Going out for a meal and drinking a bottle of wine is one of the most enjoyable things a human can do. But, as with most of life's pleasures, it comes at a cost: ordering the damn thing. Even as someone that knows a few fucks about wine, picking a wine at dinner comes with a certain amount of pressure, which is totally not chill. I like always feeling chill, so here's how I stay chill while everyone expects me to order out of a 20-page, leather bound book of wineries that sound like fictional JK Rowling private schools.
What's for Dinner? Wine is meant to complement food, so it's important to take that into consideration. The old "reds with reds" and "whites with whites" isn't a bad place to start when you know jack shit about wine, because it's generally true—except for spicy food, for which I always recommend Rieslings. It's also good to know that acidic wines are great for cutting rich foods, but those same wines can become extremely bitter with salty dishes. Old World food always goes with Old World wines, starches go with everything, and Brussels sprouts pair with nothing, so don't even bother.
If you're anything like me, you'll have a bottle before you even pick up a fork, so skip this whole section and order whatever without even considering the shit you're gonna shove in your face.
Is There a Theme Here? If the place is 95 percent Italian wines, you should probably order an Italian wine. Those three French wines are just there to please that one couple a night that "only likes French wines", but rest assured that the establishment does not give a fuck about those French wines. The wines that they have the most of are most likely what the restaurant curates with the most care.
Talk That Talk You've drank wine before, and you obviously like it, otherwise you wouldn't care to order it. So, what do you like about wine? What kind of body do you like? What kind of flavors? What kind of texture? Take those characteristics to your sommelier or waiter: things like "a big, peppery red," or "a crisp, floral white," or "a totally not terrible rosé". You're bound to get some good suggestions, and now you look opinionated but adventurous, which is tight.
Do Not Order the Second Cheapest Bottle Everyone goes for the second cheapest bottle of wine, but generally the second cheapest bottle is the worst value. Restaurants know that you don't want to look cheap, so if they take a cheap wholesale bottle and price it as the second cheapest, they will make more money on it. You're better off buying the actual cheapest if price is a factor.
Be Real—Price Is Always a Factor You should always be honest with your sommelier or waiter about what you're willing to spend. If you want to get real sneaky, open the menu and say, "Do you have anything else like this you'd recommend?" and point to a price you're cool with. Everyone else at the table will think you're pointing at a Bordeaux or some shit, and your server will get it. I mean, it's a risk, because there are unexpected oblivious assholes everywhere, but from my experience, they will smile and gracefully point you to a beautiful bottle.
Do You Dude, if you love California wines, and you're like, "OH SHIT, THEY GOT MY SHIT! YA'ALL KNOW I LOVE THAT SCRIBE PINOT!" Just order it. You know you want to. Hell, I want to.
Just Ask Whether you're dealing with a sommelier or a waiter, they are guaranteed to know the wine list pretty well. Be confident in your ignorance and give yourself over to the pros. My personal go-to: "Listen, I don't know any of these wines. What is your favorite on the menu that isn't a million dollars?" The staff usually laughs and gives you something delicious and mid-priced.
ALSO: FUCK IT. GO WILD. ORDER WHATEVER YOU WANT. IT'S YOUR DINNER AND YOU'RE A GROWN-ASS ADULT.