Rumors regarding the current state of Kylie Jenner and Timothée Chalamet’s relationship have existed for the entirety of the three years they’ve been together — usually with sources predicting there’s either a breakup pending or an engagement. Following an awards season that saw the Marty Supreme star shouting out his partner and answering questions regarding marriage and having children, the tables have turned once again, with alleged insiders predicting the end is near and revealing what Chalamet’s family supposedly thinks about The Kardashians star.
Kylie Jenner and Timothée Chalamet are “definitely” heading for a breakup, according to sources for OK! Magazine (something we’ve heard before, so take it with a grain of salt). The actor’s family and inner circle — including sister Pauline Chalamet — have allegedly questioned the couple’s compatibility since the beginning, with a family source reporting:
From the outside looking in, Timothée and Kylie's relationship has always puzzled those closest to him. There is a genuine sense of confusion about what draws them together on a deeper level, because their worlds, priorities, and ways of thinking appear so far apart.
Timothée Chalamet did appear to give Pauline a warning when he and Kylie Jenner bumped into his sister at the Oscars, allegedly telling the Sex Lives of College Girls star to “go easy” on his partner, which, if true, would suggest there’s been some tension — or at least distance — between Jenner and Chalamet’s family for the past few years.
The family source said it’s exactly that:
Among family and friends, there has long been a quiet but persistent feeling that they are fundamentally mismatched – almost like two people moving in entirely different directions who have somehow ended up side by side.
Despite the near-constant speculation of drama, however, there aren’t really any obvious indicators of trouble in this celebrity relationship. The couple has been spotted in New York recently, catching NBA games and going to dinner with Kylie Jenner’s longtime friend Jordyn Woods. Kylie even broke away for a night to share a “free the nipple” moment with sister Kendall at the Met Gala while Timmy snuck away to the Knicks game (Ben Stiller wasn’t so lucky).
Despite seemingly different backgrounds, some sources have said they balance each other really well and have a “wholesome” and “stable” relationship.
Aside from the somewhat awkward interaction with Pauline Chalamet at the Academy Awards, there have been some indications that the Kardashian-Jenner family gets along with Timothée Chalamet’s mom Nicole Flender. Kylie Jenner gave up her spot at the 2025 Oscars so that Flender could sit by her son when his category was called. Fans have also noticed Kris Jenner commenting on Flender’s Instagram posts.
Only time will tell what the future has in store for these two, and it’s definitely possible that the reports are true about Timothée Chalamet’s family having their concerns about the relationship. That doesn’t necessarily mean a split is coming — they’ve made it three years, haven’t they?
If you want to see more of Kylie Jenner’s life, check out The Kardashians with your Hulu subscription, though you won’t find Timothée Chalamet joining her there. You can find him in Marty Supreme, which is available to stream with an HBO Max subscription.
