We are the same way...we always end up going to the same places:
The Plaza, San Angel Inn, Nine Dragons, Ohana, Boma, Yak & Yeti, and Mama Melrose's.
A couple of years ago we tried to "branch out" and made ressies for Biergarten and Boatwrights. We never made it to either! I called and cancelled them the morning of so that someone else could have the spots. When we went this past year, we traded in Nine Dragons for Tutto Italia and we were not disappointed so for our trip this October, I'm trading in Ohana for Cape May, and Mama's for Hollywood & Vine. My brother in law was in the CP and worked at H & V last fall... when he came home and got a job at another restaurant, he was appalled that every restaurant doesn't operate the way H & V does! We've never been there and we had read some pretty bad reviews but we're willing to give it a try. If we don't like it, we don't have to go back!
We are also giving up Planet Hollywood for Bongos this year. PH has always been our "first night" restaurant but the Bongos menu made my mouth water so we're gonna try it out and hope for the best!