The Hollywood couple made their red carpet debut at the David di Donatello Awards, but an onstage kiss gone wrong left fans cringing.
May 9, 2025: Kylie Jenner and Timothée Chalamet’s big red carpet moment turned a little awkward during the David di Donatello Awards in Rome on Wednesday night — and the internet didn’t miss a beat.
The couple, who have been dating since 2023, made their official red carpet debut in coordinating black ensembles. But the spotlight moment took a cringeworthy turn when Chalamet, 29, stood up to accept his David Award for Cinematic Excellence. As he leaned in for a kiss, Jenner appeared to go in for a second peck — which the actor completely missed.
The subtle PDA slip-up quickly went viral, with social media users describing the moment as “embarrassing” and “hard to watch.” “The ICK I felt during this video,” one Reddit user wrote, while another commented, “Ah, the kiss pull-away moment is so embarrassing for her.”
kylie wanted to give him another kiss and i can't blame her 💞pic.twitter.com/OixjcW2XTz
— 𓍯ᥱ⳽ƚɾᥱꙆꙆɩƚᥲ (@estrellithee) May 7, 2025
Despite the awkward moment, the two looked loved-up on the red carpet. Chalamet wrapped his arm around the 27-year-old beauty mogul’s waist, and Jenner was seen whispering into his ear as they posed for photos. The Kardashians star wore a sleek black Schiaparelli gown, while Chalamet sported a velvet tux in matching tones.
The couple has kept their relationship mostly private, though they’ve been spotted together throughout awards season — including the Oscars, Golden Globes, and Vanity Fair after-parties. Jenner, however, missed the opportunity for a winner’s kiss at the Oscars, where Chalamet lost the Best Actor trophy to Adrien Brody.
Jenner and Chalamet were first romantically linked in April 2023 when her car was spotted in the actor’s driveway. They confirmed their relationship in September that year with a public kiss at Beyoncé’s Renaissance World Tour.
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According to sources close to Jenner, the relationship feels “new and exciting” for her and is a refreshing shift from her past high-profile romances.
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Kylie Jenner, Timothée Chalamet, Kylie Chalamet kiss, Italian Awards 2025, David di Donatello Awards, celebrity PDA, awkward red carpet moments, Kylie Jenner fashion, Timothée Chalamet awards