I don't know about
him, but I know a case of somebody who has failed to chase the
younger sister, ending up chasing the older sister.
Well, it could be a possibility in your case as well.
Regardless of his intent, I guess if you are uncomfortable with
him, you don't have to consider so much, since you are not
responsible in any ways to make him feel good. Of course, you don't
have to trash him; some people just need to know the truth and you
could learn to keep his pain short and decisive. 
Cheers
