The Craigslist ad beckoned to me – pouring and selling wine as an independent contractor around Southern Maryland? I’ve never been much of a salesperson, but how hard can that be? Wine practically sells itself. All I had to do was invite people to taste.

I responded to the ad and received a request days later for a Skype interview. Weird, but I did it, and the job was mine.

I had to buy some supplies before my first assignment: an ice bucket, plastic sample-sized cups, and a particular type of corkscrew – they were very particular about the corkscrew, and it wasn’t the type I normally used. I had to dress a certain way: all black, professional. And I needed to learn more about wine, so I bought a massive book detailing all the wine regions, vintages, terminology, etc.

I never gave much thought before to descriptors such as fruit forward, mouthfeel, soft tannins, hints of leather, buttery finish. I had to learn all this stuff so I could talk about the wines that I poured in a way that made people feel that I knew what I was doing, a true professional.

My first tasting was on an October evening at a liquor store in Prince Frederick. Italian wines. I was unfamiliar with the winery, and I absolutely had never heard of Montepulciano. I remember looking it up on Wikipedia so I could listen to a recording on the pronunciation.

Then there was the day, shortly before Christmas, when I was sent to a specialty grocery store in Waldorf to sell Amarula, which isn’t even wine. It’s a liqueur, similar to Irish cream in flavor, that’s made from the Amarula fruit that grows in Africa. That was my best sales day. Even better, I had a nearly full bottle afterwards that I took home with me.

Whatever I was selling, I never had much of a problem making the quota. Sure, there were people who were only interested in the samples. They would sip, thank me, throw away their cup, and leave. I’ve done my fair share of that, too. And even I didn’t completely love all the wine I sold. (I was encouraged to take the first tastes from each bottle to make sure they didn’t have cork taint.) But there is an audience for every wine, and I never had a problem finding my audience.

One night, at a liquor store in Dunkirk, I was featuring Chilean wines. The very first customer bought an entire case. Later that same night, two women walked in, already drunk, and made a beeline for my display.

“What are you pouring?” One asked.

“Wine from Chile,” I responded. “Would you like to try some?”

“Oooooh! I love chili cheese fries!” She said. She looked at her friend, and they laughed hysterically.

Naturally, I tried to convince her that wine from Chile was absolutely made to go with chili cheese fries. Anything to make a sale.

I remember the woman who complained that I was pouring wine from the wrong country. “I won’t buy your wine,” she said. “It’s not from California.” And then there was the guy who tried to correct my pronunciation of “Chee-leh,” insisting that it is “Chill-ee.”

Wine people can be the best people, but they can also be kind of weird.

My short-lived career in wine sales ended about six months after it began, after a night that yielded zero sales. That was a first, and it was the company’s policy that a night of no sales resulted in termination. Had I been determined to keep doing it, I would have bought a couple of bottles myself to make the quota.

So, I said goodbye to being on the pouring side of the tasting table. It’s more fun being the taster, anyway.

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