Kendall Jenner & Devin Booker’s Relationship Timeline From Start To Finish

The two have reportedly split again after two years of dating, but they still plan to “keep in touch.”

Written by Jake Viswanath
Originally Published: 
Kendall Jenner & Devin Booker's Relationship Timeline Will Continue On Hulu's 'The Kardashians' Seri...
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After more than two years of dating, Kendall Jenner and Devin Booker have reportedly split — again. On Nov. 21, PEOPLE reported that the two quietly split sometime in October, attributing the decision to their demanding careers. Bustle reached out to Jenner's representative, who had no comment at this time. Booker's representative did not give an immediate response.

They first split in mid-June after returning from Kourtney Kardashian and Travis Barker’s wedding in Italy. They “hit a rough patch recently and have been split for about a week and a half,” a source close to the couple told E! News on June 22. However, the breakup appeared to only be temporary, as the couple had already hinted at a reconciliation just a few weeks later. E! News reported on July 19 that the model and NBA player were “fully back together,” adding that they “worked out their issues and decided they want to move forward.”

Jenner and Booker were first spotted out together on a double date in 2018 — with other people. At the time, Booker was dating Kylie Jenner’s former best friend Jordyn Woods. Kendall, however, was involved in an on-again, off-again relationship with Philadelphia 76ers star Ben Simmons. So, how did Jenner and Booker go from friends on double dates to a full-on couple to splitsville, before falling in love again? Let’s take a look at their complete relationship timeline.

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Devin Booker and Kendall Jenner at the US Open in September 2022.Gotham/GC Images/Getty Images

May 2018: First Time Spotted Together

Jenner and Simmons met up with Booker and Woods in Los Angeles for dinner in May 2018, which marked the first time that the model and the Phoenix Suns player were ever spotted together. Their relationship was platonic at the time, but in hindsight, the double date seemingly backfired because they wound up dating each other instead of the people that they originally came with.

April 2020: Road Trip

Jenner and Booker weren’t spotted together again until two years later. In photos published by TMZ, the duo was spotted on a road trip together to Sedona, Ariz., in April 2020. That same month, the model was criticized for mainly dating basketball players. “They act like I’m not in full control of where I throw this cooch,” Jenner wrote in response to a tweet that suggested that basketball players were “passing” her around.

May 2020: Picking Him Up From The Airport

Rumors about a romance continued to swirl in May, and the duo didn’t do much to hamper them. In fact, the Keeping Up With the Kardashians star was spotted picking the athlete up from the Van Nuys Airport in Los Angeles, leading fans to wonder if their rumored romance was getting serious.

June 2020: “They’re Not Serious”

“They’re hooking up, but they’re not serious,” a source told Us Weekly in June 2020. “She’s talking to a couple different guys. She has so many men after her it’s crazy.” This update came after Jenner briefly reconciled with Simmons earlier in the year, but according to the magazine, the two were “not officially back together.” “They both like having a no-strings-attached type of relationship with each other, for the most part,” a source previously told Us Weekly of Jenner’s past relationship with Simmons. “They both work and travel frequently and don’t find it very realistic to be in an exclusive relationship with one another.”

August 2020: Getting Flirty On Instagram

Nothing says romance like flirty messages on Instagram. When Jenner captioned a photo of herself with a strawberry emoji in August 2020, Booker slid into the comments of the post. “I like strawberries,” he wrote. In response, the reality star sent back four additional strawberry emojis, confirming that at the very least, they were into each other.

A Us Weekly insider reported that “Kendall and Devin are seeing each other, but aren’t serious and are just having fun with each other.” The source added that their relationship until that point had been “easy,” especially since Booker got along so well with her family.

October 2020: Private Island Vacation

Despite trying their best to keep their relationship low-key, Jenner and Booker were spotted in the background of a photo from Kim Kardashian’s 40th birthday bash on a private island.

November 2020: Photo Booth

Instagram/Kendall Jenner

Fans knew that things were heating up between Jenner and Booker the following month when the model posted a photo with the basketball player on Instagram. The picture she shared was from the photo booth at her 25th birthday bash in Los Angeles.

January 2021: “Whew”

The couple really took their relationship to the next level after the new year. In January, Booker reportedly shared a photo of Jenner in a bikini on Instagram. Kendall, for her part, shared a picture of herself watching the athlete play against the Dallas Mavericks.

February 2021: Valentine’s Day

Instagram/Kendall Jenner

Jenner gave a rare glimpse at one of the couple’s more romantic moments. On Valentine’s Day, she shared an image of the two cuddling on the kitchen counter. Per Us Weekly, Booker also commemorated the day by sharing a video of them playing with the dog and lying on the grass.

March 2021: “Definitely An Item”

Gotham/GC Images/Getty Images

One month after showing off some Valentine’s PDA, Us Weekly reported that their relationship is becoming more serious. “They are definitely an item and care about one another immensely,” an insider said. “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.” An Entertainment Tonight source echoed that sentiment, adding that Booker makes Jenner feel “comfortable and safe.”

April 2021: Easter

Jenner captured Booker’s attention in April when she posted photos of herself in her Easter dress on Instagram. “Very beautiful…course,” he commented. Then, they were spotted holding hands while walking to dinner at New York City’s Carbone. “This is the happiest Kendall has been in a relationship,” an E! insider revealed. “It’s getting more and more serious and she is very happy.”

E!’s source also said that Booker is “quiet and not interested in being in the spotlight or a celebrity,” which could explain why they’ve tried so hard to keep their romance under the radar. “She really appreciates that about him and is attracted to that. They are really similar and love just being low-key and staying in and laughing together.”

