The first thing to consider when ordering a steak is where you are dining: if the restaurant has A-1 sauce on the table, and you go through a line to order, then you shouldn't expect much. At one of these places, who are you going to impress by ordering like a 'pro'? Really!
I'm a true omnivore; I've eaten at low places and high, on four continents. And I grew up in cattle country. I've gotten pretty good steak at a 'hole-in-the-wall', and I've also gotten an abomination (dry, probably freezer burned, with a huge vein of gristle running through it) at a well-considered steakhouse franchise. What you order and how you order it do not guarantee that that is what you will get.
So ordering means little unless the restaurant you are dining at can deliver that. Therefore, let's look at some tips for picking a good restaurant.
First: I'm not a big fan of franchised steakhouses (I prefer not to name specific names - I feel the same about all of them). They tend to be like any other franchised restaurants - Chili's, Bennigans, TGI Friday's, IHOP, etc. - except that they 'specialize' in steaks. It's a business. A high-volume, low-margin restaurant business; they will give the eating public what they will tolerate, and little if any better. And people who have never enjoyed a really great steak don't know any better. Your best bet from my experience, unless you've been recommended to a specific restaurant, is to go with either a single, family-owned place, or a higher-end restaurant. The old maxim that you get what you pay for generally applies here as well. These types of restaurants will have chefs on staff, or at least very experienced cooks - not the on-the-job-training high school kid you find at the chains. Not always, but much more likely.
That said, what you order reflects somewhat on how much of a connoisseur you are. It is generally true that steak afficianados prefer their meat rare or medium rare, depending on the cut. I know a lot of people cannot stand the thought, much less the experience, of eating a steak that oozes bloody juice. Be that as it may: a really fine piece of meat (and I am talking about beef here), properly cooked this way is an unparallelled treat. If it is an old, poor, poorly handled piece of meat, then this CAN be a fairly disgusting experience. A rare filet mignon will be well done (seared) on the surface all around, and delightfully pink, warm and juicy in the center; prime rib served any more than rare is just not prime rib anymore - it's a 'prime rib food product'.
If you are among the 'squeamish', then at least attempt to develop a taste for below-medium-well steak. Once you've started enjoying steaks that aren't so dry and tough that they require steak sauce to cover their inadequacies and allow the pieces to slide down your gullet, then you'll never go back.
How a steak is handled while being prepared can mean the difference between a perfectly good steak coming out wonderfully or horribly. First, a really fine piece of well-marbled, high-quality beef should preferably never be frozen, unless perhaps if it is vacuum packed. Second, it should never, ever, EVER be pierced: this allows the natural juices to escape, and will render the cooked steak dry. Third, marinating is fine; using meat tenderizers is just a work-around for an iffy steak. And finally steaks, especially thick cuts, should be cooked over high heat (preferrably an actual flame) to sear the surface and retain the juices.
So, 'how' to order a steak is meaningless unless you know 'where' to order the steak - unless you don't care much. Then it is simpler and cheaper to get a burger.
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