I think that every person needs to know themselves, and their kallah. I spoke to my rebbe, and decided that considering the what I've been involved in, unburdening my secret would mean burdening her with it.
So, she has a very general idea of the fact that I've had some issues in the past, and that I've known girls in my past, somewhere. She hasn't pushed for details, and I haven't offered. If she did? I think I'd tell her, staying very vague.
Dov - sorry, not gonna take you up on that one. :-[
Nevermore - in other words (I think), we need to think about tomorrow because there's planing that needs to be done...but we need to live in today, insofar as the tests of today, and not worrying now about the tests of tomorrow.