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Bad Bunny's dating history: from Kendall Jenner to long-time girlfriend Gabriela Berlingeri

The Puerto Rican rapper has even been engaged

bad bunny kendall jenner
Jenni McKnight
US Lifestyle Editor
11 March 2024
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Bad Bunny seemingly prefers long-term relationships to short-term flings – and has even been engaged. 

The Puerto Rican rapper, 29, is reportedly single now, but his most high-profile romance has been with Kendall Jenner. Before her, he was in committed relationships that lasted several years. 

Find out about his past loves below… 

Bad Bunny dating history 

Kendall Jenner 

bad bunny kendall jenner basketball© Getty Images
Bad Bunny and Kendall dated for less than a year

Bad Bunny, real name Benito Antonio Martínez Ocasio, dated The Kardashians star Kendall for less than a year after they were first spotted together in February 2023. 

They never publicly spoke about their romance, but they did little to hide it and enjoyed several PDA moments throughout 2023, including at Drake's concert in Inglewood, CA, in August. 

Kendall Jenner and Bad Bunny are seen leaving the SHOREbar © MEGA
Bad Bunny and Kendall were pictured together on multiple dates

The rapper is even believed to have referenced Kendall in his song, Un Preview, in which he refers to his love interest as a "cowgirl," which many claim is a nod to Kendall and her well-known affinity for horses. 

They appear to have remained friendly exes as they celebrated New Year's Eve together – just weeks after they called it quits in December 2023. 

Gabriela Berlingeri

bad bunny and ex girlfriend gabriela berlingeri latin billboard awards© Getty Images
Bad Bunny and Gabriela dated for five years

Bad Bunny kept his relationship with model and jewelry designer Gabriela Berlingeri under the radar for three years after meeting her in a restaurant in Puerto Rico in 2017. 

"I met her at some restaurant, while I was eating with my parents and my brothers," he told Rolling Stone in 2020. "We started talking and from there, we continued to see each other."

He added. "I am happy with her. [People] don't know she has helped me a lot in emotional aspects when I needed it the most." 

They made their first public appearance together in February 2020 at a Miami Heat and Dallas Mavericks game, before they went Instagram Official in March after he told Entertainment Tonight that he was "in love". 

bad bunny and ex girlfriend gabriela berlingeri© Getty Images
Bad Bunny and Gabriela split in 2022

The couple made their red carpet debut at the 2021 Billboard Latin Music Awards and were even rumored to be engaged after Gabriela was spotted wearing a diamond ring. 

However, Bad Bunny soon set the record straight, telling ET: "No, I'm not that married. Maybe it can be that (engagement). But I think that weddings and get[ting] married scares me. A lot." 

The couple appeared to quietly split sometime in 2022, as in August, Bad Bunny was spotted kissing another girl at a club. 

Carliz De La Cruz 

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Bad Bunny had a serious relationship with his college sweetheart, Caliz De la Cruz, for six years. They met at the University of Puerto Rico in 2011 and were engaged in 2016 before splitting in April 2017. 

Five years after their breakup, Carliz filed a lawsuit in Puerto Rico against Bad Bunny, claiming he used her voice in his music without her permission. Two of his songs, Pa Ti and Dos Mil 16, feature a soundbite of Carliz saying "Bad Bunny, baby," which she recorded for him before he became famous. 

According to the filing, a rep for the rapper contacted Carliz in May 2022 and offered her $2,000 to purchase the recording, but she declined. 

Since Bad Bunny still used it in his songs, she is suing him and his manager, Noah Kamil Assad Byrne, for $40 million. The case appears to be ongoing.

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