Kendall Jenner has been in the public eye—alongside the rest of the blended Kardashian-Jenner clan—since she was a child. If you, like me, remember the now-internationally famous model from her occasional appearances on Keeping Up With the Kardashians, it’s kind of hard to believe that she’s now old enough to collect luxury cars and have famous boyfriends. Indeed, Jenner has been romantically linked to Puerto Rican rapper and singer Bad Bunny, also known as Benito Antonio Martínez Ocasio, on and off since 2023.
Yes, the two are currently off-again, and yes, Jenner is alleged to have moved on with basketball star Devin Booker, but the Kendall-and-Bad-Bunny saga was a rich one. Below, find a semi-exhaustive chronicle of all the It couple’s ups, downs, and coordinated date-night outfits.
February 2023: First known date
Jenner and Ocasio were seen leaving Wally’s—a cheese-and-charcuterie-forward Beverly Hills restaurant with a full-on caviar menu—on February 18, 2023. Justin and Hailey Bieber were also there, pre-baby, which seemed at the time like a sign that Jenner and Ocasio were a thing. I mean, once he meets the besties, that’s officially more than a situationship!
April 2023: First couples horseback ride
Is this a traditional relationship marker? Not necessarily, unless you’re a jockey, but we loved it and continue to love it nonetheless. Let horse girls be horse girls!
May 2023: First Met Gala afterparty
Jenner and Ocasio didn’t walk the red carpet together, but they were seen together at an after-party, which is actually cooler, in a lot of ways?
August 2023: First incidence of PDA on the books
TikTok content
There’s no bigger sign that you’re falling for a softboy than cuddling with him at a Drake concert.
September 2023: First official couples’ fashion moment
Jenner and Ocasio then co-starred in an ad campaign for Gucci’s Valigeria luggage collection—basically fifth base where hot, famous people are concerned. The couple that sits front row together stays together. (Or, perhaps not…read on!)
December 2023: First alleged breakup
“Kendall and Bad Bunny have been doing their own things lately, and things slowly started to fizzle out between them,” an unnamed source told Entertainment Tonight of the couple s low-key-seeming split, adding: “They both knew going into this that it likely wouldn’t be a forever type of relationship, and that was mutually understood from the get-go.” Never say never, kids, especially when it comes to forever!
May 2024: Second Met Gala afterparty (and first round of back-together rumors)
The alleged exes were spotted “laughing while having a drink and a conversation together” at a Met Gala after-party hosted by hosted by Carlos Nazario, Emily Ratajkowski, Francesco Risso, Paloma Elsesser, Raúl Lopez of Luar, and Renell Medra, and we all know what that means.
September 2024: Second alleged breakup
Us Weekly broke the news that Jenner and Ocasio had split again and that Ocasio had been spotted on the exclusive dating app Raya, which we’re torn about. On the one hand, everyone deserves some dating-app privacy when they’re on the rebound, and on the other hand, if we saw Bad Bunny’s profile pop up on an app…
But who knows what will happen next with these two crazy kids. We’re willing to bet on at least one more round of romance and luxury brand partnerships in their future.
