I dunno, Slowly. In reading the IM traffic, it seems to me that he's grieving which can be seen as a healing step. He's grieving and sharing that grief with you.
Quote: sl what do you struggle with most? ng the sadness sl about her? ng how messed up her life is ng to pursue this against all odds ng its hard to understand ng and very sad
This sounds to me as if he sees the person she could be, but isn't.
Quote: ng yes regret that people are not more honest ng and live by inscurities ng to the point of loosing their dignity
This also sounds like he's seeing the "real OW". If he in any way idealized her, then you can see this phase as coming to terms with who she really is vs. his ideal.
I am impressed as all git out that he shares this with you. It means so much for your R. It says a lot about the kind of person you are, too. Open, honest, intelligent, trustworthy. Just by sharing this, he's telling you that you are many things she's not.