Trial and Error – How Open is Too Open?

My relationship status in an office environment is the one place I keep it on the down low.  Current co-workers always get a glossed over explanation as I have been in far too many back stabbing offices.  I have a preference for discussions of the humorous nature in a workplace, as it creates a twofold effect.  The first being the air of a friendly and positive atmosphere and the second combats my usual colder and secretive nature.  By opening up with funny little situations and anecdotes I am able to fit in a little better.
Hie, hoe, hum, what to do and say when dating?  It infuriates me when E will text a girl right in front of me and admit to it but offer absolutely no additional information.  In his mind I think it just avoids a fight and negativity, but in my mind it allows a situation to build and fester until I explode.  Vague answers drive me crazy, so clearly that is not open enough.   But what other options are there?  I tried being completely honest and open with a guy and the result was that every time we talked he would bring it up in the most negative, possessive and controlling way.  I could not really fault him as I get the temptation to react that way, but it serves at times to push me far away.  Thus there is most definitely a too open category. 
I am grateful for one thing, and that is being in a situation whereby there are very few expectations and I can test the waters a bit to find a solution that will work for me.  I want to get to the point where I can exemplify the reactions that I wish to receive.  It is not perfect or ideal for me being in a state of limbo, but the bottom line is that is where I am at and I need to make the most of a unique situation.  There are bigger stresses in my life and right now, and working on those must be the priority.  I have no answers, but I am asking the right questions so a solution is sure to present itself.

Trying to find balance between work, home and dating openness is something that takes trial and error.  Currently, lips sealed or humor in the workplace, limited in the home life and limited in the dating world.  I hope someday I can look back at this post and shout that I can be open everywhere in my life!