Just let it happen naturally - don't analyse stuff. Eventually there will come a time when you are not awkward around each other.
It is always as awkward as arse to start with. For me, it took several months of him coming round before it was natural to chat.
You will generally know when he has progressed to friendship as he'll give you ques (i.e prolonging conversations, asking you questions, laughing with you etc).
For me, I knew because my H commented that every room in my house was a different colour. (That was a compliment). He was noticing things round the house, whereas before it was strictly say hello, pick up the baby and leave.
I followed his que and I still do that now in my efforts to continue developing our R.
