Kendall Jenner & Devin Booker Relationship Timeline

For years, fans all over the world have been keenly interested in the romantic journey of Kendall Jenner and Devin Booker. Admittedly, Jenner has always preferred to keep her romantic life private. Speaking with Vogue Australia in 2019, the then-24-year-old model shared that “a relationship is only meant to be between two people.” 

However, to the joy of many fans, she’s not been completely secretive about her love life. Since 2020, Jenner and Booker have been romantically entangled. However, their relationship was on-and-off as it hit some hitches along the way. They were recently seen in the same VIP suite at the Super Bowl, prompting rumors of them rekindling their relationship. While they are no longer together, their romance is still fresh in the minds of some onlookers. Here’s a timeline of their relationship.

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While they may have met earlier, the first time this pair was spotted together was in 2018. Interestingly, it was at a double date that Jenner and Booker attended with different people. At the time, Jenner was reportedly in a relationship with basketball player Ben Simmons who was her date for the night. Also taken, Booker attended the double date with his girlfriend at the time, Jordyn Woods, Jenner's younger sister Kylie’s then-best friend.

After their double date in 2018, Jenner and Booker were not spotted together again until April 2020. The two were seen together at a rest stop during a road trip to Sedona, Arizona. At the time, much had changed as they were no longer with their partners of 2018. Also, following a cheating scandal involving Jordyn Woods and Tristan Thompson, Jenner and Woods stopped being friends. While Jenner and Booker being seen together raised eyebrows, a source told PEOPLE that the two weren’t dating.

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Subsequently, rumors and speculations of a relationship intensified. This was because Kendall Jenner and Devin Booker were repeatedly sighted together throughout the rest of 2020. For example, in August, they went to dinner at Nobu restaurant in Malibu, California, with Kylie Jenner. Also, in September, Jenner and Booker went on a fancy lake vacation with Justin and Hailey Bieber. Furthermore, in October, they attended Kim Kardashian’s 40th birthday party together. While all of this happened, fans were beside themselves with excitement, and some were completely convinced that the two were already a couple. However, an official confirmation of a relationship never came in 2020.

As the month of love rolled in, the two decided to quench the thirst of many curious fans. On Valentine’s Day, 2021, Jenner and Booker officially announced their relationship via Instagram. They both posted cute photos, and each opted to use a simple but profound heart emoji as the caption. Although there were no words written, the couple’s photos and captions said enough. Viewers certainly got the message.

After about four months of going public, Kendall Jenner and Devin Booker celebrated their first anniversary on June 12, 2021. The social media posts they shared made fans realize that they had actually started dating back in 2020. Evidently, although the couple did not confirm the rumors back then, fans were right about their secret romance. 

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Read More: Devin Booker & Kendall Jenner Call It Quits

Throughout 2021, Kendall Jenner and Devin Booker gave fans cute glimpses into their romantic life. While they were still mostly private, they showed the public enough to let them know that they were very utterly smitten. When Booker made it to the NBA finals with the Phoenix Suns in July, Jenner was there, cheering him on. During an Italian getaway in August, the two were spotted being adorable together. Also, on Jenner’s birthday in November, the basketball player proudly gushed about his girlfriend on Instagram. He posted several photos of Jenner on his Instagram story, one of which he captioned “Most beautiful woman.”

In 2022, the couple’s romantic flame continued to burn brightly, and they let fans in on it. In January, the KUWTK star shared photos of a weekend holiday with Booker. Later, the couple attended the Super Bowl together in February, and sat with the Biebers. When Booker was asked about his relationship with Jenner during an interview with Wall Street Journal in March, he said he was “enjoying life to the fullest.” Another notable point in their relationship was when Jenner brought Booker as her date to Kourtney Kardashian’s wedding in May 2022.

In June 2022, multiple sources shared with Entertainment Tonight that Kendall Jenner and Devin Booker had broken up. According to Entertainment Tonight, one source said that the two “have had discussions about their future but they are not on the same page.” Another source shared, “Kendall feels they’re on different paths.” However, later in June 2022, the two were spotted together at Soho House in Malibu. Subsequently, they were seen together a few more times between July and September. For example, paparazzi caught them heading out for a date night in August, and spending a weekend together in NYC in September. 

While it seemed like the couple was back on track after they reportedly broke up in June, it unfortunately didn’t last very long. “Both have incredibly busy schedules right now with their careers and they’ve decided to make that a priority,” one source told PEOPLE. Another source told Us Weekly that the pair broke up a month prior and that “things are amicable after the breakup, there’s no bad blood between them.”

Following their breakup, Kendall Jenner got into a relationship with Bad Bunny in early 2023. Subsequently, in April 2023, a source told Us Weekly that Booker wasn’t completely over Jenner just yet. “Devin doesn’t believe for one minute that Kendall and Bad Bunny’s relationship is that serious,” the source said. “He doesn’t think he’s her type and finds it difficult to believe there’s any longevity there between them.”

Booker’s alleged interest in getting back together with Kendall certainly excited some fans. However, if it was true, nothing ever came of it. While the two seem to have no ill feelings toward each other, they have mostly kept their distance since they broke up in 2022. Their 2024 sighting was at the Super Bowl where they happened to be in the same $1 million VIP suite. However, they did not sit together. Through a series of photos posted by Kylie Rubin (daughter of Fanatics CEO, Michael Rubin), fans noticed that Rubin was in the same suite as Jenner and Booker.

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