Kendall Jenner and Devin Booker's Relationship Timeline: A Look Back

There's only one member of the Kardashian-Jenner family who isn't splashing her love life on gossip magazines and for E!'s ever-watchful cameras: Kendall Jenner. Although the model and businesswoman has been romantically linked with some of the hottest players in the NBA and music biz, she has rarely mentioned them, posted about them, or even appeared in public with them — at least, initially. Take her relationship with her ex-boyfriend and basketball pro Devin Booker, for instance.

At first, Jenner and Booker kept things under wraps, but throughout their two-year-plus romance, we started to see an uptick in date night outings, as well as more mentions of each other on their social media and during interviews. During an appearance on The Tonight Show Starring Jimmy Fallon in 2021, Jenner shared that Booker's very into being a part of the Kardashian brood and that he especially gets along with her nieces and nephews. 

"He loves them," she said. 

It was clear by the way these two talked about each other that they were totally into one another — that is, until their breakup in 2022.

Here's a look back at Kendall Jenner and Devin Booker's relationship.

May 2018: Kendall Jenner and Devin Booker first meet

In a double date fit for Keeping Up with the Kardashians, Jenner and her then-boyfriend, Australian pro basketball player Ben Simmons, grabbed dinner with Jordyn Woods and Booker in Los Angeles. At the time, Woods and Booker had been romantically linked, but that relationship would turn sour in February 2019, reported Us Weekly. This was all before Woods became embroiled in the Kardashian family's civil war-level feud in the aftermath of Woods kissing Tristan Thompson, who was with Khloé Kardashian at the time.

April 2020: Kendall Jenner and Devin Booker are first spotted together

For the first time, Jenner and Booker make headlines as a supposed couple after going on a road trip to Sedona, Arizona, reported TMZ. Critics called her out for dating basketball players, which she promptly shut down.

"They act like I'm not in full control of where I throw this cooch," she tweeted in April 2020.

That June, sources close to the couple told Us Weekly that they were "hooking up" but "not serious." By October, internet sleuths spotted Booker in the background of one of Kim Kardashian's birthday photos — fans will remember that this is when Kim K. rented out an entire island for the festivities.

November 2020: Kendall Jenner celebrates her birthday with Devin Booker

Jenner turned 25 with Booker right beside her. A day after Halloween, she shared a snapshot of herself dressed as Pamela Anderson circa Barb Wire — and the gallery included a snapshot of Booker. 

Booker also showed Jenner some love on his social when he posted a photo of the model on his Instagram Story in January 2021, reported E!.

Apart from the occasional Instagram post, however, the couple remained pretty low-key. 

"She definitely prefers to keep her relationships on the down low, but she likes him, and she's happy to be with him right now," a source told E! when commenting on Jenner and Booker's relationship. "For now, they are together in L.A., having fun and hanging out."

February 14, 2021: Kendall Jenner and Devin Booker go Instagram official

On Valentine's Day, love was surely in the air for the couple. "They are definitely an item and care about one another immensely," an insider shared with Us Weekly. "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 confirmed the observations, saying that Booker makes Jenner feel "comfortable and safe."

April 2021: Devin Booker helps Kendall Jenner launch 818

Of course, Booker was on hand to help Jenner launch her tequila brand, 818, reported Us Weekly. 

"This is the happiest Kendall has been in a relationship," an E! source revealed. "It's getting more and more serious, and she is very happy."

They also explained that the two get along because Booker isn't looking for fame. Instead, he's "quiet and not interested in being in the spotlight or a celebrity. 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: Kendall Jenner celebrates one-year anniversary with Devin Booker

Jenner posted a rare photo of Booker to her Instagram Stories to commemorate their one-year anniversary. She captioned the shot "365."

The following month, Jenner attended the NBA Finals, which saw Booker playing with his team, the Phoenix Suns. 

"I'm not emotional, you are," she wrote in her Instagram Stories. 

She'd go on to post again when the Suns played the Milwaukee Bucks.

August 2021: Kendall Jenner and Devin Booker vacation in Italy

The couple headed to New York to fete Jenner's tequila once again. "Devin led Kendall through the crowd upon arrival and led her to her seat," an attendee told Us. "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."

Next, the two headed to Italy together, and TMZ captured some PDA.

January 2022: Kendall Jenner and Devin Booker spend New Year's together

The couple rang in the New Year together with a mountain getaway and, in doing so, sparked marriage rumors. Jenner shared a few photos of the two loved-up during a cozy escape. That February, Jenner and Booker attended the Super Bowl with Hailey and Justin Bieber. Coincidentally, they all wore matching black-and-white outfits.

March 8, 2022: Devin Booker opens up about his relationship with Kendall Jenner

Booker spoke about his relationship with Jenner during an interview with WSJ. Magazine, saying he was "enjoying life to the fullest" with her. 

"I wouldn't say hard," he said of being thrust into the spotlight because of his relationship. "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 added, "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."

May 15, 2022: Kendall Jenner brings Devin Booker as her wedding date

Jenner made a huge statement at Kourtney Kardashian and Travis Barker's wedding: she brought Booker along as her date. While the two have kept their relationship as low-key as possible, they were photographed together during the event, which took place in Portofino, Italy.

October 2022: Kendall Jenner and Devin Booker break up

By October 2022, the relationship had run its course, and the two decided to part ways. The reason for the split? A source told People, "Both have incredibly busy schedules right now with their careers, and they've decided to make that a priority." When it comes to the future, "Kendall feels like they're on different paths," a source shared with Entertainment Tonight.