Global superstar Bad Bunny, born Benito Antonio Martínez Ocasio, has always navigated the fine line between immense public visibility and guarded personal privacy. As of April 2026, the question of who he is dating has moved past the tabloid speculation of the previous years and centered on a familiar face. Following a historic performance at Super Bowl LX and a monumental win at the 2026 Grammy Awards, the evidence points toward a significant reconciliation with his longtime partner and creative collaborator, Gabriela Berlingeri.

The rumors of a rekindled romance began to gain momentum in the early months of 2026, coinciding with the most successful professional stretch of the artist's career. While his team often maintains the stance that the singer is "officially single," the public sightings and symbolic gestures of the past few months suggest a deep, personal reconnection that transcends the typical celebrity dating cycle.

The Sydney Sighting and the Australian Tour

In late February 2026, the world received its most concrete visual evidence of the current state of Benito’s heart. Ahead of his highly anticipated debut tour dates in Australia, Bad Bunny was spotted at Tamarama Beach in Sydney. He was accompanied by Gabriela Berlingeri, and witnesses described the pair as inseparable. Unlike the high-profile, paparazzi-heavy outings that defined his previous relationship with Kendall Jenner, this Sydney appearance felt markedly relaxed.

Gabriela was seen enjoying the ocean while Benito, dressed casually in a yellow hoodie, watched from the shore. The couple had reportedly arrived in the country via a private chartered jet, further signaling that Berlingeri is firmly back within his inner circle. This trip followed a romantic Valentine’s Day dinner in Buenos Aires, Argentina, just weeks prior, where the couple was photographed leaving a private dining room late into the evening. These international sightings in early 2026 mark a shift from their 2023-2024 period of "just being friends" back into a partnership that appears increasingly exclusive.

Support at the 2026 Grammys and Super Bowl LX

The month of February 2026 was a whirlwind for Bad Bunny. His latest project, Debí Tirar Más Fotos, became the first Spanish-language album to win Album of the Year at the Grammy Awards. While he walked the red carpet alone, eagle-eyed fans and industry insiders quickly noted Gabriela Berlingeri’s presence in the most exclusive VIP sections of the arena. She was captured in social media posts celebrating his historic win, often seen with his close friends and management team.

The speculation reached a fever pitch just a week later during the Super Bowl LX halftime show. Benito’s performance, which shattered global viewership records with over 4 billion views in 24 hours, featured a performance that paid deep homage to his Puerto Rican roots. Behind the scenes, Gabriela was present throughout the rehearsals and the final show. She later shared a candid photo with Lady Gaga, who was a guest performer that evening, captioned with emotional lyrics that many interpreted as a tribute to her pride in Benito’s achievements. Her presence at these two career-defining moments suggests that she remains his primary emotional anchor.

The "La Gabriela" Building and Symbolic Gestures

One of the most significant clues regarding the depth of their 2026 reconciliation lies in a project back home in Puerto Rico. In late 2025, reports surfaced that Benito had purchased and restored a historic landmark building in the Río Piedras district. The building, which once housed a major retail outlet, was reportedly renamed "La Gabriela."

This move is seen by many in Puerto Rico as the ultimate romantic gesture. For an artist who expresses his most profound emotions through his connection to the island, dedicating a physical part of that home to Berlingeri speaks volumes. This followed a period in late 2025 where he was seen frequently in the Vega Baja area with her family, suggesting that the ties between their respective families never truly frayed despite their publicized break in 2022.

Closing the Kendall Jenner Chapter

To understand the significance of the 2026 reunion, one must look back at the "Kenito" era that dominated headlines in 2023 and 2024. Bad Bunny’s relationship with supermodel Kendall Jenner was a departure from his usual pattern of dating fellow Puerto Ricans. Their romance was characterized by high-fashion campaigns, front-row seats at Milan Fashion Week, and frequent appearances at NBA games in Los Angeles.

