Downtown: Al's. Hands down my favorite place and I've been to a lot of fancy places all over the country and in Europe. It's been there for 90 yrs and has never had a printed menu. Hasn't changed one bit in the last 40 yrs (including some of the staff). Get Harold to tell you the story about when Sinatra came in. Only thing I don't like is that it's downtown.....but it's right next to the casino and you valet park.
Kreis's in Ladue is good, as Citizen Kane's in Kirkwood and Sam's near Grant's Farm. But if your lady isn't into steaks, Spiro's is a great greek place.....great ambiance and it's in Chesterfield. In the Valley go to Annie Gunn's--everything else is franchise stuff (Farato's closed last month.) Go up to Clarkson and hit Ya Ya's.......that's one of my favorites.
I disagree on the ripping on the Hill, plenty of good food but I only go there for lunch any more. Bartalino's used to be my favorite before they moved and became a hotel restaurant. But yes, Ted Drew's is gross.