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ok you wanna spend money?? 
Le Saint James Hotel (average 600$/night for a room, most expensive in Canada)
The W, The Queen Elizabeth, Sofitel, Le St-Paul, ... are all exceptional hotels.
Dinning, expensive, check out Toqué, Globe, Queue de Cheval 
Shopping, stroll on St-Catherine from Guy to the village, it can talk you all day because your girl will stop everywhere but you'll absolutely love it on Saturdays because of all the eye candy everywhere. Don't miss the shopping center Les cours Mont-Royal for some upscale shopping. Also for shopping, you can walk St-Laurent from Sherbrooke to Mont-Royal lots of good finds there too.
Going out, forget Crescent, its the home of thousands of teenage americans and ontarians invading Montreal because they can't drunk from where they come.
Go instead on St-Laurent, its way better. Time Supperclub, Myst Café and the bar at the W, Buena Notte, Sofia, to name a few are more upscale and exclusive... you need to reserve a table (with bottle).
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