Originally posted by: MovingTarget
TridenT, you fail. Just take a lesson for this. Women don't mind guys who are shy, and that can sometimes work in their favor. However, when a question like that comes up, assertiveness is what they look for. "I guess" is about the worst possible answer you could've given. Too wishy-washy. It screams "You are a friend to me who I don't think too much of and would rather keep at an arms length at all times" or that you simply do not care.
Second, back off for a while. Pushing this in its immedeate aftermath is a BAD idea. If it comes up again in conversation (again, not initiated by you), give her the answer she deserves. If not, wait until the situation has died down and approach it the exact opposite way you usually do. Again, assertiveness. Be direct and don't pussyfoot around the issue.
Third, Ladder theory is FALSE. If you know what you are doing, going between ladders can be accomplished with relative ease. The rewards can be even greater long-term doing this, but it hurts all the more if/when you fall on your ass. Tread wisely.