Ask for the sommelier or head waiter (or your own waiter, pending your best judgment based on your interactions) to choose for you based on the dishes you've decided to order. He (or she) will have tasted all the wines, will be familiar with the idiosyncracies of the chef, and will gladly to his (or her) job if asked nicely. Even if you recognize (and have enjoyed) a number of the wines on the wine list, it's quite impossible for you to be privy to the general insights and specific knowledge of the headwaiter. Do not ask the maitre d'hotel; that would be equivalent to asking the current American president to explain an arcane point of environmental policy, and you will simply end up with the most expensive bottle of wine he can think of at the moment.

It is a sign of wisdom to admit ignorance. It is a sign of foolishness to pretend wisdom. Being presented with the wine list is not an endorsement of your ability to choose well, it is an endorsement of your ability to choose to have someone else choose for you. A fine point, it must be conceded, but one that is important if one really insists on spending anywhere from $50-$200 for a bottle or two of wine with dinner and doesn't wish to be underwhelmed or disappointed.

Also, the trust and respect you accord the sommelier (or head waiter) with your request is the coin by which you acquire their goodwill. I've never been disappointed by this method.

Addendum for men seeking to impress their date with their amazing wine choosing abilities: 1) if you choose badly, and you may, that kind of defeats the purpose. 2) if you have the savoir faire to ask for the sommelier to choose for you (without sounding like a pompous bossy-boo) that's far more impressive than what I guarantee you will be a completely transparent slideshow of emotions playing across your face while you "choose" - panic, craftiness, pretend pensiveness, etc. - that will simply amuse most women, and 3) it's like asking for directions. A sign of having transcended your baser caveman Y-chromosome handicap impulses, and thus a sign that you might be a reasonably good lover. Ergo: ASK.