Tell him to not beat himself up over thinking too much. It's human nature. Tell him to concentrate on the next piece of *** instead of the one he's stuck on and will never have.
so what you are saying is, to tell him to think of a new girl but stay with the one he has now? i don't think that's being loyal! lol anyways read this, my friend told me this last night.
I am serious about this, watch Good Will Hunting. There's now two conversations going on within a day about this same circumstance.
I won't pull directly from the movie but relation and with my own life as well. You nailed it when you were talking about no father and working mother. It's the way he was brought up or the lack of. I too had a similar upbringing and found myself content thinking/talking inside to myself. His lack of communication like the gentleman touches on is extremely key. He is not able to communicate with her because he does not know for himself what is the issue, why he thinks so much, what is keeping him bound.
He must be able to come to grasp within himself. From the outside you can do a lot of speculation and bring him to realize bit by bit about the way he is. This will not be an overnight fix once the problem is found. He must want and continuously work with a mentor or teacher who cares for him so much to be there when he does start to open up about his inner most fears and doubts. This may be you. If you are willing to be there for him, you will be there for him the rest of his life because it is his life that is trapped, not this girlfriend. She may be another key factor and be the love of his life, but you mainly will be the savior of his life-or that person who helps him consistently pursue himself.
Furthermore the inability to recognize the problem lies in a long path of layers of oppression in his own mind. He must go back to his childhood to recall the days and nights where there was no one when he felt at his worst and best so he can understand what his actions were, see it from another perspective.
He was not taught how to communicate with those he truly cares about that he's not on a level with like the two of you are. The connection is there with them, the connection is different but there with the two of you. It will take time for him to open up to her, but it's inevitably you or a mentor/therapist to help find the truth behind is suppressing fears and or angers to let them out, let him cry when he realizes the truth....that'll be the beginning.
Much too much it's a consistent battle for good. Keep on being the great friend you are, seeking information to change his life. He'll always love you for it and he will make a difference in the world even more so after he's found himself.