from my experience it definitely makes a difference how well we knew each other, whether it was easy to just hang out. when you don't know each other, there is a lot of insecurity as to how to interact, and what the other will allow or expect or find uncomfortable. i guess most people in that situation will be cautious as to not appear to try to move to quickly, and that may lead to the experience you had.

what i found helpful is to not focus on romantic dates but join group activities where there is no pressure to interact directly. your friends and her friends or even some other group that you both join for some activity. there is still plenty of opportunity to get to know each other that way, because you will see how each of you act around other people.