It is your first business meeting, or your first date. You are at a fine restaurant with a wine steward. When it comes to choosing a wine, like most of us, you are a schmuck. If you want to show your worldliness, and not become a double schmuck, in every Weekend edition of the Wall Street Journal, there is a section that tells what wines are on the cutting edge of taste and popularity. Memorize part of the article and you will sound like a real wine maven. Long before I found this out, I would ask the wine steward, "for the food we are ordering, what would be your choice?" With this strategy, how can you go wrong? If the wine is bad, the schmuck is the stewardess, not you. It is one of those difficult situations in life that you can weasel out of.
In regards to tipping, in America you must consider at least 10% of it part of the cost of dinner. With poor service, I leave 10%. I don't want to create a situation where the waiter gets stiffed, but I want to let him know the service was poor, which is accomplished by tipping 10%. For an extremely attentive, personable waiter, 20% is not too much. There are areas in life where this 10-20% don't work. If you want some special request, or sucking up (ie "So nice to see you again Mr. Marcus.") At a classy restaurant, a 30-35% tip will get you this reception every time. Especially in LA and New York, eating out is a status symbol. Where you eat, where you are seated, and how you are treated matter. Especially in older restaurants, if you are seated in the rear of the restaurant, you can lose face with a date or client. Often, it is the front or nothing! In the big scheme of things, it is BS, but it is something you should know. Nearly every restaurant has a more important section. Over tipping can be as bad as under tipping. Overtipping marks you as a sucker, undertipping marks you as a chiseler.
A word of advice. In order not to be disappointed when arriving for a reservation, make sure to get the name of the person that took your reservation. This will help avoid controversy should a mistake occur.