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Originally posted by RDCollins:
Find a good wine store with knowledgeable staff, tell them what you're interested in spending, and experiment.

Ditto. Shop around and find someone you're comfortable with who seems to know what he or she is talking about. You won't know for sure right away, but eventually you will. And they should be able to explain and recommend a few things.
Also if you can get a bunch of friends together who are also interested in learning wine or already knowledgeable or both and have a big tasting party where everyone brings something different you'll get to try a lot of wines without wasting any. Note what you like and don't like and go from there.

I also used to attend wine expos to try a lot of different things but lately the crowds seem larger and more rude than they used to. I have discovered some great wines at these and most major cities have them. Lot's of wine stores also hold smaller scale tastings which may be the better way to go, you'll get more interaction than at the huge expos and if you like what you're having you can buy it right there.
Winetech has an excellent idea. Don't know where you are but in NYC most stores will have tastings very frequently. They aren't big deals, usually a distributor will open a couple of bottles but on a Thurs or Fri evening or Sat afternoon if you're not busy, see if you local stores are doing something like that. It's a good way to try a number of things. And ask them if they are sponsoring any kind of wine tasting. Especially around the holidays just passed there are many big tastings as the retailers try to generate business. Those can be extremely helpful. Best of luck.

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