Kendall Jenner's Famous Romances: From Harry Styles To Devin Booker, Here's Looking At Her Love Life

The Jenner-Kardashian clan is not new to the media; they live a life that is documented and aired for millions to watch. Kendall Jenner, however, tries to keep her life private. She keeps a low profile when it comes to her personal life and love life.

Kendall Jenner is a supermodel and an incredibly talented woman who has ruled every runway she has walked on. She is often the first choice of every designer to wear their clothes and walk their runways. Ever since their family show, Keeping Up With The Kardashians, aired in 2007, she has been familiar with life on camera.

Kendall Jenner keeps her love life private

Kendall has a pristine history of dating popstars, athletes, singers and some of the other top names of the industry. Kendall keeps her relationships under wraps and only introduces them on the show after she has been dating them for atleast an year. Jenner told Vogue Australia:

"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,"

As much of a private person as Kendall is, her sisters have been the loose lips who, on many occasions, have let out the details of her personal life. As of January 2026, she has remained single, but it is her past affairs that are to be remembered.

Kendall's romance with heartthrob Harry Styles

Kendall dated international sensation and One Direction band member, Harry Styles, from 2013-2016, making it her first public appearance with her supposed boyfriend. The rumoured couple, till the very end of their alleged romance, kept their stance of being just friends with each other. The sparks of their romance flew when the two were seen together at the restaurant Craig’s in Hollywood in November 2013.

In January 2014, their romance started picking up pace, and the two vacationed together on a ski trip with friends and also welcomed the new year together in January 2015 in St. Barth’s. Friends and companions suggested that the two had been flirting, coddling and being cosy and happy with each other, but they did not give them the label of being boyfriend and girlfriend. Neither the singer nor Kendall confirmed or denied their dating. Khloe Kardashian accidentally let it slip during an interview that the duo had been hanging out together, but she wasn’t sure if they had the talk of being boyfriend and girlfriend yet. According to her, the two had been dating since they were in St. Barth’s together.

In 2016, Harry attended Kendall’s birthday, which was also attended by NBA star Jordan Clarkson, with whom Kendall was supposedly dating since March 2016, but sources revealed that the duo were not back together. Fans wonder what happened there! However, despite their alleged romance rumours, the two have had no beef with each other and even appeared on The Late Late Show together, where Kendall asked Harry curiously which songs in his album were about her, to which Harry responded nothing. Kendall was also seen enjoying and singing at his concert with Hailey Bieber and her sister, Kylie Jenner.

Kendall allegedly dated Jordan Clarkson briefly

Ever since Jordan was spotted at her birthday party with Harry Styles in 2016, rumours had it that the two had been allegedly dating since March 2016. The Cleveland Cavaliers star Jordan Clarkson made appearances all around Hollywood and even attended Coachella with Kendall. Sources revealed that the two kept a much-needed distance when in public, but in private, they were absolutely into each other. Suffice it to say that there was nothing serious between the two romantically, but they shared a good friendship and were involved with each other’s friends' group as well

Nick Jonas and Kendall's famous alleged romance

Kendall may have been in an on-off dalliance with Harry because she was also supposedly linked with Nick Jonas in 2015. She met Nick at his brother, Joe Jonas’s concert, who was dating model Gigi Hadid at the time. An insider source claimed that the text messages between the two had a very flirty tone. A source said,

“Nick was single and looking to date, and there was an obvious attraction. He absolutely thinks she’s hot.”

When Nick was confronted about dating Jenner, he calmly denied the claims, saying that she is around all the time because of her bond with Gigi and Joe and because the former two are dating, she hangs around with the four of them as a common friend.

A$AP Rocky and Kendall's famed supposed romance

Kendall has been supposedly linked with A$AP Rocky as well from 2016 to 2017. The two were allegedly together before Rocky’s involvement with Rihanna and their welcoming of three kids together. Kendall and Rocky were often spotted together because they had been friends for some time, but it wasn’t until June 2016 that the duo was spotted having a romantic dinner in Paris at L’Avenue. In October 2016, they arrived in Los Angeles together and even attended Art Basil in Miami in December 2016 with each other. Reports claimed that Kendall was quite enjoying his company and was open to exploring the relationship further.

