Beware the "house wine." Often, this is a fancy-named rotgut making a scandalous profit for the restaurant. To avoid the trap, get the goods: If the house wine is Chardonnay, ask what brand and assess from there.
Buy smart. When the whole table wants wine, consider the value of a bottle instead of several individual glasses. Finding a wine that complements each entree may be daunting, but if you can't, who cares? Drink what you like - happiness will follow.
Assess the organization. Is the list organized by region? By varietal? By weight? "Weighted" lists are also called "progressive," meaning the wines are ranked from lightest to heaviest in flavor. A good comparison is milk: skim is light, 2 percent is medium, and 4 percent is heaviest. Think of how each type of milk feels in your mouth and you'll understand what "weight" means with wine. Weighted lists normally feature descriptions as well, so their usefulness is tenfold. Listing only the wine names raises the question, "How the hell do I know what that wine tastes like?"
Region-based wine lists are the most difficult to navigate, because they require knowledge of what grape grows where. It is especially annoying when restaurants list "Bordeaux" or "Burgundy" - most people don't know these are Merlot/Cabernet blends and Pinot Noirs/Chardonnays, respectively, but if these wines were listed under the weighted system, consumers could make more informed decisions. Same for varietal organization, although people are becoming more educated about different grapes' tastes and styles.
Don't shy away from the lowest-priced offerings. There's a psychology associated with listing the cheaper wines first. The restaurateur expects you won't order the least expensive for fear of looking cheap, and counts on your choice of the third or fourth selection. It's a game - don't play. The wine is normally already marked up 300 percent, so if you like the cheapest wine, then do some reverse psychology and save the bucks.
When flustered, seek help. If your server is a clueless plate carrier, ask the manager or owner for advice. More than likely, these enthusiastic individuals see the value in helping you. Don't be shy about asking questions like, "I'm having chicken parmigiana, what should I drink with that?" or "My price range is $30 to $40, what can you recommend in the Chardonnay area?" or "I'm not a fan of Cabernet, but I like a big wine, is there something on the wine list like that?"
If there's no help in sight, or if the atmosphere is so intimidating your palms start to sweat, go for equal weight with your food. If the food is light in flavor, then choose a light-bodied wine (for instance, Sauvignon Blanc with fish), and the opposite for heavier dishes (heavier Syrah with spicy red meat). Keep in mind that sparkling wine goes with practically everything. And if there's no brand you recognize, just order a grape type that you normally enjoy and explore.
Kendall Jackson 2002 Grand Reserve Merlot. SW = 3. $26.
This wine makes it cool to like Merlot again. Flirty and fun with a shot of raspberry. Smooth tannins allow plenty of pleasure.
Santini Asti Spumante DOCG. SW = 6. $12.
A low-alcohol sweet sparkler for those needing a deliciously fizzy sugar fix. Made from the aromatic and delicious Muscat grape, it smells and tastes like a fresh-cut Red Delicious apple, with a hint of caramel and toast on the finish. Enjoyable on a mild spring day at the park.