The Double Date they (and/or we?) deserve
– 4 min read
In the celebrity ecosystem, celebrity friendship and celebrity double dates have been foundational throughout gossip history. We love when celebrities are friends, and we love when those celebrity friends go on double dates. Few people understand this better than Taylor Swift, by the way, as evidenced by the way she has performed her celebrity through her career with all the various iterations of her squad and how she’s almost always introduced whoever she’s romancing to the members of her squad, heavily documenting each step along the way, either with song lyrics or with an assist by the paparazzi.
Every gossip generation gets the friendship and the double date they deserve. Back in the 1950s, it was the Rat Pack, led by Humphrey Bogart and then Frank Sinatra. One of their most famous double dates was when Humphrey and Lauren Bacall went out with Frank and Kim Novak on her first date after she moved to Hollywood, a legendary foursome. In the 60s, Elizabeth Taylor and Richard Burton often hung out with other famous people, like Mia Farrow and Natalie Wood. In the 70s, Warren Beatty and Jack Nicholson… well… you know. In the 80s it was the Brat Pack, they were always in movies together and dated each other. And Rob Lowe has talked about his double date with Tom Cruise back when Rob was with Melissa Gilbert and Tom was matched with Michelle Meyrink who was also in The Outsiders.
One of the most famous celebrity BFF double dates in the 90s was when Gwyneth Paltrow and Winona Ryder were inseparable for a minute and were dating Ben Affleck and Matt Damon, respectively. Then came the mess of the 2000s – Paris Hilton, Nicole Richie, Britney, Lindsay Lohan, Hyde Lounge, Teddy’s, and Les Deux. If you were around at the time or you’ve done your gossip homework, those visuals should be immediately accessible in your memory bank. They doubled with Greek heirs and minor popstars and restauranteurs and DJs. A decade later, Taylor Swift would step into the space those party girls vacated with the friends and boyfriends she collected along the way. Blake Lively and Ryan Reynolds have double dated with Taylor and Tom Hiddleston, Taylor and Joe Alwyn, Taylor and Travis Kelce. Robert Pattinson and Suki Waterhouse were part of a double during the Alwyn era. Bradley Cooper and Gigi Hadid have popped in here and there too.
So, like I said, every generation gets the double that defines gossip in their time. And now, in these times, the double that quite aptly represents the chaos of our cultural existence: Kendall and Kylie Jenner, with Jacob Elordi and Timothée Chalamet. Gen Z is getting what they deserve.
Kylie and Timmy have been together long enough. Kendall and Jacob is a 2026 thing – rumours started earlier in the year and then came into focus at Coachella when it was reported that they were making out at Justin Bieber’s after-party. Now the last week or so…
Jacob was supposed to be a jury member in Cannes but bailed because of a broken foot. He then turned up in Hawaii with Kendall, TMZ with the exclusive.
That was apparently not this past weekend but the one before. This past Saturday, Kendall and Jacob were back in LA and seen leaving a party with Kylie and Timmy, all of them “trying” to not be photographed. It was obvious that the four would have been hanging out privately – but this is the first time that they’ve been pictured together which is one more of a progression step beyond when Kendall was with Bad Bunny because there’s no doubt Benito and Timmy were spending time together while Benito was in his Kendall phase, but they managed then to not get papped when they were doing it. Benito and Timmy did sit courtside next to each other at a Knicks game one time but the Jenners were not with them on that occasion and by then I think Benito and Kendall were over.
What makes this sighting even more hilarious is the PEOPLE.com exclusive about the situation. According to PEOPLE’s source, one of the reasons this double works is because:
“[Timothée and Jacob] have the same attitude when it comes to fame. 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."
Staying out of the spotlight with two people who are the most followed and the most active on social media because they built the family brand on flooding the spotlight is funny. But we’ve talked enough about Timmy in the spotlight so can we focus here on Jacob because his whole personality is basically Adam Driver-lite and yet, and yet, every year he’s with another influencer or Zendaya, who seemed like she couldn’t get away from him fast enough. Because Tom Holland actually means it when he says he wants to stay out of the spotlight. Do we have to keep pretending that Jacob Elordi doesn’t love the smoke?
I do buy though that he’s found the Ben to his Matt, or the Matt to his Ben, LOL if we’re doing a height comparison, in that Timmy has now given him a roadmap to be as outside as he truly wants to be in his personal life, now associated with the most outside family in the business, without compromising professional success; after all, it’s not like Timmy’s working any less or nominated any less three years into his relationship with Kylie. It’s basically a blessing to be the heatscore his heart truly desires. Jacob Elordi has been Kardashianed… and also actualised, while also giving the people the double date that this wretched timeline desires and deserves.
