I think you just need to be there for your boss and support him through his difficult moments - losing your parents (especially one followed by another) is emotionally shocking.

This happened to my husband just last year - his Mom passed in November 2009 and his Dad passed in February 2010. They lived in Europe and he was not able to get to them in time to say goodbye. They were both quite aged and in poor health so their passing was not a surprise however, the finality of losing your parents is something one is never ready for, regardless of the circumstances. During this time we have also been slowly losing my mother to Alzheimer's - another reality check that no one is ever prepared for. So for our family it has been a cumulative collection of heart breaking loss and difficult feelings that appear out of nowhere some days.

Although my husband accepted the loss, his grief is still under the surface and whenever we speak of his parents, he tears up - it takes a long while to get beyond that emotion. I sometimes purposely recall a story just to get him to speak about them and if the tears come - it is a good thing. We brought his sister over for a visit this past summer - and there were painful moments of remembrance but having those moments helped.

For now having the support of friends and colleagues means a great deal to both of us. Just knowing that others understand when we get choked up because something has triggered a memory helps get us through the moment. In time, we will be able to smile with those memories but for now it is just important to embrace the reality of the loss and deal with it in our own best way.

I hope this helps you deal with the confusion somewhat.