For all his talk of feelings, Drake is either really into being single or he's had some bad luck getting partners to stick. That we know of, actually, since Drizzy has never officially confirmed any long-term relationships, which for his sake, we hope is just because he was trying to maintain a semblance of privacy, not because he hasn't had one.
What he has had, however, are a lot of dates and open flirtations.
The Recent Rumors
Most recently, there was the highly entertaining episode in which he jumped onto London rapper Stefflon Don's Instagram Live session as she and her friend were interviewing men who wanted to date her. Drake unabashedly put himself in the running.
“I can organize all your heels and your fits and your wigs for you,” Drake said, listing his dating qualities, during the November video. “I’ll make sure they’re all color coded.”
The two did know each other already, since she appeared on Drake's Scorpion track "Peak," so the offer wasn't entirely out of left field. He was reportedly spotted out with Stef in Miami in late November, but all the photographic evidence of the date has since disappeared from the internet. Since they live in such different parts of the world, we don't have high hopes for that romance, but it sure was fun to witness for 10 minutes.
Before Stef, the world was much less tickled by the rumor of another date Drake supposedly arranged. This time, it was 18-year-old model Bella Harris, whom he has apparently known since she was 16. The gossip was that he had shut down an entire restaurant in D.C. to have some quiet time with Harris, something both her camp and his vehemently denied once it leaked. Major controversy somewhat avoided.
For a hot second in April 2018, we read a few tabloid reports that Drake had been on a "string of dates" in London with 20-year-old British singer-songwriter Raye after some "late-night studio sessions." For her part, Raye pretty much brushed off the talk last fall, telling Metro UK, "I’m just excited to keep growing and these stories come and go."
Not that Drake is solely into younger women. In fact, Heidi Klum revealed that last February, he texted her shortly after Ellen DeGeneres had cornered the model into admitting she liked him. Too bad (for him) he did so the week after she met Tom Kaulitz, to whom she's now engaged.
The Pre-2019 Flirtations
Another older woman he had better luck with was Jennifer Lopez, whom he dated for maybe two months beginning in December 2016. For those of us on the outside, it was a very long two months of wondering if they were just trolling us on Instagram. But Drake seemed to confirm the rumors later with his song "Diplomatic Immunity."
If you're able to do the math, you know that early 2017 was one of the two times he hooked up with French porn star Sophie Brussaux, the mother of his baby Adonis, who was born on October 11 of that year.
Also in 2017, Drake accompanied NBC Sports reporter Rosalyn Gold-Onwude to the NBA Awards. He reportedly arranged Bella Hadid’s birthday party in June. Then he was spotted on a date with The Florida Project star Bria Vinaite in Toronto. She later told Vanity Fair that Drake was just a fan, and all they did was talk about her movie.
The "Relationships" That Fans Will Never Let Go
Now, we have traveled back in time to reach Drake's three probable/possible friends with benefits. There was Serena Williams, whom he was photographed nuzzling at a dinner date in 2015. He made a few public appearances with her, too, and was at one point blamed for making her lose the U.S. Open, but neither star ever confirmed they were more than friends.
Nicki Minaj set the record straight back in 2014 about everyone's wish for the two Young Money label-mates to couple up. Basically, it wasn’t happening, but it could have.
Which brings us to the one lady who was linked to Drake for the longest period of time: Rihanna. They first went on a date all the way back in 2009, right after her first breakup from Chris Brown. But despite the fact that the collaborated for years after that, it seemed for a while that she didn't return his unabashed love for her. That is, until 2016, when they made "Work" together, and she deigned to let him follow her around like a puppy. He frequently professed his love for Riri onstage, on Instagram, in a matching tattoo, and on a billboard.
We still don't know what happened to split up Drake and Rihanna in 2016, but it looks to us like that was his last real relationship. Did she break him? Did he cheat on her? Maybe he's just not the monogamous type, despite his sensitive image. Whatever the real story is, speculating about a man whose every song drips with sex or romance or both is just so much fun.