Kendall Jenner and Bad Bunny: A Match Made in Heaven

Kendall Jenner and Bad Bunny are supposedly back together, spotted at the 2024 Met Gala. They previously dated for less than a year before separating for a very relatable reason.

Many celebrity columns have reported Bad Bunny to be back browsing a dating app since the split. However, it seems times are changing between the former couple as their status moves into something more exclusive.

Between now and their previous break up, Kendall Jenner really embraced being single. So let’s take a look at the Jenner and Bad Bunny romance! We’ll show how the former couple have started to spend time together after their short break in Italy.

The Beginning

The rapper, whose real name is Benito Antonio Martínez Ocasio, supposedly began a romance with Kendall Jenner in Beverly Hills in February.

February 2023 put the pair in the spotlight as they were caught on a double date with Hailey and Justin Bieber at the well-known restaurant Wally’s. The rapper has previously collaborated with Justin Bieber. Also, Jenner and Hailey are long-term girlfriends. So chances are Bieber’s set the lovers up!

This February double date between Kendall Jenner and Bad Bunny get the tabloids excited and caused a flurry of gossip across social media.

First Kisses

Moving into March 2023, the couple sparked rumours of a real future together. They were spotted sharing a kiss goodbye.

Bad Bunny collaborated with the artist Eladio Carrión on the track “Coco Chanel.” In it, many believe he referenced the model suggesting they were already together a while.

Booker, a successful NBA player for Phoenix, also got his referenced on the track. While Bad Bunny never explicitly said the track was referring to Booker or Jenner, almost every source made the connection.

There is no sense of drama between Booker and Bad Bunny. These two men seem to remain on good terms. Musically, it makes sense for Booker to be mentioned since he was Jenner’s ex before meeting Bad Bunny.

“Yo no soy malo, nah, bebé, eso e’ un gimmick
Pero el sol de PR calienta má’ que el de Phoenix
Ella lo sabe

Lyrics to Coco Chanel referencing Jenner’s ex

The above lyrics translate to “I’m not bad, baby that’s a gimmick / But the sun in Puerto Rico is hotter than in Phoenix / She knows it.”

This seemingly references Booker and his previous relationship status with Jenner. In this regard, a source close to the couple explained Bunny and Jenner were not officially dating yet but were hanging out!

Later on in March, the couple continued to keep their private life to themselves yet were spotted kissing once more. Neither the face of Bad Bunny nor Kendall Jenner were clearly visible. Yet many sources, including friends, believed it to be the couple sharing a little romance.

Horsing Around

In April 2023, the couple moved away from night time dates. These two went straight for sharing a moment doing something Jenner adores: horseback riding. Fans were delighted to see Kendall and Benito starting the summer and a foreseeable future together.

The next event the duo were spotted at was a Summer staple: Coachella. It is a part of Kardashian culture that at least Kendall attends Coachella. So nobody was surprised to see Bad Bunny with her on this occasion. Despite their fame, they enjoyed time in the crowd dancing, which many saw on Instagram stories or TikTok.

Hitting Up the Big Apple

In April 2023, the pair headed to New York and appeared to be enjoying young love at Carbone. Fans saw them at the Tyler the Creator concert, too. Pergola suggested that the lovers left to continue the romance together.

Back then, Bad Bunny seemed interested in seriously dating Jenner. Yet at this stage, neither one of the lovers confirmed or made any comment on their situationship to any major outlet.

Met Gala After Party

The pair decided not to attend the Met Gala together and never made a comment on this. Both Jenner and Ocasio received enough attention for their own careers. Thus, they appeared to want space and enjoy the moment rather than make the event about their own partnership.

It was at this point that a source confirmed that the couple was hanging out more and more in life and enjoying dating pretty seriously. “They are very cute together. Kendall is happy,” the source said. “He is a fun guy. Very much a gentleman and charming. She likes his vibe. He is very chill.”

Holiday Romance

To see just how serious the couple were at this point, a source close to them stated,

“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.”

Back then, fans spotted them on a vacation in Miami with other celebrity friends. Renell Medrano caught model and the rapper in a photo together, which he later posted to his social media. However, the rapper and model were quickly taken down. Presumably, they did it to keep the date lowkey and the heat away from their time in Miami.

Around May 2023, the pair were spotted having fun courtside at the Lakers game. The celebrity date is pretty common and often used to show that a celebrity love story is becoming a little more serious. The artist and model enjoyed the occasion in the front row, both dressing up for the night and seemingly appeared to be enjoying life in love.

