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Kylie Jenner crossed paths with Timothée Chalamet's sister Pauline Chalamet during a brief exchange inside the Dolby Theatre at the 2026 Oscars Sunday night.
The moment happened as Timothée, who earned a Best Actor nomination for his role in the sports drama Marty Supreme, chatted with his sister during the ceremony hosted by Conan O'Brien.
In a clip shared by E! News, Pauline approached the Dune star while Jenner was seated nearby. After noticing Pauline, the Kylie Cosmetics founder stood up and greeted her with a hug before the pair exchanged a few quick words.
Jenner—wearing a plunging red Schiaparelli gown for Hollywood's biggest night, appeared upbeat as she complimented Pauline's look during the interaction.
"Hi," Jenner said in the video as she gestured toward Pauline's outfit. "I love this!"
Pauline, known for her role on The Sex Lives of College Girls, attended the ceremony in a short black dress featuring jeweled details along the straps and neckline.
The siblings' reunion took place as Timothée celebrated another major awards-season moment. The 30-year-old actor was nominated in the Best Actor category this year thanks to his performance in Marty Supreme.
Although Jenner and Pauline's exchange was quick, it marked another public moment involving the actor's girlfriend and his family.
Timothée has previously brought loved ones along for Hollywood's biggest night. At the 2025 ceremony, his mother Nicole Flender joined him when he received a nomination for his portrayal of Bob Dylan in A Complete Unknown.
Jenner also appeared to make space for family during last year's event. When the Best Actor nominees were announced, she reportedly switched seats with Flender so the proud mom could share the spotlight with her son while Jenner moved to a row behind them.
Off the red carpet, members of the Kardashian-Jenner family have spoken positively about the Oscar nominee. Khloe Kardashian once recalled a dinner with the couple that stretched late into the night, saying the pair seemed to have "the best time" together.
Jenner and Timothée first sparked dating rumors in 2023 and have since attended several high-profile events side by side, including the Vanity Fair Oscar Party following this year's ceremony.
