How hard could it be to bartend at the Wharf Pub?

She drew a beer the way a beer should be drawn. Surprised, Holly Nadler celebrates. A real bartender, Jade Deslauriers, watches her trainee. — Photo by David Welch

This month’s mission: bartend for a night at what Bogie in Casablanca famously called a “gin joint”. Who wouldn’t want to do that? Bartending is the coolest job there is, apart from ice cream taster at Ben & Jerry’s.

Wherever people gather to drink together, you find a happiness level ratcheted up to a glorious height. Why else do celebrations in all cultures involve alcoholic beverages? After people toss back a drink or two, they grin at each other. They huddle to discuss Aristotle’s Prior Analytics. They laugh, they dance, they buy each other more drinks.

So I was eager to partake of a roomful of sozzled campers, my only drawback being that I myself cannot drink. There’s some kind of allergy at work, and it isn’t as if I can knock back the margaritas and wait to pay the piper the next morning. Nope, my hangover starts immediately after the first sip of anything — anything! A headache forms as a revolving circle between my eyes, and it doesn’t let up, even if it’s followed by a quart of water and three Excedrins. It’s Mother Nature’s way of saying, “Don’t even think of doing that, dear.”

That doesn’t keep me from trying. At any fun gathering, I’ll mix a thimble-full of rum with a tall glass of pineapple juice, because this way I get that psychological boost of giddy pleasure. After six or seven sips spaced over a period of 20 minutes, Houston Control in my brain sends out the order: Prepare to initiate headache.

But putting aside this pesky problem, I needed to find a bar out of all the shuttered taverns on the Island in November. Immediately I thought of The Wharf in Edgartown, not only because it’s popular and made wholesome by its venerable old restaurant but, most importantly, because I’ve known 37-year-old owner Will Coogan since he was in diapers.

Actually, he was about nine when I first clapped eyes on him, so he must have been toilet-trained. His parents, Liza and the late Ed Coogan, and siblings, Geoghan (Vineyard attorney and Will’s partner in The Wharf) and baby Nell (director of this, that, and the other at Community Services), all of them once upon a time lived on Bridge Street in East Chop when the Nadlers owned their cottage near the sea.

I called Will, careful to keep the subject of diapers out of the convo, and he invited me to co-bartend on an upcoming Wednesday Trivia Night in the party-hearty back room with its own full-fledged bar.

I arrived thinking about the most sophisticated drink I’d ever encountered: the dry Rob Roy, the libation my uncle Max, a Chicago lawyer, used to order, his gaze leveled critically at the waitress. “Make sure it’s very, very dry.” Yikes! What if someone asked me to prepare one? I had no idea what a Rob was, or a Roy for that matter, nor how one went about making it not just dry but very, very dry.

The minute I met bartender Jade Deslauriers, who’s been serving up drinks at the Wharf for nine years, I knew I was in good hands. The room was packed: all 12 tables were filled with Trivia teams, with another two groups ranged along the bar, and one final set of contestants who might have been swinging from the chandelier for all I knew: I had no time to look up.

Jade got me started by pointing at a nearby table of a dozen players — all of them, it turned out, on a busman’s holiday from their waitstaff jobs at Café Moxie. Jade said, “One of the girls at the table ordered fireball shots for everyone except the girl in the grey sweater who’s not yet 21.”

I was impressed. “You’ve already carded all of them?” Jade, tall, attractive, self-confident, with brown hair pulled back in a barrette, nodded. She hauled out a bottle of Cinnamon whisky. Within half a second, she apportioned 11 shots.

“This is the most popular drink,” she said, holding up the open bottle for me to sniff. The scent took me back a hundred years to childhood: It was the fragrance of those spicy red candies we used to pop in our mouths carefully, one by one.

Trivia-meister Dan Cassidy cleared his throat into the microphone set up at a table in the southwest corner of the cavernous room.

Jade whispered, “We can give hints to favorite tables. I’m helping out the four people down at the end of the bar.”

I decided to adopt the table of 12 with the fireball shots. Dan asked for the name of the device used to record earthquakes. I’m a California girl, so I scampered over to my kids and said, “Are you thinking Richter scale?” One of the boys said, “It has to be a device.” I shrugged. “A scale’s a device.”

