Wait, Kendall Jenner and Devin Booker together in 2025? This was the last thing I would have expected to happen, but at the same time, I’m not surprised. ICYMI, over Valentine’s weekend, Jenner and Booker sparked romance rumors *again* when they were spotted at a local bistro in Aspen, Colorado. So are these two back together again?
While some may believe that romance is once again in the air for the celebs, their outing in Aspen could have just been pure coincidence. Regardless if they are back together or not, I’m sure it’ll come out sooner or later, and I can’t wait for the tea!
Jenner and Booker first sparked dating rumors in 2020 when they went to dinner with Kylie Jenner after the Phoenix Suns’s shooting guard flirted with the model on Instagram. They became Instagram official in February 2021 on Valentine’s Day, with Jenner posting a photo of Booker laying on top of her on her Instagram Story. On his IG Story, Booker shared a photo of him and Jenner cuddled up together on the grass, captioning the snapshot with a single “🧡” emoji. A few months later, the pair celebrated their one-year anniversary.
Unfortunately, Jenner and Booker’s romance didn’t last as they called it quits in June 2022. A source told Entertainment Tonight at the time that Jenner thought she and Booker were on “different paths.”
However, the two remained close with Jenner sharing Booker’s NBA 2K23 cover on her Instagram Story in July. The pair even took a tropical vacation together that same month. By September 2022, the couple were clearly back together as they showed some rare PDA at the U.S. Open before announcing their second split in November 2022.
Jenner went on to date Bad Bunny (whom she sparked dating rumors with in February 2023) until they split in December 2023. Meanwhile, Booker was rumored to be dating gymnast Suni Lee in August 2024.
In September 2024, fans clocked that both Booker and Jenner attended the gymnastics final of the 2024 Summer Olympics. They were seated on opposite sides of the stadium, but fans still thought it was a sign of rekindling.
Whether or not Jenner and Booker are dating again, seeing them back together definitely was *not* on my 2025 bingo card.