Bad Bunny's Romantic Evolution: A Timeline of Love and Fame
Puerto Rican music sensation Bad Bunny, whose real name is Benito Antonio Martínez Ocasio, has captivated global audiences not only with his chart-topping trap-reggaeton hits but also with his intriguing personal life. His romantic journey mirrors the emotional depth of his music, unfolding through innocent beginnings, profound connections, and high-profile encounters that have kept fans and media alike thoroughly engaged.
The College Sweetheart: Carliz De La Cruz Hernández
Before ascending to international stardom, Bad Bunny's love story began in the humble corridors of the University of Puerto Rico's Bayamón campus. While balancing studies and part-time work at a local Arecibo grocery store, he formed a genuine bond with classmate Carliz De La Cruz Hernández, who has since established herself as a lawyer. Their shared experiences during those formative years blossomed into a sincere young romance.
In a heartfelt gesture of commitment, Bad Bunny proposed to Carliz in January 2016, a period when his early SoundCloud tracks like "Diles" were beginning to gain traction. However, the trajectory of his life shifted dramatically upon signing with Rimas Entertainment, leading to their separation in May 2016. A brief attempt at reconciliation in 2017 could not withstand the relentless demands of his skyrocketing career, as sold-out concerts and high-profile collaborations pulled him in new directions. This chapter reflects the universal tension between first love and unstoppable ambition, a narrative that resonates deeply with many.
A Deep Connection with Gabriela Berlingeri
Fate intervened in 2017 when Bad Bunny encountered jewelry designer Gabriela Berlingeri at a cozy Puerto Rico restaurant following a Zion and Lennox concert. In a candid interview with Rolling Stone in May 2020, he recounted the meet-cute: "I met her at some restaurant, while I was eating with my parents and my brothers. We started talking and from there, we continued to see each other."
Their relationship evolved into a creative partnership as well, with Gabriela providing vocal references for his collaboration with Jennifer Lopez on "Te Gusté," as he later disclosed. After maintaining privacy for three years, subtle hints emerged during Miami Heat games in 2020, culminating in an official acknowledgment via an Instagram video from the "Yo Perreo Sola" shoot, captioned "Sorry but I had to do it." Speaking to Entertainment Tonight on March 4, 2020, Bad Bunny openly expressed his feelings: "Yeah, I feel love," and shyly confirmed, "I'm in love," emphasizing that honesty is foundational to any relationship.
Speculation about an engagement surged when Gabriela wore a diamond ring at the 2021 Billboard Latin Music Awards, but Bad Bunny humorously dismissed the rumors to Entertainment Tonight on November 26, 2020: "No, I'm not that married. Maybe it can be that (engagement). But I think that weddings and getting married scares me. A lot." Despite parting ways in 2022, the authenticity of their bond continues to echo like a memorable chorus in his life story.
The High-Profile Romance with Kendall Jenner
Early 2023 ignited widespread media buzz with rumors of a romance between Bad Bunny and supermodel Kendall Jenner, reportedly sparked through mutual friends following his relocation to Los Angeles. Their relationship unfolded with low-key beginnings at Coachella, progressing to double dates with Justin and Hailey Bieber, and affectionate moments captured by paparazzi at Sushi Park by March 7.
A horseback riding session at Kendall's Hidden Hills ranch on April 4 showcased her welcoming him into her world, with Bad Bunny riding solo as she filmed, both sharing genuine smiles. Their outings included dinners at Carbone, attending Tyler, the Creator concerts in coordinated casual attire, and mingling at Met Gala after-parties. By May 1, sources told People that the couple was "getting more serious," noting, "It was a slow start, but they spend almost every day together now. He hangs out with her friends and she hangs out with his. It's more of a relationship now. Kendall is not seeing anyone else. She really likes him."
Us Weekly added on May 11: "Things are going really well for Kendall Jenner and Bad Bunny and she definitely sees long-term potential with him. She feels like he's the complete package and he treats her like a total gentleman. They are having a great time together, and she appreciates that he gets along with all of her friends. They complement each other on so many levels and she's enjoying getting to know him better every day." Public displays of affection, such as kisses at a Drake concert in August and her voice featured in his Instagram Story alongside a "K" necklace, solidified their connection. However, by December 2023, the relationship had cooled, with mutual understanding that it was not meant to last, though lingering rumors continue to spark interest.
Looking Ahead: 2026 Super Bowl Rumors
As of February 2026, fresh speculation surrounds Bad Bunny's romantic life, with unverified rumors linking him to potential appearances or performances at the Super Bowl, adding another layer to his ever-evolving narrative. While details remain scarce, this development underscores his enduring presence in both the music industry and popular culture, ensuring that his personal and professional journeys remain topics of fascination for years to come.
