The Unofficial Timeline: What Really Happened Between Drake And Rihanna?

For over a decade, the relationship between two of music's biggest titans, Drake and Rihanna, has captivated fans and fueled endless speculation. Their chemistry, whether on stage, in music videos, or simply caught by paparazzi, was undeniable. But what exactly was the nature of their connection? Was it a passionate romance, a deep friendship, or something perpetually in between? Let's dive into the long, winding, and often mysterious timeline of Drake and Rihanna.

The Early Days: A Bowling Alley "Meet-Cute" and Budding Romance

The story of Drake and Rihanna's connection reportedly began in a way that sounds straight out of a romantic comedy: at a bowling alley. It was May 2009, just a few months after Rihanna's highly publicized and traumatic split from ex-boyfriend Chris Brown, who violently assaulted her in February 2009. The world was watching Rihanna's every move, and it didn't take long for new rumors to emerge.

According to reports from Page Six and other outlets, Rihanna was spotted making out with Drake at a Lucky Strike bowling alley in New York. This sighting, where the two were allegedly seen on a date and even shared an intimate kiss, sparked the very first romance rumors between the talented singers. It was a surprising development, given the fresh wounds from her previous relationship, but it set the stage for years of an intriguing, on-again, off-again dynamic.

From Rumors to Collaborations: The Musical Connection Deepens

While the initial bowling alley sighting was a whisper, their musical collaborations turned the volume up. Drake and Rihanna's relationship timeline is a long one, spanning from these early days when the two collabed on songs with steamy, emotional music videos. Their artistic synergy was palpable, leading to some of their most iconic hits.

Over the years, despite the public's constant curiosity, the nature of their relationship remained elusive. There were periods of intense closeness, followed by times when they seemed to drift apart. Yet, the photographic evidence often told a different story than any public denials. For instance, in 2014, the twosome were spotted in London enjoying a day out, further fueling the "are they or aren't they?" debate that defined their connection for so long.

One of the most significant musical reunions came with Rihanna's massive 2016 hit, “Work.” Fresh from collaborating on "Work," she and Drake were keeping company again, both on stage and off. Their performances of the song were electrifying, showcasing an undeniable chemistry that left fans convinced they were more than just friends. However, during this period, Rihanna often clarified her relationship status, for example, when talking with Ellen DeGeneres, suggesting she was single.

The Public Declarations and the "In Love With" Moment

The peak of their public romantic speculation came in 2016, leading up to one of the most memorable moments in MTV Video Music Awards history. Rihanna and Drake's mysterious relationship had made headlines for years, all leading up to the rapper's love declaration at the 2016 MTV Video Music Awards.

The 2016 MTV VMA Speech

At the 2016 VMAs, Drake was tasked with presenting Rihanna with the Michael Jackson Video Vanguard Award. What followed was a speech that left no doubt about his feelings. He famously declared, "She's someone I've been in love with since I was 22 years old." He continued to praise her, calling her "one of my best friends in the world" and "a living, breathing legend in our industry." The moment was incredibly raw and public, sending shockwaves through the internet and confirming what many fans had suspected for years: Drake was deeply, openly smitten with Rihanna.

Following this declaration, a source close to the "Umbrella" singer told ET that Drake and Rihanna were "definitely a couple" and "fully dating." For a brief period, it seemed like the on-and-off saga had finally settled into a confirmed romance. They were seen together frequently, enjoying time both privately and publicly, and their affection for each other was apparent.

The Unraveling: From "Couple" to "No Friendship"

Despite the public confirmation and Drake's heartfelt declaration, their "fully dating" status didn't last long. By October 10, 2016, E! News reported that Drake and Rihanna had reportedly broken up. Their source indicated that the pair “are seeing other people at the moment. They are not” together. The whirlwind romance, once again, came to an end, leaving fans to wonder what went wrong after such a public display of affection.

Their last public link together was in 2017 when Drake gave her a birthday shout-out at one of his concerts, a gesture that suggested some lingering fondness, or at least respect. However, the definitive word on their relationship came in 2018 when Rihanna addressed the situation directly in an interview with Vogue.

In that candid conversation, Rihanna revealed that she and Drake were no longer close. She specifically addressed the 2016 VMA declaration, stating, "We don't have a friendship now, but we're not enemies either. It is what it is." She elaborated on the VMA moment, admitting, "The VMAs moment, you know, he said, 'I'm in love with her' or whatever. That was a bit uncomfortable for me, because I know what it felt like to be in that position, and I've had that experience before." This statement clarified that while she appreciated his feelings, the public nature of it created a dynamic that ultimately led to the dissolution of their close bond.

Where They Stand Now: Moving On

After years of being in an on-and-off relationship, Rihanna's 2018 revelation marked a clear turning point. Minus a few interactions since their breakup, both moved on. Rihanna has since found love and started a family with A$AP Rocky, while Drake continues to navigate his highly successful music career and personal life. The intense romantic speculation surrounding them has largely subsided, replaced by a mutual respect for each other's careers and individual paths.

While the "what happened with Drake and Rihanna" question might never have a simple answer, their journey together provided a fascinating glimpse into the complexities of celebrity relationships, public declarations of love, and the challenges of maintaining a connection under intense scrutiny. Their story remains a significant chapter in pop culture history, a testament to a powerful, albeit complicated, bond.