On May 16, 2026, Kylie Jenner and her boyfriend, Oscar-nominated actor Timothée Chalamet, joined forces with Kendall Jenner and her rumored new flame, Jacob Elordi, for a double date in Los Angeles. The group was photographed leaving a party, with Elordi and Kendall in the front seat of a car and Kylie and Timothée in the back, covering their faces from paparazzi. It was the first public sighting of the two couples together, fueling excitement among fans and sparking new questions about the burgeoning romance between Kendall and the Euphoria star.
According to an insider who spoke exclusively to People, the quartet has developed a genuine bond over the past few months. "They have a lot of fun together," the source said. "They all really get along." The source attributed the easy chemistry to their "similar personalities and lifestyles," noting that both Chalamet and Elordi share a low-key approach to fame and a mutual respect for each other's careers. Chalamet and Elordi, both 30, have crossed paths during awards season and run in overlapping Hollywood circles, making the double date a natural extension of existing friendships.
The Growing Relationship Between Kendall Jenner and Jacob Elordi
Kendall Jenner, 30, and Jacob Elordi, 28, have been the subject of romantic speculation since early 2026. In April, People confirmed that the supermodel and the actor had been "hanging out and getting to know each other the last couple months" after rumors surfaced about a Coachella outing. The pair were later spotted enjoying a tropical getaway in Hawaii, which further intensified interest. Their double date with Kylie and Timothée marks the first time they have been seen together with family, suggesting the relationship is becoming more serious.
Before Elordi, Kendall was linked to Latin music star Bad Bunny, whom she dated on and off from 2023 to 2024. Prior to that, she had a two-year relationship with NBA player Devin Booker. Kendall has historically kept her personal life private, but her recent outings with Elordi indicate she is comfortable showing him off to her inner circle. "Kendall is happy," a separate source previously told People. "She’s spending time with someone who gets her lifestyle."
The Low-Key Chemistry of Timothée Chalamet and Kylie Jenner
Kylie Jenner, 28, and Timothée Chalamet have been dating since early 2023, though they have largely kept their relationship out of the spotlight. They were first linked after Kylie attended one of his film screenings, and they have since made occasional public appearances together, including at the 2025 Oscars and 2026 Oscars. The two have been spotted at awards shows, red carpets, and intimate dinners, often evading paparazzi with clever disguises. "Timothée and Kylie have a very real connection," a source close to the couple said. "They understand each other's worlds. Kylie is incredibly supportive of his acting career, and he admires her business acumen."
Chalamet, known for his roles in Call Me by Your Name, Dune, and Wonka, has been nominated for two Academy Awards and is one of the most sought-after actors of his generation. He has a reputation for being fiercely private about his personal life, which aligns with Kylie's own preference for controlling her narrative. The couple's decision to double-date with Kendall and Jacob signals a deepening of their commitment to blending their social circles.
Jacob Elordi’s Career and Romantic History
Jacob Elordi rose to fame playing Nate Jacobs in HBO's Euphoria and has since starred in films like The Kissing Booth trilogy, Priscilla, and Saltburn. His role in Saltburn earned him critical acclaim and positioned him as a versatile leading man. Off-screen, Elordi has been linked to several high-profile women. Most recently, he dated Olivia Jade on and off from December 2021 to early 2026; they were last spotted together in January 2026. Prior to that, he was romantically linked to Kaia Gerber, Zendaya, and Joey King. Elordi has often spoken about the challenges of dating in the public eye and has expressed a desire for a low-key relationship.
His friendship with Timothée Chalamet predates his romance with Kendall. The two actors met during awards season and have been spotted at industry events together. "They already know each other and were friendly before Kendall and Jacob were getting close," the source said. "They spent a lot of time around each other during the award season and naturally run in similar circles." This existing rapport likely contributed to the ease of the double date.
Family Involvement and Future Prospects
The double date in Los Angeles is not just a casual outing—it reflects a pattern of family involvement in the Jenner sisters' relationships. Kylie has been with Timothée for over three years, and Kendall has introduced Jacob to her siblings and close friends. The insider noted that Kylie is "excited" about Kendall's budding romance with Elordi. "She's likes him a lot," the source said. "She thinks they make a great match."
The group dynamic is reportedly very positive. "They all have a lot of fun together," the source reiterated. "Similar personalities and lifestyles make it easy. They all really get along." Whether this double date will become a regular occurrence remains to be seen, but given the strong chemistry and mutual respect, it seems likely that the four will continue to spend time together.
Neither Kendall nor Jacob has publicly commented on their relationship status, but the evidence—a romantic Hawaii trip, a double date with family, and glowing descriptions from insiders—points to a serious connection. Meanwhile, Kylie and Timothée continue to solidify their bond, balancing their high-profile careers with a private life they carefully curate. The world watches as these two power couples navigate fame, love, and friendship in the spotlight of Hollywood.
Source: MSN News