I've always thought that some of our best prayers are pains we feel for others.  Along this line and regarding souls that seem to be lost, maybe God has sent an answer to your pain.  I haven't quite known what to think of it.

Yesterday my nephew died in a construction accident.  He was in his later 40's and non Catholic.  But the odd thing is that for the past few weeks he has been repenting of things, apologizing and expressing firm purposes of amendment.  He didn't do this privately, but quite publicly with the people he had issues with, which is how I know he did it.  He wasn't a bad guy, that I'm aware of, so it was smaller things like not showing up for family re unions.  

I don't believe in coincidences in the first place, and even if I did this would hardly be in that category.  So maybe God has other rules we don't know about.  Then again, He made the rules, so He can do as wills with them, too.  Like laying down His own life instead of ours.  I don't know.  Just thought I'd share that in case...