Bad Bunny's Romantic History Includes Gabriela Berlingeri and Kendall Jenner

Before breaking into the music world, Bad Bunny dated Carliz De La Cruz. The couple got together in 2011 when they both were studying at the University of Puerto Rico and had jobs at a local grocery store. The couple were so serious that they got engaged in 2016; however, they seemingly drifted apart once their lives began going in separate directions. They officially broke up in 2017.

More than five years after calling it quits, Puerto Rico's NotiCel reported in March that De La Cruz was suing Bad Bunny for allegedly using her voice in his music without her permission. The rapper included audio of De La Cruz saying "Bad Bunny, baby" in two of his songs: "Pa Ti" and "Dos Mil 16." According to the lawsuit, De La Cruz recorded the line in 2015 after Bad Bunny asked her to do it. In May 2022, a rep for the star reached out to De La Cruz to buy the recording from her for $2,000, but she declined. Since Bad Bunny still used the recording, De La Cruz is now suing him and his manager, Noah Kamil Assad Byrne, for $40 million.

In a May 2020 interview with Rolling Stone, Bad Bunny revealed that he met Berlingeri 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 said, adding that they clicked instantly. "We started talking and from there, we continued to see each other."

After keeping their relationship under the radar for three years, Bad Bunny and Berlingeri made their first public appearance together by attending a Miami Heat and Dallas Mavericks game in February 2020. Of course, fans assumed they were dating, and Bad Bunny fueled the rumors that March by telling Entertainment Tonight that he was "in love." He went Instagram official with Berlingeri a few days later and then confirmed their romance in April by sharing a video of the pair kissing in a since-deleted Instagram post.

While talking to Rolling Stone that May, Bad Bunny confirmed that he and Berlingeri were quarantining together. "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," he said. "I am happy with her. [People] don't know she has helped me a lot in emotional aspects when I needed it the most."

Considering how serious their relationship seemed, fans thought the pair had gotten engaged after Berlingeri flaunted a diamond ring in an Instagram that August. However, Bad Bunny shut down the rumors that November, per Entertainment Tonight. Although they didn't have plans to walk down the aisle, Bad Bunny and Berlingeri took their relationship to the next level in September 2021 by making their red carpet debut as a couple at the 2021 Billboard Latin Music Awards.

Things between Bad Bunny and Berlingeri appeared to be going smoothly until August 2022 when Bad Bunny was spotted kissing another girl at a club. While some fans thought that he and Berlingeri had broken up, others speculated the pair were in an open relationship. After he was seen hanging out with another mystery woman in January 2023, however, Bad Bunny and Berlingeri appeared to have split for good.

Dating rumors between Bad Bunny and Jenner began on Feb. 17 when the celebrity gossip account DeuxMoi shared that they had received an anonymous tip about the pair seemingly kissing at a club in Los Angeles. The rumors only intensified when TMZ shared photos of the stars leaving the same restaurant together on Feb. 19. The following day, a source told People that Bad Bunny and Jenner had only recently started hanging out after the rapper moved to Los Angeles in January. "They were introduced by friends," the source said. "[Jenner] likes him and is having fun. He is different from guys that she dated in the past. He is very charming."

On March 8, Bad Bunny and Jenner seemingly confirmed their relationship by showing PDA following a sushi date. TMZ posted photos of the stars getting cozy before they said goodbye to each other for the night. In the following weeks, Bad Bunny and Jenner continued to flaunt their relationship by attending Coachella together on April 15 and 16 and then going to Tyler, The Creator's Los Angeles concert on April 27. After months of date-night photographs, Bad Bunny and Jenner finally made their first public appearance together at a Lakers vs. Warriors playoff game on May 12. The stars were photographed sitting side by side and whispering into each other's ears during the game.

Bad Bunny addressed the dating rumors between him and Jenner for the first time in a June 21 interview with Rolling Stone. However, he played coy when discussing his status with the model. "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," he said. "In the end, the only thing I have is my privacy."

That same day, Jenner also refused to confirm or deny their relationship while speaking to WSJ. She told the publication that when it comes to her love life, she prefers to keep those details "sacred," explaining, "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."

On Aug. 13, Bad Bunny and Jenner were spotted kissing at a Drake concert, proving they're still going strong. Then, in October, Bad Bunny appeared to reference Jenner in his single "Fina," on which he raps about getting intimate at one of her sister's homes, though he never mentions Jenner by name.