Mess Hall on Sherbrooke (nice n small upscale resto), then head to Dairy Queen a few metres away (you can enjoy it on the terasse or continue walking with it, use your judgment), then take a stroll through Westmount Park (very beautiful and costs you nothing) and walk right up to the big pond where all the people gather... sit, touch her vadge, and by the time you get home she'll be nice n wet.
If you still have some energy, after you can take a drive up to Summit Circle to check out all the insane houses... it always sparks major conversation, keep going up to the highest point until you hit summit park, you should hit the white-marble lookout. Stop your car and get out for a little gander.
Works everytime.