Bad Bunny, the global reggaeton sensation whose real name is Benito Antonio Martínez Ocasio, remains one of the most talked-about celebrities when it comes to his romantic relationships. As of 2025, the 31-year-old Puerto Rican artist is officially single, but his love life continues to generate headlines and speculation among fans worldwide. The Grammy-winning musician has been notably private about his personal relationships, once telling Vanity Fair that he has “no commitment to clarify anything to anyone” regarding his romantic life.
Throughout his career, Bad Bunny has been linked to several high-profile relationships, most notably with model Kendall Jenner and jewelry designer Gabriela Berlingeri. His dating history has been a rollercoaster of public appearances, breakups, reconciliations, and ongoing speculation about potential rekindled romances. The artist’s approach to love mirrors his artistic expression—passionate, authentic, and deeply connected to his Puerto Rican roots.
What makes Bad Bunny’s romantic timeline particularly intriguing is how his relationships often interweave with his music and public appearances. From subtle lyrical references to coordinated fashion week appearances, every aspect of his love life becomes part of a larger narrative that fans eagerly follow. As we enter 2025, the question of who Bad Bunny is dating remains as as ever, with recent developments suggesting that his past may hold the key to his romantic future.
Current Relationship Status: Officially Single
Bad Bunny (Image via Getty)
Bad Bunny entered 2025 as a single man, having ended his on-and-off relationship with Kendall Jenner in September 2024. The breakup marked the end of a tumultuous romance that had fans since early 2023. According to sources close to the situation, Jenner was the one who “decided she wanted space” after their summer together in Europe, with insiders noting that “she wants to stay single for now” and “isn’t ready to be tied down at the moment.”
The decision to remain single appears to align with both celebrities’ current life priorities. Bad Bunny has been focusing intensively on his music career, releasing his latest album “Debí Tirar Más Fotos” in January 2025, which has been interpreted by fans as a love letter to Puerto Rico and potentially to his past relationships. Meanwhile, Jenner has been described as “enjoying this era” of independence and taking time to focus on her modeling career and business ventures.
Despite their official single status, both Bad Bunny and Jenner have been spotted at various events throughout 2025, leading to continued speculation about their relationship dynamics. Their ability to maintain a “friendly” relationship post-breakup has kept fans hopeful for a potential reconciliation, especially given their history of breaking up and getting back together.
The Kendall Jenner Chapter: A Timeline of On-and-Off Romance
The relationship between Bad Bunny and Kendall Jenner has been one of the most closely watched celebrity romances of recent years. Their story began in February 2023 when they were first spotted together at Wally’s restaurant in Beverly Hills, potentially on a double date with Hailey and Justin Bieber. What started as casual dating quickly evolved into something more serious, with the couple making their relationship increasingly public throughout 2023.
Their romance reached its peak during the 2023 Met Gala season, where they attended after-parties together and were described by sources as becoming “more serious.” The summer of 2023 saw them traveling together, attending Lakers games courtside, and integrating into each other’s social circles. Bad Bunny even referenced their relationship in his music, with lyrics on Eladio Carrión’s track “Coco Chanel” that appeared to reference Jenner’s zodiac sign and her ex-boyfriend Devin Booker’s basketball team.
However, their first breakup came in December 2023, only to be followed by a reconciliation at the 2024 Met Gala. A source told People at the time that “it’s like they needed the break to miss each other enough to figure things out” and that “they always had this crazy attraction to each other.” Their rekindled romance included romantic dates in Paris and Puerto Rico throughout the summer of 2024, but ultimately ended again in September 2024.
The most recent development in their relationship timeline occurred in February 2025, when both attended the Calvin Klein Collection show during New York Fashion Week. Bad Bunny was spotted in the front row while Jenner walked the runway, leading to viral TikTok videos and renewed speculation about their connection.
Gabriela Berlingeri: The Puerto Rican Connection
Bad Bunny (Image via Getty)
Perhaps the most significant relationship in Bad Bunny’s romantic history is with Gabriela Berlingeri, a Puerto Rican model and jewelry designer who founded the brand Diciembre Veintinueve. Their love story began in April 2017 when they met at a restaurant in Puerto Rico after Bad Bunny performed as a surprise guest at a Zion and Lennox concert. What started as a chance encounter evolved into a five-year relationship that would deeply influence Bad Bunny’s music and personal growth.