I missed the answer to that one: I was busy learning to swoosh out beer on tap. Jade demonstrated from a fountain of half-a-dozen levers. You pull the thing, tumbler tipped beneath the spigot to keep the foam at bay. My first few tries looked like Lucille Ball’s washing machine spilling over with suds. At last I got the hang of it: You yank that baby down hard, at the last moment hoisting the glass to a perpendicular angle until you arrive at what they call in the trade “a nickel head,” when the foam at the top is just a smear the size of a coin.

Oh dear heavens, was I tracking! I poured perfect Blue Moons with a slice of orange tacked over the rim, PBR’s (Pabst Blue Ribbon to the uninitiated), and Oktoberfests. Seriously, someone should have filmed a demo of me for bartenders of the future.

What kept me from morphing into the perfect barkeep (aside from my having never attended bartending school) is that the trivia questions caused me to drift off to Never Never Land. “I know that one!” I’d murmur, staring off into space, my senior memory caught in that sinkhole.

At one point, though, I really aced it with my table. From a tiny photograph of two men on ground-scooping Harleys, I identified Peter Fonda and Dennis Hopper in Easy Rider. “How’d you know that?!” asked the same young man who’d questioned The Richter Scale. I said, “I grew up with that movie! I saw it fresh!”

Other highlights: I watched Jade shake up a cucumber martini made from cucumber vodka, a squeeze of lemon, and St. Germaine elderberry liqueur. Jade jostled it mightily in a tin cylinder. James Bond would have frowned. He may also have been wrong all this time.

Meanwhile, for myself, because, as I’ve explained, I pretend I’m drinking, I squirted out a tall glass of seltzer, then dolloped in an iddie-biddie drop of vodka. It occurred to me that if people used Red Bull to fight hangovers, why not add a goodly splash, and get cranking on the hangover in advance?

But who had time to drink? The odd glass of wine and a tank of shots and ales had to be served. Jade’s co-bartender-and-waitress, Amelia Ball, originally from the north of England, dashed over to tell me something. Adorable, blue-eyed, with a high-sculpted crown of prematurely silver hair, she cried out, “Holly, you gave my mother a tarot reading on Tivoli Day!”

So many people to get to know! From my table of adoptees, one of them, a French girl who resembled a young Anouk Aimee, leaned over the bar counter to describe her memoir-in-progress about her bilingual bicultural life, having spent half her time here, half in Fountainbleu, southwest of Paris.

But zut alors! Did I think I could just schmooze like Ted Danson in Cheers? Jade swooped in to ask me to bring free shots to the table that won best team name. Presiding over that table, artist Hawken Lee Morrison, who’s inked-and-pierced face and body could itself be featured in an exhibition at the Whitney, refused to tell me the sobriquet that won him and his buds the comp-ed drinks.

“It’s about the Philippines. It’s horrible,” he assured me with a groan and a grin.

Dan Cassidy announced the winners: “‘Best team name goes to ‘Thousands Dead, Hundreds in Damages.'” The crowd exploded in laughter and derision, “Too soon!”

Before the evening was over, one of the Trivia puzzlers turned my head around. Dan posed the serendipitous question, “What ingredients go into a Rob Roy?”

The answer came quickly: Scotch, sweet vermouth, and a maraschino cherry. Hmm, my Uncle Max would have expected dry vermouth and NO cherry, but there’s no way I could double-check with him, outside of sending a query via Ouija board.

I scurried to catch the last bus home — the 9:50 out of Edgartown — so Jade was left to punch in all those mystifying color codes and drink names and bar totals on her two computer screens. But she was up to the task. Nothing rattled her. And she’d been to bartending school!

And what became of my own clever mixture of Vodka Spritzer with Red Bull? Well, after a few slugs, the headache began to wind between my eyes like a YouTube video slowly loading. A couple of Excedrins when I got home busted it out of there, and the only downside was the caffeine in that aspirin compound that kept me up half the night.

Of all the gin joints in all the world, I had to walk into this one.