Originally Posted by ratbastid

Here's the thing about death: EVERYBODY'S awkward. There's no right thing to say. If there was ANYTHING you could magically say to make them feel better, everyone would know what it was, and somebody would have said it by now and things would be fine. But there's not.

They know that. They know you're just trying to be helpful and friendly, and that while you'd give your right arm for everything to be okay, there's nothing really to be done. And if you do say something and they immediately burst into tears, it's not what you said, it's the death. So relax.

You might ask your good friend (but probably not his family), "How you holding up?", and then be prepared to just listen to whatever he needs to say, and to get him whatever he needs, from emotional support to physical support (cleaning his house, say), to a good stiff drink conveyed to him in a subtle manner.