I think you should just go and talk to him in a friendly way,
saying "hi" is a great way to start off...
I used to be like you, eveything also scared, scared this scared
that... Then one day i thought to myself, "I've been regretting not
doing certain things all my life, I won't let myself regret again".
So i instilled a new mentality into myself, which is "Live each day
to its fullest, without regrets."
Have you ever thought wat if tml he gets sacked or something, then
you'll never get the chance to see him again, you will then regret
not even talking to him for the rest of your life.
So just go and say "Hi!" if nothing happens, you won't lose
anything. Nike says it best: " JUST DO IT! " 
