Timothée Chalamet had a star-studded evening at the Vanity Fair Oscars afterparty, where he spent time catching up with girlfriend Kylie Jenner’s famous family.
The 29-year-old actor, who was nominated for Best Actor, was spotted chatting with Kim Kardashian and Kendall Jenner at the high-profile event in Los Angeles.
Despite the crowded venue filled with photographers eager to capture every moment, Timothée seemed at ease as he engaged in conversation with the reality TV icons.
His interaction with Kylie’s sisters came just hours after he and the beauty mogul showcased their affection during the Oscars ceremony.
Stunning Red Carpet Looks
Even though Kendall didn’t attend the actual awards show, she made a striking entrance at the afterparty in a sheer black gown with long sleeves and an internal corset.
Meanwhile, Kim opted for a dramatic Balenciaga dress inspired by bridal fashion, featuring a fitted bodice and an extravagant voluminous skirt.
Kylie and Timothée, who had already been turning heads with their affectionate moments throughout the night, continued to flaunt their romance at the afterparty.
Kylie, 27, leaned into the actor and nuzzled her face against his neck, proving their bond was stronger than ever.
Outfit Changes for the Afterparty
For the afterparty, both Kylie and Timothée switched up their outfits.
Kylie dazzled in a figure-hugging nude and black lace corset gown, while Timothée ditched his bold yellow suit from the Oscars ceremony for a more understated black satin dinner jacket.
Avoiding an Awkward Encounter?
Earlier in the evening, eagle-eyed fans noticed that Timothée and Kylie were absent when his ex-girlfriend, Lily-Rose Depp, took the stage to present the award for Best Costume Design.
Lily-Rose, 25, was joined by other actresses to hand the trophy to Wicked’s Paul Tazewell, but the loved-up couple had seemingly left their seats just moments before.
Social media users quickly picked up on their absence, with one Reddit user calling it “insane” that Timothée and Kylie weren’t in the audience when Lily was on stage.
Others speculated that it was intentional, suggesting he may have wanted to avoid any awkwardness.
Some, however, defended the move, saying it was a smart way to avoid unnecessary media attention.
Timothée’s Past with Lily-Rose Depp
Timothée and Lily-Rose famously dated for about two years after starring together in the 2019 film The King.
Their relationship was relatively private, but their breakup became public when Timothée referred to himself as “currently single” in a 2020 interview.
Looking back on their romance, he once admitted feeling embarrassed when paparazzi photos of them kissing on a yacht went viral.
He recalled thinking it was one of the best days of his life, only to wake up to a media frenzy that made him feel “like a real nob.”
Lily-Rose has since moved on and has been dating rapper-singer 070 Shake (Danielle Balbuena) since 2023.
A Subtle Tribute or a Coincidence?
Interestingly, during the Oscars, Lily-Rose was seen standing in front of a massive illustration of Timothée while Elle Fanning paid tribute to Arianne Phillips, the costume designer for A Complete Unknown—the Bob Dylan biopic in which Timothée stars.
The moment didn’t go unnoticed by viewers, who called it “messy” and speculated whether it was a coincidence or an intentional placement.
Kylie’s Oscars Etiquette Criticized
Kylie also found herself under scrutiny when a video surfaced of her meeting Sir Elton John during a commercial break.
Instead of standing to greet the music legend, she remained seated and extended her hand for him to kiss.
This gesture sparked backlash online, with many viewers calling it disrespectful.
One outraged fan commented, “That is SIR Elton John! You stand when you greet him!”
Others echoed the sentiment, emphasizing that standing to greet someone is a basic sign of respect.
2025 Oscars: Big Winners of the Night
While the afterparty drama made headlines, the Oscars themselves celebrated some incredible talent. Here are some of the major winners:
- Best Picture: Anora
- Best Actor: Adrien Brody (The Brutalist)
- Best Actress: Mikey Madison (Anora)
- Best Supporting Actor: Kieran Culkin (A Real Pain)
- Best Supporting Actress: Zoe Saldaña (Emilia Pérez)
- Best Director: Sean Baker (Anora)
- Best Original Screenplay: Sean Baker (Anora)
- Best Adapted Screenplay: Peter Straughan (Conclave)
- Best International Feature Film: I’m Still Here (Brazil)
- Best Documentary Feature Film: No Other Land
- Best Costume Design: Paul Tazewell (Wicked)
From career milestones to red carpet drama, this year’s Oscars had it all.
With Timothée and Kylie’s romance still a hot topic, fans will undoubtedly keep their eyes on Hollywood’s most talked-about couple.