I am nervous of giving input, but a few questions came to mind when I read your posts... Do you mind?
I was wondering if you are trying to knock H off the fence on a lot of issues at once. OW... being his friend , wedding, OG, him facing your family and friends... Only you know if you need resolution on all these matters now, because you could be understandably fed up. I am only worried for you that it might be gentler (on YOU, too) if you broke these all up into little events to plan out and "pull the trigger" one by one after H catches up to each? IE, since he brought it up - start with wedding... if he goes, let him face the family then wait and then carry out the detaching plan...
I only worry cause my H seems to "overload" when he's had too much stimuli at once - comments, questions, events, interactions, ANYTHING...And I have not been very good at seeing this happening or conttrolling MY contribution to it (another lightbulb moment)... I hope that doesn't happen for you, unless it is what you want.
Does that make any sense? Feel free (anyone) to tell me if I am wrong.