The couple’s long-awaited red carpet debut in Rome was nearly flawless—until an awkward moment of missed affection was caught on camera.
In a glamorous moment turned slightly awkward, Timothée Chalamet and Kylie Jenner made headlines during their red carpet debut at the 70th David di Donatello Awards in Rome on Wednesday, May 7, 2025—not just for their stunning appearance, but for a blink-and-you’ll-miss-it public display of affection gone awry.
The couple, who have been romantically linked since early 2023, attended the prestigious Italian film awards in chic coordination: Jenner, 27, wore a curve-hugging black Schiaparelli gown with statement earrings and a velvet black-and-gold clutch, while Chalamet, 29, exuded quiet luxury in a sleek velvet suit.
However, as Chalamet was announced the winner of the David Award for Cinematic Excellence for his role in A Complete Unknown, he leaned in to kiss Jenner—only to accidentally dodge her second attempt at a smooch. The actor, focused on the moment, had already turned to shake hands with two men seated behind them, inadvertently leaving Jenner leaning in solo.
Footage of the brief but noticeable moment, shared by Italian streaming platform RaiPlay, quickly circulated online. Still, Jenner handled the moment with grace, watching proudly from the audience as Chalamet made his way to the stage. When the ceremony host mentioned her by name, Jenner smiled, waved, and clapped, radiating support.
The award marked a major moment for Chalamet, who has received accolades throughout the season for his portrayal of Bob Dylan. Though the actor skipped the 2025 Met Gala just two days prior, Jenner turned heads solo in New York before reuniting with Chalamet in Rome.
Jenner later shared a behind-the-scenes glimpse of her awards night prep on Instagram, where she boasts over 393 million followers. The carousel included makeup touch-ups (done by Jenner herself), mirror selfies, and champagne toasts. “Rome in Schiaparelli,” she captioned the post, adding playfully, “Makeup by meeeee 🥰.” Her mom Kris Jenner responded with a row of black heart emojis.
This awards season has seen Jenner and Chalamet attend several major ceremonies together—including the Golden Globes, the BAFTAs, and the Oscars—but their David di Donatello appearance marks their first official red carpet walk as a couple.
Though the missed kiss may have sparked chatter online, it didn’t detract from the couple’s radiant presence. From private concerts to prestigious film festivals, Jenner and Chalamet continue to be one of the most talked-about duos in Hollywood—awkward kisses and all.
