Okay, I fear this might actually be becoming a thing, Pop Tellers. Despite everyone insisting it was “just Coachella vibes,” Kendall Jenner and Jacob Elordi keep popping up together like the universe is personally trying to break our hearts (Jacob = our forever crush). Mood:
And let me tell you, the progression from festival flirting to private Hawaii getaway happened FAST. Like, one minute there were random DeuxMoi whispers, and the next we apparently have beach hangs, breakfast dates, and double dates with Kylie Jenner and Timothée Chalamet. These Kardashian-Jenners really do get the crème de la crème of Hollywood men!
Anyway, if you’re wondering how Kendall seemingly went from Bad Bunny to Jacob Elordi, and how Jacob somehow pivoted from Olivia Jade to Kendall Jenner, buckle up, because this relationship timeline is kind of impossible to look away from.
March 15, 2026
These two (very good looking) popular stars were first linked together (publicly) during the Vanity Fair Oscars after-party. Kendall and Jacob were photographed deep in conversation, and fans immidietely started shipping a potential romance.
April 12, 2026
This whole saga then continued during the first weekend of Coachella. According to multiple DeuxMoi submissions, Kendall and Jacob were spotted spending a lot of time together at the festival. And this time, they weren’t just chatting together, but…
The biggest piece of gossip? A tipster claimed the two were allegedly making out at one of Justin Bieber’s Coachella parties.
April 14, 2026
A few days later, reports started rolling in trying to downplay the situation. The Daily Mail basically said nobody should expect these two to become the next power couple because “late at night at Coachella isn’t usually the place to start a new love.” Brutal.
Another source claimed Jacob “isn’t her [Kendall’s] type,” which is funny because Kendall’s “type” changes every six business days according to the internet.
Still, insiders admitted there was obvious flirting happening between them and that neither of them seemed bothered by the dating rumors.
Then things got even funnier because suddenly Kylie entered the chat.
Apparently, Kylie was “rooting for something to happen” between Kendall and Jacob because she wanted cute double dates with Timothée. Very younger-sister-coded!
“Kylie would fully support a relationship between the two as she has mentioned on many occasions that they could do a bunch of fun double dates,” the source adds. “They both can have their Oscar-nominated men and just have the best times ever.”
Like imagine your sister aggressively shipping you with an Oscar-nominated actor because she wants coordinated dinner reservations.
April 15, 2026
Just when everyone thought the Coachella flirting might’ve been a one-night thing, The Sun claimed Jacob spent more time with Kendall the following day too.
One source allegedly said Kendall is “100 percent Jacob’s type.” They added, “I heard they’re having fun and he hung out with her Sunday, too.” Also thrown into the mix? Claims that Jacob and Olivia Jade were officially over. The timing of all this gossip was…convenient, to say the least.
April 21, 2026
At this point, insiders started acting like this wasn’t even new information anymore.
A source told People that Kendall and Jacob had actually been hanging out for “a couple of months,” which immediately made everyone collectively crash tf out. This has been a slow-burn situation happening behind the scenes (!!).
April 22, 2026
And then came the plot twist. Another Daily Mail insider claimed Kendall and Jacob had already been together privately for a couple of months and that things were “going well.” According to the report, “They were an item as far back as early February, so it’s been a while.”
That source also said spending so much time in Los Angeles helped them get closer, which makes sense considering celebrity relationships basically survive on proximity and private SUVs.
Oh and if you’re wondering how Kendall and Jacob even met—Kylie allegedly played matchmaker.
“Kylie is the alpha sister and pushed Kenny to start a romance with Jacob because she wanted to set up double dates with Timothée,” the source added. “She thought it would be fun if she and Timothée and Kenny and Jacob all hung out together. ‘Though Kylie is younger, she is really the leader between those two, she has dominant Leo energy for sure, while her sister is more casual. Kenny’s house is where all the parties happen, a lot of action there, so the four of them got close there. And Kenny found out she just clicked with Jacob… there was chemistry.”
So basically: Kylie Jenner said you two should kiss and the universe listened.
May 16, 2026
Vacation status already? Oh this escalated quickly.
Fast forward to May, and suddenly Kendall and Jacob were reportedly spending time together in Kauai, Hawaii.
DeuxMoi shared reports claiming the pair stopped by Nourish Hanalei for breakfast while visiting the island, and fans who saw them together apparently described them as “really cute.”
I mean, should we just call this a hard-launch or what? Because once strangers start calling you cute together in public? It’s serious enough.
May 18, 2026
Just when people thought the Hawaii rumors couldn’t get more couple-coded, photos surfaced appearing to show Kendall and Jacob enjoying a super low-key beach day together.
At this point, I genuinely don’t know how anyone is still calling this casual.
May 18, 2026
And then came the viral double-date pics.
DeuxMoi later posted photos that allegedly showed Kendall and Jacob hiding out in a car alongside Kylie and Timothée after a night out together in L.A.
Which means the rumored group dynamic might actually be real, Pop Tellers!
Knowing Timothée and Jacob might be bro-in-laws was definitely not on my 2026 bingo card, but here we are, and it’s very real! All I wanna know is if Timmy has informed Jacob about the Kardashian curse, because, you know, joining this family *may* have some consequences!
Stay tuned for more updates!
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