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.