Kendall Jenner’s Boyfriend: All About Her Romance With Ex Devin Booker & Past Relationships

Kendall Jenner is a single lady, after breaking up with Devin Booker again. Learn everything about their relationship, and all the men who the supermodel has dated right here.

Devin Booker, Kendall Jenner
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  • Kendall Jenner and Devin Booker began dating around Apr. 2020
  • The model and the NBA player are reportedly focusing on their careers
  • Kendall’s other famous exes include the NBA’s Ben Simmons and singer Harry Styles

Game over. Kendall Jenner and NBA star Devin Booker tried to make their relationship work, but it wasn’t meant to be. News that the pair split once and for all emerged on Nov. 21, 2022 via People. “Both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority,” an insider revealed about the breakup, which happened a month earlier.

Devin Booker, Kendall Jenner
Kendall Jenner and Devin Booker enjoy halftime of Super Bowl LVI between the Los Angeles Rams and the Cincinnati Bengals at SoFi Stadium in Los Angeles on February 13, 2022. (Shutterstock)

Kendall and Devin have been on and off for a minute. They reportedly broke up in June 2022, because of his commitment issues, but just weeks later they were seen getting cozy together on vacation and in Malibu.

So is it really over, and what lead to the end? Learn everything there is about Kendall Jenner and Devin Booker’s relationship, and her previous boyfriends right here.

Kendall Jenner & Devin Booker

Their Final Breakup

The model and NBA pro quietly split in Oct. 2022, an insider confirmed to HollywoodLife. It seems both were ready to focus on their careers. “Both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority,” another source told People. One more added, “They have a lot of love and respect for each other and wish only the best.”

Things seemed to be going fine for the duo around late Oct. Kendall posted an Instagram for “Birthday Boy” Devin on Halloween. Before that, they’d put on a PDA-packed display at the US Open.

After their initial June breakup, insiders said Devin was more dedicated than ever. “He’s been laser-focused on making her happy ever since,” the source told HollywoodLife EXCLUSIVELY in July. “It’s like they’re back in the honeymoon stage. Her friends and family are thrilled that they’re back together; everyone would love to see them get married.”

Their First Split

Kendall first pulled the plug on the relationship after Devin failed to impress during sister Kourtney Kardashian’s wedding to Travis Barker in Italy in May 2022. A source EXCLUSIVELY told HollywoodLife, “Kendall broke up with him because she didn’t think he was taking the relationship as seriously as she was.

 

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One of the first public sightings of Kendall and Devin. (BACKGRID)

“Kendall felt like it was a really big deal to bring him with her to Kourtney’s wedding and she thought it would be super romantic. But it didn’t turn out like that at all, and he couldn’t have seemed more disconnected from the love and romantic aspect of it.”

Kendall & Devin’s Quiet Beginning

The couple sparked romance rumors when they were seen outside a rest stop in Sedona, Arizona on April 28, 2020, escaping Los Angeles amid the COVID-19 pandemic. They officially started dating in June 2020, which Kendall confirmed by posting about their one-year anniversary on Instagram. However, she also opened up on the KUWTK reunion about why she’s chosen to keep her relationship with her “boyfriend” private despite being in the public eye so much.

“I feel like it’s always worked better for me that way,” Kendall admitted in front of her sisters. “And no offense to my older sisters at all, but I think that Kylie [Jenner] and I specifically have had the opportunity to watch my older sisters go through marriages and relationships and breakups and all these things and do them pretty publicly.”

She added, “Again, no offense to you guys at all, but I think it was a personal preference from a really young age that I didn’t really want to like… I think it makes my life a lot easier and our relationship a lot better to be completely honest. I just feel like it’s a private matter. It’s not really for anybody else to judge or know.”

Kendall & Devin’s Time Together

Kendall and Ben were all about having fun during their two-plus years together. In addition to their many road trips and vacations, Kendall was also seen supporting him at his games with the Phoenix Suns, with fans snapping pics of her in the stands watching her man play ball.

