Every male who is out of college should have at least thought this through. Initiation is not manipulating the situation so that while you're officially "asking her out" there's no actual risk of rejection or embarrassment. It means that you as the man take the first step, risk and all. 'Doesn't that mean that she can just tell me no and leave me twisting in the wind? But whatever the circumstances, her role is as responder, not initiator.
If you're not ready to marry, you're not ready to date.
In my view, if you can't happily picture yourself married within a year, you're not in a position to date.
Third, once you decide that you are ready to date, look to God's Word to decide the kind of person to date, and evaluate potential dating partners on those criteria, rather than relying primarily on the world's treatment of ideas like "attraction" and "chemistry." I wrote at some length on this in my article, "Brother, You're Like a Six." For you busy singles with time for only one mildly irritating column per day, the summary is this: Pick a potential dating partner with an eye toward godly manhood and womanhood — with an eye toward who would make a good husband or wife, defined by those characteristics esteems in His Word, not the ones Hollywood likes.
Ultimately, this means learning to trust God's goodness and sovereignty.
Clearly, this is not the popular secular view of the "liberated" woman's role.