It's time to add another split to the Kendall Jenner and Devin Booker timeline. The couple has been off and on since April 2020, and five years later, with a Bad Bunny in between, things are still not working out.
After sparking reconciliation rumors in September 2024, the hot-and-cold pair were spotted taking a break from the slopes in Aspen just after Valentine’s Day, on February 17, 2025.
Two days later, a source told Us Weekly they were “very much together” and officially back. But things fizzled out fast - according to a new Us Weekly report, the two quietly broke up “over a month ago.”
As for what went wrong this time? A source said they have "communication issues." “It always comes down to them both being busy, navigating schedules and just not being on the same page,” they explained.
Jenner went back to Booker following her high-profile relationship with Bad Bunny. But the timeline wasn’t exactly clean. While the reality star and Bad Bunny called it quits in late 2023, she was already reconnecting with Booker by February 2024.
That same month, reports said she and Devin were "rekindling their relationship" and "navigating a restart."
But just a couple of months later, in May, she was photographed sitting close to Bad Bunny and whispering with him at a Met Gala afterparty.
Two weeks after that, she was seen dancing at his concert in Orlando, and by the end of May, sources confirmed they were officially back together. One insider even noted that Bad Bunny had “not been happy” about her reconnecting with Devin and had been wanting her back.
She and Bad Bunny called it quits for the last time sometime after that, and she was spotted having dinner with Booker in Miami in September 2024.
Will the couple get back together... AGAIN? Time will tell.