What he wants is someone to listen to him and validate his feelings. He's not looking for a fix to the problem. He knows that he's the one that has to figure it out and let it go. You can continue to say that you are sorry he feels the way that he does and then drop it. At some point he may very well speak to her about how he feels. However, he needs to come up with the solution on his own.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.
