I am thinking that i will initiate with something simple and then ensure I take a pressure free stance. I know I have a different attitude now and I feel sure I can do this in a more detached mode.

However, just initiating might be pressuring. I guess I could ask him if he minds that i initiate.

In previous times H would get annoyed with me because I was a people pleaser and never made a decision, always waiting on others so perhaps being decisive is a good thing.