Kendall Jenner and Bad Bunny‘s relationship caused the internet to completely 🌀🌀🌀 back in February 2023—but it looks like they might be over after less than a year of dating…maybe. Idk, our heads are kinda scrambled after these two are rumored to have spent the New Year together, so ¯_(ツ)_/¯. Anyway! Check out a handy dandy timeline on everything that’s happened between these two, from when things were moving fast/furious, to where they stand now.
February 16, 2023
DeuxMoi drops a blind item about Kendall Jenner and Bad Bunny making out at a club. The blind in question? “This single, famous model sister was seen playing tonsil hockey with Bad Bunny at a private L.A. club last night.”
DeuxMoi herself revealed the identity of the “famous model sister,” saying, “So I’m revealing it was Kendall Jenner and Bad Bunny. I have witnesses on the scene who saw her in the club.”
February 18, 2023
Kendall and Bad Bunny are spotted leaving the same restaurant after a double date with Hailey and Justin Bieber, according to TMZ. It’s all happening!
February 20, 2023
A source tells People that Kendall and Bad Bunny “are spending time together” and that “Kendall recently started hanging out with him. They were introduced by friends. He moved to L.A. a few weeks ago and bought a house. She likes him and is having fun. He is different from guys that she dated in the past. He is very charming.” Not-ed!
March 7, 2023
The duo are finally (!!) caught red-handed and in the same frame as they head out of Sushi Park in WeHo with a number of their friends and Kenny’s younger sister, Kylie Jenner.
Just outside of the celeb hot spot, the model and musician are captured parting ways and looking v cozy as they hug goodbye after reaching Kendall’s waiting SUV. 👀
March 9, 2023
Status update! A source tells Entertainment Tonight, “They’re taking things slow for now and seeing where things go in the future. They both really like each other and are just hanging out and having a good time. They get along very well and have mutual friends, so the people around them really like them together. Her family is supportive of their relationship. Everyone is happy that Kendall’s happy.”
March 12, 2023
Kay, this sighting might just be the nail in the coffin for those of you (me) who were kinda on the fence (in denial) about this whole Kendall and Bad Bunny sitch for the past few weeks. 😭 Apparently, the two were spotted on Hollywood’s biggest night getting into the same car after spending some time at Beyoncé and Jay-Z’s after-party, which…kay, sick invite. Anyway!! Although it’s unclear whether or not the supermodel and Latin pop star showed up to the star-studded affair as a unit, they were most certainly captured hopping into the same Maybach at the end of the night. See the pics and get ready to weep right this way.
March 14, 2023
Hi, so according to an Us Weekly insider, Kendall wasn’t “really looking to date anybody” after her breakup with Devin Booker, but her “feelings are starting to grow” for Bad Bunny. If you need me, I’ll be in the fetal position.
April 4, 2023
TMZ publishes truly amazing photos of Kendall and Bad Bunny riding a horse together, which you’ll want to head over this way to feast your eyes upon.
April 16, 2023
Kendall and Bad Bunny are spotted at Coachella! Alllll the details this way:
April 30, 2023
They’re spotted leaving Carbone!
May 1, 2023
A source tells People that Kenny and Bad Bunny are “getting more serious” and that “it was a slow start, but they spend almost every day together now. He hangs out with her friends and she hangs out with his. It’s more of a relationship now. Kendall is not seeing anyone else. She really likes him.”
May 11, 2023
Things are progressing! This time, a source tells Us Weekly that “things are going really well for Kendall and Bad Bunny and she definitely sees long-term potential with him. She feels like he’s the complete package and he treats her like a total gentleman.”
The insider adds that “they are having a great time together, and she appreciates that he gets along with all of her friends. They complement each other on so many levels and she’s enjoying getting to know him better every day.”
May 12, 2023
Kendall and Benito make their first public appearance together—courtside! In matching boots!
