My boss at work just confided in me that his wife left him last night. I've offered to be a listening ear if he needs it, but I don't know what else to say. He's very clearly (obviously, understandably) distressed and I really really want to do something to help. I care about him just as much as a friend as a boss. We've always had very casual and open communication... not your usual boss/employee relationship. Any advice?
I would just let him talk to you about things, and ask if there is anything else that you can do to help him through this time. It's great that you are willing to be there for him through this tough time
I think that's the very best thing you can do for him - to make the offer and mean it. Be there for him and give him time and space to talk about it. Feelings of loss will be particularly acute and it will take time for him to move beyond those feelings, so while he's going through that process just keep checking with him. Show warmth, consideration and empathy and respond to what he is telling you. Very often, we imagine there is a need for us to say something or do something to try to make things right (you can almost bet your last $ that everyone will be trying to 'rescue' him in some way), when all that's really needed is to listen attentively and respond. It might seem a little passive, but that's what really makes the difference. It's tried and tested. At this early stage, just pay careful attention to his mood, as he will be hurting a lot. If he says he is "fine" or "okay", but his general mood or appearance says otherwise, don't be afraid to double check and ask if he is really fine/okay. Hope this makes sense.
Why not offer to take him for a drink after work? He may open up a bit more and you can provide an empathetic ear. Even if he refuses I am sure that he would appreciate the offer.