You could ask him about the insurance, but that's really all you can do. Is there a free clinic or something of that nature around you that you might be able to get meds through? If and when someone files, he could be required to provide you with health insurance. It's definately something you should ask for if that happens.
The friends thing can be tough. Since there are no kids perhaps there is a group that meets in your area that you all have similar interests. There are sites on the web (no, not dating sites) too. I've looked into some of these types of activities, but I have teenage D's that live with me and my time isn't always my own (umm, more like rarely).
I don't know about your friend "mediating" though. Pointedly, what good do you see coming out of it. I've got some good friends that know both of us and one with a background that could be helpful and I still wouldn't do it with them. Maybe it's just me. Sounds like your friend wants to help you stop hurting, which is very altruistic I guess, but I think her agenda would be to see you "move on" more than anything. IMO you don't need a sit down with her and him to get there. It takes time. There is no clock that's the same for any two people.
