EXCLUSIVE: Kylie Jenner is Demanding a Ring! Why the Billionaire Makeup Mogul is 'Pressuring' Boyfriend Timothée Chalamet to Propose After Two Years of Dating

Kylie Jenner is pressuring Timothée Chalamet for a proposal after two years of dating, stirring attention.
Sept. 24 2025, Published 6:30 a.m. ET
Jittery Kylie Jenner is pressuring Timothée Chalamet to get more serious about their 18-month romance and move in with her – but he's loving his freedom as a footloose movie star, RadarOnline.com can reveal.
L.A.-based Kylie, 28, and A Complete Unknown actor, 29, spent weeks apart this summer while Chalamet filmed Dune: Part Three in Budapest, Hungary – causing the needy reality TV babe to fly nearly 6,000 miles for a face-to-face showdown about their future, sources shared.

Travis Scott shares two children with Kylie Jenner, who now wants Timothée to move in.
"They had an entire month apart, and it was tough on Kylie – especially as rumors were circulating that Timmy was having a fine time without her and partying with the crew during breaks," an insider confided.
"She's very affected by social media rumors, which is why she insisted on flying out when he had a break and asking for some reassurances about where they're at and how things will work when he's back in the States."
According to the insider, the makeup mogul — who shares two young kids with rapper ex Travis Scott – isn't pressuring Chalamet to propose, but she's desperate to shack up with her stud and is even willing to foot the bill.
"He's caught between a rock and a hard place because he does like his independence, but the last thing he wants to do is to drive Kylie away by being too noncommittal," the insider explained.

Chalamet filmed 'Dune: Part Three' in Budapest while spending weeks apart from Jenner.
But sources said Timothée has seen his family turn up their noses over him dating a member of the Kardashian clan — and he's also struggling to keep up with his galpal's lavish lifestyle as her $670 million purse dwarfs his $25 million fortune.
The insider noted: "Timmy and Kylie have bonded on these expensive trips and vacations they've taken. But he does feel the pinch when he's splurging on Kylie, who demands and gets only the best.
"They both love high-end experiences and luxury accommodations, and Timmy's fame can open doors to the finer things in life – but somebody has to pay for all of this, and it's usually Timmy.
"He's just too proud of his own success to ever want to ride Kylie's coattails financially, and that's been the dynamic between them from the beginning."

Family of Chalamet reportedly disapproves of his relationship with Jenner.

According to the source, the young couple's uneven assets are a "big test" of Timothée's "ego and self-esteem," but the smitten star knows that "this relationship is done if he ever shows any insecurity."