When I bring people who have never been to PIttsburgh before to Pittsburgh, here is what we do:
We go to the Gandy Dancer and get drinks and get a lite dinner. Gandy Dancer is the definition of casual upscale. Dark, warm, polished....feels comfortable and refined but not pretentious. Their Brie plate is great (if they still have it) as is their fish chowder and their rolls. I haven't had much else but all this treats me well.
Then, after drinks, we peek our heads in the Grand Concourse, marvel at it, be glad we did not spend the money to eat *there*. Then, we head up the incline to the top of Mount Washington where we go to the Georgetown Inn and grab an after dinner drink, and marvel at the view.
Then we leave.
This, is Pittsburgh that I love.