ellen DeGeneres Show.
Discussing future commitments with Vogue Australia in 2019, Jenner hinted at the possibility of marriage someday.
Definitely not now, but maybe one day,
she shared.
I got a glimpse of how my sisters dealt with [the attention] and it’s cool to learn from that.
The relationship ended later that same year, following what sources described as a natural conclusion.
They’re on a break. The relationship ran its course. She’s spending time with her friends and back to being in fun mode,
a close source disclosed. Despite the split, the two maintained a friendly rapport into the New Year period.
Significant Relationship with Devin Booker
Jenner’s romance with Phoenix Suns player Devin Booker began in early 2020, with the couple initially sparking dating rumors after a joint road trip to Arizona.
As their relationship progressed, insiders observed Jenner’s happiness and Booker’s integration with her family circle.
Devin is very sweet to her. He spends a lot of time with Kendall’s family and friends too. They both seem to enjoy the quiet time together,
a source noted in September 2020.
Breaking from her usual discretion, Jenner publicly acknowledged the relationship by going Instagram official on Valentine’s Day 2021.
What first seemed like a fun hookup is now a relationship. They are exclusive and Kendall is very happy with Devin,
a source confirmed.
Their one-year anniversary in June 2021 was marked by affectionate social media posts, reflecting Jenner’s deep affection.
She has never looked happier. Her whole family loves Devin too,
a source said.
Following two years together, the couple experienced a brief split in mid-2022 but reconciled soon after, sharing a tropical vacation and public appearances. By September 2022, they were seen together again at the U.S. Open exhibiting rare public displays of affection.
However, by October 2022, Jenner and Booker parted ways quietly due to demanding careers.
Both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority,
a source stated.
They have a lot of love and respect for each other and wish only the best.
Short Lived Romance with Bad Bunny
In early 2023, Jenner’s dating life made headlines again following sightings with rapper Bad Bunny. They were first spotted together leaving a restaurant in Los Angeles and reportedly went on a double date with Justin and Hailey Bieber.
Sources revealed their budding connection, mentioning,
Kendall recently started hanging out with him. They were introduced by friends. He moved to L.A. a few weeks ago and bought a house.
Additionally,
She likes him and is having fun. He is different from guys that she dated in the past. He is very charming.
Their relationship included public moments such as horseback riding at the Hidden Hills Equestrian Center, indicating a romantic bond. However, tensions emerged later in the year, notably highlighted when Bad Bunny appeared to allude to Booker in his track “Coco Chanel.” Booker’s Instagram response added fuel to speculation about rivalry.
Despite some speculation about rekindling, Jenner and Bad Bunny officially ended their relationship by December 2023. Rumors of reconciliation surfaced following appearances together in early 2024, including a Met Gala afterparty and a concert in Orlando, but the couple separated again shortly thereafter.