Berlingeri and Bad Bunny kept their relationship private for the first three years, only going public in 2020 when they were spotted together at a Miami basketball game. During the pandemic, they shared glimpses of their life together in Puerto Rico through social media, and Berlingeri even contributed to Bad Bunny’s music, recording references for Jennifer Lopez’s vocals on the track “Te Gusté.” Their relationship reached a milestone when they made their red carpet debut at the 2021 Billboard Latin Music Awards and adopted a puppy together in 2022.
The couple’s relationship was characterized by its deep connection to Puerto Rican culture and Bad Bunny’s artistic evolution. Berlingeri appeared in several of his music videos, most notably as his bride in the “Titi Me Preguntó” video in June 2022. However, by August 2022, they had split, with Bad Bunny being spotted with another woman at a club.
2025 Reconciliation Rumors and Recent Developments
The release of Bad Bunny’s album “Debí Tirar Más Fotos” in January 2025 has sparked intense speculation about a potential reconciliation with Gabriela Berlingeri. Fans have analyzed the album’s lyrics, particularly the track “BAILE INOLVIDABLE,” which appears to reference their relationship. The song describes a woman who taught him to dance and care, with the music video featuring Bad Bunny in a light blue suit reminiscent of what he wore to his 2021 red carpet debut with Berlingeri.
Adding fuel to reconciliation rumors, Berlingeri attended the album’s listening party in January 2025, though she wasn’t photographed with Bad Bunny. Later that month, both were spotted separately at an Elvis Crespo concert in Puerto Rico, with Bad Bunny maintaining an incognito appearance while Berlingeri was seen enjoying the show.
The timing of these appearances, combined with the album’s seemingly personal lyrics, has led fans to speculate that Bad Bunny and Berlingeri may be quietly rekindling their romance. Their history of maintaining a friendship after their breakup, with Bad Bunny previously stating that “Gabriela and I are best friends,” suggests that a reconciliation wouldn’t be entirely unexpected.
Other Rumored Connections
Bad Bunny (Image via Getty)
While Bad Bunny’s most significant relationships have been with Jenner and Berlingeri, he’s also been the subject of various dating rumors throughout 2025. Most notably, speculation arose about a potential romantic connection with Becky G following their reunion at the 2025 iHeart Music Awards. The two artists, who collaborated on the hit song “Mayores” in 2017, shared what observers described as an “undeniably warm” reunion, complete with a heartfelt hug.
However, these rumors appear to be unfounded, with sources confirming that there’s “no confirmation or solid evidence suggesting a romantic connection” between Bad Bunny and Becky G. Their interaction at the awards show seems to have been purely friendly, highlighting the tendency for fans and media to analyze every public interaction involving the Puerto Rican superstar.
Country music superstar Kenny Chesney has long fascinated audiences with his chart-topping hits and electrifying performances, but his romantic life has remained largely shrouded in mystery. The 57-year-old “She Thinks My Tractor’s Sexy” singer has experienced both public heartbreak and private relationships throughout his career, leaving fans constantly wondering about his current dating status. From his highly publicized four-month marriage to Academy Award-winning actress Renée Zellweger to rumored relationships with various women in the entertainment industry, Chesney’s love life has been a subject of intense speculation.
Recent developments in 2025 have sparked renewed interest in the country star’s romantic endeavors, with conflicting reports and viral conspiracy theories creating confusion among fans and media outlets alike. While some sources suggest he’s been in a long-term relationship since 2012, others point to new romantic connections that have emerged in recent months. The singer’s preference for privacy has only fueled more speculation, as he rarely discusses his personal relationships in interviews or on social media.
Adding to the intrigue are recent viral TikTok theories and paparazzi sightings that have country music fans dissecting every photo and social media post for clues about Chesney’s romantic status. With multiple conflicting reports circulating about his dating life, separating fact from fiction has become increasingly challenging. This comprehensive look at Kenny Chesney’s relationship history and current romantic status aims to clarify the confusion surrounding one of country music’s most eligible bachelors.
Kenny Chesney’s Relationship History
Kenny Chesney (Image via Getty)
Kenny Chesney’s most notable romantic relationship was his brief but highly publicized marriage to actress Renée Zellweger in 2005. The couple met just five months before their Caribbean island wedding ceremony in May 2005, surprising fans and media with their whirlwind romance. However, their marriage lasted only four months, ending in September 2005 when they announced their separation and subsequent annulment.
The annulment became particularly controversial when Zellweger cited “fraud” as the reason, sparking widespread speculation and rumors about Chesney’s sexuality. In a later interview with Oprah Winfrey, Chesney explained that he “panicked” and wasn’t ready for marriage, citing his grueling touring schedule and passion for music as factors that left little time for relationships. Zellweger later clarified that the term “fraud” was simply legal language and didn’t reflect negatively on Kenny’s character.
