Back in December 2015, the rapper shared a pic of him and NBA sports broadcaster Rosalyn to Instagram and cheekily captioned the pic: “When the post game makes you forget about what happened during the actual game @rosgo21.” The status of their relationship was never confirmed and no one knows if these two are still on good terms.
However, following the Drake and Pusha T drama, Rosalyn retweeted a tweet in agreement with Pusha T.



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. Maybe he's just not the monogamous type, despite his sensitive image.
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 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.
If there’s one thing that’s for sure is that when it comes to Drake’s love life he is fiercely private, seeing him with a woman that he’s dating is a very rare sighting.