Ordering wine at a restaurant doesn’t have to be so daunting. Ray Isle goes undercover as a sommelier and shares seven tips for a better wine experience during your next night on the town.

By Ray Isle
June 24, 2019

It was the Thursday before Christmas and I was at Oceana in New York City pretending to be a sommelier. Around me the floor was bustling: family dinners, end-of-year get-togethers, dates; servers and captains racing around; the somm team uncorking bottle after bottle; a manager wheeling a 10-pound king crab, like a prehistoric hubcap with legs, through the dining room on a cart. I was at table 42, a deuce. Middle-aged guy, bearded, jacket for the evening, architect glasses—much younger dining companion. He had the vaguely overwhelmed look people get when trying to figure out what wine to order, but he tried to sound confident: “I’m thinking white ... maybe a Sancerre?”

I felt for him: There is little in this world more effective at making people feel uncertain than a restaurant wine list. Instead of coming off the way I tend to think of them—gateway to fun! cornucopia of wild possibilities! fascinating insight into wine director’s mind!—wine lists baffle and daunt most people.

That was why I’d put on a suit, armed myself with my favorite corkscrew, and headed out to spend several weeks selling wine in restaurants around the country. What I hoped to do was come up with some strategies to help diners feel less helpless and more savvy when the sommelier asks for their wine order. I bounced from a white-tablecloth midtown Manhattan seafood hot (Oceana) to an ambitious neighborhood Mediterranean bistro (Allora, in Sacramento, California) to an extravagant, 3,500-bottle-list Texas steakhouse (Mastro’s at The Post Oak Hotel, in Houston, Texas). I pulled corks, poured, talked, listened, and watched, and came away with the following seven pieces of advice.

Kati Szilagyi

1. Abandon your comfort zone

Call it the Sancerre moment, as exemplified by the fellow I was waiting on at Oceana. It’s when people flip through a wine list, first interested, then overwhelmed, until their brain solves the problem in the most expedient way possible and they blurt out, “Sancerre!” or “Santa Margherita Pinot Grigio!” or “Meiomi!” Safe, familiar, known. Andrew O’Reilly, the wine director at Oceana, says, “For us it’s California Chardonnay and Sancerre. Those are comfort s for people.”

But what the heck, a lot of life is a debate between comfort and excitement. Let’s see, for today’s activity, afternoon in the spa or shark-cage diving? Wine lists, conveniently, offer the possibility of novelty and excitement without actual danger. You’re not apt to get your arm chewed off if you go wild and order a Grenache from the mountains near Madrid, for instance.

Nor am I dismissing comfort. The familiar can be very satisfying. You want a cheeseburger, order a cheeseburger; so what if there’s linguine with sea urchin roe on the menu. But make your decision a conscious one. Be aware, when looking at a wine list, of the point at which you start to think, “I’m lost—I’ll just go back to something I’ve had before.”

And if you are lost in the wilderness of wine, remember that you have a trained guide. Sommeliers want you to experience something cool and amazing: the aurora borealis, not a random streetlight. My advice is to follow the lead of Santhoosh, a tech consultant I waited on in Houston, who told me, “My feeling is, I can get Caymus at home, I can get it anywhere—so where can you take me that’s an exploration?”

2. Skip the wine words

“It’s so agonizing—raspberries? I didn’t smell any raspberries. Am I supposed to smell them? I have a friend who was studying for a sommelier degree, and he’d be like, ‘What do you smell?’ And I’d say, ‘I don’t know, man! I don’t know what I smell.’”

Don, the young finance guy I was chatting with at Allora, had a fair point (which he punctuated by ordering a beer). Raspberries and blackberries, minerality and terroir; wine has its own language, and like most specialized languages—from particle physics to plumbing—it sounds arcane to outsiders. The confusion is compounded by the fact that most sommeliers occasionally drift into wine-speak when talking to guests. Hearing that a wine is “site-expressive” is, for most people, like hearing a plumber say, “Yeah, you’ll probably need some 2-inch CPVC there.”

The answer, as a guest, is simply not to worry about the words. Explain what you like in your own language. Even a statement that pretty much makes no sense—like “a sweet, dry red wine that isn’t too bitter but still has a bold flavor,” as one guest told Chris McFall, a member of the sommelier team at Mastro’s—is still a doorway to a conversation. In that particular case, McFall replied, “Great. So tell me the last wine you had that’s like that. 19 Crimes? All right then. Let me give you a couple of options.”

