A Complete Timeline of Kendall Jenner and Devin Booker's Relationship

The most private Kardashian-Jenner sibling keeps her romance under wraps.

There's only one member of the Kardashian-Jenner family that isn't splashing her love life on gossip magazines and for E!'s ever-watchful cameras: Kendall Jenner. The secretive sister has been dating her beau, basketball pro Devin Booker, have been dating for more than a year, but it's rare that she mentions him, posts about him, or even appears in public with him. But sources say the love is real — not reality TV fodder. Here's everything you need to know, from an unexpected double date to their Italian getaway.

Kendall Jenner Devin Booker
Photo by Gotham/GC Images

May 2018

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 L.A. At the time, Woods and Booker had been romantically linked, but that relationship would turn sour in February 2019. This was all before Woods would become embroiled in the Kardashian family's civil war-level feud that came in the aftermath of Woods kissing Tristan Thompson, who was with Khloé Kardashian at the time.

Jenner and Simmons dated on and off until February 2020.

April 2020

For the first time, Jenner and Booker make headlines as a supposed couple. 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.

Booker joined Jenner on a road trip to Sedona, Arizona.

June 2020

Sources close to the couple told Us that they were "hooking up," but "not serious."

October 2020

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

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

January 2021

Booker posts a photo of Jenner on his Instagram Story.

"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! at the time. "For now, they are together in L.A. having fun and hanging out."

February 2021

Us adds that their relationship starts to get more serious.

"They are definitely an item and care about one another immensely," an insider shared. "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

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

"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."

E!'s source 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

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

July 2021

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

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."

The two head to Italy together and TMZ has the evidence, including all the PDA.

September 2021

During an appearance on The Late Show Starring Jimmy Fallon, 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.

January 2022

The couple rang in the New Year together with a mountain getaway. Jenner shared a few photos of the two loved up during a cozy escape.

February 2022

Jenner and Booker attended the Super Bowl with Hailey and Justin Bieber. Coincidentally, they all wore matching black-and-white outfits.

March 2022

Booker spoke about his relationship with Jenner during an interview with WSJ. Magazine, saying that he's "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."

"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," he finished.

May 2022

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.

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