Latest Shocking Entertainment News: Kendall Jenner and Devin Booker's Relationship Timeline
Kendall Jenner went through plenty of ups and downs in her relationship with Devin Booker.
Jenner and Booker were first spotted on a double date — with other people — in May 2018. While the model was seeing Ben Simmons at the time, Booker was linked to Kylie Jenner’s then-best friend Jordyn Woods.
Us Weekly confirmed in February 2019 that Booker and Woods’ relationship quietly fizzled out before she was caught kissing Khloé Kardashian’s on-again, off-again boyfriend, Tristan Thompson, at a party. The scandal, which prompted Kardashian and Thompson to split, also resulted in the end of Woods and Kylie’s friendship. (Kardashian and Thompson got back together in August 2020.)
Kendall and Simmons, meanwhile, continued to date on and off. After more than two years of dating, however, sources told Us that Kendall and Booker pulled the plug on their romance — but only for a few weeks. Two months after their June 2022 split, Us confirmed that the pair were back together. However, they called it quits again that fall. In February 2025, an insider told Us that the pair were back together.
Scroll through to see Kendall and Booker’s timeline:
May 2018
Kendall, Woods, Booker and Simmons dined together in Los Angeles in May 2018.
April 2020
The twosome were spotted on a road trip to Sedona, Arizona, on April 29, 2020.
June 2020
A source told Us in June 2020 that Kendall and Booker were “hooking up,” but “not serious” about their romance.
August 2020
After the twosome were spotted together several times during the summer of 2020, Us confirmed that they were “still seeing each other.” An insider told Us in August 2020, “It’s easy because they get along well and he also gets along great with her family.”
November 2020
The model cuddled up to the athlete at her 25th birthday party in November 2020.
January 2021
The duo proved to be going strong in the new year after Booker reposted a steamy snap of Kendall in a bikini in January 2021 via Instagram. That same month, the reality TV personality posted a pic watching her man and the Phoenix Suns take on the Dallas Mavericks on the social media platform.
February 2021
Kendall and Booker gave fans a closer look at their romance on Valentine’s Day in February 2021. While she posted a pic cuddling with him on her kitchen countertop via Instagram Stories, Booker posted a video of her playing with a dog and the twosome taking a nap on the grass.
March 2021
"They are definitely an item and care about one another immensely,” a source told Us in March 2021, less than a month after the pair went Instagram official. “But it's not like they will be getting engaged any time soon. Kendall likes the pace at which things are going at the moment and has no plans to elevate things so quickly."
April 2021
When Jenner posted photos of her Easter Sunday dress via Instagram, Booker commented, "Very beautiful ... course."
April 2021
The pair attended a launch party for Jenner's new 818 Tequila at the Nice Guy in West Hollywood.
June 2021
Jenner celebrated her one-year anniversary with the athlete by sharing a few intimate photos on her Instagram Story, simply captioned “365.” The two cuddled on a private jet in one shot, and they entertained Booker’s dog, Haven, in another pic.
July 2021
Jenner showed her support for Booker during his NBA Finals debut with the Phoenix Suns. "I'm not emotional, you are," she wrote via her Instagram Stories, sharing a video taken from inside the arena. She also posted a photo of herself decked out head-to-toe in Suns orange.
July 2021
The reality star was spotted cheering on her boyfriend in Arizona on July 17 as his team faced off against the Milwaukee Bucks.
August 2021
The couple toasted Jenner’s successful 818 Tequila brand in New York with a beachside bash. "Devin led Kendall through the crowd upon arrival and led her to her seat,” an eyewitness exclusively told Us of the event. “They kept making eye contact throughout the night and never strayed far away from each other. At the end of the night, they walked out together hand in hand with nothing but smiles."
August 2021
The duo were spotted kissing and cuddling while on vacation in Italy in photos obtained by TMZ.
August 2021
A fan posted a video of the couple talking with Booker's grandmother as Jenner met the athlete's family member for the first time. Mister Cartoon, who was working with Booker to design two basketball courts in Moss Point, exclusively told Us that the duo seemed like "a perfect match" during their visit.
September 2021
“Limoncello ,” Jenner captioned a series of photos from Italy via Instagram, including a snap of her and Booker on a romantic stroll.
October 2021
Kendall shared a look at her pumpkin carving date night with Booker ahead of Halloween. However, the athlete has rules for jack-o-lanterns. "Pumpkin dont count if you used a stencil," he tweeted. His girlfriend quoted his message and jokingly added, "I feel personally attacked."
October 2021
The couple shared a sweet victory kiss after Booker’s team beat the Los Angeles Lakers on October 24.
October 2021
“Yer corpse bride,” Jenner captioned an Instagram gallery of images from a lingerie photoshoot, which left her boyfriend in awe. “Don’t forget!” Booker commented on October 27.
November 2021
Booker gushed over his girlfriend on her 26th birthday, calling her the "most beautiful woman" in a sweet Instagram Story tribute.
December 2021
Booker made it to the gingerbread house. Kendall's mother, Kris Jenner, is known for sending elaborate Christmas cookie creations to her loved ones, and Booker's name was included on Kendall's confectionary gift alongside her dogs' names.
