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Behold: A Journey Through Bad Bunny's Entire Dating History

Behold: A Journey Through Bad Bunny's Entire Dating History

It's pretty safe to say that over the years, Bad Bunny's relationship status has historically caused the masses to completely 🌀🌀🌀 she says with the fierce assurance of someone who knows exactly where she was when *that* Kendall Jenner DeuxMoi post dropped.

So if you, dear reader, have ever found yourself with a Diet Coke in hand and 30+ tabs open with searches like “Celebrities Who Have Dated Their Fans,” dw—we've fully been there lol. Luckily, after fully combing through the internet in the name of ~research~, we've put all the deets of Bad Bunny's prior romances in one space for you to hyper fixate on and/or profusely cry over. ¯\_(ツ)_/¯

Let's get into it, shall we?!

[table-of-contents] stripped

Kendall Jenner (2023-2024)

Something cataclysmic happened the day DeuxMoi was sent an anonymous tip on February 16, 2023 that read, “This single famous model sister was seen playing tonsil tennis with Bad Bunny at a private club in LA.” Like, to say we truly haven't known peace is a serious understatement. After all, this was practically everyone's collective mood when the bombshell rumor dropped...

Eventually, chatty sources revealed the two had indeed been “spending time together.” “Kendall recently started hanging out with him,” said another insider close to the sitch before revealing, “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.”

However, it didn't take long for people close to the celebs to dish that the two miiiiight be more than a fling. “Kendall and Bad Bunny are attracted to each other and definitely have a flirty vibe,” one person confessed to Entertainment Tonight on February 20, 2023. “It is still new, but they’re enjoying each other’s company and like each other. They have mutual friends and had dinner with Hailey, Justin and friends at Wally’s in Beverly Hills on Saturday night. It’s been fun for both of them so far.”

Eventually, we all got to see the 'ship in action for ourselves with the two being spotted on everything from casual date nights to after-parties for the freakin' Met Gala!

bad bunny and kendall jenner
Shareif Ziyadat - Getty Images
kendall jenner and bad bunny
Gotham - Getty Images

Oh, and in September 2023, the celebs proved they were still going strong in a gorgeous ad campaign for Gucci together.

And when Bad Bunny released his most recent album Nadie Sabe Lo Que Va a Pasar Mañana a month later, a buncha fans noted that some of the tracks appeared to be about Kenny. 👀

Regardless, it seemed as though things cooled off between the two in the winter of 2023, after the supermodel dropped a somewhat cryptic Instagram post alongside the caption “what's meant for me, will simply find me.”

Everyone's suspicions were eventually confirmed by People, which reported on December 15, 2023, that the two had split. At the time, an Entertainment Tonight source came through with the following additional details: “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.”

That! Said!!!! Reconciliation rumors swiftly began after the two seemingly rang in 2024 together with a group of mutual friends in Barbados, per TMZ.

Buuuuut then Kenny sparked dating rumors with *checks notes* her ex-boyfriend Devin Booker in news that legit left us all like 👁👄👁. Anyway!!! To get the scoop on that sitch, head right on over this way:

Gabriela Berlingeri (2017-2022)

Bad Bunny and Gabriela Berlingeri were in an on-and-off relationship from 2017 to 2022. According to a May 2020 interview with Rolling Stone, the musician dished that he and the jewelry designer initially met when he traveled to Puerto Rico in 2017 to perform at a Zion and Lennox concert. “I met her at some restaurant, while I was eating with my parents and my brothers,” he recalled before adding, “We started talking and from there, we continued to see each other.”

The two maintained a relatively low-key 'ship for a whopping three years before making their first public appearance in February 2020 at a Miami Heat vs. Dallas Mavericks basketball game. And, yes, the pics are fully still engrained in our minds even four years after, TYVM:

bad bunny and gabriela berlingeri at a miami heat game
Michael Reaves - Getty Images

Just a few months later, in May 2020, the musician gushed about his girlfriend during a candid interview with Rolling Stone: “I am happy with her...[People] don't know she has helped me a lot in emotional aspects when I needed it the most.” During the convo, he also separately opened up about their quarantine experience and mused, “Do people really think I'm spending quarantine alone? No! I am with someone, she is very special in my life. This quarantine has made me understand that she is the best companion I could have.”

Fast-forward to August 2020, and fans noticed Gabriela was rocking a diamond ring on *that* finger in a video that Bad Bunny recorded.

In case you missed the moment, here's a general sense of the vibe once the clip dropped:

However, Bad Bunny eventually set the record straight on those marriage rumors in November of that year during an interview with Entertainment Tonight in which he said, “No, I'm not that married.” However, he then said, “Maybe it can be [an engagement]. But I think that weddings and get[ting] married scares me. A lot.”

The musician also made it clear that his 'ship with Gabriela was going well: “Yeah I'm still in love. I think [it's been] perfect. My perfect quarantine partner.” Good! To! Know!!!

Eventually, the two took their romance public public and walked their first red carpet together in 2021:

bad bunny and gabriela berlingeri
Telemundo - Getty Images

Oh, and during their 'ship, Gabriela even collaborated with Bad Bunny and was featured on a number of his tracks, including his 2022 hit “El Apagón” from his forever iconic album Un Verano Sin Tí and “En Casita” from his 2020 project Las queue no iban a salir.

During that same aforementioned Rolling Stone convo, Bad Bunny spoke about their history of making music together, which is truly just so 🥺❤️:

“After the pair released 'En Casita,' Assad urged Berlingeri to get a proper, public Instagram profile — for this may not be the last time we’ll hear her voice. 'Nobody knows this, but when I did [‘Te Gusté’], the song with J. Lo,' says Martínez, 'Gabriela recorded references for J. Lo’s vocals.'”

Eventually, the two sparked breakup rumors in August 2022 after the rapper was spotted kissing another girl at a club. And though die-hard fans (me) were hoping they would reconcile, we all know how the story ended up: with Bad Bunny dating *drumroll, pls* Kendall Jenner.

Carliz De La Cruz (2011-2017)

Bad Bunny and Carliz De La Cruz began dating after meeting in college when they were both studying at the University of Puerto Rico. Things between the former couple seemed to get pretty serious while they were together, with the musician even proposing (!!!!) to the now-lawyer in January 2016, according to the Associated Press. However, by May of that year, the two wound up going their separate ways, and things kinda sorta remained that way (with the exception of a brieeeeeef reconciliation in 2017, that is 👀).

P.S. All you Bad Bunny historians out there likely already know about Carliz's lawsuit, but for those of you who don't, let us fill you in. Ahem: The rapper's ex is famously the voice behind the ad-lib “Bad Bunny, baby,” which is featured in two of his tracks: “Pa Ti” and “Dos Mil 16.” According to the lawsuit, Carliz recorded the line in 2015 while she was with Bad Bunny because...well, because he'd asked her to lol.

How-ev-er!!! In 2023, she wound up suing Bad Bunny for $40 million, per the Associated Press, which noted that the lawsuit states her “distinguishable voice” has *also* been used without her consent for promotions, worldwide concerts, television, radio, and social media platforms. Reportedly, Bad Bunny’s team offered to buy the recording from Carliz for $2,000 in 2022, but she allegedly declined and a deal was never reached, yet the recording was still used.

Truly yikes!

Aaaaaand that's pretty much all we know for now! Brb, manifesting that we end up on this list next 🕯🕯🕯.

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