Buy him a hooker?

Haha, that would be a waste of good money. The boy still couldn't seal the deal!

Doesn't Toronto have a Chinatown and Little Italy? Places like that would be cool unless he is from somewhere like NYC or San Fran or something, then it might be old hat. I don't know what to suggest about the gamer part though - surely he has other interests.

I guess you could buy him a hooker in a computer game.

The only place I know near Toronto is a place to pull off and smoke a bowl in a really pretty setting but I forget where it is.

You could go to a baseball game.

fenriq, that's funny.

Sass, I can't give you any specifics, but like weretable says, Toronto does have a fantastic area for Italian food (around College and...dammit, I can't recall. Someone else who knows the city should be able to help)

Look for Cafe Diplomatico. I have been a number of times with my kid brother, and have never been disappointed.

Also, head up and over to the Danforth area for some WICKED Greek food. I don't even have a single suggestion for names for this one, as I have been once in about 500 years, but we had some amazing Greek food while waiting to go see Neko Case.

Oomonia on the Danforth between Chester and Pape had some pretty spectacular food when I there a few years ago. Although, that was a while ago and things change.

The Ontario Science Center? I hear they have some pretty cool exhibits although I haven't seen them myself.

Also, Honest Ed's (Bloor and Bathurst) has to be one of the coolest places to find stuff ever. I can spend hours lost in that maze of a store, buy three bags worth of stuff and not spend more than $30. That place is amazing.