Heh, I think the bottom-line is that men were never meant to analyze relationships and doing so just drives us to melancholy.
Look at it this way...do you have some close friends? Think of one. How do you feel about your relationship with him?
If you're like me, you probably had to think about it a little bit. I mean, you know what you like about a person, you know what you DON'T like, but you don't really feel a need to define (or try to shape) the context of the "relationship." It just takes care of itself.
It should be the same way with women, just with sex. I think you're thinking about it too much, planning "scenarios", analyzing "best-case situations", evaluating your feelings, trying to decide what shape you want a relationship to take.
That all needs to go. Your mind and spirit could do so much more for you devoted to something else. Just associate with women and let it lead where it leads. Stop analyzing Kate and Nicole. Just hang out with them. If you enjoy her company, be friends with her. If she turns you on, then lay your mack down on her. If she bores you, find something/someone else to do.
But stop worrying about "where this is going." You might've had a "bad acid trip" with a previous girl and you're concerned about where this one will go, but when you come right down to it, it's going to go that way whether you like it or not, and all you can do is either buckle in and ride or find someone else. So stop stressing over it. It takes all the fun out of it.