5 Shocking Times Kendall Jenner And Bad Bunny Reunited In 2025—Unpacking Their On-Again, Off-Again Romance

The relationship saga between supermodel Kendall Jenner and global music sensation Bad Bunny (Benito Antonio Martínez Ocasio) is one of Hollywood’s most intriguing and private celebrity pairings, constantly shifting between "on" and "off." As of late December 2025, the question of their relationship status remains a hot topic, fueled by a series of high-profile, unexpected reunions that have occurred throughout the year, suggesting their connection is far from over.

This deep dive explores the complete timeline, from their initial private dates to their surprising split and the most recent, undeniable public sightings in 2025 that have reignited reconciliation rumors. The freshest news centers on their joint appearances at major fashion events, proving that even after a reported breakup, the model and the *reggeaton* star can’t seem to quit each other.

The Power Couple Profile: Kendall Jenner and Bad Bunny Biography

To understand the magnitude of this pairing, one must first look at the individual global empires they command. Kendall Jenner and Bad Bunny are two of the most influential figures in their respective industries, fashion and music, making their relationship a true cultural phenomenon.

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Kendall Jenner: Model, Socialite, and Businesswoman

• Full Name: Kendall Nicole Jenner
• Date of Birth: November 3, 1995
• Place of Birth: Los Angeles, California, U.S.
• Known For: Rising to fame on the reality television show *Keeping Up with the Kardashians*, she established herself as a high-fashion supermodel, walking for every major design house, including Chanel, Versace, and Marc Jacobs. She is also a successful businesswoman and socialite.
• Key Entities: *The Kardashians*, Kylie Jenner, Kris Jenner, high-fashion modeling, 818 Tequila, *Vogue*.

Bad Bunny (Benito Antonio Martínez Ocasio): Global Music Icon

• Full Name: Benito Antonio Martínez Ocasio
• Date of Birth: March 10, 1994
• Place of Birth: Vega Baja, Puerto Rico
• Known For: A pioneer in the Latin trap and *reggeaton* genres, Bad Bunny is one of the world's most-streamed artists. His music, often characterized by his unique blend of genres and bold fashion sense, has broken language barriers to achieve massive global success.
• Key Entities: *Un Verano Sin Ti*, Latin trap, *reggeaton*, Puerto Rico, Grammy Awards, World Wrestling Entertainment (WWE).

The Turbulent Timeline: Breakups and Reconciliation Rumors

The relationship between the model and the musician began in a famously private manner, yet its twists and turns have been intensely scrutinized by the public and media. Their romance was characterized by low-key dates, subtle social media nods, and a shared love for privacy, which only amplified the curiosity surrounding them.

The Initial Spark and the December 2023 Split

Dating rumors first surfaced in early 2023, quickly followed by public sightings that confirmed their status as a couple. Over the course of the year, they were seen together at major events like the Met Gala, NBA games, and various fashion shows, including a high-profile front-row appearance at Gucci’s Spring/Summer 2024 show.

However, the initial whirlwind romance hit a snag. Reports confirmed that Kendall Jenner and Bad Bunny had called it quits in December 2023, just before the holidays. Sources at the time suggested the split was amicable, attributing it to their demanding schedules and the difficulty of maintaining a serious relationship while navigating two massive global careers.

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The May 2024 Reconciliation

The break was short-lived. By May 2024, the couple was reportedly back together, confirming their reconciliation with a series of joint outings. This "on-again" phase saw them attending events and being photographed sharing intimate moments, suggesting they were more serious than ever.

Despite the reunion, a second, more quiet split was rumored in late 2024. Insiders suggested that Jenner wanted to be single again, though they remained friendly. This second separation set the stage for the most confusing and buzz-worthy events of the following year.

The 2025 Reunion: 5 Times They Sparked Fresh Rumors

Despite the conflicting reports of a late 2024 breakup, the first half of 2025 delivered a series of undeniable public sightings that have completely reframed the narrative. These appearances suggest that while their relationship may not be traditionally defined, the bond between Kendall and Benito remains strong.

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1. New York Fashion Week (February 2025)

One of the earliest and most shocking reunions of the year occurred in February 2025. Both Kendall Jenner and Bad Bunny were spotted crossing paths at Calvin Klein’s Fall 2025 runway show during New York Fashion Week. While they did not walk the red carpet together, their presence at the same high-profile, industry-specific event immediately fueled speculation that the "former flames" were reconnecting.

2. The Met Gala After-Party (May 2025)

Fashion’s biggest night, the Met Gala, has historically been a significant marker in their relationship timeline. The 2025 event proved no different. While they arrived separately, sources confirmed that the pair reunited at a private after-party. This cozy sighting, months after their rumored split, was a clear signal to fans that they were still in each other's orbit, even if they weren't officially a couple.

3. Private Dinner Sightings in Los Angeles

Throughout the spring of 2025, reports of them being seen at exclusive, low-key restaurants in Los Angeles began to surface. These private romance sightings, often involving attempts to dodge the paparazzi, reinforced the idea that they were prioritizing discretion while spending quality time together.

4. Subtle Social Media Interaction

Though both are known for keeping their personal lives off social media, eagle-eyed fans noted subtle interactions on platforms like Instagram in mid-2025. A brief "like" on an old photo or a shared location tag, though minor, are often interpreted as cryptic hints about their current status, keeping the mystery alive.

5. The Late-Year "Reconnecting" Source Report

As 2025 drew to a close, a source close to the pair told media outlets that the exes were "reconnecting again" and actively spending time together, suggesting a potential third attempt at a full-fledged relationship. This report, coming after the high-profile fashion week and Met Gala reunions, indicates a clear pattern of attraction that neither star can easily walk away from.

The Evolving Nature of Their Private Romance

The dynamic between Kendall Jenner and Bad Bunny is a perfect example of a modern celebrity relationship that defies traditional labels. Their constant back-and-forth, coupled with their efforts to maintain privacy, suggests a deep connection that transcends the demands of their public lives.

For Kendall, who has always valued her personal space, the relationship with Benito Antonio Martínez Ocasio was arguably her most public yet, but still fiercely guarded. The intense media scrutiny and the pressure of the *Kardashians* franchise likely play a role in her desire for an "off" switch when things get too intense.

For Bad Bunny, whose music often reflects his personal experiences and emotions, the relationship with Kendall has been a source of inspiration and, at times, speculation. Fans often dissect his new tracks for subtle shade or hidden messages directed at the supermodel, a common occurrence in the world of Latin trap.

Ultimately, the latest 2025 sightings at major events like the New York Fashion Week and the Met Gala are the strongest evidence available. They confirm that whether they are officially "dating" or simply very close friends, Kendall Jenner and Bad Bunny remain deeply connected. Their story is a continuous, evolving saga of two global icons who are navigating fame, fashion, and a highly scrutinized, yet very private, romance.

The next chapter in the Kendall-Benito relationship timeline is likely to be written at the next major international event, keeping fans and media alike on the edge of their seats for the next undeniable public sighting.