Rudd, I love what your doing and reading about it. I would like to hear more about what you did on the date and if the girls approve even pictures!! I don't think you should have to take a girl out more than once...what if you really don't feel that spark? Don't feel obligated to ask the girl out again unless you really dig her. That's my little suggestions.
Feedback numba 2:
I second the motion on pictures! As well as not needing more than one date, b/c that would just lead a girl on if you didn't feel anything for her. I like the princess idea personally and I think going to different cities would definitely make it more adventurous. And if the dates don't turn out as great, then you've at least gotten familiar with a new place.