Saying what you want is more powerful than asking them what they want. When in doubt, ask questions. Winter believes this so-called rule is total garbage. So own the fact that you want to have the conversation. But sometimes, we get lucky and meet someone that we want to keep around. The whole point of the conversation was to map out the boundaries of your relationship, so remembering to stick to them is half the battle. Can you live with what the other person wants?