Having just found this thread, and reading through it all, I"ll grant your "friend" has a problem, if not several.
However, as "Cold" as this might sound, those are His problems, not Yours!  And, though I'm all for altruism, they are things He has to deal with, and it's not Your responsibility to take on any/all of His baggage!
Let's also be Truthful here.  The fact that you feel some kind of "duty", to possibly help this guy figure out his own uncertainties, suggests you hold more than a casual interest in Him!
If you are finding that so uncomfortable, I urge you to take a deep look at your own feelings/desires, in regard to Him, and seriously consider a "reset"!
It seems you have as much of an attraction to Him, as He (seemingly/obviously) does to You!
You're allowing yourself to be drawn into a "No Win" situation!  It's not just Him.  It's Both of you!
For your own sake, I'd highly recommend, as difficult as it might be for You, to put that guy on personal "Ignore"!
He will Never by "Yours", or You "His", as much as you're granting him control of you as if you are "His".
Be social.  Be friendly.  Be pleasant.  But that's it!  
You have allowed this dude to get under your skin, and into your Heart, where he doesn't belong, and sounds like he never will.
On the other hand, since Time is so short, and none of us are going to survive Life anyway, if you'd be willing to abandon your own morals, with the gravity of "morals" being questionable in the long run (What's the Real point?), it also sounds like you might be passing up the opportunity of a "Lifetime", to "Bag" a Hot "Straight" Man, on "The Down Low", and fuck each other, like bunnies, curl each others' toes, and make some Awesome stories to remember in both your old ages!  
 
   
   
   
Do not loose sight that those choices are Yours to make.  And, nothing is written in stone.
All the more reasons to ... No Matter What ...
Keep Smilin'!!  
 
  
Chaz  
