And on June 3, 2021, Jenner attended Booker’s basketball game in Los Angeles. InstagramJenner and Booker’s relationship was serious and exclusive in March 2021, with Jenner’s family approving of her dating Booker. InstagramInstagramInstagramInstagramInstagramInstagramOne year into dating Booker, Jenner was “crazy” about him—and became seriously involved with him long before anyone knew. Kendall Jenner // InstagramBooker spoke about dating Jenner for the first time to WSJ in March 2022. In July 2026, Booker sparked dating speculation after photos and videos surfaced on social media of him and model Irina Shayk spending time in the Hamptons.