Benito Antonio Martínez Ocasio, known to the world as Bad Bunny turns 32. The Puerto Rican superstar is entering his new year at the absolute peak of his powers, fresh off a historic Super Bowl halftime performance and a dominant sweep at the Grammys. While his musical evolution continues to shatter records, his personal life remains a source of endless fascination. Despite his famous plea to “stop dating people who don’t get your music,” Benito’s own romantic journey has been a mix of long-term loyalty, whirlwind celebrity flings, and deep-seated privacy.
Carliz De La Cruz: The College Sweetheart
Long before the Grammys and the global stadium tours, there was Carliz De La Cruz. The pair met in 2011 while studying at the University of Puerto Rico and even worked together as baggers at an Econo grocery store. Their six-year relationship was so serious that they were engaged to be married in 2016. However, as Benito’s SoundCloud tracks began to go viral, the pressures of his skyrocketing fame led to a split in 2017. Their relationship made headlines again recently due to a high-profile lawsuit Carliz filed regarding the use of her voice in his songs.
Gabriela Berlingeri: The “Best Friend” and Muse
Gabriela Berlingeri attends the Cult Gaia RE24 Runway Show on November 14, 2023 in Los Angeles, California. (Photo by Steven Simione/Getty Images)
In 2017, fate intervened at a restaurant in Puerto Rico where Benito was dining with his family. It was there he met jewelry designer Gabriela Berlingeri. For years, she was his most consistent partner and creative collaborator, providing reference vocals for hits like “Te Gusté” and appearing as his bride in the “Tití Me Preguntó” music video. Though they sparked breakup rumors in 2022 and Benito famously claimed they were just “best friends” who could date whoever they wanted, their bond has proven unbreakable.
Kendall Jenner: The Whirlwind Romance
Bad Bunny and Kendall Jenner are seen at Gucci Ancora during Milan Fashion Week on September 22, 2023 in Milan, Italy. (Photo by Jacopo M. Raule/Getty Images for Gucci)
In early 2023, the internet nearly broke when reports surfaced that Bad Bunny was dating supermodel Kendall Jenner. The “Kenito” era saw the pair courtside at NBA games, horseback riding in Hidden Hills, and even starring in a joint Gucci campaign. It was a rare moment where the singer stepped fully into the Hollywood spotlight. However, the cross-cultural romance reportedly “fizzled out” by late 2024, with insiders citing their “crazy-busy schedules” as the primary reason for the split.
The 2026 Reconnection: Back with Gabriela?
As of his 32nd birthday, all signs point to a major romantic reconciliation. Following his Super Bowl performance in February 2026, Benito was spotted on a series of intimate dates with Gabriela Berlingeri in Buenos Aires and Sydney. Most recently, Gabriela was seen accompanying him to Tokyo for his “Billions Club” celebration. Sources close to the artist suggest that after a brief stint in the high-intensity world of Hollywood dating, the singer has found comfort in returning to his roots with the woman who has supported him since the very beginning.
Whether he is officially “off the market” or enjoying his birthday as a single man, Bad Bunny continues to prove that his most enduring relationship is with his craft and his identity as a Puerto Rican icon.
