Odd as this may sound, I bust out the BBQ.
BBQ'd chicken that you then place into a caesar salad works well. Another one would be porkchops, kettle cooked corn on the cob, and baked potato. All usually served with some "fancy" fruit juice. Or a beer depending on her stance and the "mood."
Everyone else I know does the whole "romantic Italian" thing, but I cook what I cook best. If the food sucks, she's not going to be impressed, right?
What can I say? I'm a hick