June 2021: The First Anniversary

June was a big month for Jenner and Booker, as they were celebrating their first anniversary. To honor the occasion, she shared a series of photos of her beau on Instagram. Kendall kept the captions simple, writing “365” and “52” on two of the pictures to mark the number of days and weeks that they were in a relationship. Later that month, Us Weekly reported that Booker “practically moved in” with Jenner. “They really respect each other’s careers and give each other space to focus on her modeling or his basketball career,” a source said. “That’s probably what makes their relationship work so well is that they have that work-life balance.”

Instagram/Kendall Jenner

In Part 2 of the KUWTK reunion special, which aired on June 20, Kendall also revealed why she likes to keep her relationships so private. “No offense to my older sisters at all, but I think that Kylie [Jenner] and I specifically have had the opportunity to watch our older sisters go through marriages and relationships and breakups and do them pretty publicly,” she said, adding that keeping things on the down-low makes her life “a lot easier.”

July 2021: The NBA Finals

Instagram/Kendall Jenner

When Booker played against the Milwaukee Bucks during the NBA Finals, Jenner showed up to show her support. Alongside a video of a lit-up arena, Kendall wrote: “I’m not emotional, you are.” When the Suns made it to game 5, Jenner took to her Instagram Stories to share a photo of her wearing a Phoenix Suns jacket.

August 2021: Business Celebrations

The couple closed out the summer by celebrating Jenner’s 818 Tequila brand. “They kept making eye contact throughout the night and never strayed far away from each other,” an eye witness at the event told Us Weekly. At the end of the night, they walked out together hand in hand with nothing but smiles.” That same month, Booker shared a photo of a bikini-clad Kendall on a boat wearing the gold medal that he and the rest of Team USA won at the 2021 Olympics in Tokyo.

September 2021: Opening Up (On Tv)

Fast forward to September and it seems that Jenner and Booker are stronger than ever. During an appearance on The Late Show Starring Jimmy Fallon, Jenner said that the basketball star gets along great with her family — especially her nieces and nephews. “He loves them,” she said.

In that same interview, the reality star revealed that her boyfriend brings out her competitive side. “We were playing in the pool, and he just took it way too seriously—as did I, by the way,” she said of their water-basketball game. “I had the ball, and he was guarding me, and it was a whole thing. He actually ended up cutting my hand open a little bit with his nail because he took it a little too seriously.” Fortunately, Jenner said that she was on the mend.

October 2021: Halloween

If we know one thing about the Kardashian-Jenners, it’s that they go hard for Halloween. So hard, in fact, that they typically start sharing photos of their activities and costumes long before Oct. 31. This year, Jenner and Booker kicked off the festivities with some pumpkin carving. But the NBA star totally let it slip that the model needed some guidance. “Pumpkin dont count if you used a stencil,” he tweeted. In response, Kendall quoted his message and wrote that she felt “personally attacked.”

On Oct. 27, the Halloween spirit continued when Jenner shared pictures from a photo shoot of her dressed in spooky lingerie. “yer corpse bride,” she wrote alongside several images of her in a wedding veil and a white lace thong. Booker, for his part, seemed to really like the photos and the bridal theme. “Don’t forget!” he wrote. Oh, don’t worry. We won’t.

March 2022: Talking To The WSJ

Booker spoke about his relationship with Jenner for the very first time in a March 8 interview with WSJ. When asked what it’s like dating one of the most famous women in the world, the basketball player answered honestly. “I wouldn’t say [it’s been] hard,” he said. “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. 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.”

Although they are very happy together, a source told E! that marriage is not a consideration at the moment. “Kendall and Devin’s relationship is going strong, but they are in no rush to settle down and tie the knot,” the insider said, explaining that an engagement is not something weighing on the model’s mind. “Kendall is not a conventional or traditional type of girl and doesn’t even care about having a huge elaborate wedding,” the source said. “She is very much content with how things are with Devin right now.”

April 2022: Booker’s Basketball Games

During an appearance on Jimmy Kimmel Live! with her mother and sisters, the model was asked if she watches Booker’s basketball 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 said. She also said that she’s always been a fan of the sport and used to attend Lakers games with her older sister Khloé Kardashian.

June 2022: Jenner & Booker Reportedly Split

After two years of dating, Jenner and Booker reportedly broke up in mid-June due to them realizing “they have very different lifestyles” after returning from Kourtney Kardashian and Travis Barker’s wedding in Italy. They “hit a rough patch recently and have been split for about a week and a half,” a source close to the couple told E! News. The split appears to be amicable — and possibly not permanent. “They both hope to make it work, but as of now, they are split,” the source added.

July 2022: Jenner & Booker Reconcile

On July 19, E! News reported that Jenner and Booker were “fully back together” after spending more quality time with each other. “They worked out their issues and decided they want to move forward and be together,” a source told the outlet. Jenner first hinted at the reconciliation on her Instagram Story, when she shared a picture with Booker at her friend Lauren’s Napa wedding, and the source confirmed that he was indeed her date.

A couple weeks later, Jenner posted a video of Booker axe-throwing in the woods, which he also shared on his stories, adding a bullseye emoji. Clearly, their reunion is going strong.

November 2022: Jenner & Booker Split — Again

On Nov. 21, PEOPLE reported that Jenner and Booker had quietly broke up yet again a month prior. “Both have incredibly busy schedules right now with their careers and they've decided to make that a priority,” a source told the outlet, adding that the two “have a lot of love and respect for each other and wish only the best.” A separate insider said their decision to split was mutual and simply came down to timing, adding that they plan to keep in touch. Given how they’ve reconciled before, it seems that the door could be open to that possibility again.

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