Are Bad Bunny, Kendall Jenner Dating? Super Bowl Headliner Keeps Fans Guessing Over 'Secret' New Girlfriend

Bad Bunny sat completely frozen when they called his name at the Grammys. Didn't move. Just sat there with his hand over his face, processing the fact that he'd just won Album of the Year. And then Twitter lost its mind - not about the trophy, but about the ring on his left hand. That, and the woman sitting in the VIP section who wasn't Kendall Jenner.

Officially? He's single. Been that way since last September when Jenner walked. But Gabriela Berlingeri turning up at the ceremony has complicated that story considerably. The jewellery designer dated him for five years before they split in 2022. She wasn't just there that night - she had Premium access, stood with his inner circle, and later posted his win to Instagram alongside photos of champagne toasts.

Three years on from their split, that's not exactly casual support from afar.

Bad Bunny's Grammy Ring Sparks Marriage Rumours

The internet did its thing. Secret weddings in Puerto Rico. Theories about them getting back together that nobody would confirm, but plenty of people seemed convinced were true.

His team moved quickly to shut it down, as per Hola! The ring's just Cartier, they said. He collects vintage watches and statement pieces, and it means nothing.

Fair enough. Except it still doesn't explain why she was there, or why she felt the need to share his achievement hours later when she was photographed standing amongst the people closest to him. Fans spotted videos of her cheering when he accepted the award.

Bad Bunny hasn't said a word about any of it. He never does. The man kept their entire five-year relationship mostly private. Why would he start explaining himself now?

Bad Bunny and Kendall Jenner's Complicated Timeline

Kendall's been rather vocal about being single, actually. Told the In Your Dreams podcast last month, she'd spent her entire twenties jumping from one relationship to another without taking proper time for herself. At 29, she decided enough was enough. This would be her 'me year' - no boyfriends, no drama, just focusing on herself.

She and Bad Bunny lasted about 18 months. High-profile stuff - Met Gala, Lakers games, that Gucci campaign. Then it fizzled. Yahoo Entertainment reported that they wanted different things. He craves privacy. She stars in a reality show. Not exactly compatible, is it?

Bad Bunny's Dating History Shows Pattern of Privacy

Privacy's always been his thing. His first serious girlfriend was Carliz De La Cruz Hernandez, whom he met at university. They dated from 2011 to 2017, got engaged in 2016, then split when he signed his record deal. She later sued him over using her voice in his songs without permission. Not exactly an amicable ending.

Gabriela showed up in 2017. They met at a restaurant where he was eating with his dad and brother. She stuck around through the mad early years of global fame, even appearing in his music video for 'Titi Me Pregunto' in 2022 as the bride. Then silence. They'd split by the end of that year.

During lockdown, he told Rolling Stone she was his ideal partner, the person who kept him grounded emotionally when everything else was chaos. Coming from someone who rarely discusses his personal life, that meant something.

Now he has headlined the Super Bowl halftime show with a massive global audience, one of the biggest stages in entertainment, and nobody has a clue who's actually in his life. Fans are desperate for answers. He's not giving them any. There's something almost refreshing about that level of boundary-setting, even if it drives people mad.