People love to ask me, "How did you learn so much about wine?" usually followed by, "I wish I knew more about wine," or "I obviously just don't taste as well as you do."
The answer is easy. I wanted to learn about wine, so I found people that knew more than I did and listened to them talk about it. That really is the easiest way, and it takes no special tasting skills. Seek out or start a wine club, or go to your local restaurant with a good wine list and engage the sommelier.
Every restaurant has a highest-ranking cork dork, even if it is just the waiter that drinks the most. Have him recommend a wine and then discuss why he likes it. Of course not at 7:30pm on a Thursday. But early/late in service on slower nights is always good. My only warning on this is: the minute you find a guy that brings up hours of daylight, slope, elevation, biodynamic, or great extraction from pump-over rather than punch-down cap maintenance, end the conversation, pick a color (white or red), pay in the $30 range and cut your losses. It's ok to discuss that stuff but you should lead that conversation, when you find it interesting. All he is really saying by going to those places unprovoked is: “I have read books, I geek out on process, and I have generally missed the nuanced beauty that is wine. But still I can dazzle!”
When you do find a guy that works well at your level and helps you find wines you enjoy, talk about them with him. The more wines you find you like and the more you discuss them, the more you will be able to explain to strangers the kind of wine you love. Once you start doing this, it is easy to find more wine and talk about what makes you love or hate it. Knowing you like a big red is far better then knowing you like red, and knowing you like fruit-forward big red wine with enough tannic structure may be a little cliché, but will make you able to get what you want.
The best part about this process is it makes you a regular at his place. When I found Paul Grieco at Gramercy Tavern, I would show up on Wednesdays and Thursdays around 2:30 in the afternoon, when I wasn't working, and order a roasted chicken and a glass of Pinot Noir. Sooner or later Paul would show up and meet the guys trying to sell him wine and they would discuss them. I would listen, usually Paul would notice me listening, recognize my face, and send me a taste of what they were having. After listening to two pros discuss it, I would taste the wine and look for things I understood. When I would dine at Gramercy, I would ask for Paul and have him help or just choose our wine and discuss it a little. Drinking juice with Paul is still one of my favorite pastimes. Now we do it at his restaurant, Hearth, his legacy sticks I now know a lot more about wine and am very familiar with the staffs of two of NY's best restaurants because I paid attention to a pro and asked him do his job.
Six years later, I can discuss pump-over with any agro-geek in the world, I can find the value on most of NY's better wine lists, and when I call GT or Hearth they think of me as a good customer that loves wine, which is so true.