On May 24, a source gave more detail to Entertainment Tonight about how Jenner and Bunny’s more serious relationship was progressing. “He is not only spending more time with Kendall, but with the rest of the family as well,” the source said.

Well, we all know how much Kendall Jenner values her mother and her input, as well as her friends, so this all seemed to clarify that the love story between Jenner and the artist was more than just a fleeting moment.

Keeping Things Under Wraps

June 2023, Bad Bunny appeared with Rolling Stone and confirms that he wants to keep his romance with Jenner private. “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.”

This is totally understandable and something many fans seem to miss. Every photo, comment and moment of these young celebrities’ lives gets analyzed by everybody, so it becomes easier to either stay single or try to keep who you date under wraps!

It was around this time that Jenner appeared to share the same sentiment and miss being able to keep her private time private as she gave WSJ Magazine “no comment” on her relationship with Bad Bunny.

Another Romantic Getaway

A source close to the pair disclosed the lovers had snuck away on another short break to enjoy hanging out away from prying eyes. The source explained they are “really cute” and “so happy together,” adding, “They definitely seem in happy, and super serious. They’re really friendly. Kendall is so low key that plenty of guests don’t even know who she was.”

Bad Bunny and Jenner grabbed a quick sushi date on their return and seemed to be enjoying hanging out with shared friends.

This day was also the reveal of another episode of Keeping Up With The Kardashians, where the popular entertainment show shared that Kris was manifesting Kendall as the next sibling to get tied down to her partner.

“She put an engagement ring in mine, because she thought it was manifesting an engagement for me,” she said in a confessional. “So if that tells you anything about where my mom wants me to be in life.”

The reveal certainly shows that the earlier Summer of dating has made a mark on the whole family, who appear to like Bad Bunny and his recently more public partnership with Kendall Jenner.

August showed the pair seemingly tied at the hip as they put on a real PDA at a Drake concert. It was also around this time that Bad Bunny chose to soft launch his girlfriend by showing a social media post that appeared to feature Kendall Jenner.

Dating culture certainly saw a rise in the “soft launch” vs the “hard launch”, seeing celebrities post sneaky previews of a partner before going public or going full-on Sabrina Carpenter and showing off a new boyfriend in a music video!

Milan Fashion Week and the Met Opera

September was a high point in the year’s public appearances from Kendall Jenner and Ocasio as they appeared together in Milan at the Gucci Fashion Show. September and it’s Milan Fashion Week is an absolute must for Jenner since her main career is actually a model, so it’s only natural that she brings her boyfriend!

Compared to earlier in the year, in September in Milan, the partners appeared in the public eye more than ever. September also showed Bad Bunny speaking to Vanity Fair about his courting of Jenner. Italy is definitely a romantic location, with Milan in particular being called “a city of passion”, so it’s nice to think of the two sneaking off around Italy in between public appearances.

The newest Gucci advert was also previewed, featuring Jenner and Ocasio in their September campaign for the first time. This September campaign is the first time we have seen the two together in a work environment, and we have to say the two really work well together!

SNL, Instagram and Halloween

October brings us to Ocasio’s October appearance on SNL. After the weekly entertainment show, fans snapped him partying with Jenner. In particular, they spent time at the club L’Avenue—and then, grabbed brunch after the Kardashian Halloween Party.

Breakup Rumours

November was roughly when the rumours began to flourish, with Jenner making cryptic Instagram posts. However, nobody actually confirmed or denied the rumours. Moverover, a source told Us Weekly that Jenner’s girlfriends weren’t confident if she and Bunny would last.

“Kendall’s girlfriends don’t think she’ll be with Bad Bunny forever.”

December Heartbreak

December confirmed the two young lovers were no longer together, and many called it time for Jenner to stay single and enjoy herself. With people beginning to question what happened, it says tabloids asking, “Will they get back together?” which sparked negative comments such as “Who the fuck cares”.

Despite this December heartache, it looks like change was just around the corner…

New Year, New Beginnings

After Bad Bunny was spotted on a dating app, it was reported the former lovers were back together! A source close to the lovers recently said,

“…at the end of the day, if she’s happy, then of course they support her and whoever she decides to date.”

The source above and buddies of the former couple seem to be more than pleased to see them reconcile and look forward to seeing where the lovebirds take their partnership next!