Kylie Jenner Dropping Hints About Engagement Rings to Boyfriend Timothee Chalamet: She’s ‘Very Picky’

After two years of dating, Kylie Jenner and Timothée Chalamet made their long-awaited red carpet debut at the 70th annual David di Donatello Awards in Rome on May 7. It was a special night for the 29-year-old actor, who received this year’s Cinematic Excellence trophy as his girlfriend, 27, looked on adoringly. Now, a source exclusively tells Life & Style that Kylie appears eager to score some new hardware of her own — eyeing up engagement rings and dropping not-so-subtle hints that she’s ready to accept a proposal from Timothée.

“Friends say Kylie is very picky about what jewelry she likes, so as much as she loves the idea of Timothée [choosing] her ring, the truth is she would rather have some input,” admits the source, calling the reality TV star a “perfectionist ” at heart. “Kylie has a vision for everything … and has gone so far as to show Timothée photos of the [ring] styles she likes.”

While the beauty mogul would no doubt want a sizeable bauble she can wear proudly, says the source, at the end of the day, the price tag isn’t all that important to her. Admits the source, “It’s just about being Timothée’s wife.”

Some fans thought Kylie and Timothée might use the Met Gala on May 5 for their big red carpet debut as a couple after she joined him at several high-profile events throughout awards season.

Kylie Jenner and Timothee Chalamet Make Red Carpet Debut: Photos

However, the cosmetics queen arrived on the arm of Ferragamo designer Maximilian Davis at the New York City event. Kylie donned a plunging silver bralette top with sheer black mesh corset and a low-slung skirt had a thigh-high slit by the design house.

Little did fans know that just two days later, Kylie and Timothée would hit their first red carpet in Italy.

The couple walked onto the red carpet holding hands, as the mom of two wowed in a plunging black gown. Kylie and Timothée put on quite a PDA display, as she leaned into him from behind, while the A Complete Unknown actor put his arm around her waist. The entrepreneur then sweetly put her hand over her boyfriend’s in an adoring display.

The duo has come a long way from the beginning of their romance, when they were photographed leaving each other’s homes in April and June of 2023, keeping their connection on the downlow.

Kylie and Timothée confirmed speculation about their relationship by attending the U.S. Open tennis tournament in New York together in September 2023. The couple shared kisses and weren’t shy about cuddling up while watching the action on the court.

While Kylie attended the Golden Globes in 2024 as Timothée’s date, she didn’t join him on the red carpet. The same arrangement went down at the awards show in January, where Kylie joined Timothée once he was inside the event.

The California native made her biggest awards show appearance yet, scoring a seat alongside her boyfriend at the Oscars in March, when he was nominated for Best Actor. While Timothée lost to Adrian Brody, the couple went on to have a loved-up display once they were inside the Vanity Fair afterparty.

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The following month, a source exclusively told Life & Style that Kylie’s mom, Kris Jenner, wants to be a part of any engagement plans Kylie has with the Dune star.

“Kris is determined to have her way,” the insider said about how Kylie’s love life could provide The Kardashians with a huge rating boost. “She’s seeing a huge opportunity for a televised event, photos and video of the proposal, sponsors for the wedding and reception.”

“As far as Kris is concerned, Kylie and Timothée will have to play by her rules. It’s a benefit to them as well as her,” the source added about the momager.