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To OP: Great post man. Just great stuff.
Certain parts of your post actually reminded me of an experience I had when I started out.
I took the girl shopping for a day 2, and when I didn't ask her to go back to my place after two and a half hours (:lol: the poor girl...we were so tired from walking around and I just didn't know how to ask her to come to my house), she flat out told me "come on lets get out of here". I was lucky enough to be with a girl that knew how things were supposed to go, and was willing to help me along when I needed a nudge.
I can understand you perfecty and I have been a victim of this problem..