Add in the extra pressure of ordering the wine when out on a date –that is, ordering the right wine with the right price tag with the right food– it can make you want to hide under the table until the waiter comes to bring the check. Fortunately, though, ordering wine doesn’t have to be an ordeal. Wine should taste simply wonderful… it shouldn’t taste like the bitterness of embarrassment.

First things first; don’t invent an expertise where none exists. In other words, it’s okay if you’re not an expert in wines. Most people, your date included, know only what they like, but know very little about wine in general. Pretending to know more than you do will make you appear insecure and more than a bit obnoxious.
Even if you do know about wines, consider yourself an expert, and know just what to order to go with the chicken cordon bleu, do ask your date about his or her first choice. Something like “I’ve had the 2002 Santa Margretha before and it goes beautifully with chicken; shall I go ahead and order some?” is perfectly okay.
As with anything, it can take time to learn what you like. Buying different wines, both white and red, to try at home is a great way to develop your taste and figure out what you like and what you don’t. As you become familiar with the wines of different countries and wine regions choosing wine for someone else will become less and less awkward.
Resist the urge to order the most expensive wine on the menu in the hopes that your date will be impressed. Chances are he or she will just be uncomfortable. You don’t have to order the cheapest bottle either; feel free to go up in price. Just realize that at a certain point your date’s opinion of you may go from ‘impressed’ to ‘what a showoff!’!
Really, it’s okay to order the house wine if you want to. If you’re not sure how your date will feel about it, just ask first. “I’m not picky and am fine with a house red. That sound okay to you?” It won’t make you look cheap… it’ll make you look relaxed and down-to-earth.
When in doubt about what wine to order, there’s no better person to consult than the server. Though some people are afraid this will make them look stupid, nothing is further from the truth. If you’re planning to order prime rib, asking the server for a full bodied, medium priced red wine will make you look self assured and will get you the perfect bottle of wine with your dinner.
Let’s face it, life is just far too short to spend much time worrying about impressing your date with your wine knowledge. Being relaxed about the whole process means your date will be relaxed too; and you can spend the time enjoying each other’s company.

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