I don't know T.. I recall him discussing some rather personal stuff with you recently so I don't think number 3 is really out of the question... besides, his input on that is also kind of interesting from a db perspective. But I do think number 4 is also a good idea to speak with him about too.
What's taking you to NYC in December? Or is it a BF specific trip? If there are set dates in December that you are going for something and the plan is in place I don't think it's a bad idea to mention that you're doing such and such in NY at that time. I think I would see his response and if he mentions getting together or what his plans are.. and if nothing is said from his end.. then the next time you two communicate (a little closer to December) mention meeting up.