June 22, 2023
Kendall Jenner is on the cover of WSJ Magazine and is obvi asked about her relationship with Benito. But the vibe is sadly “no comment,” although Kendall does explain, “I try [to] find the balance of keeping things private and keeping things sacred [and] also not letting the unfortunate frustration and stress of everyone trying to get in on it stop me from enjoying my side.” She continues, “Does that make sense? I’ll go out of my way to do things as privately as possible because I just think that that’s the healthier way of dealing with relationships anyway.”
Meanwhile, Bad Bunny is also asked about their romance for his recent Rolling Stone cover and muses, “I know something is going to come out. I know [people are] going to say something. People know everything about me, so what’s left for me to protect? My private life, my personal life. That’s the only answer. In the end, the only thing I have is my privacy.”
“We’re in the worst time, the worst moment for the privacy of other humans, not just artists but human beings. Today, no one respects the privacy or life of anyone.…I keep living. Fans are always going to want to know more, but I don’t focus on that. I’m always going to keep living my way,” he adds. Not-ed!
July 20, 2023
A source tells Entertainment Tonight that “Things are definitely progressing between them. Things are becoming more serious and their relationship is on the upswing.” Oh, and Kendall and Bad Bunny are “both super into each other and have a ton of chemistry. Their friends and families are really happy for them and like them as a couple.” Plus, they’re vacationing in Idaho!
August 1, 2023
Kendall and Benito enjoy a date night in Los Angeles, in semi-matching fits, no less.
August 13, 2023
Here’s some footage of them being allll over each other at a Drake show, for all the doubters out there!
August 27, 2023
Kendall’s voice shows up on Bad Bunny’s Instagram Story!
September 15, 2023
Kendall and Bad Bunny are spotted chilling in NYC together (side note: Kendall def got the fall Mary Jane memo):
September 22, 2023
The couple make their first front row fashion week appearance at Gucci Ancora!
September 26, 2023
Things just keep getting more and more serious! Benito just dropped the music video for his new song “Un Preview,” and we just can’t help but notice how deeply Kendall-Coded it all is.
October 1, 2023
Kendall and Bad Bunny go Gucci campaign official:
October 19, 2023
Bad Bunny references his and Kendall Jenner’s viral mosquito video with his SNL promo:
October 22, 2023
Kendall is seen at the SNL after-party!
November 14, 2023
Kendall drops a somewhat cryptic Instagram post, which some people randomly decide to read into (think: comments like “sounds like a breakup post”). But literally it’s…just a pic of a sunset with a contemplative musing so, probs nothing to see here!
December 17, 2023
People reports that Bad Bunny and Kendall have split, and an Entertainment Tonight source comes through with some additional details, saying “Kendall and Bad Bunny have been doing their own things lately and things slowly started to fizzle out between them. 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. They have crazy busy schedules and know they’re still young and have a lot more to experience individually before settling down.”
December 18, 2023
Us Weekly speaks with an insider who says “Friends aren’t surprised that Kendall and Bad Bunny have broken up. They never really saw their relationship going the distance anyway. Of course, they want the best for their friend, but they really didn’t feel like Kendall was as compatible with Bad Bunny as she was in past relationships with other people. At the same time, Kendall has had a few on-off relationships in the past, so they wouldn’t be totally surprised if she got back together with him at some point.”
January 3, 2024
Kenny and Bad Bunny reportedly ring in 2024 together with a group of mutual friends in Barbados, per TMZ—news that leaves us all 👁👄👁.
Interestingly enough, people were already speculating about the reunion given that in a clip of NYE fireworks posted by one of Kendall’s friends, you can clearly hear Bad Bunny wishing everyone a Happy New Year in Spanish.
Sources with “direct knowledge” clarify the sitch to the outlet and maintain that the supermodel and singer continue to remain cool despite their recent breakup, so this outing with their friends (which btw included Justin and Hailey Bieber) is kinda sorta no biggie.
Aaand that brings us up to date. Stay tuned!
Mehera Bonner is a celebrity and entertainment news writer who enjoys Bravo and Antiques Roadshow with equal enthusiasm, She was previously entertainment editor at Marie Claire and has covered pop culture for over a decade.
