Benito Antonio Martínez Ocasio doesn't do things the normal way. Not his music, not his fashion, and definitely not his love life. If you’ve spent any time on TikTok or Twitter over the last few years, you’ve seen the chaos. One day he’s supposedly engaged to a long-time girlfriend from Puerto Rico, the next he’s courtside at a Lakers game with a Kardashian-Jenner. It’s a lot. People want to know the Bad Bunny dating history because, honestly, he’s the biggest superstar on the planet right now, and his lyrics are basically a giant puzzle about his exes.
He’s private. Like, really private. But he’s also a master of "trolling" the media. You can’t always take a song lyric at face value, but you also can’t ignore the paparazzi photos from Carbone in New York.
The Carliz de la Cruz Era: More Than Just a Muse
Before the Grammys and the stadium tours, there was Carliz. This isn't just a footnote; it’s the foundation. They started dating around 2011. They worked together at a grocery store in Puerto Rico. Think about that for a second. The man who just sold out arenas was bagging groceries while Carliz was right there by his side.
They were together for about six years. It was serious. Like, "let’s get married" serious. They even applied for a marriage license and scheduled a wedding for July 2016. But fame is a weird thing. It changes the math of a relationship. They broke up shortly before the wedding, though they tried to make it work again in 2017 before calling it quits for good.
The messy part? The voice. If you’ve heard "Pa Ti" or "Dos Mil 16," you know that feminine voice saying "Bad Bunny, baby." That’s Carliz. She actually sued him recently for $40 million, claiming he used her voice memo without permission. It’s a legal headache that proves just how intertwined their lives were. You can’t talk about his rise to power without mentioning her, even if the relationship ended just as he became a household name.
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Gabriela Berlingeri: The "Best Friend" Mystery
Then came Gabriela. This is where the Bad Bunny dating history gets confusing for the casual fan. They met at a restaurant in 2017. For years, she was the only woman on his Instagram. She was in the "Antes Que El Mundo Se Acabe" music video. She even took the cover photo for his Rolling Stone feature during the pandemic.
They were inseparable.
But Benito did something strange. In an Instagram Live in 2022, he told thousands of viewers that Gabriela was just his "best friend." He said, "We are best friends. If she wants to have a boyfriend, she can. If I want to have a girlfriend, I can."
People lost their minds. Was it an open relationship? Was it a PR stunt? Was he just protecting her from the toxic corners of the internet? Honestly, it felt like a mix of all three. They stayed close even when the rumors started swirling about other women. She was even spotted at his concerts long after the "best friend" comment. It’s a modern, fluid type of bond that doesn't fit into a neat little box.
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The Kendall Jenner Chapter: A Cultural Reset
Nobody saw the Kendall Jenner thing coming. In early 2023, gossip accounts like DeuxMoi started posting sightings of them at a club in Los Angeles. Then came the horseback riding dates. Then the Gucci campaign. Suddenly, the "Latino Gang" leader was dating a member of the most famous reality TV family in history.
The internet's reaction was... polarized.
- Fans in Puerto Rico felt he was "selling out."
- Fashionistas loved the aesthetic.
- Paparazzi had a field day.
They were together for most of 2023. They looked comfortable. It didn't seem like a frantic PR move; it seemed like two people who are incredibly famous finding comfort in someone who understands that specific level of scrutiny. But by December 2023, reports surfaced that they had split. Sources told People and Entertainment Tonight that they were "doing their own things."
However, because this is Benito, nothing is ever truly over. They were seen together again at a Met Gala afterparty in 2024, and then again later that summer. It’s a classic "on-again, off-again" situation. It keeps the fans guessing, which is exactly how he likes it. He thrives in the gray area.
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Why We Get the Bad Bunny Dating History Wrong
We try to apply 1990s celebrity rules to a 2026 artist. It doesn't work. Benito doesn't feel the need to confirm anything to a magazine. He communicates through fashion and music. If he wears a certain piece of jewelry, fans dissect it. If he changes a lyric during a live show, it becomes a news cycle.
The biggest misconception is that every woman he is seen with is a "girlfriend." In reality, his circle is tight. He values loyalty over labels. Whether it’s rumored flings with jewelry designers or brief sightings with models, he rarely gives the public the satisfaction of a "hard launch" on social media anymore. He learned his lesson after the public nature of his early years.
How to Track the Narrative Moving Forward
If you want to know who is actually in his life, stop looking at the tabloids and start looking at the credits. Benito involves the people he loves in his work.
- Check the credits: He often uses his inner circle for creative input.
- Watch the "Easter Eggs": He loves hiding references to his personal life in his music videos.
- Monitor the inner circle: His childhood friends from PR are the real gatekeepers of his personal life.
The reality of his dating life is that it’s likely a lot more low-key than the headlines suggest. Between recording albums and filming movies, he spends a lot of time in a "work mode" that doesn't leave room for the constant dating-around lifestyle the media portrays. He’s an artist who uses his heart as his primary source of material—even if that heart is currently a bit of a mystery to the rest of us.
When looking at the Bad Bunny dating history, the most important thing to remember is that he’s in control of the story. He tells us what he wants us to know, usually three minutes at a time over a reggaeton beat. If you want the truth, listen to the lyrics, but remember that he’s also a storyteller. Sometimes a song is just a song, and a "best friend" is exactly that.
To stay updated on the most accurate shifts in his public life, follow the official primary sources like his WhatsApp channel or his infrequent, yet revealing, Instagram Lives. Avoid the speculative TikTok "tea" accounts that often recycle old photos from 2018 as "new" evidence. Stick to verified sightings and his own lyrical admissions for the most authentic view of his journey.