Kendall and Devin on a date night. (BACKGRID)

They made some PDA-packed appearances in 2021, spotted walking hand in hand while en route to NYC hotspot Carbone or West Coast celeb favorite Nobu. They also attended several high-profile sporting events, like the U.S. Open men’s tennis championship and the 2022 Super Bowl. Devin came to Italy with Kendall for Kourtney Kardashian’s wedding, but according to insiders the romantic trip only made Kendall realize he wasn’t “as serious as she was.”

What Kendall Wants Now

Back around Kendall and Devin’s first breakup, the model seemed worried about big things, like getting married and starting a family. “Kendall does love Devin, but she does not feel like they are on the same page in terms of their feelings for each other and in terms of what they ultimately want out of a relationship,” a source close to Kendall told HollywoodLife EXCLUSIVELY.

“All of Kendall‘s sisters (and brother Rob even) have children now and Kendall is the only one that is still not even close to getting there. This just makes her feel slightly like the odd one out. Her mom and sisters are always asking her, ‘So when are you going to have children?’ Her answer is always the same, which is that she doesn’t know.”

Kendall Jenner’s Past Relationships

Before Devin came along, Kendall had romanced a few high-profile men over the years. From her on-and-off relationship with former One Direction heartthrob Harry Styles, to the other NBA players she’s courted, Kendall’s relationships have always been a point of interest for fans.

Nick Jonas

Disney Channel star Nick Jonas was linked to the supermodel back in 2015 when his older brother Joe Jonas was dating Kendall’s BFF Gigi Hadid. It was reported at the time that Gigi set up the pair, however, the Jonas Brothers star denied the claims. “We’re not dating. Kendall is great, and naturally, with 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,” Nick told E! at the time.

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Kendall with Harry Styles. Image: Shutterstock

Kendall’s relationship with “Watermelon Sugar” chart-topper Harry Styles was big news in the early 2010s. The pair were first linked when they were spotted having dinner together in Los Angeles in November 2013, but it was reported that they parted ways a few months later. Things weren’t over for the duo, who spent New Years’ Eve 2014 canoodling on a yacht together.

Kendall’s big sis Khloe Kardashian seemingly confirmed the romance. “Do I think they’re dating? Yes,” she told Entertainment Weekly. “I don’t know if they’re like boyfriend-girlfriend. Nowadays I don’t know. People are weird with stuff. So, I don’t know their title.” Fans didn’t see much from them until they were spotted shopping together in April 2016, however, they split later that year. It seems the pair ended on good terms, as they appeared on James Corden‘s The Late Late Show together in 2019, and even joked about their past romance.

After Harry

Kendall casually dated NBA player Jordan Clarkson in July 2016. They were reportedly seen cozying up to each other at Drake’s 2016 American Music Awards after-party. She then sparked romance rumors with rapper A$AP Rocky after they attended Kanye West’s Yeezy fashion show together in August 2016, and were later spotted together at the 2017 Met Gala.

A few months later, Kendall reportedly began dating NBA star Blake Griffin. Although their romance was brief, she opened up about their relationship in a March 2018 Vogue interview. “I’m happy. He’s very nice,” she said. “I have someone being very nice to me.” The two were spotted out and about together for around seven months before calling it quits in April 2018.

Ben Simmons

The supermodel’s last beau before Devin was Australian-born basketball player Ben Simmons. Kendall had an on-again, off-again relationship with the Philadelphia 76ers star for nearly two years, breaking up for the first time in May 2019 before rekindling their relationship.

Kendall Jenner, Ben Simmons
Kendall Jenner and Ben Simmons out and about during New York Fashion Week Feb. 2019. (Shutterstock)

She even confirmed that they dated on a February 2019 episode of The Ellen DeGeneres Show. Things began heating up again in early 2020 when she spent time with his parents during a Sixers game in Philadelphia. They appeared to call it quits shortly afterward as the coronavirus pandemic began.

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