I recommend eating at a Ruth's Chris's Steakhouse, and a Del Frisco's at least once. Other local steakhouses around the nation can be better, for sure. Donovan's in La Jolla has an excellent house salad, and some amazing peppercorn gravy.
Ribeye, bone in, or Porterhouse.
Philly style is good with a nice rub. Otherwise Med-Rare and you only need a little salt and pepper.
Garlic mashed potatoes, sometimes cheesy. Very customizable dish.
Seafood also makes a great side for a steak. Oysters, crab, lobster, or clams. A 'steak oscar' is crab meat and melted cheese on top of the steak.
Corn on the cob, grilled with chili and lime juice.
I'll pay good money for a good meal, but I find that when we all get together to have some home cooking, we have some amazing meals off the home grill.