a nice wine
I'd really suggest going to an LCBO with a decent sized Vintages and speaking to the people there. Summerhill, the mother ship on Lakeshore, any larger Vintages with a dedicated staffer. Once you've decided on wine and/or cheese combinations, you can buy appropriately.
I had two bad experiences of late at the Alex Farms on Danforth. I ordered a Riopelle, and then a Calvados Camembert, only to find they were both stale. I usually taste before I buy, but was in a hurry the first time, and bought a wheel of the Camembert. I understand that the stores have been franchised. About Cheese on Church Street is my new fave. On the wine pairing, a simple rule of thumb is to choose cheese and wine from the same region.
Maybe as a very general rule of thumb. I tend to agree with Beppi Crosarial's position that sometimes long-distance pairing works better (see his artical at link). For instance, I'd rather have an amarone with epoisses, as he suggests, than a Burgundy where the cheese is made. I'd prefer port with stilton than, um, whatever wine is made in central England.
Are you in Toronto? A lot of your posts are on the Montreal board.
Either way, I suggest you go to a good cheese shop and ask the staff there for advice for a suitable cheese based on your budget and your friend's taste. Once you've chosen your cheese, the staff there will very likely have recommendations for a wine pairing. Or you can go to a wine shop or good lcbo store and they may be able to recommend a pairing (or come back here and let us know what kind of cheese you ended up with).
Here are a few cheese shops in Toronto -
Cheese Boutique – Etobicoke
Leslieville Cheese Market – Queen East http://www.leslievillecheese.com
La Fromagerie - College
Scheffler’s – St Lawrence Market
About Cheese – Church, Yonge
Alex Farm – Danforth, Bayview, etc
Thin Blue Line - Roncesvalles http://www.thinbluelinecheese.ca