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Are Timothee Chalamet and Kylie Jenner contemplating their next big steps?

From the start of their entanglement, these two hotties have kept things conspicuously private.

That’s smart!

But now, Timmy is dropping hints that he’s ready to become engaged — and perhaps have kids.

TimothÃ©e Chalamet and Kylie Jenner look on during a sports game at Yankee Stadium on October 08, 2025. (Photo Credit: Ishika Samant/Getty Images)

Are Timothee Chalamet and Kylie Jenner moving towards an engagement?

Vogue published an interview with Timothee Chalamet, whose hair seems to get worse every time that we see him lately.

To be clear, he did not delve into his romance with Kylie Jenner in the cover interview.

But he did address how little he was addressing it.

Timmy explained that he was not keeping quiet about his Kylie romance out of “any fear.”

Instead, he claimed that he does not “have anything to say.”

Timothee Chalamet and Kylie Jenner attend a sports game at Gainbridge Fieldhouse on May 31, 2025. (Photo Credit: Gregory Shamus/Getty Images)

That attitude did not last very long, it seems.

Timothee did hint that having children one day “could be on the radar.”

This came up because he had seen someone online “bragging about not having kids and how much time it afforded them to do other stuff.”

Being childfree is, for many, still a revolutionary idea — even as it becomes an economic necessity for growing numbers of Americans who would love to have children, but cannot afford to.

However, Timothee simply labeled the mindset of enjoying one’s life without children to be “bleak.”

Actor Timothee Chalamet and Kylie Jenner sit court-side during a sports game at Madison Square Garden on May 12, 2025. (Photo Credit: Elsa/Getty Images)

A lot of Timmy’s peers are engaged or married, even though he’s still in his 20s

Timothee Chalamet noted that he feels that he is in a “new stage of life.”

He was born in 1995, and turned 30 in December. Yes, he’s just under two months younger than recent birthday girl Kendall Jenner.

And Timmy is not the only one in his social — or professional — circle who is marking certain milestones.

Referring to Dune co-stars, he noted: “Zendaya is engaged. Anya is married.”

Zendaya and Tom Holland became engaged in December 2024. Anya Taylor-Joy (who is playing Timothee’s character’s younger sister, the pre-born abomination Alia Atreides) married musician Malcolm McRae in April 2022.

Timothee Chalamet and Kylie Jenner attend the red carpet during the 70th David Di Donatello at Cinecitta Studios on May 07, 2025. (Photo Credit: Vittorio Zunino Celotto/Getty Images)

When many of the people your age are engaged, you might feel like it’s an age-appropriate time for you to look at marriage yourself.

Similarly, when you’ve spent two years dating someone who has kids, you’re more likely to imagine yourself in a parental role — whether it’s as a stepparent or not.

We wouldn’t necessarily say that the average 29-and-almost-30-year-old is engaged or married.

But with Timothee’s immediate professional and social orbit filling up with people who are engaged, married, or are parents, it is natural that he’d have these things on his mind.

And it definitely sounds like he’s hinting at plans for the future — perhaps even the near future — with Kylie. He did not, however, just come right out and say that.

Kylie Jenner and TimothÃ©e Chalamet (when he still had nice hair) attend the WSJ. Magazine 2023 Innovator Awards on November 01, 2023. (Photo Credit: Dimitrios Kambouris/Getty Images for WSJ. Magazine Innovators Awards)

Yeah, he kind of put his foot in his mouth with that one comment

Much like the hairstyle that Timothee Chalamet is sporting these days, his comments on childfree folks being “bleak” is not a good look.

Some people talk about how happy they are without kids because they, through economic or biological or other factors, cannot have them — so they’ve learned to be vocal about the silver lining about what might be a sad situation.

And others are just enjoying their lives being complete people unto themselves. Someone being happy without children (or without a partner, for that matter) is not “bleak,” it’s their life and their joy. What’s the problem with that?

Perhaps he misspoke. Maybe Timmy is so wrapped up in imagining a future with Kylie Jenner that he’s having a hard time connecting with anyone else’s happiness.

Kids are amazing. If having kids one day makes him happy, more power to him. But he could be more tasteful when he’s effectively dismissing millions of his own fans as “bleak.”

Timothee Chalamet Hints at Engagement, Baby Plans with Kylie Jenner was originally published on The Hollywood Gossip.

The Hollywood Gossip