As weird it may seems, when I am in the mood to try something, I pick one of the restaurants in this guy's list:
http://jamiesarner.com/toronto-restaurant-reviews/. I am really fond of European food, but I am looking forward to try some Japanese dishes (I read Haruki Murakami's books and he mentions the food that the characters eat way too often.)
Since I really love Italian food, among my top favourite restaurants are:
Trattoria Giancarlo’s
Little Italy, 41 Clinton Street at College
Mercatto
330 Bay Street
La Bettola di Terroni
Downtown, 106 Victoria Street