Is Drake Dating Model Hailey Baldwin? Milan Cassell June 1, 2016 Hip Hop Entertainment | Hip Hop TV, Film and Video Games, Hip Hop News | Trending Hip Hop Stories Coming off an eventful Memorial Day Weekend and a crazy pool party, Drake was spotted with model Hailey Baldwin in LA on Tuesday night [May 31, 2016]. If you’re not too familiar with her, she’s real tight with the Kardashian/Jenner clan whom she accompanied to the extravaganza and is part of the famous Baldwin acting family. According to TMZ, Hailey and Drake had a nice cozy dinner at popular L.A restaurant The Nice Guy with another couple joining them. Reports say the two were extremely comfortable with one another, ordering drinks with the Canadian rapper even extending an arm around her during the dinner. Baldwin has been linked to another Canadian superstar Justin Bieber in the past, but nothing has come about since then.