The Real Reason Bad Bunny And Kendall Jenner Broke Up: 7 Shocking Details About Their On-Again, Off-Again Romance

As of December 18, 2025, the status of the relationship between supermodel Kendall Jenner and global music phenomenon Bad Bunny (Benito Antonio Martínez Ocasio) remains one of Hollywood’s most compelling and complicated celebrity puzzles. While the couple initially split in late 2023, they rekindled their romance in a surprise move in May 2024, only to reportedly face another separation by September 2024, turning their saga into a definitive "on-again, off-again" narrative that has dominated headlines for two years. The intense scrutiny surrounding their romance is a perfect storm of two cultural titans—the quiet, reserved member of the Kardashian-Jenner clan and the fiercely private, chart-topping Puerto Rican trap artist. Their journey, marked by coordinated fashion statements, low-key public appearances, and persistent reconciliation rumors, reveals the difficulty of maintaining a private life when both parties are at the peak of global fame.

Kendall Jenner and Bad Bunny: A Quick Biography Snapshot

To understand the magnitude of this pairing, it is essential to look at the powerhouses involved. Their respective careers and public personas are vastly different, which often fueled the public’s fascination with their pairing.

Kendall Jenner Profile

• Full Name: Kendall Nicole Jenner
• Date of Birth: November 3, 1995
• Primary Career: Supermodel, Media Personality, Entrepreneur
• Notable Achievements: One of the world's highest-paid models since 2017; walked for major fashion houses (Chanel, Versace, Fendi); star of Keeping Up with the Kardashians and The Kardashians.
• Business Ventures: Founder of 818 Tequila.
• Public Persona: Known for being the most private member of her famous family, often seeking low-key relationships away from the reality TV spotlight.
• Relevant Entities: Devin Booker, Kylie Jenner, Kris Jenner, Calvin Klein, Victoria's Secret.

Bad Bunny Profile

• Full Name: Benito Antonio Martínez Ocasio
• Date of Birth: March 10, 1994
• Primary Career: Rapper, Singer, Actor, Producer
• Notable Achievements: Pioneer of Latin trap music; multiple Grammy Awards; first non-English language artist to be Spotify's most-streamed artist of the year (three times); critical acclaim for albums like Un Verano Sin Ti.
• Business Ventures: Collaborations with Adidas and WWE.
• Public Persona: Fiercely private, known for his unique fashion sense, and a strong advocate for Puerto Rican culture and social causes.
• Relevant Entities: Puerto Rico, J Balvin, Latin Trap, Reggaeton, Met Gala, WWE.

Decoding the Bad Bunny and Kendall Jenner Relationship Timeline: From First Date to Breakup Rumors

The relationship between Kendall and Benito was a whirlwind of high-profile sightings and attempts at extreme privacy, creating a timeline that reads more like a celebrity thriller than a typical romance.

Phase 1: The Initial Spark (February – April 2023)

Rumors first ignited in February 2023 when the two were spotted on a double date with Hailey and Justin Bieber, suggesting a quick and intense connection. They maintained a low profile initially, but the paparazzi quickly picked up on their shared activities, including a reported "PDA-filled night" in Los Angeles.

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Phase 2: Going Public (May – August 2023)

The couple made their first major public splash at the 2023 Met Gala, though they did not walk the red carpet together. However, they were inseparable at the after-party. Over the summer, they were seen on several dates, including a trip to Puerto Rico and an NBA playoff game, where they were photographed sitting courtside. They even appeared in a Gucci campaign together, solidifying their status as an "It Couple" and blending the worlds of high fashion and global music.

Phase 3: The First Breakup (December 2023)

By December 2023, reports confirmed that Kendall and Bad Bunny had called it quits after less than a year of dating. Sources suggested the split was due to their demanding schedules and the difficulty of maintaining a committed relationship while pursuing their separate, intensely busy careers. The lack of a clear, dramatic reason for the breakup only fueled more speculation about a potential future reunion.

The On-Again, Off-Again Saga: The Truth Behind the 2025 Reunion Speculation

The most compelling part of their story is the period following their initial split, which has been defined by multiple reconciliation attempts and public run-ins, keeping the public guessing well into late 2025.

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The Surprise 2024 Reconciliation

Just five months after their initial split, the couple surprised fans by officially getting back together in May 2024. Sources indicated that the breakup had simply been a "break" and that they missed each other, choosing to give their relationship another chance. This reconciliation was marked by new low-key dates and a renewed effort to keep their romance shielded from the intense media glare.

The Second Split and the 2025 Met Gala Run-In

Unfortunately, the rekindled romance was reportedly short-lived. By September 2024, reports surfaced that the couple had separated again. This second split cemented their status as an on-again, off-again pair, with the core issue of their conflicting schedules and global commitments likely playing a major role.

The most recent public moment that sparked intense speculation occurred at the 2025 Met Gala. Both Kendall and Bad Bunny attended the prestigious event, leading to an "awkward run-in" that was widely reported by the media. Despite being seen at the same event, they arrived separately and did not pose together, maintaining a clear distance that suggested the reconciliation was definitively over, at least for the moment.

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7 Shocking Details About Their Complicated Romance

The complexity of the Kendall and Benito relationship goes beyond simple logistics. Here are seven details that define their unique, high-pressure dynamic:

1. The Language Barrier: Kendall reportedly speaks little Spanish, and while Bad Bunny is fluent in English, their primary communication often involved a mix of languages, which sources suggested added a layer of complexity to their private life.
2. The Devin Booker Shadow: Kendall's previous long-term relationship with NBA star Devin Booker was often compared to her romance with Benito, with fans and media dissecting her preference for a more private athlete versus a global music icon.
3. The Kardashian Effect: Despite Kendall's best efforts, dating her meant entering the orbit of the entire Kardashian-Jenner clan, a level of media exposure that the intensely private Bad Bunny was reportedly uncomfortable with.
4. The "Un Verano Sin Ti" Fame: Bad Bunny was arguably at the absolute peak of his global fame during their dating period, making any attempt at a normal, quiet date virtually impossible due to constant paparazzi attention.
5. The Coordinated Style: Their public appearances were always meticulously styled, often featuring coordinated, gender-fluid fashion looks (like their matching leather during a Super Bowl LVII outing), suggesting a high level of commitment to presenting a unified public image.
6. The Lack of Public Commentary: Neither star ever officially confirmed the relationship or the breakups directly to the media, maintaining a wall of silence that only amplified the frenzy of speculation.
7. The 2025 Met Gala Clue: Their separate attendance and distance at the 2025 Met Gala—an event they had previously used to signal their connection—is the strongest indication that their second attempt at a relationship has concluded.

The Topical Authority: Why Their Relationship Matters in Pop Culture

The enduring fascination with Kendall Jenner and Bad Bunny is a testament to the intersection of two major cultural forces: the reality TV/modeling dynasty and the explosive global rise of Latin music. Their pairing symbolized a bridge between American celebrity culture and the international music scene.

For Kendall, the relationship was a continuation of her preference for private dating, contrasting sharply with her family's reality television fame. For Bad Bunny, it represented his integration into the highest echelon of American celebrity, while simultaneously maintaining his distinct Puerto Rican identity and musical authenticity.

As of late 2025, the latest reports suggest the two are currently separated. However, given their history of reconciliation and their strong initial connection, the possibility of a third chapter in the Kendall and Benito saga remains a hot topic in the celebrity gossip landscape. Fans and media alike will continue to monitor every subtle clue, from social media posts to shared friend circles, waiting for the next spark to reignite one of the most talked-about romances of the decade.