Devin Booker Spotted With Kendall Jenner Again: How Many Times Have They Broken Up and Reconciled?
The Kardashian and Jenner sisters rarely have a shortage of relationship drama. Over the last several years, fans’ eyes have been glued to Kim Kardashian and Khloe Kardashian’s relationship statuses. Their romantic lives seemed to be the most up in the air. As it turns out, everyone should have been paying more attention to one of the younger siblings. Kendall Jenner has been quietly riding a rollercoaster romance of her own. Kendall Jenner, a model, and Devin Booker, an NBA superstar, have been on and off for years. Recent reports suggest the pair are back at it again, but do you know how many times they’ve split up in he past? We did the math.
Kendall Jenner sparks relationship speculation
Kendall Jenner and Devin Booker might be back together again after a tumultuous summer. In September, just weeks before the NBA season kicked off, Booker and Jenner sparked romance rumors when they exited the same New York City hotel. While the pair didn’t exit together, it hardly seems like a coincidence that they were staying in the same place.
There have been other hints that Booker and Jenner might be considering the possibility of rekindling their romance over the summer, too. Some insiders claim they’ve been sort of together for the last several months. Radar Online alleges that Jenner is trying to keep things casual with Booker out of fear of ending up in a relationship like her older sisters. While she isn’t speaking on the topic, the reports that the former flames have gotten back together and broken up several times in the last few months would certainly make more sense if they were keeping their relationship open.
How many times have Kendall Jenner and Devin Booker broken up?
Devin Booker and Kendall Jenner were first spotted together in 2020, but didn’t make their relationship publicly official until 2021. After making things Instagram official, the young pair appeared to happily float along together. Trouble was coming, though. Rumors of a rough patch between the pair began in June 2022, shortly after they attended Kourtney Kardashian’s wedding in Italy together. According to several sources, they quietly split that month because of differing lifestyles and schedules. It didn’t last long, though. They were spotted together again in July 2022 and carried on as if nothing had happened. The pair never confirmed the breakup.
In November 2022, however, things clearly went south. The former flames were no longer seen together, and insiders revealed that they were quietly navigating a second split. Everything between them fell quiet. Jenner moved on with a short-lived romance with Bad Bunny. Then, in early 2024, Booker and Jenner linked back up. A source told People that they were taking things slow and seeing if there was still something there.
Kendall Jenner and Devin Booker tried to make it work again until September 2024, when they were said to have split yet again. Again, the breakup wasn’t forever. Over the summer of 2025, they were seen spending time together and have been spending time together this fall, too. Still, they refuse to confirm the romance. According to the U.S. Sun, Booker’s lack of commitment might be the problem. An alleged insider spoke to the outlet and revealed that Jenner would like to make things work with Booker, but that he’s reluctant to settle down just yet.
They have broken up at least 3 times since going public with their relationship in 2021. Could there be more turmoil to come? It seems likely. Still, Jenner seems most interested in conducting her relationship offline these days, so online sleuths may never know.
