Timothée Chalamet and Kylie Jenner made their long-awaited red carpet debut as a couple on Wednesday, May 7, at the prestigious David Di Donatello Awards in Rome but the night didn’t go off without a slightly awkward moment that quickly caught the internet’s attention.
The Dune star, 29, and the Kardashians reality mogul, 27, appeared together publicly for the first time at the awards ceremony, where Chalamet was honored with the David Speciale award, recognizing his contributions as a “great actor of quality and innovative films.”
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Their glamorous debut, however, took a slightly uncomfortable turn when Chalamet appeared to miss a second kiss from Jenner just before heading to the stage.
A viral video circulating on social media shows the moment his name was announced. Chalamet rose from his seat and shared a brief kiss with Jenner. As she leaned in for a second kiss, Chalamet turned to shake hands with people seated behind him, unintentionally leaving Jenner hanging.

The brief exchange sparked a wave of reactions from fans online. “Awkward double kiss,” one TikTok user commented under the now-viral clip. “Hahaha she wanted more,” another joked. A third viewer came to Chalamet’s defense, writing, “Someone was talking to Timothée at the back, he didn’t notice the second kiss.”
Despite the slightly misaligned moment, the evening was a major milestone for the couple, who have been quietly dating for over two years. The Rome appearance marked the first time they walked a red carpet together, solidifying their relationship in the public eye after months of speculation and low-key outings.
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Chalamet looked dapper in a sleek, dark suit, while Jenner stunned in an elegant, floor-length gown, turning heads as they posed for photographers and smiled for the cameras.
The couple’s relationship, long kept out of the spotlight, has now officially entered a new phase, with fans eagerly watching their every move. While the red carpet moment wasn’t flawless, it offered a rare glimpse into the dynamic between the famously private actor and the high-profile entrepreneur.
For Chalamet, the night was still a resounding success, as he accepted the David Speciale award and added yet another accolade to his already impressive resume. As for Jenner, she stood proudly by his side, missed kiss and all, on what was clearly a meaningful night for them both.
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