Hollywood’s favorite new couple, Kylie Jenner and Timothée Chalamet, finally made their red carpet debut — and it was anything but ordinary. The pair stepped out in style at the 70th David Di Donatello Awards in Rome on May 7, 2025, but one brief, awkward PDA moment quickly became the talk of the night.
Chalamet, 29, was honored with the prestigious David Award for Cinematic Excellence, and as he stood up to receive his award, he leaned in to kiss Jenner, 27. While the first kiss landed perfectly, Kylie appeared to lean in for a second — only to realize Timothée had already turned away to greet guests behind them. The quick exchange was captured on camera and shared widely online, sparking lighthearted reactions from fans.
Despite the minor hiccup, the couple looked every bit the fashion-forward duo. Kylie stunned in a sculpted Schiaparelli gown, complete with a black-and-gold clutch and bold earrings. Meanwhile, Timothée kept it classic in a velvet suit, exuding old-Hollywood charm.
During the award show, one of the hosts gave a nod to Jenner, prompting the beauty mogul to smile, wave, and clap proudly from her seat. Footage also showed Kylie watching Chalamet’s acceptance speech with admiration.
Behind the Glam: Kylie Shares Her Personal Touch
Ahead of the event, Kylie gave fans a behind-the-scenes look at her evening prep via Instagram. With nearly 400 million followers, she posted a series of photos showing her doing her own makeup, sipping champagne, and posing in the mirror. She captioned the carousel, “Rome in Schiaparelli. Makeup by meeeee 🥰,” earning supportive comments — including a trio of black heart emojis from mom Kris Jenner.
Relationship Timeline: From Rumors to Red Carpets
Kylie Jenner and Timothée Chalamet were first romantically linked in April 2023, but kept their relationship largely private until September of that year, when they were spotted kissing at a Beyoncé concert in Los Angeles. Since then, Kylie has accompanied Timothée to several major award ceremonies, including the Golden Globes, BAFTAs, and the Oscars, where he’s been recognized for his performance as Bob Dylan in A Complete Unknown.
However, their appearance at the David Di Donatello Awards marks the first time the couple has walked the red carpet together, making it a memorable milestone — awkward moment and all.
