How to order wine at a restaurant
While buying wine presents plenty of potential pitfalls, ordering wine while dining out is distinctly trickier, not least because you don't control the field. The list may be unwieldy, or specialized in a region you've never heard of, or skewed toward the astronomically expensive. It might just be limited and boring, or lacking in anything that can justify the typical 300% mark-up (yup, that's the standard if you were wondering). Moreover, if you're out for a meal, you're likely in the company of at least one companion whom you risk disappointing with either your radical chic oxidized Jura vin jaune or your mom-jeans in a bottle California Merlot. Obviously, if anyone orders the latter, I cannot take responsibility for the massacre that will likely ensue.
Here are a few rules for making sure both you and your companions drink well and never feel the need to scream about each other's bad taste in wine:
1. Know your audience. I don't espouse caving to the underdeveloped palate of your average American (no spicy, no recognizable animal parts, no fish with eyes still present, no unpronounceable cheese, and definitely no raw anything), but remember, you're the one who is going to have to go back inside and re-tip your server after your colleagues send back the Riesling because "it tastes like juice!" So identify what people like: if your group thinks red is the only color of good wine, don't force a full-bodied white on them just to make a point (or at least, see my post on Winter Whites first); if your aunt loves buttery California Chardonnay, don't order Chablis just to be sure she knows her version is inferior to yours (it is); if people are there to celebrate but couldn't tell a grower champagne from a lemon-flavored seltzer, find something cheap and sparkly and let everyone enjoy equally without getting annoyed about the price point.
2. Plan if you can, and especially if you need to show off. Is this dinner a situation à la This Means War in which the only way to win the love of your life from your best friend is to show a superior knowledge of all things cultural while maintaining a secret double-life as a CIA agent? (Did you think it was a coincidence that Chris Pine knows how to get a good table and a good bottle of wine AND gets the girl? While Tom Hardy, who prefers a warm beer at a casual local pub, is left to reconcile with his unforgiving ex-wife and weakling child? Please.) Most restaurants publish a sample or even their complete wine list on their website, so download it in advance, pick a few bottles of different colors in your price range and learn something about them. Then when it comes time to order, pretend to peruse before stumbling upon "an old favorite" and sit back and enjoy the raised eyebrows and impressed looks on everyone else's faces.
3. Think outside the box. The cruel and unusual mark-up on retail price (e.g. $50 for a bottle that retails at $18) that you see at a restaurant is how most places cover their thin margins on food, and there's rarely a way to get around this semi-consensual gouging. However, if you're not afraid to try things you've never heard of, it'll be much easier for you to find a deal. The less likely someone is to order the bottle, the more likely it'll be priced to move, and this can add up to some spectacular value. Ignore the California Cabernet Sauvignon (unless you're at a steakhouse, it's only on the list because someone held a gun to the sommelier's head) and head for exotic, or at least less popular regions. Just by trading Bordeaux or Burgundy for the Loire Valley, Tuscany or Piedmont for Campania, and California for Washington or Oregon, you'll almost certainly find something that delivers more excitement per dollar spent, and you'll look good doing it.
4. Don't forget you're paying for a service, so take advantage of it. It's not your job to know about wine, it's theirs. Ask the sommelier to come to your table, tell them what you usually like to drink and how much you want to spend (NB: do NOT feel obligated to go big, there are good wines at every price point), and ask them to point you to a bottle. Even if it's not the kind of place to have a professional wine expert on the floor, ask your server, as they will almost certainly have been given a chance to taste some of the wines on the list and will be glad to share what they know. If they're good at their job, nothing will make them happier than making you happy, especially if you're willing to try something new.
5. Finally, even after you've decided what to drink, don't drop the reins. First, make sure of the price or use the bin number (the number sometimes included next to the wine name that indicates where it's kept in their cellar) to confirm that you're ordering the wine you want at the cost you expect. When the bottle comes, make sure it's what you ordered and if you're not sure, ask, or double check it against the list (vintage is the most common thing that gets lost in translation/changed without consulting the client, so look out for that especially). If you picked it and it doesn't taste good, ask the somm or server if they think it's flawed; if they picked it and you don't like it, tell them what you don't like about it, and ask them (nicely) to try again. As long as you don't scream and flip over the table in your rage they won't mind--the opened bottle will be sold by the glass at a still higher mark up, so it's a low risk operation for everyone involved.