We do have our favourites that we always go back to and know we will not be disappointed:
The Drake - We have been going here for awhile. I love their brunch menu (now especially because of the Little Drake for $6 for kids), but also their dinner menu. They have a great patio both at street level and on the roof. It's trendy, it's on the west side, and is always a great place to take guests.
Pizzeria Libretto (Ossington) - This is the best pizza place in the city. Other places make Neapolitan style pizza, but this is my favourite place. And I always save room for dessert, their affogato (gelato with espresso poured overtop) is amazing. This is a great family restaurant too, although they do not take reservations, so you usually need to be prepared to wait.
Real Sports - One of the best sports bars in North America. When it first opened we went all the time, then it got a little too crazy and pretentious, impossible to get a table, set seating times, etc. But it's calmed down a bit and is a great place to go before a Raptors/Jays game (we never go to the Leafs), or to watch a game. They have a pretty good menu all around, but we usually get wings, and beer, of course. The music is loud when the game isn't playing, and E is always entertained by that and the numerous televisions.
The Harbord Room - The Harbord Room makes the best burger I've ever had in my life, no word of a lie. They also have oysters and fun cocktails, so I'm all set. It's small and if you don't have a reservation you may have to wait. Sitting at the bar is always fun too since you get to interact with the bartender. This is not a place I would take E, too small and always busy, not the right crowd.
Honourable mentions go to the Biermarkt on King West, Fresh on Crawford, Queen Margherita Pizza, The Keg (Haunted Mansion and York St.), Beer Bistro, and Barque