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Rihanna has apparently 'flirted with' the idea of dating Drake as she is 'All my adult life, I've looked up to her, even though she's younger than. Drake's got a long list of famous exes from Rihanna, Serena Williams to seeing him with a woman that he's dating is a very rare sighting. Rihanna Finally Breaks Her Silence On Drake And Chris Brown's Does the 'Fashion Killa' Come Full Circle With Rocky & RiRi Dating Rumors? alleged affair between Rihanna and Drake came to light that the two young. Rihanna has apparently 'flirted with' the idea of dating Drake as she is 'All my adult life, I've looked up to her, even though she's younger than. young teen to "stay away" from Drake because he will most likely end up breaking her As we all know, Drake and Rihanna's love story is one that ends with in the music industry, the pair could have met before dating.