3. When baffled, ask questions

“We actually know something about wine, but we don’t know a single thing on this list!” That was Raghuraman, who, when not being perplexed by the wine list at Allora, is an anthropology professor at Sacramento State. In other words, a smart, capable, wine-savvy person—who was looking at a list without one single wine he recognized on it.

I’d been working at Allora for three days at that point, and this was not the first time I’d heard something to that effect. Wine director (and co-owner) Elizabeth-Rose Mandalou’s 19-page list has no comfort choices: no California Cabernets or Chardonnays, no Veuve Clicquot or Whispering Angel. What it does have, to go with the Mediterranean-inspired menu created by her husband, Deneb Williams, is a fascinating abundance of Italian, Slovenian, and Greek varieties, many of them little-known and almost all from small, family-owned wineries. It’s a list that is designed intentionally, Mandalou said, to encourage guests to reach out to the staff.

“Just talk to me,” Mandalou said post-service one night over a glass of Pallagrello, an obscure (but delicious) variety from Italy’s equally obscure Terre del Volturno wine region. “That’s the whole idea. No matter what, I’ll find you a wine that you’ll love. We have a lot of people come in who like Caymus Cabernet—that’s fine. I don’t have anything like that on my list. But I do have a Nino Negri Sfursat from the Valtellina that’s a fantastic option for someone who likes that wine.”

Essentially, there are two ways to react to a lack of comfort choices: freak out or have fun. My advice is the latter. Put yourself in the hands of the (ideally well- trained) staff, and odds are you’ll end up like a woman I spoke to on my last night at Allora. She was waiting by the front door for her coat, and I asked her what she’d been drinking with dinner. “It was some northern Greek wine you have,” she said. “It was red—”

“Xinomavro?”

“Yes!” she exclaimed. “We just took one look at your list, handed it right back, and went with whatever you all suggested. I loved it.”

4. Distill your options

“You know,” McFall said during a rare quiet moment in the midst of Valentine’s Day service at Mastro’s, “we scare the hell out of some people who aren’t used to opening a 114-page War and Peace wine list.”

His comment made me think of a famous psychological experiment conducted back in 2000. One day, shoppers at a grocery store were confronted by a display of 24 kinds of gourmet jam. Those who tried some got a coupon for $1 off. The next day, the display only had six kinds of jam. The result of the study? Shoppers who saw the large display were far less likely to buy jam than those who saw the small display; there were just too many options. It was a classic demonstration of what’s now called “the paradox of choice.”

To which I’d say, “Jam? Give me a break. Try a wine list.”

At Mastro’s, the list has more than 3,500 choices ranging in price from $35 a bottle to $80,000 (for an 1825 Château Gruaud Larose—odds are it’s still there, if you’re feeling flush). It’s amazing, but the average customer, reading through it, would doubtless feel (a) utterly overwhelmed and (b) lonely, because the person they were dining with would have gotten up and left long ago. (And even so, Mastro's list only offers a portion of the30,000 bottles in the cellar at the Post Oak Hotel at Uptown Houston, where the restaurant is located; the place is truly a mecca for the wine-passionate.)

So here’s my advice when dealing with a giant list. First, spend no more than five to seven minutes looking at it (unless you have a really tolerant spouse, or you’re obsessively into wine). Flip through. Find three bottles that intrigue you. Use the fingers of your left hand as bookmarks for those pages as you flip. Then ask for the sommelier and say, “I’m interested in these, but I’m curious what you think.” The somm will likely suggest a couple of other possibilities, and there you are: You’ve winnowed down several thousand selections to about five. Now, enjoy your jam.

5. Don’t worry (too much) about pairing

There are two ways to handle the question of what wine to drink with the food you’re going to eat. The first is to be like the table of 12 guys I waited on during my first night at Mastro’s who were in Houston for NAPE, a massive oil and gas industry conference. Their solution: Order something you know (Caymus Cabernet, once again!) with something you feel like eating (seafood towers, in this case) and don’t give the matter another thought. Do raw oysters and Napa Cabernet go together? Not in the slightest. Do you care? Dude, are you kidding? I’m busy thinking about Permian Basin pipeline build-outs.

