Player! See the list of women Drake has dated in the past (Very Prolific!)

2. Rihanna

Rihanna is Drake’s most on-and-off relationship. The two first got together way back in 2009 when Drake was first entering the public eye, linking once again in 2014 on the European leg of his Would You Like A Tour. In summer 2016, the couple seemed to have reunited for a time after working on new music together, with Drake proclaiming at the VMAs “She is someone I’ve been in love with since I was 22 years old.”