The Fractured History Of Drake & Rihanna

Certain kinds of relationships don't end so much as they continue to echo. It isn't because they're caught up in romance or unresolved feelings, but because one person doesn't seem to want to let go. The lingering space between Drake and Rihanna fills somewhere in there. It's been labeled as a man talking to someone who has long since stopped answering.

Their names haven’t been linked romantically in years. Rihanna is raising three children with A$AP Rocky. She hasn’t released an album since ANTI. She moves on her own time, with her own map. Yet, every few years, Drake adjusts the rearview mirror. Often, it's through a lyric, and sometimes, through a pointed omission. Every time, it stirs something.

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After For All the Dogs dropped in 2023, it wasn’t long before listeners picked up on “Fear of Heights.” A few lines aimed at a woman from the past. “Why they make it sound like I’m still hung up on you? / That could never be." It was a reference nobody had to squint to catch, but Rihanna's name was soon entangled in gossip once again. She didn’t respond, but the echoes got louder.

Then, Rocky released "Don’t Be Dumb" last month and made sure to defend his lady and the mother of his kids. He didn’t need to say much. “First you stole my flow, so I stole yo’ b*tch." This was never a love triangle. One man stands accused of keeping reaching backward. One woman has moved forward to a blissful family life. Still, when their names appear together in headlines, it causes prying eyes to recall their convoluted history.

They reportedly met in 2005 when Rihanna was filming the music video for "Pon de Replay" in Toronto. The two crossed paths in Drizzy's hometown before they took over the industry. Things would heat up around 2009 when Rihanna was an international superstar with a growing catalog. She was also physically and emotionally recovering after the domestic assault by Chris Brown, a public trauma that turned her personal life into a paparazzi circus.

Around that time, Page Six reported that Rihanna and Drake had been spotted together at Lucky Strike bowling alley in Manhattan. The rumors moved fast, and there was no confirmation. Still, it was one of the first times his name appeared beside hers in a romantic context.

Drake would later describe that night to The New York Times, but his version had less to do with her and more to do with how the moment made him feel. He claimed she used him as a "pawn." He said, "You know what she was doing to me? She was doing exactly what I’ve done to so many women throughout my life. She was showing me how it feels." He also referenced the rumor on his track, "Fireworks": "Who could've predicted Lucky Strikes would have you stuck with me / What happened between us that night it always seems to trouble me."

It wasn’t the first time he spoke publicly about Rihanna, but it was the first time he positioned himself as the wounded one. The framing mattered—although Rihanna didn’t offer a counter-narrative. She rarely does. However, from the start, he spoke as if her presence in his life needed to mean something profound.

Even amid the drama unfolding, Rihanna and Drake released “What’s My Name?” in 2010. The song was flirtatious and clean enough for radio but charged enough to suggest something beneath the surface. Their performance at the 2011 Grammys added fuel to the fire. Fans claimed he watched her as if he believed the fantasy while she performed like a woman doing her job.

Then came “Take Care.” It remains one of Drake’s strongest collaborations with Rih. Again, listeners assumed closeness and reconciliation, but it was Drake’s voice doing the talking. By 2016, “Work” reconnected them sonically, but not emotionally. The lead single off Rihanna's ANTI was a massive hit. They performed it together at the BRIT Awards and again at Rihanna’s tour stops. The videos went viral. The audience read it all as seduction.

That same year, at the MTV Video Music Awards, Drake presented Rihanna with the Michael Jackson Vanguard Award. He delivered a speech about unrequited love and appreciation. “She’s someone I’ve been in love with since I was 22 years old.” It was framed as a tribute, but it read like a claim. He looked as if he attempted to kiss her on stage, but she dodged the moment.

Rihanna later clarified how she felt about the moment. “Waiting through that speech was probably the most uncomfortable part,” she told Vogue in 2018. “I don’t like too many compliments. I don’t like to be put on blast.” Rih added, "We don't have a friendship now, but we're not enemies either. It is what it is."

While Rihanna would refrain from speaking about the OVO boss, Drake continued to drop hints. “Fear of Heights” was a vibe, but the lyrics carried the same tone Drake always uses when he’s trying not to sound wounded. "Gyal can’t run me," he rapped. On "Virginia Beach," Drake spit bars about someone "drawin’ conclusions like you got a Parsons degree or somethin’." Again, a direct Rihanna reference, as she received an honorary degree from Parsons School of Design

He even referenced ANTI, mockingly, repeating "anti" several times on the track. It wasn’t a direct attack, and it didn’t need to be. Drake has always been more invested in insinuation than confrontation. His music doesn’t necessarily call people out. It circles them. Once again, Rihanna didn’t respond.

A$AP Rocky decided to step in on Rihanna's behalf when he dropped Don’t Be Dumb. He never named Drake, but the meaning wasn’t hidden. “This thing between us, it’s not real smoke, but I just don’t f*ck with him,” Rocky told Ebro Darden about his rift with Drake. “We was once friends. I feel like it’s over females. I feel like he wasn’t happy, and he expressed that.”

There’s a version of Drizzy and RihRih's story that still lives online. It's a timeline built from music videos, old interviews, soft glances on stage, and blog tabloid headlines. It’s been edited and re-shared so many times that people forget how little of it was ever confirmed. The real story never had a clean arc. It started asymmetrically and ended without ease.

Rocky didn’t bring a new conflict. He closed the window with Rihanna by his side as the plan the future of their family. Drake, meanwhile, continues his Certified Lover Boy, "Papi" status, with many anticipating what he has in store for Iceman, a release that has kept his fans on their toes. Whether he'll continue the sneak-mention Rihanna trend remains to be seen, but we know listeners will be keeping an ear out to hear if this saga continues.