Bad Bunny and Kendall Jenner Are Back: A Dive Into His Love Life, Past and Present

All the muses behind the Puerto Rican rapper's catchy hits.

Ever since Puerto Rican rapper Bad Bunny rose to pop star status with his 2018 breakout hit “Te Boté,” his name has been splashed across headlines for everything from his catchy, top-charting tracks and his gender-bending, effortlessly cool streetwear style to his on-again, off-again love affair with model and 818 founder Kendall Jenner. The pair have had their ups and downs, to be sure, but recent confirmation of a rekindled romance has us wondering: is she the one?

Over the years, the Grammy award winner has tried his best to keep a low profile when it comes to his significant others. But curiosity surrounding his love life hit a fever pitch in February 2023 following reports that he was seeing Jenner. The duo only lasted a few months in the spotlight, however: breakup rumors were confirmed that December.

Of course, now we know that the pair's story didn't end there. The romance is officially back on, and the couple couldn't be in a better place, according to Entertainment Tonight. Still, Bad Bunny does everything he can to safeguard his privacy, an issue he explained during a June 2023 interview with Rolling Stone. "I know something is going to come out. I know [people are] going to say something. People know everything about me, so what’s left for me to protect? My private life, my personal life," he told the publication. He added, "That’s the only answer. In the end, the only thing I have is my privacy."

The Bullet Train star has, however, let some information slip through the cracks over the course of several years and three relationships. See ahead for everything we know about Bad Bunny’s ex flames, and the latest on his rekindled romance with Jenner.

2011-2017: Carliz De La Cruz Hernández

Hernández and Bad Bunny first became an item in 2011. A year later, they began studying at the University of Puerto Rico and working at a local grocery store together. Also during this time, the rapper was focused on launching his music career. As he made songs and beats, he enlisted De La Cruz’s help, who offered feedback, scheduled his parties, and handled his invoices and contracts.

Over the years, both their relationship and Bad Bunny’s career developed, and on January 1, 2016, the rapper, then 21 years old, popped the question. The couple planned to be wed in July 2016, but in April of that year, Bad Bunny scored a record deal with Rimas Entertainment and De La Cruz was accepted into the University of Puerto Rico’s law school. As a result, she called off the wedding and their relationship.

The pair rekindled their romance in 2017 but once again called it quits. And, in March 2023, things went sour when De La Cruz sued the pop star for $40 million over the use of her voice in his songs. According to AP, Bad Bunny included a 2015 recording of his ex-flame saying “Bad Bunny, baby” in his tracks “Pa Ti” and “Dos Mil 16” without her consent. The lawsuit stated Bad Bunny offered Hernández $2,000 for the recording in 2022, but she declined; he released the songs anyway.

2017-2023: Gabriela Berlingeri

Bad Bunny’s relationship with the jewelry designer started off low profile, as they kept things private for the first three years of seeing each other. The pair went public in February 2020 at a Miami Heat and Dallas Mavericks game, and Bad Bunny shared some insight into their bond shortly after during a May 2020 interview with Rolling Stone.

The Grammy award winner explained it all happened in 2017 after he performed at a Zion & Lennox concert in Puerto Rico. Following his performance, he went to dinner with his family at a local restaurant, where he encountered Berlingeri. “We started talking and from there, we continued to see each other."

He gushed about her at the time, saying, "I am happy with her. [People] don't know she has helped me a lot in emotional aspects when I needed it the most."

Bad Bunny and Berlingeri made their red carpet debut at the 2021 Billboard Latin Music Awards and started showing off their love on social media thereafter with frequent posts of each other. Berlingeri even served as Bad Bunny’s muse for his 2022 album Un Verano Sin Ti and was featured in several tracks and music videos. However, split rumors began to spread that same year, although they never publicly confirmed their breakup.

2023-2024: Kendall Jenner

A Kendall Jenner-Bad Bunny fling was a surprise on many people’s 2023 bingo cards. The unexpected pairing took the world by storm in February 2023 after a report was published to gossip social media account DeuxMoi, now deleted, that stated "This single, famous model sister was seen playing tonsil hockey with Bad Bunny at a private L.A. club last night,” and then followed up by confirming the “famous model sister” in question was indeed Kendall Jenner.

Shortly after, TMZ published photos of the two leaving the same restaurant in Beverly Hills and People confirmed the pair was “hanging out” and “having fun.” Then, to put any lingering speculation to rest, the two were photographed kissing in March 2023. Once the PDA started, it didn’t stop. Over two months, the pair shared lots of sweet moments at Coachella, enjoyed a hot date-night at the Met Gala after-party, made a smiley public debut at a Los Angeles Lakers vs. Golden State Warriors game, made out at a Drake concert, and showed off their sleek coordinated couples’ style during several date nights.

The couple took their relationship up a notch in September when they starred in a Gucci ad campaign—looking more loved up than ever. One photo sees Bad Bunny grinning ear-to-ear while hugging Jenner from behind as she sits on a stack of Gucci Savoy luggages, also flashing her pearly whites.

By the end of the year, however, an insider confirmed to People that the couple had called it quits on December 17, 2023, after less than a year of dating. Even so, Bad Bunny and Jenner kept things cordial, as they even spent New Year’s together as friends.

The split didn't last long: in May, Bad Bunny and Jenner were all smiles at a 2024 MET Gala after-party. Later that same month, they were spotted together again, this time in Miami. Jenner was at several of the singer's shows and they also dined together not once, but twice, over the course of the weekend.

It won't come as a surprise that soon after their Miami rendezvous, the couple confirmed the rumors: love is in the air. According to Entertainment Tonight, Bad Bunny and Jenner are "totally back together."

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