Two days ago was the birthday of his sister, who died in a car wreck a few years ago. He's been taking it really hard. Just by the types of replied I'm getting, I think he's depressed (I suffer from depression as well, although I've been much much better for a long time). He keeps saying he has a lot on his mind and needs to "work through it alone." We're meeting after I get off work today, and I assume he's going to break up with me. Don't get me wrong, it's his life and he can make his own decisions. But I know this choice isn't coming from somewhere healthy. His self harm takes the form of recklessness, and I think this is one of those things. 

Can anyone think of something I can do or say that could make him understand that this is a mistake? I feel like I could really be a positive force for him right now, given my experience with this type of thing. It just seems stupid to throw away something that makes you happy just for the sake of throwing it away.