Timothée Chalamet and Kylie Jenner share sweet moment at Oscars afterparty despite his defeat

Timothée Chalamet and Kylie Jenner were all smiles and affection at the Vanity Fair Oscar afterparty on Sunday, despite the actor’s high-profile loss in the Best Actor category. 

The pair displayed undeniable closeness, with Chalamet wrapping his arms around Jenner’s waist, planting kisses on her cheek, and carefully adjusting the train of her dress for photos.

Chalamet, nominated for his role in ‘Marty Supreme,’ lost the Oscar to Michael B. Jordan for ‘Sinners.’ During the ceremony, he sat next to Jenner, before rising to applaud Jordan’s win. 

The actor’s defeat was not only personal. ‘Marty Supreme,’ directed by Josh Safdie and produced by Chalamet, ended the night without a single win despite nine nominations, including Best Picture and Best Director. 

© JEAN BAPTISTE LACROIX

The film’s zero-outcome puts it alongside cinematic heavyweights like ‘The Color Purple’ and ‘The Irishman’ in Oscar history. Its dismal run had already been foreshadowed at the BAFTAs, where it went 0 for 11.

Chalamet’s loss also marked a shift in momentum. Though he was initially favored after winning the Golden Globe and Critics’ Choice Awards, the tide turned in Michael B. Jordan’s favor following his SAG Awards victories. 

© John Shearer/98th Oscars

The night wasn’t without drama. Chalamet’s previous remarks that “nobody cares about ballet or opera” became a focal point of discussion, drawing criticism from figures such as Steven Spielberg, Andrea Bocelli, and Misty Copeland. 

Comedian Conan O’Brien also targeted Chalamet during the opening monologue, joking about extreme security precautions in case ballet and opera communities were offended. 

© Rich Polk

One winner of the Live Action Short Film even subtly called out the sentiment in their acceptance speech, emphasizing that art and performance do indeed have societal impact. Despite these setbacks, Chalamet still made history as the youngest actor to receive three Best Actor Oscar nominations before turning 30.

Jenner, who has been dating Chalamet for roughly three years, captured attention with two distinct outfits during the Oscars weekend. At the ceremony, she wore a custom red Schiaparelli gown designed by Daniel Roseberry, featuring a deep halter neckline and a chest-opening lock detail. 

© Christopher Polk/2026GG

She paired the look with over 200 carats of Lorraine Schwartz diamonds. Later, at the Vanity Fair afterparty, she changed into a black sequined Alexander McQueen gown with a high hip cut and dramatic feathered train, accessorized with a striking 20-carat black diamond ring, also from Lorraine Schwartz. 

Since going public in April 2023, Chalamet and Jenner have evolved from a low-profile couple into one of Hollywood’s most visible pairings. Throughout the 2026 awards season, Jenner has accompanied Chalamet to all major events, including the Golden Globes, BAFTAs, and Oscars, despite his preference for walking the red carpet solo to keep the focus on his work.