Following his divorce, Chesney dated several women, including Miss Tennessee 2005 Amy Colley and ESPN broadcaster Jenn Brown, who made history as the first female correspondent for Inside The NFL. However, these relationships didn’t develop into anything serious, as the country star seemed to focus primarily on his music career.
The Mary Nolan Connection
Since 2012, Kenny Chesney has reportedly been in a relationship with Mary Nolan, a woman who has largely stayed out of the public spotlight. Their relationship has been characterized by extreme privacy, with the couple rarely being photographed together or making public appearances as a pair. Mary Nolan was first publicly identified as Chesney’s girlfriend when reports emerged of them being spotted together, including on an Italian vacation.
The couple made one of their few public appearances together at the 2016 Country Music Association Awards ceremony, where Chesney received the prestigious Pinnacle Award and Nolan was photographed giving him a congratulatory kiss. Prior to that, in 2014, they were spotted at the American Country Countdown Awards in Nashville, though Nolan sat behind Chesney in the audience rather than beside him.
One of the most telling signs of their relationship came in December 2022, when Chesney posted a heartfelt tribute on Instagram to Nolan’s deceased dog, Ruby. The emotional post revealed the depth of their connection, as Chesney wrote about how Ruby and Mary “ended up saving each other” when she adopted the dog from a shelter. He even dedicated a song called “Da Ruba Girl” to Ruby and other rescued dogs, demonstrating how intertwined their lives had become.
Recent Developments and Conflicting Reports
Kenny Chesney (Image via Getty)
The year 2025 has brought conflicting information about Kenny Chesney’s romantic status. One report suggests that Chesney made his red carpet debut with a new girlfriend named Sarah Johnson at the 2025 CMA Awards. According to this source, Johnson is described as a “stunning blonde beauty who works as a nurse in Nashville,” and the couple had reportedly been dating for over a year before going public.
However, the reliability of this information is questionable, as other sources continue to reference his long-term relationship with Mary Nolan. The lack of recent photographs or confirmed sightings of Chesney with either woman has made it difficult to verify his current relationship status.
Viral Conspiracy Theories and Social Media Speculation
Adding to the confusion surrounding Chesney’s love life are recent viral conspiracy theories that have emerged on social media platforms, particularly TikTok. In early 2025, a particularly outlandish theory gained traction, suggesting that Chesney was romantically involved with fellow country artist Megan Moroney.
The conspiracy theory originated from a TikTok user who noticed that Moroney had been posting numerous island and boat pictures, similar to Chesney’s lifestyle preferences. The theorist also pointed to the fact that they had toured together and that Moroney had recently posted about one of Chesney’s songs as evidence of their supposed relationship. However, this theory appears to be purely speculative, as Moroney has been more credibly linked to country singer Riley Green, with evidence including suspicious social media activity and tropical vacation photos.
Kenny Chesney’s Approach to Privacy
Kenny Chesney (Image via Getty)
Throughout his career, Kenny Chesney has maintained a notably private approach to his personal relationships. Unlike many celebrities who share details of their romantic lives on social media or in interviews, Chesney has consistently chosen to keep his dating life away from public scrutiny. This preference for privacy has been evident in his relationship with Mary Nolan, where both parties have avoided the spotlight and rarely made public appearances together.
Chesney’s commitment to privacy extends beyond just avoiding paparazzi; he rarely discusses relationships in interviews and maintains strict boundaries between his public persona and personal life. This approach has likely contributed to the longevity of his relationship with Nolan, allowing them to develop their connection away from media pressure and public speculation.
Current Status and Future Outlook
As of June 2025, Kenny Chesney’s exact relationship status remains somewhat unclear due to conflicting reports and his preference for privacy. While some sources suggest he may have moved on to a new relationship with Sarah Johnson, others indicate that his long-term relationship with Mary Nolan may still be ongoing. The lack of recent confirmed sightings or official statements from Chesney himself makes it impossible to definitively determine his current romantic situation.
What remains clear is that Kenny Chesney continues to prioritize his music career while maintaining his desire for privacy in personal matters. Whether he’s single, in a long-term relationship, or exploring new romantic connections, the country star seems committed to keeping those details away from public consumption. Fans will likely have to wait for official confirmation or more concrete evidence before knowing the true status of Kenny Chesney’s love life.
