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It’s So Clear Why People Still Talk About Drake’s Relationships

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Drake’s love life has generated nearly as much conversation as his chart-topping catalog, and the receipts go back over a decade.

The rapper born Aubrey Drake Graham built an empire on vulnerability, turning breakups, flings, and one very famous almost-romance into some of his biggest records. A new Nicki Swift feature, “It’s So Clear Why People Still Talk About Drake’s Relationships,” retraces that timeline — from a Toronto video shoot in 2005 to a paternity reveal in 2018 — and lays out exactly why fans still can’t stop dissecting his dating history.

• Drake and Rihanna first crossed paths in Toronto in 2005 during the shoot for her “Pon de Replay” video, reportedly grew romantic around 2009 at Lucky Strike, and inspired collaborations including “What’s My Name?” and “Work.”
• At the 2016 MTV Video Music Awards, Drake told the crowd he’d been in love with Rihanna “since I was 22 years old,” but by 2018 Rihanna said the two were no longer speaking.
• Drake’s 2018 fatherhood reveal with French artist Sophie Brussaux, mother of his son Adonis, became public alongside long-running speculation over Keshia Chanté as the “Keke” referenced in “In My Feelings.”

The Rihanna Timeline That Won’t Quit

No name comes up faster in a Drake relationship rundown than Rihanna’s. Their connection dates back to 2005, when a teenage Drake was on set in Toronto for her “Pon de Replay” video, and the pair reportedly turned romantic years later in 2009 at the Los Angeles bowling alley-lounge Lucky Strike. What followed was a professional and personal loop that produced “What’s My Name?” and “Work,” two of the biggest crossover records either artist has had.

The relationship’s most quoted moment came at the 2016 VMAs, where Drake presented Rihanna with the Video Vanguard Award and told the room, in front of cameras and everyone, that he’d been in love with her “since I was 22 years old.” It’s the line that cemented Rihanna’s status as the one Drake fans still bring up first.

“I’ve been in love with her since I was 22 years old” — Drake, presenting Rihanna with the Video Vanguard Award at the 2016 VMAs.

The fairy-tale framing didn’t hold. By 2018, Rihanna had confirmed publicly that the two were no longer on speaking terms, closing the loop on what’s still described as the one that got away.

The Early Flames and Recurring Muses

Long before the Rihanna saga, Drake’s love life was already fodder for speculation. Canadian singer Keshia Chanté has been tied for years to “Keke,” the name Drake repeats throughout “In My Feelings,” while wedding planner Jade Lee is remembered as one of his early, lower-profile relationships. Those teenage-era connections set the template for a career built partly on turning real names and real heartbreak into radio hits.

From there, the list of rumored entanglements only grew louder: Nicki Minaj, Jennifer Lopez, and Kylie Jenner have all been linked to Drake at various points, each pairing generating its own tabloid cycle. It’s the same dynamic that’s made relationship retrospectives on stars like Megan Fox such reliable reading — famous names dating famous names tends to write its own headlines.

Fatherhood Changes the Story

The most consequential development in Drake’s personal history arrived in 2018, when his private relationship with French artist Sophie Brussaux became public knowledge — along with the fact that the two share a son, Adonis. It was a shift from tabloid romance to something more permanent, and it reframed how fans read every love song that came after it.

Put together, the Rihanna arc, the early flames, the rumored A-list flings, and the Adonis reveal are why Drake earned the “certified lover boy” label long before he made it an album title — his discography and his dating history have always been the same document, just told two different ways.