A Timeline of Kendall Jenner and Devin Booker’s Romance Amid Reconciliation Rumors

April 2020

Kendall and Devin sparked romance rumors during a road trip in April 2020.

September 2020

Kendall was spotted picking Devin up from LAX in September 2020.

October 2020

The following month, he also joined Kenny on a trip to Tahiti for sister Kim’s birthday.

October 2020

In October 2020, Devin attended Kendall’s Halloween-themed birthday party. The couple even took a sexy picture together in a photo booth at the bash.

January 2021

Devin gushed over Kendall’s toned bikini body on his Instagram Stories in January 2021.

January 2021

The model shared a Boomerang of her TV while watching one of her man’s games in January 2021. Supporting bae!

February 2021

The KUWTK star was spotted wearing a Phoenix Sun sweatshirt while running errands in Beverly Hills in February 2021. Clearly, Kendall is all about supporting her man.

February 2021

Aww! Kenny and Devin made their relationship Instagram official on Valentine’s Day. The supermodel shared this cuddled up photo on her Story and added a white heart emoji.

February 2021

Kendall showed off a sweet Louis Vuitton box full of white roses with her and her boyfriend’s initials (KJ&DB) monogrammed on the leather handle. So sentimental!

March 2021

On March 13, Kenny shared an Instagram Story video in which she followed her boyfriend’s dog around so she could capture the athlete’s last name and number on the puppy’s back. A few hours later, Devin reposted the footage to his own Instagram Stories and added the caption, “Big guard.”

May 2021

During a Poosh video with Kourtney Kardashian, Kendall pranked her family and claimed she and Devin were engaged — and pregnant. “It’s believable so I will do it,” she said during the YouTube video.

May 2021

The same month, the NBA star decorated his girlfriend’s backyard in a lavish display in honor of her 818 Tequila launch.

June 2021

In June 2021, Kendall and Devin shared a stunning snapshot from where they had their one-year anniversary date. So dreamy!

June 2021

Later that month, Kendall opened up about her relationship with the athlete for the first time — and noted that they like keeping their romance private.

“I feel like it’s always worked better for me that way, and no offense to my older sisters at all, but I think like Kylie [Jenner] and I specifically have had the opportunity to watch my older sisters go through marriages and relationships and breakups and all these things and do it pretty publicly,” she explained on the KUWTK series reunion. “I think it makes my life a lot easier and our relationship a lot better to be completely honest. I just feel like it’s a private matter and not for anyone to judge or know.”

August 2021

The model supported her man during his incredible gold medal win at the 2021 Olympic Games in Tokyo.

October 2021

Sealed with a kiss! The A-list couple shared their first public smooch during Devin’s NBA game in Los Angeles on October 22.

October 2021

All smiles! Kendall posted a sweet 25th birthday tribute for Devin on her Instagram Stories on October 30, calling him her “best friend.”

October 2021

Kendall posted another Instagram Story on October 30 of her beau. In it, Devin was wearing a Nike headband and red T-shirt. Kendall sealed her caption with three heart emojis.

November 2021

Devin posted a sweet birthday tribute for Kendall on November 3. “Most beautiful woman,” the NBA player wrote for a photo of Kendall looking away, with another photo of his arms around the model.

December 2021

Kendall and Devin spent the holiday season together, including a cozy cabin getaway for New Year’s. “They’re so in love,” a source exclusively told Life & Style, noting “it’s only a matter of time” before they get engaged. 

April 2022

Kendall gave further insight into her romance with the NBA player when she and her mom and sisters appeared on Jimmy Kimmel Live! She watches “every game” no matter where she is.

May 2022

Kendall tagged her beau in a snap that she shared via her Instagram Stories in May 2022, featuring the vintage Sorry! board game they were playing for their date night. Shortly afterward, Kendall declared she won alongside a photo of her four blue pawns.

August 2022

Kenny proved she and Devin were fully back on by sharing a photo of herself curled up on his lap while they enjoyed a serene vacation on August 2.

September 2022

Athletic date day! Devin and Kendall attended the U.S. Open tennis tournament on September 11, sitting close together and getting cozy as they watched the men’s final match between Casper Ruud and Carlos Alcaraz.

October 2022

Kendall wished Devin a happy 26th birthday in a sweet Instagram post on October 30, sharing a photo from their summer vacation to a Wyoming rodeo and writing “Birthday boy” while including a red heart emoji.

November 2022

Life & Style confirmed that the former couple called it quits the month prior. According to People, they “amicably split.”

February 2025

Kendall and Devin reunited over Valentine’s Day weekend in Aspen, Colorado, in February 2025. Photos circulated on social media that showed the pair bundled up in beanies and snow goggles as they sat side by side in a local bistro.

Neither Kendall nor Devin have publicly confirmed the status of their relationship, though their reunion made many fans wonder if they’re back together.