Ordering wine at a restaurant should be simple, but the list is too long, the markup feels criminal, and there's a quiet pressure to pick something that works for four different dishes and six different opinions. Most people default to the same two or three moves every time. Those moves are often wrong — not catastrophically, but enough that you're leaving better wine on the table. Here are the seven mistakes and the better moves.
1. Ordering the Second-Cheapest Bottle
This is the most famous wine-ordering "hack" in existence: don't order the cheapest bottle (you'll look cheap), order the second cheapest (you'll look smart). Restaurants know this. They've known it for years.
Some wine directors deliberately put a low-value wine in that second slot — something with a high wholesale cost and a minimal markup, or something that's just mediocre but sells by the truckload because of its position on the list. You're not gaming the system. The system is gaming you.
The better move: Look at the $45-65 range (or whatever the middle third of the list is). Restaurants apply the highest percentage markups to their cheapest bottles — a $10 wholesale wine becomes $40 on the list. But a $25 wholesale wine might only become $55. You're getting significantly better wine for a modest bump in price. That $50-ish zone is where the quality-to-markup ratio is best.
2. Ignoring the By-the-Glass List
People treat the by-the-glass section like the kid's menu — something you order when you can't commit to a real bottle. That's backwards.
Yes, by-the-glass pours are more expensive per ounce than buying a full bottle. A glass that costs $16 might come from a bottle the restaurant sells for $48. But you're not paying for volume. You're paying for flexibility.
If the wine list is unfamiliar, or you and your dining companion want totally different styles, two different glasses beat one safe bottle every time. You each get exactly what works with your food instead of a compromise that half-works for everyone. And if you hate what you ordered, you're out $16, not $55.
The better move: Start with a glass each while you look at the food menu. Once you know what everyone's eating, decide whether a bottle makes sense. Sometimes three different glasses across the table is the smarter play.
3. Matching Wine to the Table, Not Your Dish
Four people sit down. One orders salmon, one orders a burger, one orders a mushroom risotto, one orders a salad with grilled chicken. Someone says, "Should we just get a bottle of Pinot Noir?"
That Pinot will be fine with the salmon and okay with the mushrooms. It'll be too light for the burger and it won't do much for the salad. You've just bought a bottle that truly satisfies one person and sort of works for the rest. That's not a pairing. That's a surrender.
The better move: If the table's dishes are all over the map, skip the single bottle. Two half-bottles (if the restaurant offers them) cover more ground. Or just go with individual glasses — the risotto person gets a Nebbiolo, the burger person gets a Malbec, the salmon person gets a white Burgundy. Everyone's happier. The per-glass premium is worth it when the alternative is a wine that doesn't really match anything.
4. Being Afraid to Ask the Server
This is the big one. People would rather stare at a wine list for ten minutes, pick something they half-recognize, and hope for the best — rather than ask the server for help. The fear is looking unsophisticated. The reality is that the server (or sommelier, if the restaurant has one) wants you to ask. It's their literal job. Good servers get excited about this part.
You don't need to know anything about wine to get a great recommendation. You just need to communicate three things.
Script 1 (easiest): "I'm having the short ribs. What wine would you pair with that in the $50-60 range?" You've given them the dish and the budget. That's all they need.
Script 2 (preference-based): "I usually drink Malbec but I'm open to trying something different. What do you like on this list?" Now they know your taste profile and can push you somewhere interesting without going off a cliff.
Script 3 (adventurous): "What's the most interesting wine on this list that nobody orders?" Every good server has an answer to this question. And it's almost always a phenomenal value, because unpopular bottles don't get marked up as aggressively.
If the server just says "everything's good" or can't give you a specific answer, that tells you something about the restaurant's wine program. Adjust expectations accordingly.
5. Skipping the Unusual Regions
You see France, Italy, California, maybe Argentina. Familiar. Comfortable. Then you see a section labeled "Portugal" or "Greece" or "Slovenia" and your eyes slide right past it.
Those are usually the best values on the entire list.
Here's why: restaurants put wines from unusual regions on the list because someone — the wine director, the sommelier — genuinely loves them. They're not there because they sell well. Someone tasted a Xinomavro from Naoussa or an Assyrtiko from Santorini and thought, "People need to drink this." And because these wines aren't in high demand, the markup is often lower.
A $40 bottle of Barolo is probably marked up 3x from wholesale. A $40 bottle of Baga from Luís Pato in Bairrada, Portugal? Might be marked up only 2x — and it's just as interesting and often better suited to a wide range of food.
The better move: Next time you're scanning the list, go straight to the regions you don't recognize. South Africa's Swartland is producing Chenin Blancs and Syrahs that rival bottles at twice the price. Greek whites are some of the most food-friendly wines on earth. Ask the server about these sections — that's usually where their enthusiasm lives too.
6. Overthinking the Vintage
"Is 2019 or 2021 better for Côtes du Rhône?"
At a Tuesday dinner with a $45 bottle? It genuinely does not matter.
Vintage variation is real at the top end — a 2010 versus 2013 Barolo is a meaningful difference. But for wines under $80 at a restaurant, the vintage year is one of the least important factors in whether you'll enjoy it. The grape, the producer, and the region matter more. Whether the wine goes with your food matters more. Five minutes agonizing over the 2020 versus 2022 Sancerre is five minutes you could have spent drinking it.
The better move: Ignore the vintage unless you're spending over $100 or you have specific knowledge about a particular year and region. If the restaurant lists two vintages of the same wine, ask the server which they prefer. Otherwise, just pick and move on.
7. Not Checking the Wine Before Committing
The server pours a small taste in your glass. You nod and say "that's great" before the wine has even hit your tongue. Everyone does this. It feels awkward to actually evaluate the wine with someone standing there watching.
But that tasting ritual exists for a reason, and the reason isn't to test whether you like the wine's style. It's to check whether the wine is flawed. Corked wine (wet cardboard smell), oxidized wine (flat and stale), wine cooked by bad storage — these affect roughly 3-5% of bottles sealed with natural cork.
If the wine smells off, you're allowed to say so. You're allowed to send it back. That's not being difficult. That's the system working as intended. The restaurant returns the flawed bottle to the distributor. Nobody loses except the cork that failed.
The better move: When the server pours the taste, actually smell it. You don't need to swirl it theatrically or hold it up to a candle. Just put your nose in the glass and breathe. Does it smell clean? Like fruit, earth, minerals, flowers — anything that seems intentional? Good. Does it smell like a wet dog, a damp basement, or vinegar? Say something. A simple "I think this might be off — would you mind checking it?" is all you need. A good server will smell it themselves, agree, and bring a new bottle without any drama.
This is exactly the kind of thing PairScan was built for. You're at the restaurant, the wine list is in front of you, and you don't want to make mistakes 1 through 7 all in the same meal. Scan the menu, tell the app what you're ordering, and it recommends specific wines from the list — with prices, so you can hit that value sweet spot without doing mental math while your server waits.