However, by late 2024, the relationship had reached a definitive end. Sources close to the singer indicated that the "lifestyle differences" and the intense media circus surrounding the Kardashian-Jenner clan were often at odds with Benito’s desire for a quieter life in Puerto Rico. While they were spotted together briefly at a 2025 Met Gala after-party, the relationship was officially described as "friendly exes" by the time his 2026 tour began. The consensus among those in his circle is that while the romance with Jenner was a significant moment in his global crossover, it lacked the deep cultural and creative shared history that he possesses with Berlingeri.

The Mystery of the Cartier Band

During his 2026 Grammy acceptance speech, many viewers noticed a prominent diamond Cartier band on Bad Bunny’s left ring finger. This immediately sparked rumors of a secret engagement to Gabriela. However, sources familiar with the singer were quick to clarify to major news outlets that the ring was not an engagement piece but rather a custom gift from the jewelry brand following the success of his album.

Bad Bunny has a long history of wearing statement jewelry, and he has often used rings as part of his performance aesthetic. When asked about his marital status or engagement rumors in the past, he has consistently maintained a stance of total privacy. In a famous 2023 interview, he stated that he has "no commitment to clarify anything to anyone" regarding his personal life. This philosophy appears to hold true in 2026; while he is happy to be seen with Gabriela in public, he remains uninterested in providing a formal title or a press release to satisfy public curiosity.

Gabriela Berlingeri: More Than a Partner

It is essential to recognize that Gabriela Berlingeri has always been more than just a romantic interest to Bad Bunny. Their relationship, which began in 2017 after meeting at a restaurant in Puerto Rico, has been a collaborative partnership. She has provided vocals for his tracks (such as "En Casita" and "El Apagón"), photographed him for a historic Rolling Stone cover during the 2020 lockdowns, and served as his creative muse for some of his most vulnerable lyrics.

In his 2026 album, Debí Tirar Más Fotos, several tracks appear to reference the peace and stability he finds in a partner who understands his roots. Fans have pointed to lyrics that speak of "returning to the place where I was happiest" as a clear nod to his rekindled relationship with Gabriela. Unlike his previous flings, his connection with Berlingeri is rooted in their shared identity as Puerto Ricans navigating the sudden pressures of global fame.

The History with Carliz de la Cruz

Before Gabriela, the most significant woman in Benito’s life was Carliz de la Cruz, his college sweetheart whom he dated from 2011 to 2017. Their relationship spanned the years before his rise to superstardom, and they were reportedly engaged in 2016. However, that chapter ended on a complex note, culminating in a 2023-2024 legal battle over the unauthorized use of her voice in his early recordings.

The resolution of this lawsuit in early 2025 seemed to clear the air for Benito, allowing him to focus on his future without the lingering legal and emotional weight of his first major relationship. This closure arguably paved the way for him to revisit his connection with Gabriela with a fresh perspective.

Is Bad Bunny Single or Taken in 2026?

As of April 21, 2026, the technical answer depends on who you ask. If you look at official statements from his representatives, Bad Bunny is a single man focused on his global tour and the promotion of his Grammy-winning album. He avoids the "boyfriend" label in interviews and continues to speak about his life in terms of "freedom" and "privacy."

However, the reality of his day-to-day life tells a different story. Since the start of 2026, he has not been seen with any other romantic interests. Every major milestone—the Super Bowl, the Grammys, his world tour kickoff—has been shared with Gabriela Berlingeri. Whether they choose to label it for the public or not, it is clear that they have chosen each other once again. For fans of the artist, this version of Benito appears more grounded and at peace than he did during the height of the media frenzy in 2023.

In the ever-evolving world of celebrity dating, Bad Bunny continues to write his own rules. He refuses to conform to the expectations of the "Hollywood couple" and instead chooses to surround himself with those who knew him before the world knew Bad Bunny. In 2026, that person is undeniably Gabriela Berlingeri.