A commenter over at Zuska offers up a much more coherent version of what I was trying to say back here.

You need to be willing to do the unspoken emotional work and social barometer-reading that our culture expects women to do. If you are paying attention to the object of your affections as a person, and reading and responding to her with unfeigned respect for her feelings, you're already most of the way to avoiding the jerk trap.

I also hadn't thought this deeply about compliments that really make me feel good, but I love this rule of thumb:

Learn the different levels of compliments:

Things that are not intrinsic to her person, and that she has control over are safest: "That's a great haircut."

Things that are intrinsic to her and she has no control over need to wait until you've established that your attentions are welcome: "You have incredible eyes."

I don't know that I necessarily need them as different levels of familiarity, but, at least in my case, compliments regarding something I make a conscious decision about are way, way more flattering.