As a server who has worked in four restaurants I don't mind how someone orders their food.  My biggest annoyance is people who don't understand what the different terms mean as far as restaurant chefs are concerned.  Here is what we tell guests who ask:

Extra Rare or Blue - Very red and cold
Rare - Cold red center, soft
Medium Rare - Warm red center, firmer
Medium - Pink and firm
Medium Well - Small amount of pink in the center
Well - Gray, brown throughout - no pink
Very Well - Blackened throughout, hard

Almost every restaurant follows this with the exception of some high-end steak houses which refuse to cook anything higher than medium well.  Some servers I know will also ring in well done steaks as medium well to avoid getting a comp on one of their checks since some people mistakenly believe a well done steak will come out with a little bit of pink.  That's why some guests who truly want a well done steak have to tell the kitchen to burn it in order to get it cooked the way they like.

I hope this helps people get the steaks they truly want when they go out to eat.