Actually, you may already be a chocolate connoisseur, who am I to say? It's a largely subjective term. But I'm pretty sure you're NOT one if your definition of "fine chocolate" includes anything available in a vending machine. Don't worry, though, it's never to late to learn!
I suggest starting with a quick read: "The Chocolate Connoisseur," by Chloe Doutre-Roussel, which I've spotted on the shelves of several gourmet chocolate shops as well as in the big bookstores.
For further reading, the Library of Congress has compiled this useful guide to chocolate-related books and Web sites. If you're interested in food history, I especially recommend the book "The True History of Chocolate," by Sophie and Michael Coe. (Or you can read a briefer history of chocolate online here.)
Of course, Valentine's Day is only a day away, and maybe you don't have time to study before you shop. Here's a little cheat sheet:
1. Don't just grab the prettiest box of chocolates you see: Read the label. Look for the percentage of cacao (pronounced "ka-kow") and aim for something between 40 and 70 percent, keeping in mind that higher numbers will generally taste more bitter, or "dark." Taste and texture also depend on the proportion of cacao butter to solids (more butter generally makes the chocolate richer and smoother, as you'd expect), but the label won't necessarily tell you those numbers. Looks like you'll have no choice but to taste-test a few!
2. There are four main types of cacao: Forastero, Trinitario, Criollo, and Nacional (though some argue that Nacional is really just an obscure variety of Forastero). The flavors and aroma of each one are slightly different, and can also vary between growing regions, so ask a salesperson to let you sample some single-origin chocolates to get a sense of your personal preference. The majority of mass-market chocolate is made from the hardy, high-yielding Forastero tree—which isn't to say it's all bad, but you've probably had it before. Splurge on Criollo for a change.
3. Consider savory chocolate, a growing trend that's really nothing new when you consider that the Mayans were putting spices in their chocolate about two millennia ago. I'm a big fan of dark chocolate, even more so when there's a little kick of chili in there. Most recently, I fell for the "warm clove" truffle from Alexandria, Virginia-based J. Chocolatier, which incorporates cloves, vanilla, cinnamon and ancho chili. I found that here in DC at a little shop called Biagio Fine Chocolate (check our their website's "Chocolate 101" page), and I suspect part of the reason it was so good was that it hadn't traveled far. Which brings me to my next point...
4. Seek out local or regional chocolate makers, or at least a locally owned shop, before succumbing to the big chains or (shudder) drugstore chocolate boxes. You'll likely get better service and a better product.
5. Think about the environmental, economic and ethical implications of your purchase. Cacao is grown mostly in developing countries around the equator, and unfortunately, reports of child and slave labor are not uncommon in several of those places. Look for products labeled "Fair Trade Certified" to be sure that the cacao farmers abided by labor and environmental standards and received a fair price for their product.
P.S. If you're in DC this weekend, check out the chocolate festival at the National Museum of the American Indian -- you can read more about that at our sister blog, Around the Mall.