Lily-Rose Depp’s Oscars debut plunges into awkwardness as ex-boyfriend Timothée Chalamet attends the event with girlfriend Kylie Jenner.
The Oscars 2025 was in full swing, and in an intriguing parallel to the past, Lily-Rose Depp has found herself in Jennifer Aniston’s shoes. Any actress would accept such a fate in other circumstances.
Lily-Rose Depp in Nosferatu | Credits: Universal Pictures
However, when it comes to the awkward post-divorce encounters between her and Brad Pitt, that’s a different ball game altogether. Unfortunately, the world bore witness to such an incident during the Oscars 2009 with increasing discomfort by the second.
Now, Lily-Rose Depp presenting at The Oscars 2025 with ex Timothée Chalamet and Kylie Jenner in attendance, is reminding people of that awkward Jennifer Aniston-Brad Pitt encounter.
Lily-Rose Depp finds herself in Jennifer Aniston’s shoes as ex Timothée Chalamet attends ceremony with Kylie Jenner
Fans have been excited about Lily-Rose Depp presenting the Best Costume Design Award at The Oscars 2025 ever since it was announced. Not only because it would mark her debut at the prestigious award ceremony, but also because her own movie Nosferatu was nominated in the same category due to Linda Muir’s phenomenal work.
Lily-Rose Depp’s film Nosferatu was nominated for the Best Costume Design Award at The Oscars 2025 | Credits: Universal Pictures
As such, her appearance on the red carpet wearing a custom couture Chanel halter neck black lace gown (via Vogue) created appropriate buzz among fans.
Unfortunately, though, no one was prepared for the awkwardness that would follow her taking the stage during the presentation at the ceremony. As per Style Caster, Depp and Timothée Chalamet dated from 2018 to 2020 after meeting on the sets of The King.
Although both of them have seemingly moved on with Chalamet dating Kylie Jenner and Depp dating rapper O70 Shake (People), a meeting between the exes is bound to create some awkwardness. However, belonging to the same industry means that it was bound to happen at some point or another.
The Oscars 2025 became the platform for the awkward encounter to take place as along with Lily-Rose Depp, Timothée Chalamet, too, was present at the ceremony as a nominee in the Best Actor Category with girlfriend Kylie Jenner. Things became even more uncomfortable when Depp took the stage as a presenter.
Although it is unclear whether Chalamet and Jenner were inhabiting their seats at the time, it must have made way for some difficult conversation between the couple for sure. Interestingly, this incident is also reminding people of something similar occurring between Jennifer Aniston and Brad Pitt after their divorce.
Fans are aware that the once happy couple split after the entrance of Angelina Jolie in their lives. However, they came face to face during a similar situation to Depp when Aniston appeared as a presenter during the 2009 Oscars, with Brangelina front and center in the audience, as per Mirror UK.
With the latter’s frozen grins, and Aniston forgetting herself on stage in her hurry to get away from there, it made for an exceedingly discomfiting situation. Although Lily-Rose Depp was smooth in her set, the situation still brought back flashbacks for many.
Fans comment on exes Lily-Rose Depp and Timothée Chalamet attending The Oscars 2025
Much like Jennifer Aniston and Brad Pitt, Lily-Rose Depp and Timothée Chalamet used to be the hot couple back in the day. As a result, their break up broke many fans’ hearts who had hoped that the former co-stars were in for the long haul.
Timothée Chalamet in a still from A Complete Unknown | Credits: Searchlight Pictures
In any case, the actors moved on, and so did the fans with Chalamet and his current girlfriend Kylie Jenner soon turning into the new power couple. Which, again, paralleled Pitt and Jolie dominating the Hollywood circles for years until their eventual, bitter split.
However, seeing the exes attending the same event is suddenly reminding fans of what could have been, which is only adding to their awkwardness.
So awkward seeing Lily Rose Depp onstage with a huge blowup images of her ex behind her, and her actual real life ex sitting front row in front of her lol #Oscars
— 𓃭 LOEWE Lioness (@GgV0gue) March 3, 2025
lily rose depp presenting infront of timothee chalamet… yes i still care, no I won’t move on. #Oscars
— eli (@nogafs) March 3, 2025
timothee chalamet and kylie jenner watching lily rose depp on the oscars stage right now is CRAZY #theoscars
— lola (@lolasayshii) March 3, 2025
Hmm Timothee Chalamet not being present at his seat while Lily Ross Depp presented is funny #Oscars
— Ashanay (@ashanaydalmar) March 3, 2025
lily-rose depp presenting right in front of timothée and kylie at the #oscars… pic.twitter.com/vG1hlNOvpk
— َ (@chlmtslut) March 3, 2025
Much like Lily-Rose Depp’s Nosferatu, Chalamet’s A Complete Unknown, too, was a nominee for the Best Costume Design award. In a historical move, though, Wicked’s Paul Tazewell became the first Black costume designer to win the prestigious award as per USA Today.
