With his Super Bowl halftime show looming and controversy swirling, Bad Bunny has now given fans something else to obsess over: is he secretly off the market?
The Puerto Rican sensation is at the absolute peak of his career, which so far includes being crowned the most-streamed artist in the world, a historic three Grammy win, and even a brief but high-profile romance with Kendall Jenner.
The pair first set tongues wagging when they were spotted together repeatedly in 2023, fueling months of speculation that the reggaeton superstar had entered a new phase of global celebrity.
That relationship, however, appears to have quietly run its course, though neither have confirmed the split or exactly when it happened.
Since then, amid his ongoing success and the constant spotlight, Bad Bunny has kept his romantic life on the down low.
That was until the singer set off the rumor mill once more at the Grammys last weekend, when eagle-eyed fans picked up on subtle hints that he may no longer be single.
Bad Bunny has sparked a fresh love-life frenzy ahead of his Super Bowl halftime show, with fans obsessing over whether the superstar is secretly off the market
The Latin superstar has been romantically linked to Kendall Jenner and Puerto Rican jewelry designer Gabriela Berlingeri, pictured right at the Billboard Latin Music Awards in 2021
Bad Bunny’s former longtime girlfriend Gabriela Berlingeri, who knew him well before he was selling out stadiums, suddenly resurfaced in his orbit, prompting fans to wonder whether they were hooking up once again – or if they might even be secretly engaged or married.
Berlingeri, 32, a Puerto Rican model and jewelry designer, met Bad Bunny in 2017 in Puerto Rico and even appeared as his bride in his ‘Tití Me Preguntó’ music video before the two broke it off quietly in 2022. He went on to date Jenner the following year.
Berlingeri made an unexpected but low-key appearance at the award show Sunday, confirmed only by clues pieced together online sleuths.
Almost immediately, the internet was flooded with fans parsing seating charts at the Grammys, freeze-framing backstage videos, zooming in on jewelry, and reading emotional subtext into who claps, who stands, and who is allowed within arm’s length of the 31-year-old rapper who was born Benito Antonio Martinez Ocasio.
Although she did not walk the red carpet with the singer, she publicly showed her support by sharing his Album of the Year win for Debi Tirar Mas Photos on her Instagram story that night.
Fans were also quick to clock a telling detail in her Instagram post: a glimpse of Berlingeri’s Crypto.com Arena wristband, confirming she had been inside the venue where the Grammys are held.
Fans went into detective mode after Bad Bunny appeared on the Grammys red carpet wearing what some claimed looked suspiciously like a wedding ring
Dressed in a custom Schiaparelli haute couture tuxedo, the singer wore a single gold ring that remained visible throughout the night and sparked speculation that he may have quietly tied the knot
With fans going into detective mode, videos later emerged on social media showing a proud Berlingeri in the crowd, cheering as Benito accepted his award on stage.
But it was Bad Bunny’s interesting choice to accessory that truly sent the internet into a frenzy.
The Reggaetonero wore a single gold ring on his left ring finger to complement his custom Schiaparelli haute couture tuxedo – a detail that remained visible throughout the night and quickly sparked speculation that he may have quietly tied the knot.
‘Wedding bells are ringing in the reggaeton world! The rumors are louder than ever: Bad Bunny and Gabriela Berlingeri are said to be engaged,’ wrote one typically breathless poster on X Monday.
Other fan accounts and celebrity gossip sites also shared unverified reports that the the two secretly rekindled their romance and got engaged and married in Puerto Rico some time last summer.
Of course, those rumors included some other wild theories, including allegations that Bad Bunny’s more high profile romances are just beard situations to camouflage that the occasional drag-wearing superstar is gay.
Further fueling speculation, Berlingeri publicly showed her support for her ex-boyfriend’s historic Grammy win and shared an Instagram photo giving a glimpse of her Crypto.com Arena wristband – confirming she was at the venue
Eagle-eyed fans soon spotted a familiar face from his past in the crowd as Benito accepted his award on stage
The couple, who had shared social photos together throughout their relationship, met in 2017 but broke it off quietly in 2022
‘I think he’s pretty straight,’ an ad agency executive in San Juan, Puerto Rico who’s known Bad Bunny and some of his team peripherally since the rapper launched his career a decade ago.
‘This is a guy who was bagging groceries 10 years in Vega Baja, which is basically the Bronx of PR,’ the source told the Daily Mail.
