Timothee Chalamet Took ‘Flack’ For Dating Kylie Jenner, But Their Relationship Helped Him ‘Mature’

It was an acceptance speech for the books. After being awarded the Best Actor trophy for his work in Marty Supreme at the Critics’ Choice Awards Jan. 4, an emotional Timothée Chalamet thanked his team and director Josh Safdie before turning his focus to his girlfriend, Kylie Jenner. “Lastly, I’ll just say thank you to my partner of three years. Thank you for our foundation,” he said to a beaming Kylie. “I love you. I couldn’t do this without you. Thank you from the bottom of my heart.”

The shout-out was a major milestone for the couple. The 30-year-old actor and the reality star, 28, have been slowly making their relationship more public since they quietly began dating in early 2023. Despite their differences — he’s an acclaimed actor; she’s known for plastic surgery — the romance has gotten increasingly more serious, and now a source tells Star that if Timothée triumphs during the 2026 awards season, he will pop the question to the mom of two (she shares Stormi, 7, and Aire, 3, with her rapper ex Travis Scott).

“It was a big deal that Timmy decided to shout his love for Kylie from the rooftop,” says the source, noting that a summer wedding could be in the cards. “Winning an Academy Award and sealing the deal with the girl of his dreams would be the icing on the cake for Timmy and a perfect way for him to kick off 2026.”

Surprisingly In Sync

From the beginning, people said it wouldn’t last between the New York City–raised thespian and the L.A.-based makeup mogul, who shot to fame on reality TV as part of the Kardashian-Jenner family, including mom Kris and sisters Kendall, Kim, Khloé and Kourtney. But the source says Timothée is “in awe” of Kylie’s business sense (her Kylie Cosmetics line was projected to make $400 million in 2025). “He’s seen how incredibly smart, accomplished and driven to succeed she is,” the source reveals.

He also loves how dedicated she is to her loved ones. “Kylie is not the vapid, superficial type. She’s sincere, loyal and is all about family,” the source says. “He says she’s a fabulous mom and a real deep thinker, which is a big reason why they match so well.” (The source says Timothée gets along great with Kylie’s kids but “is very mindful” that Travis is their dad and “at the forefront of their lives.”)

His friends are saying the relationship has helped the Dune star grow up. “Timmy’s taken a fair amount of flack for dating Kylie, but ultimately it’s made him a more mature and serious person,” says the source. Indeed, Kylie talked about how she feels older than her years during a recent appearance on her sister’s podcast, Khloé in Wonder Land, saying, “I feel 45. I have two kids, I have a million jobs, I have a business that just turned 10 years old. Of course I feel 45.”

She’s helped him up his game, especially when it comes to navigating the social media world. After all, she has 391 million Instagram followers to his 20.6 mil. While promoting Marty Supreme, for instance, Timothée generated major buzz when he appeared at surprise pop-up events featuring limited edition merch (which he co-designed). “There’s no doubt she’s helped him with that,” says the source.

Wedding Planning

It took some time for his inner circle to come around, but now they embrace Kylie. “Timmy’s family was wary at first,” says the source, noting that there are lingering concerns “that he could get sucked into the reality TV world, but so far there’s been no sign of that happening.”

Kylie’s family, meanwhile, couldn’t be more thrilled — especially Kris. The momager even showed her support by displaying a Marty Supreme jacket on Instagram in early December. His name was also included on the family’s holiday gingerbread house in a photo shared on social media. Says the source, “It’s an open secret Kris considers Timmy a dream son-in-law.”

Kylie’s sisters are ready to wedding plan. “They’re chiming in,” says the source. “The consensus is that the sooner Timmy proposes, the sooner their dream wedding can be planned. And if all goes well, it can happen this summer.”

According to projection sites, the star has an 85 percent chance of taking home the Oscar in March. Adds the source: “Everyone’s waiting with baited breath for the official engagement news.”