At Coachella, people say Kendall and Rocky all cosied up with each other and had the time of their lives at the music festival. In May 2016, Kendall was seen standing cheek to cheek with the singer in her famous bathroom photo from the Met Gala. But obviously, their unofficial relationship didn’t last, and the two grew apart.

Kendall's first official Instagram relationship with Blake Griffin

In May 2016, after her famous photo with A$AP Rocky, a few months later, she was spotted with Blake Griffin, who is yet another NBA player. Throughout summer 2016, the two went on dates and, according to inside sources, were a full-fledged serious couple. In October 2017, the couple defined their relationship and became a proper couple. Kendall was often seen at his games, and the two spent some quality time when Griffin was in town. She attended Halloween Horror Nights with Griffin, her sister Kylie, and Kylie’s then-boyfriend, Travis Scott. She was also seen in public, cheering for him on at a Clippers game. A source told People:

 “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.”

During a 2018 interview that took place just after Valentine’s Day, Kendall denied all speculations about their dating and claimed that she liked having someone being very nice to her and that her private life is private. The alleged romance fizzled out when Griffin got traded from the LA Clippers to the Detroit Pistons, and the two grew apart due to long distance.

Kendall Jenner with NBA star Ben Simmons

In May 2018, we saw Kendall with yet another NBA star, Ben Simmons, on lunch dates and the duo dated on-and-off for a year. Jenner made her relationship with Simmons official when she appeared on the Ellen DeGeneres Show in February 2019. The host DeGeneres asked Kendall about how long she been dating this guy from the 76ers? To which she replied that she has been dating him for a bit now. In May 2019, when Vogue Australia questioned Kendall on her thoughts about marriage, she said:

“Definitely not now, but maybe one day,”

Safe to say that the couple did not end up together, and the relationship came to an end later in May, and the model was back to spending time with friends and family.

Devin Booker and Kendall have been an on-and-off couple since 2020

Kendall has been in an on-and-off relationship with Devin Booker since 2020. The duo were together from 2020 to 2022, and the rumours of them casually flirting with each other have been flying over social media again since the end of 2025.

In April 2020, Jenner was spotted road tripping with a Phoenix Suns player through Arizona. Later, in September 2020, she took a lake trip with Devin and her friends Justin and Hailey Bieber. In an unprecedented move, Kendall made their relationship Instagram official in February 2021 when she spoke about him on Valentine’s Day. A source said:

“What first seemed like a fun hookup is now a relationship,”

In June 2021, Kendall posted multiple pictures with him marking their first anniversary. They went on to date for yet another year until their split in summer 2022. The duo went on different paths and wanted different things in life, and after a long discussion on what they wanted from their relationship, the duo decided to separate.

In October 2022, the duo broke up again after reconciling from their first breakup in the summer. The duo has tight schedules and just could not take up the responsibility of a relationship. However, when Jenner and rapper Bad Bunny split in late 2023, it was rumoured she might be spending quality time with Booker yet again. After Jenner and Bunny split in September 2024, Jenner was linked with Booker again in mid-February 2025. Jenner really liked his personality and humour, and the two were solid as a rock.

Kendall's romance with Bad Bunny and his diss with Devin Booker

After her not-so-brief dalliance with Devin, Kendall got together with Bad Bunny in 2023 after he moved to Los Angeles. Shortly after, the pair was spending time together after being introduced through friends. Bad Bunny and Booker got in a heated battle in March 2023, taking shots at one another. 

Bad Bunny dissed Devin on his track, Coco Chanel with the lyrics Sun in Puerto Rico is hotter than in Phoenix, and she knows it, referencing it to Booker’s basketball team. To respond to this, Devin wrote that ''he worried about another man again'' in an Instagram post, which he later deleted. The next month, the pair was spotted packing on the PDA at Coachella and taking a romantic horseback ride on Jenner's horse, Arizona. Weeks after that, they had their first public date, sitting court-side at the NBA playoff match between the Los Angeles Lakers and the Golden State Warriors. In October 2023, they were captured getting cosy at a Saturday Night Live after party, following Bad Bunny's appearance as both host and musical guest. The duo split in December 2023, for reasons known only to the couple.

Despite being a top model, an impeccable beauty, and a dating history that reads like a rap sheet, Kendall is an ace businesswoman. She is an avid lover of horses and often sees herself coddling her horses and enjoying riding. Kendall also started her own Tequila Brand, 818 and is extensively involved in its marketing.

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