‘His rise has been insane and it makes total sense to me he’d go back to a girl who was with him before he made it. Puerto Rico is everything to him.
‘I’m not surprised that he’s playing things close to the vest, though. He’s always understood the power of withholding to make you wonder about them, especially when it comes to his personal life.’
When contacted by the Daily Mail, Bad Bunny’s mother, Lysaurie Ocasio had only this to say about her son’s meteoric rise: ‘I’m very proud of my son.’
Bad Bunny and Berlingeri’s relationship, which began when they met at a restaurant in Puerto Rico where he was having dinner with his family after a Zion and Lennox concert, was never flashy.
Gabriela appeared as Benito’s bride in his 2023 music video for Titi Me Pregunto
Berlingeri’s relationship with Bad Bunny was never flashy, and was widely supported by fans
They two met after Bad Bunny’s first serious relationship with Carliz de la Cruz Hernandez, who’s currently an attorney in San Juan.
Bad Bunny and Carliz met when they were both students at the University of Puerto Rico and were reportedly engaged in 2016 before eventually splitting in 2017.
After the breakup, De La Cruz filed a lawsuit in 2023 alleging unauthorized use of her voice in some of his early songs.
Bad Bunny and Gabriela didn’t really go public for about three years despite collaborating together on music.
Gabriela was featured in Bad Bunny songs like ‘La Casita’ and ‘El Apagón’ and she photographed him for his Rolling Stone cover story in June 2020.
When he was asked about his relationship with Berlingeri in a 2020 interview with Entertainment Tonight, he said, ‘Yeah, I feel love’ but didn’t mention Gabriela by name.
Bad Bunny previously dated Carliz de la Cruz, while they were both students in Puerto Rico
De La Cruz, pictured more recently, later sued her singer ex for using a recording of her voice in one of his songs in 2023 without her consent
Born in and raised in Vega Baja, Puerto Rico, the singer still draws on his island roots in his music and personal style
He did say that every good relationship stems from trust.
‘(It’s) always about being honest,’ he said.
But fans didn’t take to the next woman after Gabriela, Kendall Jenner, with whom Bad Bunny had a high-profile but fairly brief fling in 2023.
Fans were brutal, calling Bad Bunny a hypocrite for choosing someone who symbolized the polar opposite of his anti-colonial, anti-imperialistic and anti-materialistic views.
The two further cemented their status that year most unexpected celebrity couplings, when they appeared together in a Gucci ad campaign.
The relationship seemed to fade out in 2024 with no drama, no postmortems and no explanations from Bad Bunny – but leaving a bad aftertaste for some of his most loyal fans.
The rapper is resolutely private about where he lives as well.
Public records indicate one of his addresses is an inexpensive lot of land in his hometown of Vega Baja where his parents, Benito Martinez, a truck driver, and Lysaurie Ocasio, a retired schoolteacher, raised him and where they still live.
He reportedly owns an expensive home in San Juan which he uses as his base and is thought to own at least two high-end estates in the Hollywood Hills.
In 2023, Bad Bunny rented a penthouse in Manhattan’s West Chelsea neighborhood for approximately $150,000 per month, one of the most expensive residential rentals in New York City at the time.
Most recently, Bad Bunny dated Kendall Jenner in a brief but highly publicized romance that divided fans before quietly fizzling out
The pair were even featured together in a high-fashion advertising campaign for Gucci in late 2023, cementing their status as one of the most unexpected celebrity couplings that year
Bad Bunny had a 30-date concert residency at the Coliseo de Puerto Rico last summer
It was later sold and there is no indication that he has a regular home in the New York area now.
Bad Bunny’s preference for keeping his personal life fluid and out of view now stands in stark contrast to what comes next: his highly anticipated performance at Super Bowl LX’s halftime show.
His music, however, may be overshadowed by the reactions of the MAGA crowd, who have protested the decision to have a Spanish-singing artist perform.
The world’s biggest artist – at least according to recent Spotify streaming data – is fresh off a historic three-Grammy Award win and is expected to bring Puerto Rican pride and anti-ICE stance to the planet’s biggest performance venue.
President Trump called the decision to make Bad Bunny the headliner ‘absolutely ridiculous’ and encouraged people to tune in instead to a parallel event called ‘The All-American Halftime Show’ starring Kid Rock and organized by the conservative Turning Point USA.
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