A good place to start for info on ''fine dining'' in any city is Chowhound, here's the link for the quebec/montreal board:
http://chowhound.chow.com/boards/22
Now if you want ''high end'' with ''eye candy'' that won't necessarily equate quality dining.
You can always hit the supperclubs on St-Laurent just past Sherbrooke (Buena Notte, MED, Globe, etc...), load of high heels and miniskirts there let's say...
There are also a couple of spots in the old port where you are bound to have a decent drink/meal and fall upon some beautiful (though most likely unattainable - haha) ladies (Velvet, Garde-Manger, Confessional, etc).
Otherwise for a classy/stylish 5 à 7 afterwork drink kind of spot I'd say Baldwin Barmacy (the owners also just reopened Dominion Pub), Bily Kun/Plan B, La Porte Rouge, etc... all in the Plateau or Mile End neighbourhoods.