Bad Bunny dating history: From college sweethearts to Gabriela Berlingeri, Kendall Jenner and 2026 Super Bowl rumors

Puerto Rican rapper and singer Bad Bunny, born Benito Antonio Martínez Ocasio, weaves the same heartfelt passion from his trap-reggaeton tracks into his real-life romances. His dating stories hit like a late-night playlist, innocent beginnings, deep trusts, whirlwind thrills, and those honest confessions that make him feel like the friend spilling tea over drinks.

Back at the University of Puerto Rico’s Bayamón campus, before dropping out for music, Bad Bunny connected with classmate Carliz De La Cruz Hernández, now a lawyer. They shared shifts at a local Arecibo grocery store, chatting through mundane days that sparked real young love.He proposed to Carliz De La Cruz Hernández in January 2016, full of dreams as his SoundCloud tracks like “Diles” gained traction. But his Rimas Entertainment deal changed everything, leading to a May 2016 split. A hopeful 2017 reunion couldn’t outrun his exploding career, sold-out gigs and collabs pulled him away. It’s that tender ache when first love meets unstoppable ambition, a story so many know too well.

Early 2023 buzzed with Kendall Jenner, sparked by mutual friends after his L.A. move. They kicked off low-key at Coachella, double dates with the Biebers, and Sushi Park hugs caught on camera by March 7. Horseback rides at her Hidden Hills ranch on April 4 showed her opening her world, he rode solo while she filmed, grinning. Carbone dinners, Tyler, the Creator concerts in matching casual fits, and Met Gala after-parties heated up. By May 1, according to People they were “getting more serious”: “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 on May 11 added: “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.” Drake concert kisses in August and her voice on his Instagram Story with a “K” necklace sealed the vibe. It fizzled by December 2023, a mutual understanding it wasn’t forever, though sparks lingered in rumors.