Bad Bunny's dating history explored amid Kendall Jenner's rekindling romance rumors 

Bad Bunny Most Wanted Tour Night Two - Atlanta, GA - Source: Getty
Bad Bunny Most Wanted Tour Night Two - Atlanta. (Image via Getty/Paras Griffin)

Bad Bunny, or Benito Ocasio, is arguably one of the most booked and busy celebrities out there. Besides his sold-out concerts, luxury brand campaigns, and appearances at A-list events, the rapper also makes news for his dating life. The King of Latin Trap is no stranger to public scrutiny but this hasn't prevented him from dating in public.

The multiple Grammy-winning star has mostly been in long-term relationships and openly expressed affection for his partners. However, the Yo Perreo Sola singer has stayed tight-lipped about his rumored girlfriend Kendall Jenner. It will be interesting to see if Bad Bunny opens up about his current love life, till then here is a look back at his dating history.


The Relationship Timeline of Bad Bunny

1) Carliz De La Cruz ( 2011-2017)

Carliz De La Cruz and the Bad Bunny met in 2011 at the University of Puerto Rico. They dated from 2011 to 2016. As per Harper's Bazaar, the rapper proposed to Carliz in 2016, but they broke up the next year.

In March 2023, almost six years after their breakup, Cruz sued Bad Bunny for $40 million for using her voice recording that she had sent him early into his career. Cruz, who is an attorney, claims that her voice sample in which she says “Bad Bunny, baby” was used in two hit songs Pa Ti and Dos Mil 16. The lawsuit claims the recording was used without her consent on not just the songs but for other promotional material on television, radio, and social media platforms.

She won the lawsuit in May 2024, as per El Diario Nueva York, the largest Spanish newspaper in the USA.


2) Gabriela Berlingeri ( 2017-2022)

Bad Bunny started seeing jewelry designer Gabriela Berlingeri in 2017. In a May 2020 interview with Rolling Stone, the 30-year-old recalled how he met Gabriela and said:

“It was after I sang at a Zion and Lennox concert, here in Puerto Rico. I met her at some restaurant, while I was eating with my parents and my brothers. We started talking and from there, we continued to see each other.”

He shared that being with Gabriela during the quarantine made him appreciate her more and remarked:

“This quarantine has made me understand that she is the best companion I could have,”

This Rolling Stone cover story confirmed their relationship. In 2021, the couple attended the Billboard Latin Music Awards which was their first red carpet appearance.

In 2022, Bad Bunny's album Un Verano Sin Ti featured Gabriela. In conversation with People Magazine, he shared why Gabriela participated in the video:

" This new album revolves a lot around my life, around her as well. She has always been a big part of my projects, my ideas, behind everything. I always ask for her ideas, her opinion and she's an important part."

Despite the public declarations of love, by the end of 2022, the couple was no longer seen together, leading fans to speculate that they had gone their separate ways.


3) Kendall Jenner ( 2023- present)

The dating rumors of model Kendall Jenner and Bad Bunny began in 2023. The couple was first spotted together at a restaurant in late February 2023, accompanied by another high-profile pair, Hailey and Justin Bieber.

Their dating rumor got a boost when it was widely theorized that Bad Bunny dissed basketball player Devin Booker, who was Kendall Jenner's ex, in his song Coco Chanel.

The lyrics, roughly translated from Spanish, were:

"Im not bad, baby that's a gimmick / But the sun in Puerto Rico is hotter than in Phoenix / She knows it."

The rapper mentioned "Phoenix", and Devin Booker's basketball team is Phoenix Suns. He further raps, "las de escorpio son peligro," which roughly translates to" Scorpio women are dangerous." Jenner, born on Nov. 3, 1995, has Scorpio as her zodiac sign.

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Kendall was seen at Coachella in April 2023, dancing to Bunny's songs. Moreover, the pair was spotted having a good time together at that annual music festival. From May to August 2023, the couple was frequently seen together at various events, ranging from the Met Gala after-party to front-row fashion shows.

In September 2023, Bad Bunny and Kendall Jenner shared a screen for a Gucci advertisement.

In October 2023, they were last seen together at the Saturday Night Live after-party. However, by December, a source confirmed their breakup to People Magazine. It is important to note that neither of them ever denied nor confirmed their romance.

Back in May 2024, Bad Bunny and Kendall Jenner were spotted partying at Emily Ratajkowski’s Met Gala after-party. Throughout May, the couple was seen in Miami, Puerto Rico, and Orlando.

In May, some sources told to Entertainment Tonight that Bad Bunny and Kendall are not exclusive but their relationship is "casual, easy, and comfortable."

Edited by Niharika Dabral
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