Boy, this is such a tough choice. I've had some awesome steak dinners while dining out, but I have to say my home-cooked pan fry ribeyes are close to their equal.
The other night, I found a great deal on a couple of ribeyes, about 14 oz. each, which cost me $13 and change for both. I marinated them for about an hour, pan-fried them in my cast iron skillet, and served them with home fries cut from a giant leftover baked potato and asparagus (99 cents a pound).
The cost for the two of us was, with beer and a slice of pie for dessert, was less than 10 bucks each. The steaks and accompaniments were out of this world, IMHO.
Now, you can get a marginally better meal featuring the same ingredients while dining out, but it would run you maybe $75, give or take $10 either way.
So my final answer is this: If it is just the two of us, I opt for staying home. For a party of four or more, the hassle of cooking isn't worth it, and it's more fun with a larger party. Plus, your guests can order whatever they want and what do you care (unless you're paying!).