Have a good trip Mutatio. What a beautiful weekend to be going to Boston! Its' probably too late now as you are most likely already traveling, but I was going to suggest an audio book for the car ride if its a long trip- maybe something positive or funny to fill the silence.
I also struggle with the thought that the silence might be reinforcing H's perception that there is nothing left between us. But that can apply to any aspect of DB. If I don't pursue, will he think its over. If I do pursue, will he be turned off. If I GAL will he think I don't need him and then its over. If I don't GAL will he think its more of the same. Its hard to know what to think, so I am sticking with DB, because obviously if my instincts were right I wouldn't be in this situation to start with.