2. Aubrey Plaza
Aside from having the same first name (…think about it) we believe these two would make a magical comedic duo. Drizzy prides himself on being able to make his women of past and present giggle, and Aubrey’s proven love of sweaters means they’re already compatible.
So… the next time they both touch down in New York, Drake will take her out for lobsters and shrimp at the Oyster Bar in Grand Central (it’s not touristy, it’s classic) and then head to a late night show at the Upright Citizens Brigade. Plaza is a pro, but Drake’s improvisational and sketch comedy skills could use some work, so he’d be happy to sit in the audience–plus, he likes a woman who is confident in her abilities and popping off on her own. After the show, they’ll carouse with mutual friend Judd Apatow and the cast of his latest movie until the wee hours. Drake may or may not try too hard to make people laugh.