1. Rihanna
It was always going come back to bad girl RiRi for the number one spot. Their relationship has also had something of an on-and-off nature; they were first linked in 2009 through to 2010, as both of them were finding their feet in the industry and starting to experience real fame for the first time. She, however, was reportedly not looking for anything serious, and quickly broke it off. Drake has stated since that it hit him hard, and it shows; they are still occasionally snapped together in nightclubs getting cosy. It seems that he just can’t let this one go.
Source: Cosmopolitan, Therichest
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