Drake Hogestyn
Hogestyn married his childhood sweetheart Victoria. The couple have four children: three daughters, Whitney, Alexandra and Rachael; and one son, Ben.
Keshia Chanté
In 2009, Drake was asked by MuchMusic's VJ Sarah Taylor on his past relationship with Chanté when they were 16 years old. Drake said he would be "proud to call [Chanté] an ex-girlfriend".