Bad Bunny's Dating History – 30+ Bright Photos

When Bad Bunny took over the Super Bowl halftime stage, familiar names from his dating history were also in attendance.

It was a rare moment when different chapters of his personal life appeared in the same place at the same time.

Those chapters stretch back more than a decade, beginning long before stadium crowds and international headlines.

Before His Music Career Took Shape

Bad Bunny's earliest publicly known relationship began years before his rise to fame and later became the subject of a legal dispute.

He started dating Carliz De La Cruz Hernández in 2011 while living in Puerto Rico. They studied at the University of Puerto Rico in Arecibo and worked together at a nearby grocery store.

During that period, De La Cruz was closely involved in his day-to-day life as Bad Bunny worked on music outside of school and work.

According to later court filings, she offered feedback on his songs and helped manage practical matters, including scheduling, invoices, and contracts.

De La Cruz later attended the University of Puerto Rico's law school and became a lawyer.

The Recording That Followed Him for Years

In 2015, De La Cruz recorded herself saying "Bad Bunny, baby" while staying with a friend, choosing a bathroom because it was the least noisy place, the lawsuit states.

At the time, Bad Bunny had not yet signed a major record deal. Years later, that same recording appeared in his songs "Pa Ti" and "Dos Mil 16."

"Pa Ti" has more than 355 million views on YouTube and over 235 million streams on Spotify, while "Dos Mil 16" has surpassed 60 million views on YouTube and 280 million streams on Spotify.

A Proposal and a Breakup

On January 1, 2016, Bad Bunny proposed to De La Cruz, and they planned to marry in July of that year. Within months, their circumstances changed.

Bad Bunny signed with Rimas Entertainment in April 2016, and De La Cruz was accepted into law school. The relationship ended in May of the same year. They briefly reunited in 2017 before separating again.

The Lawsuit Filed Years Later

In March 2023, De La Cruz filed a lawsuit in Puerto Rico seeking at least 40 million dollars. The suit alleges her voice was used without permission across songs, promotions, concerts, and broadcasts.

According to the Associated Press, Bad Bunny representatives contacted her in May 2022 and offered $2,000 to purchase the recording.

She declined, and no agreement was reached. A later offer from someone at Rimas Entertainment also did not result in an agreement, according to the filing.

However, the recording was later released anyway, without her consent. It is not publicly known whether the case is still ongoing.

A Relationship That Spanned His Rise

By 2017, Bad Bunny was dating Gabriela Berlingeri. The Puerto Rican jewelry designer and model became a consistent presence as his career expanded.

Multiple outlets have reported that the pair were in an on-again, off-again relationship until 2022.

During that period, Berlingeri appeared in his music videos, attended award shows, and was frequently photographed with him at industry events.

Bad Bunny and Kendall Jenner

Following his breakup with Berlingeri, Bad Bunny was first publicly linked to supermodel Kendall Jenner in early 2023. They dated for less than one year before ending their relationship in December 2023.

In May 2024, they were seen together at the Met Gala in New York. They later traveled together across Europe during the summer. By September 2024, the relationship had cooled.

"They're still friendly but have taken a step back and aren't dating," a source told Us Weekly at the time.

The source added that the pair were more serious after a brief break earlier that year, but the relationship did not continue long-term.

More than a year later, Bad Bunny's high-profile appearances placed former partners back in the same public frame.

Grammy Night Activity and the Super Bowl Moment

In early February 2026, two of the biggest nights of Bad Bunny's career unfolded within days of each other, and both carried unexpected echoes of his past relationships.

After Bad Bunny won Album of the Year at the Grammys on February 1, 2026, Berlingeri reposted the Recording Academy's announcement and shared a photo showing herself wearing a VIP wristband from Crypto.com Arena, where the ceremony took place, according to Cosmopolitan.

Days later, Bad Bunny headlined the Super Bowl halftime show. Sports Illustrated reported that Berlingeri attended the game and later posted an image of the stadium field showing "PERREO" on the Jumbotron to her Instagram story.

Jenner was also present at the game and was filmed moving along to the music during the halftime performance, as seen in a video shared on X.

While his dating life has drawn attention, Bad Bunny has spoken about his sense of self in ways not defined by his relationships.

"I have always felt like there [was] a part of me that is very feminine," he said in a Rolling Stone cover story. "But I never felt as masculine as I did the day I dressed up like a drag queen."

He added, "I may not be gay, but I'm a human who cares."

Where Things Stand

Bad Bunny has not publicly confirmed a current relationship.

What remains visible are the moments that surfaced over time through court records, interviews, and publicly reported appearances.