Kylie Jenner and Timothée Chalamet may look picture-perfect on red carpets, but behind the scenes, things are reportedly far more complicated. Nearly three years into their headline-making romance, insiders claim the beauty mogul has reached her breaking point—allegedly demanding a marriage proposal or preparing to walk away for good.
According to sources close to the situation, Jenner, 28, feels she’s been patient long enough while waiting for the Oscar-nominated actor to make a lasting commitment. As their relationship approaches its third anniversary, she’s reportedly ready for clarity. One insider claims Kylie believes she has shown unwavering support—standing by him at premieres, awards shows, and high-profile events—yet hasn’t seen the same level of certainty reflected back.
The couple first sparked dating rumors in April 2023 after Jenner’s split from Travis Scott, with whom she shares two children, Stormi and Aire. While their relationship has largely unfolded out of the spotlight, they’ve stepped out together for major moments, including Beyoncé’s Renaissance tour and multiple Hollywood award ceremonies. Most recently, Chalamet referred to Jenner as his “partner of three years” during a Critics Choice Awards speech, a public acknowledgment that briefly quieted speculation.
Still, insiders say that public validation hasn’t erased private doubts. Jenner has reportedly grown frustrated by what she sees as an imbalance in effort. While Chalamet has been welcomed into her family circle—and is said to spend time with her children—sources claim she has yet to feel fully embraced by his inner world. Rumors have swirled that some of his friends and relatives were initially skeptical of the relationship, though more recent reports suggest tensions may have eased.
Adding to the intrigue are conflicting reports about the couple’s future. Some outlets recently claimed they were discussing engagement plans for 2026, with Jenner even jokingly referring to him as her “husband.” Meanwhile, other insiders describe a very different dynamic—one in which Kylie feels she’s done waiting. The suggestion that she’s issued a firm ultimatum has only intensified the buzz.
For Jenner, who built a cosmetics empire worth hundreds of millions and commands one of the largest social media followings in the world, the stakes are less about status and more about certainty. Whether the ultimatum rumors are exaggerated or not, one thing is clear: fans are watching closely to see if Chalamet takes the next step—or if one of Hollywood’s most unexpected love stories is headed for a dramatic finale.
