Magic, There will be times that he'll test you and see where your head is at and then there will be times when he's just being himself. For some unknown reason, you now perceive everything he does as baiting you. Asking you if you want a coffee or going out for a drink is not baiting you. It's just asking you out. Now, if he begins to get nosey about your dating, then that's another story. That's your business and if you choose not to tell him what you are doing, then don't...but you are under no obligation to live like a nun for the rest of your life.
If you aren't comfortable w/relationship talks, then tell him that you aren't going to discuss it and walk away or change the subject...but at some point relationship talks may have to happen. You do tend to pick and choose from the conversations what you want to acknowledge and hear. I might be interpreting your postings incorrectly on this, but that's how it comes across. The best thing to do is listen and replay the entire conversation, not just certain parts of it.
As for Pearl, when she worked on herself and came to realize that no matter what happens she would be okay, that's when things began to change for her. Dropping the rope, accepting the situation and becoming all you can be are the keys. Learning to respect yourself first and then looking at the relationship for what it was and is now is also part of it.
It didn't take long for the new and improved you that you carried away from your retreat to go by the wayside. Magic, you have to be determined to work on you and you alone. Dig deep for that self respect and if you respect yourself and set your boundaries, then others will learn to respect you for the intelligent person that you are.
As for your SO, keep your conversations to work and don't engage in relationship talks right now. Your focus has to be on the financials and on you and your daughter. If your SO truly wanted things to change, he would have been doing the work by now. I don't see any of that in your postings. He's all talk and nothing more.
Let's try to keep the focus on you and try to break the habit of blow by blow of the activities/interactions you have w/him. The sooner you let him go and think of him as just a co-worker, the better.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.