03/10/2014 11:39 am ET Updated May 10, 2014

A Perfect Fit: Uncovering the Right Wine

I tip-toed into a fitting room while shopping today, to see if the last dress, waiting to be tried on by someone else, was my size. I got caught and although it wasn't life altering, it was uncomfortably weird. By this point, a great number of us have experienced an awkward moment in which you realize you have done something regrettably wrong.

While I could walk away and never see this person again, it isn't always easy to get out of a sticky situation so effortlessly. I was lucky enough to save a good friend of mine from the shame of his, and it so happens to be a great point to begin my story.

One afternoon I was casually conversing with a friend, we'll call him Roman, about love, life and the pursuit of happiness and as we wrapped up the outstanding topics of the day, including the design for my new website, he casually switches topics to his "Oh, no." moment. "Hey, so speaking of wine, I accidentally drank someone's bottle at the Supperclub last night. What's a good red to replace it with?" I managed to suppress my initial reaction -- laughter, of course -- and managed to compose myself with empathy as I began my line of questioning.

"What did you take?", I asked. "I don't know, he said it was a gift, from far away. Probably something blended with Icelandic tears and polar bear blood."

Well that was helpful, I thought -- his response was vague and sarcastic. "Well you drank it; what did it taste like?" I asked. "It tasted like a gift. Smooth, medium." Now we're getting somewhere; "Who did you take it from?" I asked.

"He owns a gaming company and he pops his collar all the time. He was probably just letting it breath." Roam responded. It turned out this guy was a gaming entrepreneur and investor, and I'd guess that he wasn't kidding about his description. "What is your price range for a replacement?" "Around 40 bucks."

After collecting a few more details to support the loose, sarcastic ones, he actually did pretty well for not knowing what he drank, I provided my instructions:

"I got one better. Go to PlumpJack Wines in Noe Valley and buy the Clos Saron Syrah blend. I called and they have it in stock. It's $34.99."

Clos Saron had all the attributes he was describing -- it was complex yet smooth, elegant, and full bodied, but was drinkable for the non-wine expert as well. Given the background of the person for whom he'd replace the wine, as an added, yet superficial bonus, this extremely small production bottle immediately reeked prestige. From the batch and bottle number handwritten on the label, to the simplistic yet elegant branding, Clos Saron would be sure to please. He loved it.

How did I do it? I knew the audience. I've seen quite frequently that there is a correlation between wine, age group, and demographic. During my wine tastings I've educated dozens of eager young techies on how to taste wine. I have been able to pick up themes and qualities that repeat themselves.

Secondly, price does not always reflect great wine. Case and point, Sine Qua Non. Yes, its well balanced, uber cult wines whose proprietor changes labels each year with a funky spin on branding are tasty, but I can't say they were light years better than the more economical $72 bottle of Donum -- which just happens to have a female president and winegrower.

Lastly, I know wine. I have tasted hundreds wines from over 2 dozen wine regions so after a while I began to call wines like one might sense the taste of common foods, like an apple or a hamburger.

Whether you are fortunate enough to be one of the few who's never had an embarrassing "Oh, no." Wine moment (kudos to you) or you are the majority of us who have experienced this slightly embarrassing, immensely awkward situation, hopefully this gives perspective on the process of making informed decisions on wine.