Kendall Jenner and Jacob Elordi Go on Double Date with Kylie Jenner and Timothée Chalamet

Kendall Jenner and Jacob Elordi appear to be taking their rumored romance into a more serious phase after joining Kylie Jenner and Timothée Chalamet for a night out in Los Angeles. The outing came days after Kendall and Elordi were spotted together on a tropical getaway in Hawaii.

Kendall Jenner and Jacob Elordi are continuing to fuel romance speculation, and this time the model appears to be bringing family into the mix.

The pair were photographed in Los Angeles on Saturday, May 16, 2026, during a night out that also included Kylie Jenner and her longtime boyfriend, Timothée Chalamet. Photos shared online showed the four stars leaving a party together while trying to avoid paparazzi cameras.

Jacob, 28, was seen driving with Kendall, 30, seated beside him in the front of the vehicle. Kylie, 28, and Timothée, 30, sat in the backseat as the group departed the event together.

Kendall Jenner and Jacob Elordi Continue to Spark Romance Rumors

Neither Kendall nor Elordi has publicly addressed reports about their relationship. However, the pair have been photographed together multiple times in recent weeks.

Just days before the Los Angeles outing, the two were spotted vacationing in Hawaii together. The tropical getaway quickly drew attention online and added to growing speculation that the two celebrities had become romantically involved.

According to a source who spoke to PEOPLE, the relationship between Kendall and the “Euphoria” actor has developed naturally. “They have a lot of fun together,” the source said of the rumored couple and their dynamic with Kylie and Timothée.

The insider added that the four celebrities “all really get along” because they share “similar personalities and lifestyles.”

The source also explained that Timothée and Jacob already knew each other before Kendall and Jacob reportedly became close.

Oscar nominees Timothée and Jacob "already know each other and were friendly before Kendall and Jacob were getting close,” the source noted. “They spent a lot of time around each other during the award season and naturally run in similar circles.”

Timothée Chalamet and Jacob Elordi Reportedly Bonded Before the Romance

Although Kendall and Jacob's rumored romance has become a recent topic of conversation, Timothée and Jacob reportedly had an existing friendship through Hollywood events and awards season appearances.

The source said the two actors also share a similar outlook when it comes to fame and public attention.

“They have the same attitude when it comes to fame,” the insider said. “They’re both actually pretty low-key. They like to stay out of the spotlight when they can. They have a lot of respect for each other.”

That approach appears to extend to the couples’ personal lives as well. While all four stars are among the most recognizable names in entertainment and fashion, they have largely kept their relationships private.

Kylie and Timothée have been linked since 2023, though they rarely speak publicly about their romance. Over the past several years, the couple has been photographed together at awards shows, sporting events, and private vacations while maintaining a relatively low profile.

Kylie has also reportedly gotten to know Jacob through Kendall. According to the source, Kylie “really likes him” and is “excited Kendall is spending time with him.”

Kendall Jenner’s Dating History Has Drawn Attention for Years

Kendall’s relationships have long generated headlines, though the reality star and model has typically kept details about her personal life out of the public eye.

Most recently, Kendall was linked to rapper Bad Bunny. The pair dated on and off between 2023 and 2024 before eventually splitting.

Before her relationship with Bad Bunny, Kendall was involved with NBA player Devin Booker. The two dated for about two years and frequently appeared together at public events before ending their relationship.

Jacob has also been linked to several high-profile names over the years.

The Australian actor most recently dated Olivia Jade. Their relationship began in December 2021 and continued on and off for several years. The two were last photographed together in January 2026.

Prior to Olivia Jade, Jacob was romantically linked to Kaia Gerber, Zendaya, and Joey King.

Despite the intense public interest surrounding his dating life, Jacob has often avoided discussing relationships in interviews.

Kylie Jenner and Timothée Chalamet Keep Their Relationship Private

While Kendall and Jacob are now attracting attention as a possible new couple, Kylie and Timothée have spent the last several years navigating public fascination surrounding their own relationship.

The beauty mogul and the Oscar-nominated actor first sparked dating rumors in 2023. Since then, they have attended several major entertainment events together, including awards ceremonies and high-profile industry gatherings.

Although they have occasionally appeared together publicly, the pair have mostly avoided sharing details about their relationship online or in interviews.

The Hawaii Vacation Appears to Have Intensified Speculation

The timing of the Los Angeles outing has only increased interest in Kendall and Jacob's status.

Photos of the pair in Hawaii circulated days earlier, prompting fans to question whether the two had officially become a couple. Although neither has commented publicly, the back-to-back appearances have led many to believe the relationship may be progressing.

For now, both stars appear focused on keeping things relatively private despite widespread attention.

The same can be said for Kylie and Timothée, whose relationship has remained largely out of the spotlight even as they continue appearing together at select public events.

As rumors continue to build around Kendall and Jacob, their recent outing with Kylie and Timothée suggests the pair are becoming more comfortable spending time together publicly, even if they are not ready to confirm anything officially.

With Hollywood fans closely watching every appearance, the double date only added more intrigue to what may be one of entertainment’s newest high-profile romances.