As Bad Bunny gets ready to take over the Super Bowl halftime stage, it feels like the perfect moment to revisit the most talked-about subplot of his career: his famously private love life.
Public curiosity peaked in 2023 when the six-time Grammy winner was linked to Kendall Jenner. Around the same time, he told Vanity Fair he was “not interested” in discussing his relationships publicly, a boundary that makes sense given the intensity of the attention surrounding their romance.
The pair are believed to have split in 2024. Even so, as Bad Bunny’s star continues to rise, interest in who he dates has only grown.
That curiosity peaked again at the Grammys last week, where Debí Tirar Más Fotos made history with an all-Spanish Album of the Year win. He arrived wearing a diamond Cartier ring on his left ring finger, a small detail that immediately sent the internet into a spin. Probably just an accessory. But naturally, people had questions.
Curious? Here is a definitive look back at Bad Bunny’s elusive dating history.
Who Is Bad Bunny Dating Now?
As far as the public record suggests, Bad Bunny is currently single. Over the years, though, his romantic history has included two long-term relationships, alongside a brief, high-profile chapter with Kendall Jenner.
His most formative relationship was with Carliz De La Cruz Hernández, whom he dated for more than six years while the pair were students at the University of Puerto Rico and working together at a local grocery store. The couple were reportedly engaged in early 2016 before quietly parting ways a few months later.
Following their split, Bad Bunny began dating Gabriela Berlingeri, whom he allegedly met at a restaurant. They went public in 2020, quarantined together during COVID-19 and collaborated on music, before parting ways in 2022.
Still, the Grammys sparked fresh speculation. Berlingeri was in attendance at the ceremony and, while she did not walk the red carpet with the singer, she shared his Album of the Year win on Instagram later that night.
Have the two reconciled? It is impossible to say. What is clear is that the pair appear to be on good terms, a rare and quietly refreshing outcome in celebrity breakups.
Bad Bunny’s Dating History: From 2011 To Now
Kendall Jenner, 2023-2024
Reports that Bad Bunny was dating Kendall Jenner began swirling in early 2023, after celebrity gossip account DeuxMoi claimed the pair had been spotted getting close at a private club in Los Angeles.
Soon after, sources told People they were “spending time together,” with one insider noting Jenner was enjoying the connection and that Bunny felt refreshingly different to her past relationships.
By late February, Entertainment Tonight described a flirty new romance, with the pair spotted out to dinner with Hailey and Justin Bieber in Beverly Hills.
Sightings followed throughout 2023, from leaving Carbone together to slipping into a Met Gala after-party.
Their first official public appearance came front row at Gucci’s Milan show, later linked to the brand’s campaign. Breakup rumours surfaced in late 2023, with People confirming a split in December.
They were later seen together in Barbados and at Met Gala after-parties in 2024, before quietly parting ways again that September.
Gabriela Berlingeri, 2017-2022
Jewellery designer Gabriela Berlingeri, founder of DiciembreVeintinueve (D29), began dating Bad Bunny in 2017, with their relationship unfolding largely out of the spotlight until his global profile surged.
In a 2020 interview with Rolling Stone, the artist recalled meeting Berlingeri in Puerto Rico after a Zion y Lennox concert, striking up a conversation at a restaurant while dining with his family.
The connection quickly deepened, and during the pandemic, the pair quarantined together, with Bad Bunny crediting Berlingeri for providing emotional support during a pivotal moment in his career.
Their relationship extended into his creative world. Berlingeri recorded reference vocals for Jennifer Lopez on Te Gusté and later appeared on Bad Bunny’s tracks En Casita and El Apagón. Public appearances followed, including court-side at a Miami Heat game in 2020 and red carpet moments in 2021.
Engagement rumours surfaced briefly that year, which the singer dismissed. By August 2022, the couple appeared to have quietly parted ways.
Fast-forward to 2026, and Berlingeri subtly acknowledged Bad Bunny’s major Grammys night, resharing the Recording Academy’s post announcing his Album of the Year win. Fans also clocked a celebratory snap on her social media later that evening, in which she appeared to be wearing a VIP wristband from the inside the ceremony venue.
While neither has hinted at a romantic reconciliation, the gestures suggest a relationship that has, at the very least, ended on good terms.
Carliz De La Cruz Hernández, 2011-2017
Bad Bunny met Carliz De La Cruz Hernández while they were students at the University of Puerto Rico, where they also worked together at a grocery store in Arecibo. The pair dated for six years, spanning the early years of his rise to fame.
They were reportedly engaged in 2016, before quietly parting ways a few months later as their paths diverged, with Bad Bunny signing to Rimas Music and De La Cruz Hernández beginning law school. A brief reconciliation followed in 2017, but the relationship ended for good soon after.
Years later, the former couple made headlines again when De La Cruz Hernández filed a lawsuit in 2023 over the use of a voice recording she had made before his rise to fame, which later appeared in the tracks Pa Ti and Dos Mil 16. The case concluded in 2024, with the court ruling in her favour.