January 2022
The couple got cozy during a winter getaway for New Year's, and they both shared photos via Instagram of their vacation. They went to a rustic location for an intimate weekend in the countryside, sharing wine and nights by the roaring fire.
January 2022
“Y’all know I wanna see #DevinBooker play in the All-Star Game #NBAAllStar ,,” the supermodel tweeted on January 7.
February 2022
Booker recalled taking a road trip with his love to Roden Crater, a landmark created by an extinct volcano outside Flagstaff, Arizona, as the COVID-19 pandemic began. The visit gave them an opportunity to bond over the artwork created there by artist James Turrell.“We visited Roden Crater and were astonished by the experience,” Booker told Architectural Digest in February 2022. He even bought a piece by Turrell to remind him of the getaway.
February 2022
The model and the athlete attended Super Bowl LVI in Inglewood, California.
March 2022
Booker gushed over his relationship during an interview with WSJ. Magazine, noting that it wasn't "hard" to manage the public interest in his love life. "Honestly, I'm enjoying life to the fullest, and that came off my tongue so easily because it wasn't always this way, but I feel like I'm in a good place right now," he told the outlet. "I love my family, I love the people around me, and I love the impact that I get to have on this world, the younger generation under me and the kids who look up to me."
April 2022
During an appearance on Jimmy Kimmel Live! with her mother and sisters, the host asked the model whether she tunes into Booker’s NBA games. “I watch every game unless I have — last night, I had a dinner, but all my friends and family know that I, like, sit with my phone [in front of me] wherever I am with the game on,” she replied, adding that she’s been a basketball fan since going to Lakers games with Khloé Kardashian.
April 2022
Though the couple have become more comfortable sharing their relationship over the years, Jenner has no interest in including the athlete on The Kardashians. "We’ll see Kendall with her friends more than you did in Keeping Up [With the Kardashians]," showrunner Danielle King told Variety when asked about Booker appearing on the show. "But she is keeping her relationship private."
May 2022
While promoting a new episode of Hulu's The Kardashians, Jenner revealed that her phone background is a black-and-white photo of Booker getting ready to hit the court during a basketball game.
May 2022
The Rebels: City of Indra author shared a glimpse into the pair’s May 14 date night, where they played “Sorry!” together, which she ultimately won.
May 2022
The duo went to Italy to celebrate Kourtney Kardashian and Travis Barker's wedding.
June 2022
A source told Us that the twosome hit pause on their relationship as they “figure out if a future together is what’s meant to be.” Per the insider, Booker and Jenner are “still super amicable and supportive of each other.
June 2022
Booker raised eyebrows when he “liked” a cheeky photo of Jenner sunbathing nude, which she posted via Instagram on June 26. The same day, the twosome sparked reconciliation speculation when they were spotted hanging out in Malibu together. The pair were seen smiling and getting close on the balcony of the Soho House.
July 2022
Weeks after Us reported the pair pumped the brakes on their relationship, they were spotted together multiple times, from a Hamptons getaway to a weekend wedding in Napa, California.
August 2022
"Kendall and Devin are 100 percent back together," an insider exclusively told Us. "They spent some time apart but are back to a good place and are really happy with each other."
August 2022
The model shared a glimpse of a rural summer getaway with Booker via her Instagram Story, posting a photo of herself sitting on her beau's lap and drinking a beer.
August 2022
The athlete was left speechless after Jenner shared a series of sizzling bikini pics. Booker kept his reaction simple, dropping a sweaty emoji in her Instagram comments.
September 2022
After attending multiple New York Fashion Week events together, Jenner and Booker packed on the PDA while watching the men's final at the U.S. Open.
October 2022
Booker celebrated his girlfriend by commenting on Kim Kardashian’s Instagram snap of herself with Kris and Kendall. “Middle,” he wrote, pointing out that the 818 founder was front and center for the family snap. Kendall, for her part, showed she appreciated the support from her beau by "liking" his comment.
October 2022
Kendall kicked off the start of the new basketball season by cheering on her boyfriend during his game against the Los Angeles Clippers. Kendall brought Caitlyn Jenner with her to the Crypto.com Arena to root for Booker’s eventual win.
October 2022
Jenner shared a sweet snap with the athlete on his 26th birthday, simply writing, “Birthday boy,” with a red heart emoji via Instagram Stories.
November 2022
Us confirmed that the duo called it quits once again. "Things are amicable after the breakup, there's no bad blood between them," an insider revealed, noting that the split happened "a little over a month" prior.
April 2023
Months after their split, a source exclusively told Us that Booker was still harboring feelings for his ex. "Devin still thinks about Kendall on occasion and a piece of him still misses her. He has no idea what the future holds and although maybe their timing wasn’t right, [that] doesn’t mean it can’t happen at some point down the line," the insider noted, explaining the athlete “is not completely over her." The source explained: "He’s not actively trying to get back with her but isn’t exactly opposed to the idea either.”
February 2025
A source exclusively told Us that Kendall and Booker are “very much together,” adding, “Kendall thinks Devin is really funny, and they seem very solid right now.” The insider noted that Kendall and Booker had been in New York City for a friend’s dinner party and were “making out and being very affectionate.” Despite their PDA, the source shared that the pair “like to keep their relationship private.” The insider added, “But they are very touchy-feely when they’re with friends.”
by Sarah Hearon
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