Kylie Jenner goes on a double date with one of her sisters: Here’s who joined her and Timothée Chalamet

Nobody saw this coming, but we are happy that it happened. Four of Hollywood’s most talked-about names were spotted packed into one car cruising through Los Angeles. On May 16, Kylie Jenner, Timothée Chalamet, Kendall Jenner, and Jacob Elordi were photographed driving around the city in pictures obtained by DeuxMoi. 

According to the photos, Jacob appeared to be behind the wheel while Kendall sat in the front passenger seat. Kylie and Timothée occupied the backseat alongside photographer and longtime Kardashian-Jenner friend Renell Medrano. 

© Christopher Polk/NBC

Even though the group attempted to shield themselves from paparazzi cameras with their phones, their smiles and laughter were still visible. The candid energy of the outing drew comparisons to the legendary 2006 paparazzi photos featuring Britney Spears, Lindsay Lohan, and Paris Hilton piled into a car.

While Kylie and Timothée have been in a stable relationship for a while, Kendall and Jacob are bringing a bigger source of speculation, as rumors surrounding the model and the “Euphoria” actor have been growing steadily over the past few months.

 Fans first started connecting the dots after the pair were spotted together at the Vanity Fair Oscars after-party in March. Then in April, they were seen again during the Coachella Valley Music and Arts Festival while attending Justin Bieber’s performance.

© Getty Images

While online chatter, starring attendees and social media users, claimed the two looked especially close throughout the event, neither Kendall nor Jacob has publicly addressed the romance speculation. 

Jacob previously dated Olivia Jade Giannulli on and off for several years before reports surfaced about their split last August. Kendall, meanwhile, has consistently kept her past relationships with Devin Booker and Bad Bunny largely private.

© The Grosby Group

Despite all the rumors, Kendall has recently made it clear she is focused on enjoying this chapter of her life on her own terms. “I want to have some, but not right away,” Kendall told Vogue France in an interview published Feb. 24 while discussing future plans for children. “I want to make sure I can dedicate a lot of time to them, and for now, I'm still too busy.”

She also shared the mindset she hopes to carry throughout 2026. “The most important thing will be to stay true to myself and continue having a good time,” Kendall said. “It might sound like a cliché, but it's very important to me.”