The second way—which I have to say I prefer—is to talk to the sommelier. It’s their job to spend time pondering which wine pairs best with which dish. They know the menu backward and forward, and the wine list with similar familiarity, and they want your meal to be as memorable as it possibly can be.

As a restaurant guest, why not take advantage of that? But note that sommeliers aren’t mind readers—to suggest a wine to go with your food, they have to know what food you’re going to order. But then again, you could always order a glass of Champagne—you deserve one, right?—while you figure that part out.

6. Be clear about budget

No matter where I was working, the most common things customers said to me about how much they wanted to spend on wine were statements like, “Oh, something about in the middle,” or “Let’s keep it sort of reasonable,” or “You know, kind of moderately priced.” This presents the sommelier—me, in this case—with a quandary, since “reasonable” for you is not necessarily “reasonable” for the brain surgeon at the next table. So unless you are flashing status markers like a Patek Philippe watch or a wad of hundreds, I’m probably going to take you to something in the sweet for that restaurant: about $90 a bottle at Allora, or more like $150 at Oceana.

But you will make the sommelier your friend, and cause yourself less stress, if you are simply clear about how much you want to spend. One way is to do what Lorie, a guest at Oceana hosting a table of five coworkers, did: Point to a bottle on the list and say, “We’d like a red around this price.”

Alternatively, you can do what Julie Dalton at Mastro’s suggests: “Tell me what the last bottle you enjoyed was. That gives me price point and style. Then I know exactly where to take you.” One note: Many people feel wary of sommeliers and worry that their mission is to get you to spend more money than you would like. My experience is that most sommeliers are actually more likely to downsell than upsell people. Even so, as Lorie, my customer at Oceana, also said, “I’ve been in weirdly expensive restaurants where the sommelier is just tone-deaf. You say, ‘I’m looking at one of these,’ and he’ll suggest something three times as much.” She’s right; this happens. When it does, be firm. However, note that this doesn’t mean saying something like, “Hey, peanut-head! I said 100 dollars. What’s your problem?” Which brings me to my last bit of advice.

7. Be human

If there’s one bit of insight I could pass along to people outside the sommelier world from my brief stint inside, it’s that being a sommelier is a job. It’s hard work. For all the blind-tasting exploits and opportunities to taste pricey bottles, there are days of hauling cases of wine up staircases with a clipboard in your teeth, inventory tasks that numb the brain, and the simple labor of being on your feet for eight or more hours straight. As Nikki Palladino at Oceana said, “Seriously, it should be required that all sommeliers are issued Rollerblades.” Plus, it’s service: Try talking, in a truly engaged way, to 70 or 80 new people every night. No one who doesn’t like people could survive in the sommelier world very long.

But your love of humanity can sure get tested. So I would suggest—because these are all things I saw—the following: Do not grab the sommelier by the arm to get his or her attention. Do not hit on the sommelier. Do not give your order to the female sommelier then turn to the random (possibly a sommelier) guy standing behind her (me) and say, “So, is she doing a good job?” Similarly, do not say to the female sommelier, “Hey, darlin’, will you be my valentine?” when your actual date is sitting right across the table from you (unless, of course, you’re curious to know what it’s like to have your date stick you with a steak knife). Just think of things this way: If you were at your workplace, would you want someone to yank you, poke you, make a pass at you, or insult you? I didn’t think so.

Wine is fermented grape juice, but it’s also a medium for connection—to the people you’re dining with, but also to the person who’s helping you decide on a bottle, who’s pouring you that first taste. Every sommelier I know is in the business because they love the stuff; wine really is their passion, not just their profession. As Tara Tretola, a member of the somm team at Oceana, said to me, “Before I came here I was working at a nightclub, and you’re selling liquor at tables for what, a thousand dollars a bottle? It was killing my soul. Now I pour things like Roulot Meursault. It’s like, this is what I’m actually supposed to do.”

Pouring things for people—that’s what sommeliers do. But not alone. You’re part of the equation, too. So if you want a great bottle of wine with your meal, here’s my final advice: Be active, not passive; engage and ask questions; and rather than thinking of that wine list you’re holding as an impenetrable tome, look at it as an adventure, a travel guide for your senses, one that can take you, by means of a bottle, somewhere you’ve never been before.

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