Two New York Times restaurant critics, Peter Wells and Tejao Ral, explain how they decide what to order when they go to a restaurant. (It’s behind a paywall so I will summarize)
- Be skeptical about a dish the menu highlights. It’s probably a big-ticket item (low cost, high margin) and less interesting than other options.
- Seek out dishes that are original or surprising
- Order soup. It’s never a big seller so there is a reason the chef put it on the menu.
- Steaks and burgers are played out—not much new and exciting there.
- Order what is in season.
- Order something you wouldn’t cook at home.
- Rely on server’s suggestions only if it’s clear they really know the menu.
- Push yourself out of your comfort zone.
This is all good advice. “Order something you wouldn’t cook at home” is the big one for me. Nothing is more disappointing than perusing a menu and finding nothing there I couldn’t cook myself.
Exploring the Philosophy of Food and Wine 
Dwight,
I have a couple things I typically do at the restaurant.
1. Ask the server’s name, and occasionally introduce ourselves.
2. Re menu: Select something that is freshly made as opposed to stews or other preparations from the freezer.
3. If no details on the menu, then quiz server on the entree’s main ingredient and the herbs and spices.
4. Offer the server or Manager a taste of the wine if I brought it.
5. Tip generously if appropriate.
Tom