I think you might actually be more interested in yourself than in anyone else.
Most single people who want to be in a couple suffer from a problem of desire but an unwillingness to discover the other person inside the skin shell. The division of male/female in your mind is the primary cause of you not being able to relate. The division is mostly an illusion, for when you decide you don't desire anyone or anything and you see the world as a giant interconnected beast that doesn't care about your ego, you will easily find everything to satisfy you, and more. Basically, at that point, it will be a matter of which fantasy to make into reality...
Plus, I thought you mentioned something about wanting escorts? If you are into vapid exchanges of physical encounters, then perhaps dating is not really meant for you. Nothing in your behavior points to you being actually interested in this woman. It does however point to the fact that you're too wrapped up in your ego, self-esteem and identity to bother getting to know your date.