When I found out, he was remorseful, and willing to do all the things to make us work.
Obviously he wasn’t actually remorseful. He was regretful for being caught. Real remorse is persistent, consistent and dedicated and cannot be demonstrated in just 3-weeks.
Then he got frustrated with having to tell me what he was doing all the time
Remorse is lovingly patient. It’s patient because it uses empathy to assuage itself and re-engage during setbacks, when it gets frustrated. It uses empathy to predict your needs and patterns of behavior.
I found out a week later he started back up with her.
Even when remorse gets frustrated, it would never dream of re-inflicting that very pain upon you that he claims has caused him so much remorse.
Some days he tells me he wants to do whatever it will take but doesn’t know if he can and doesn’t want to hurt me more.
That’s just a cop out. He doesn’t hesitate hurting you by breaking NC, but acts all so concerned about hurting you here.
It is sometimes like pulling teeth to get him to be open and honest with me.
You won’t get anywhere in R without a whole new level of intimacy that begins with him opening up and being honest. Trusting you with his truths, making himself vulnerable to you with the uncomfortable truths. Sharing his intimate discoveries with you while on his journey of self examination is very binding.
How do I know how long to wait for him to figure out if he’s up for this or not?
There are certain things you don’t have to wait one minute for such as: NC, full transparency, STD testing, getting himself into IC, boundaries.
Then there are things that do take a bit of time such as: full disclosure, The Timeline, therapeutic outcomes and results, the evolution of a more refined approach to R usually learned from books and counseling.
Your expectations should have applicable consequences for failure that are mutually understood. Breaking NC is a deal breaker for many. Your expectations are not to manipulate him into doing thy bidding, they’re boundaries or trigger points for you so you don’t keep making concessions at your expense. Boundaries help you measure his performance (actions) and level of remorse objectively so that you can more accurately read through his talky-talk shiber-shabber.
Having a WS accept the precious fleeting gift of R and then give you the soggy milk toast reply of "I’m not sure I can do it…sniffle wha" is not encouraging.