Hey Dr. E W,
Good to see you!
Places:
Underground shopping mall (thursday and friday stores opened till 9
m + st-catherine street (everrything some stripclubs and as time passes mostly clothing
((...boring
Crescent street and surrounding streets (bars, dance clubs and restaurants); also Mcgibbins irish pub on Mckay is good. Their hamburgers are great. Their are many good irish pubs...but that one is my fav.
St-Laurent street (below sherbrooke: chinatown filled with restaurants chinese and vietnamese, cleos (intersection st-catherine; although area is being destroyed by the city for a corporate tower) + (above sherbrooke: night clubs and restaurants; lots of life after 12)
Old montreal (a bit of everything; many restaurants; for a good steak you could go to Gibby's).
St-Denis (mostly restaurants)
Mont-Royal (plateau) some restaurants and bars
Food:
I agree with the schwartz's suggestion (on st-laurent north of sherbrooke)
Also you should give poutine a try; a good place is la banquise on Rachel (it is opened 24 hrs) or any belle province is pretty good
Montreal steamie hot-dogs and fries (belle province)
Montreal has many vietnamese and chinese restaurants ( you could find many in chinatown although they are scattered throughout the city
Hope this list helps