Kendall Jenner went through plenty of ups and downs in her relationship with Devin Booker.
Jenner and Booker were first spotted on a double date — with other people — in May 2018. While the model was seeing Ben Simmons at the time, Booker was linked to Kylie Jenner’s then-best friend Jordyn Woods.
Us Weekly confirmed in February 2019 that Booker and Woods’ relationship quietly fizzled out before she was caught kissing Khloé Kardashian’s on-again, off-again boyfriend, Tristan Thompson, at a party. The scandal, which prompted Kardashian and Thompson to split, also resulted in the end of Woods and Kylie’s friendship. (Kardashian and Thompson got back together in August 2020.)
Kendall and Simmons, meanwhile, continued to date on and off. After more than two years of dating, however, sources told Us that Kendall and Booker pulled the plug on their romance — but only for a few weeks. Two months after their June 2022 split, Us confirmed that the pair were back together. However, they called it quits again that fall. In February 2025, an insider told Us that the pair were back together.
Scroll through to see Kendall and Booker’s timeline:
