My best meal for two was at the Yachtsman Steakhouse at the Yacht Club. It was a splurge about four years ago. Very good steaks, attentive service, a more adult atmosphere but casual enough. We wore shorts and collared shirts.
The garlic spread for the bread was absolutely fantastic. My husband is a bread lover and he smeared this stuff all over and I called him Garlic Boy for the next couple of days! Excellent.
This was four years ago but our cost for the meal, including the cheapest bottle of wine, was $110. Our entrees were in the mid $30 range, the wine was $24.
We've also done California Grill as a splurge and I didn't like it as much. Too noisy for me. But the service was very good - when we couldn't decide on one appetizer, the server asked if we were in a hurry. When we said no, he brought out one appetizer first and when we finished that, brought out the second one. He even heard me say that the sauce for the mussels was fantastic so he took me up to the chef to get the recipe. Cost there was $100.