Drake and Rihanna are both international superstars, and it goes with the territory that both have been involved in some very high-profile romances, yet all of their relationships have paled in comparison to the level of attention their involvement with one another has garnered. Which is ironic considering they were never officially official—emotional rollercoaster aside.

While on paper, the Barbadian songstress and Toronto rapper make a hot, unstoppable match, something has always fallen short of, well, follow-through, am I right? The fact is, RiRi and Drake had to toy with one another (and by extension, with their fans) for many years before finally maturing enough as individuals to call a spade a spade and recognize their limitations as a pair.

How the Rihanna-Drake saga all began

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Drake met Rihanna for the first time in 2005 when she was shooting the music video for “Pon De Replay” at a restaurant in Toronto. He was introduced as Drake, the guy who “played background music at the restaurant as people ate their dinner.” It was the beginning of a tumultuous and multi-faceted relationship.

Fast forward to 2009, not long after Rihanna’s disastrous split from Chris Brown after he violently assaulted her, and Drake and Rihanna were spotted out on the town in NYC, where she was “making out with him all night.”

Years later Drake would stand up at the 2016 MTV Video Music Awards to present Rihanna with the Video Vanguard Award while taking the opportunity to tell this story of their first encounter and profess his love for all the world to hear.

And who can forget their amazing chemistry on their collaboration for her song “Work,” which convinced the whole world that the two must be together.

So what went wrong?

Why it didn’t work out

Before we begin parsing out how and why it never really worked out between Drake and Rihanna, it’s first worth acknowledging the fact that they were never officially a couple, seemingly due to longterm hesitation and confusion stemming from both sides.

Between 2009, just months after their first date, up until very recently, anyone who’s paid attention to the spectacle of their romance has been bombarded with an endless stream of alleged makeups, breakups, hot dates, steamy collaborations, declarations of (sort of) togetherness, declarations that their relationship was open, sordid stories of cheating or wandering eyes…

And as though to put a big ol’ cherry on top, there’s the persistent denial that they were ever a thing to begin with, mostly but not entirely on Rihanna’s end.

In a famous 2010 interview with The New York Times, Drake confessed he felt used by Rihanna:

I was a pawn. You know what she was doing to me? She was doing exactly what I’ve done to so many women throughout my life, which is show them quality time, then disappear. I was like, ‘Wow, this feels terrible.’

But then in a followup interview, he dialed it back a bit, saying that Rihanna is an “overwhelming and incredible person.” Of course, Rihanna dispelled the notion that she’d used Drake at all, using ‘we’ statements all the way.

“I definitely was attracted to Drake, but I think it is what it is, like it was what it was. We didn’t want to take it any further. It was at a really fragile time in my life, so I just didn’t want to get too serious with anything or anyone at that time.”

Autonomous over amorousness…x2?

Drake has taken advantage of many an interview to detail how his ambition and his passion for music make him hyper independent, which in turn makes finding a romantic partner challenging. Ultimately, what it comes down to is that he’s single because he loves his freedom.

“I love my space,” he says. “I love my work and I love my routine, and for me to break that for somebody it would just have to be like a really special person that fits into that puzzle and that is supportive of the things I’m doing…” Drake confessed.

It has to be someone that has taste in music, it has to be somebody, you know, that I get along with so much to the point when we’re separate I’m feeling like I can’t function properly without their presence.

“Hopefully I can find somebody that can just stand beside me at the wheel and help me steer while we keep the journey going as opposed to me having to pull over because that person is getting seasick,” he continued.

On being called a “hopeless romantic,” Drake explained that it was his response to being told, “You can’t be single forever.” The fact that he hasn’t settled down with anyone has made him the subject of multiple inquiries. In a moment of vulnerability, Drake admitted that he has doubts about relationships.

You look behind the curtain at some people’s relationships and they’re not as peachy as they seem.

Rihanna is similarly in bed with her independence, having stated that she’s both “not looking for a man,” and that she would “‘wait forever’ if that’s what it takes for a man she can actually connect with to show up.”

Much like Drake, she also has expressed very similar issues with valuing her independence and also wanting someone she could trust.

And I get fearful of relationships because I feel guilty about wanting someone to be completely faithful and loyal, when I can’t even give them 10 percent of the attention that they need. It’s just the reality of my time, my life, my schedule.

After attempting to reignite the flame in 2016, Drake and Rihanna abruptly called it quits in October of that year, not long after Drake declared his love at the MTV Video Music Awards, a stunt of which RiRi later said, “Waiting through that speech was probably the most
uncomfortable part. I don’t like too many compliments; I don’t like to be put on blast.” Ouch.

Around that time it was reported that, “Rihanna and Drake are seeing other people at the moment. They are not exclusive anymore. They still love each other, but their schedules have gotten in the way.”

Friends does not mean the ends

In 2018, Rihanna was very matter-of-fact when she stated that she and Drake were no longer even friends , saying, “We don’t have a friendship now, but we’re not enemies either. It is what it is.”

Yet if history has taught us anything, it’s that RiRi and Drake are forever unfolding. For starters, Rihanna’s recent breakup with Saudi businessman Hassan Jameel back in January seems to have coincided with a reconnection with Drake.

At the very least, they’re back on actively friendly terms, as evidenced by the fact that she spent “several hours” at his birthday party this past October before her breakup, and he seemed pretty happy about it.

Perhaps this is a simple testament to the old adage “time heals all wounds.” Following the party, the now-notorious pair made waves when they were seen attending the Yams Day benefit concert together in Brooklyn.

They didn’t appear romantically linked, however, plus RiRi was also spotted getting cozy with A$AP Rocky. The gossip mill aside, Drake and Rihanna seem capable of being friends these days, which means that even if their love boat sailed long ago, they’ve matured as individuals and still see good in each other.

Bottom line: there is profound value in understanding why relationships don’t work out. Where there is learning, there is no such thing as failure. So while yes, there’s been drama surrounding both their romance and their many breakups, over time they both got to know themselves better, and are surely better off for it.

Since they’re both super ambitious, independent, and not into compromising their ideals, it’s nigh on impossible for them to be compatible rather then competitive. Instead, they seem content to take their time playing the field until they meet their better halves.

Read about Rihanna’s powerful confession on motherhood here and Drake’s incredible approach to being a father here.

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