How are you going to get the critical mass that makes a dating site worth using? Thats your number one problem and you need to solve that before thinking up things like matching.
You hit the nail on the head. Right now our approach is focusing on a very small number of geos where we can pound the pavement and do some guerrilla marketing to get that critical mass for that specific region. As we grow we'll be expanding to more markets with the same approach.