As a guy, I try not to treat going out as a date, because you will have more fun, and become more comfortable with being yourself. If she is down to earth, she will roll with you (so to speak).. on the other hand, if she doesn't find that comforting, it is time to focus on another person.

I think highly of my self-worth, so she would be fortunate to go out with me (and vice versa). It can be a turn off to woman with this mind set, but it acts as a natural filter to narrow in on the woman that can truly bring you happiness (and that you can make her happy too)