>>1 I'm a pretty awkward guy myself. So I will see what I can do.
Can he talk to you normally, so to speak? If so, you could advice him on certain things that you can relate to yourself. Try to convince him that talking to that friend is like talking to you.
Of course, it wont be the same, so advice him to improvise. How? I'm not an expert and I really dont know him. So try your best to give a sensible advice.
Since you truly want to advice him. Try researching on socially awkward people and so on.