Kylie Jenner Suffers 'Embarrassing' Moment As She Tries To Kiss Timothée Chalamet At Award Show

However, it is an awkward missed kiss moment between the duo that has gone viral and has fans questioning their chemistry.

According to reports, Timothée Chalamet and Kylie Jenner chose not to attend the Met Gala together, prioritizing privacy and personal interests.

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Kylie Jenner Left Hanging By Timothée Chalamet During Awkward Kiss Moment At Award Show

Timothee Chalamet And Kylie Jenner In Rome, Italy
ZUMAPRESS.com / MEGA

Jenner recently experienced an awkward moment that quickly went viral after being captured on live television.

She traveled to Rome to support her boyfriend, Chalamet, who was receiving an award at the 70th David di Donatello Awards – often referred to as Italy’s version of the Oscars.

Although they have gone to various events together before, this occasion marked their first official appearance together on the red carpet as a couple. Chalamet, 29, was honored with the esteemed David for Cinematic Excellence, which recognized his entire body of work, focusing on his recent performances in “Dune: Part Two” and “A Complete Unknown.”

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During Chalamet’s significant moment at the awards ceremony, Jenner found herself in a slightly awkward situation. When his name was called out and the audience cheered, the couple exchanged a brief celebratory kiss.

But when she leaned in again for a second one, Chalamet caught up in the excitement and turned his attention instead to greeting friends seated nearby.

Left hanging, the makeup mogul quietly sat back down as Chalamet made his way to the stage, unintentionally leaving her momentarily sidelined.

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Fans React To The Duo’s Awkward Kiss Moment

Timothee Chalamet And Kylie Jenner In Rome, Italy
ZUMAPRESS.com / MEGA

Fans were quick to react to the awkward moment, with many taking to Reddit to share their secondhand embarrassment. One user wrote, “The ICK I felt during this video.”

Others echoed the sentiment, suggesting a lack of spark between the couple. “No chemistry whatsoever. And he can’t even fake it,” one commenter said, per The U.S. Sun.

Another noted, “Ah, the kiss pull-away moment is so embarrassing for her.” A different user chimed in with, “Literally and forced to kiss her, and the fact he rejected the second kiss lmaoooo.”

Despite the awkward moment, Jenner turned heads in a stunning floor-length black gown featuring her signature plunging neckline and shimmering crystal embellishments woven into the fabric. She wore her hair in a sleek, tight bun.

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Chalamet complemented her effortlessly, opting for a sharp black velvet double-breasted blazer paired with tailored pants, polished leather loafers, and a statement floral brooch.

Why Timothée Chalamet Skipped The Met Gala Despite Red Carpet Debut Rumors

Timothee Chalamet at Vanity Fair Oscar Party 2025
OConnor-Arroyo / AFF-USA.com / MEGA

Earlier this week, fans wondered if Jenner and Chalamet would make their official red carpet debut at the Met Gala, given they’ve only been seen together at private events and after-parties so far.

According to Daily Mail, Chalamet had considered attending but ultimately chose to skip the glamorous evening in favor of watching his beloved New York Knicks play.

“Timothée did consider going to the Met Gala,” a source shared. “But he is a huge Knicks fan, and Kylie knows this. Kylie didn’t bother him to go with her, and that’s something he appreciates about her. She allows him to do his own thing.”

The Insider added that while the couple did entertain the idea of attending together, they ultimately felt it wasn’t the right setting.

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“They didn’t want to do the whole song and dance of it all together because it would have felt more like a chore over a fun date night,” the source explained. “If it was Kylie’s first Met Gala, or an event where she was being honored for something, then he would have been there 100 per cent, but they decided to do their own thing.”

Timothée Chalamet Reportedly Sets Strict Boundaries To Keep Relationship With Kylie Jenner Private

Timothee Chalamet and Kylie Jenner at Lakers Vs. Timberwolves - Game 5
ZUMAPRESS.com / MEGA

Last week, insiders revealed that Jenner and Chalamet’s relationship, which has been going strong since 2023, thrives thanks to some carefully set boundaries, especially regarding public exposure.

A source told the Daily Mail that the couple’s success largely stems from mutual respect for privacy, with Chalamet drawing a firm line when it comes to Jenner’s reality TV world.

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