Interesting. Similar to some of my experiences, although I'm guessing you're about his age, and I'm 30 years older now. You can like or even love this guy, but don't fall for him too hard. And don't try and fix him by loving him better. Only he can do that. Most of my relationships were with broken people who I thought I could help. I never imagined it possible to be loved for myself. Still don't. But as a older woman past the menopause who never married and has no family, all I will say is that life passes us by faster than we think. You care for him and might invest a lot in him, but what about you? Do you want to marry and have a family? What do you want out of your life? Is he able to give you that? It doesn't sound like it from what you've said. His story is very sad and I understand the depth of your feeling to care and to support. But don't go too deep. See if you can help him get professional help. Stay close friends if you can't stop your feelings, but DONT sleep with him. That would be the slide downwards into chaos and heartbreak. Care for yourself too.