I don't know the first real thing about the dating game. I don't know how to talk to a specific person and connect. I just think you have to go to person by person and do the best you can with people in general.
Someone able to carry on a conversation whether the topic is silly or serious. Knowing enough about life so that you always have something to say is a definite bonus
Never assume that the guy understands that you and he have a relationship.