Kim,
I'm sorry I didn't get to this earlier, and hope that my answer can still help a little. Your roommate reminds me of something I've just learned. I'm rather borderline too, and I'm a self-injurer. I use self injury to deal with emotions that I can't handle. What I have learned recently is that when I tell someone that I want to hurt myself, that is not the same thing as expressing my feelings. I thought that it was though, and since I couldn't deal with feelings I used that instead and offered it in place of talking about my feelings.
What I am wondering if if maybe your roommate, when he is having difficulty with his feelings, says those things thinking that he is expessing what he is feeling. If that is it, then you could tell him that saying things like that doesn't tell you about his emotions or feelings, and ask him to tell you "I feel ___ because ___" instead. That might be hard for him to do, but if he has support he will be able to work it out.
Let me know if you try it, how it works, ok?
Rap
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“We should always pray for help, but we should always listen for inspiration and impression to proceed in ways different from those we may have thought of.”
– John H. Groberg
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