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

9. Kat Dennings

Drake and Kat went on one date, as he recalled on a 2013 appearance on Ellen. Unfortunately, he didn’t win her over. 

“I just always had a huge crush on Kat Dennings and she was kind enough one night to oblige me and we went out for dinner,” he said. “They don’t call me back after one date according to this.”