Kendall Jenner, Devin Booker's Relationship Timeline (2024)

Has Kendall Jenner found The One? The Keeping Up With the Kardashians star 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.“I’m very young and right now I feel like relationships aren’t always super-certain and I don’t want to bring too much attention to something if you don’t really know long term [what it’s going to be]," she told Vogue in May 2019. "A relationship is only meant to be between two people, and the second you make it the world’s business is when it starts messing with the two people mentally. Like once everyone is let in, you’re letting all these opinions into your relationships, and I don’t think that’s fair.”[sendtonews type="float" key="Xt19F341m4-2841874-14453"]Kendall and Simmons were last spotted together in February 2020.“A lot of the relationships have taught me more about myself, which is the most valuable,” she said during a behind-the-scenes video for a Calvin Klein campaign at the time. “And like, what I want from a person or from a relationship.”That April, the E! personality was spotted out with Booker. Woods was subsequently accused of throwing shade via Twitter.“Haha good morning,” the influencer wrote alongside three trash can emojis in a since-deleted tweet.Kendall, for her part, never acknowledged Woods’ alleged shade. She did, however, fire back at social media users who accused her of “passing around” NBA players after she was seen with the Phoenix Suns player.“They act like I’m not in full control of where I throw this cooch,” Kendall, who has also been linked to Blake Griffin, tweeted in April 2020.After more than two years of dating, however, sources told Us that Kendall and Booker pulled the plug — but only for a few weeks. Two months after their June 2022 split, Us Weekly confirmed that the pair were back together. However, they called it quits again that fall.Scroll through to see Kendall and Booker’s timeline:

Has Kendall Jenner found The One? The Keeping Up With the Kardashians star 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.“I’m very young and right now I feel like relationships aren’t always super-certain and I don’t want to bring too much attention to something if you don’t really know long term [what it’s going to be]," she told Vogue in May 2019. "A relationship is only meant to be between two people, and the second you make it the world’s business is when it starts messing with the two people mentally. Like once everyone is let in, you’re letting all these opinions into your relationships, and I don’t think that’s fair.”[sendtonews type="float" key="Xt19F341m4-2841874-14453"]Kendall and Simmons were last spotted together in February 2020.“A lot of the relationships have taught me more about myself, which is the most valuable,” she said during a behind-the-scenes video for a Calvin Klein campaign at the time. “And like, what I want from a person or from a relationship.”That April, the E! personality was spotted out with Booker. Woods was subsequently accused of throwing shade via Twitter.“Haha good morning,” the influencer wrote alongside three trash can emojis in a since-deleted tweet.Kendall, for her part, never acknowledged Woods’ alleged shade. She did, however, fire back at social media users who accused her of “passing around” NBA players after she was seen with the Phoenix Suns player.“They act like I’m not in full control of where I throw this cooch,” Kendall, who has also been linked to Blake Griffin, tweeted in April 2020.After more than two years of dating, however, sources told Us that Kendall and Booker pulled the plug — but only for a few weeks. Two months after their June 2022 split, Us Weekly confirmed that the pair were back together. However, they called it quits again that fall.Scroll through to see Kendall and Booker’s timeline:

Kendall, Woods, Booker and Simmons dined together in Los Angeles in May 2018.

The twosome were spotted on a road trip to Sedona, Arizona, on April 29, 2020.

A source told Us in June 2020 that Kendall and Booker were “hooking up,” but “not serious” about their romance.

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.”

The model cuddled up to the athlete at her 25th birthday party in November 2020.

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.

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.

"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."

When Jenner posted photos of her Easter Sunday dress via Instagram, Booker commented, "Very beautiful ... course."

The pair attended a launch party for Jenner's new 818 Tequila at the Nice Guy in West Hollywood.

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.

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.

The reality star was spotted cheering on her boyfriend in Arizona on July 17 as his team faced off against the Milwaukee Bucks.

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."

The duo were spotted kissing and cuddling while on vacation in Italy in photos obtained by TMZ.

“Limoncello,” Jenner captioned a series of photos from Italy via Instagram, including a snap of her and Booker on a romantic stroll.

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."

The couple shared a sweet victory kiss after Booker’s team beat the Los Angeles Lakers on October 24.

“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.

Booker gushed over his girlfriend on her 26th birthday, calling her the "most beautiful woman" in a sweet Instagram Story tribute.

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.

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.

“Y’all know I wanna see #DevinBooker play in the All-Star Game #NBAAllStar,,” the supermodel tweeted on January 7.

The model and the athlete attended Super Bowl LVI in Inglewood, California.

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."

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.

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."

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.

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.

The duo went to Italy to celebrate Kourtney Kardashian and Travis Barker's wedding.

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.

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.

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.

"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."

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.

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.

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.

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.

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.

Jenner shared a sweet snap with the athlete on his 26th birthday, simply writing, “Birthday boy,” with a red heart emoji via Instagram Stories.

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.

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.”