For those of you DB’ing, how many times did you f’up and regress before you actually started doing it successfully? And when is it too late?

I ask because last night I had a friend visiting from out of town so I had our nanny stay with the kids so I could have dinner with her. His house is on the way back to my house. Yeah, I could have taken the longer route and should have, but I didn’t. I passed by his house in my way home at 10 pm and noticed the lights out and his car wasn’t there. I started to let my mind go crazy with thoughts of where he could be and with who. I got home and sent him a random text message related to an unimportant conversation we had the other day. He replied, but not until midnight. Ugh.

I feel like I try to detatch and after a few days of not hearing from him or getting cold text messages from him I go back to pursuing. Then he’s nice again and I find the confidence to detatch again...until he goes silent or cold again. I worry that he will eventually think “Well, haven’t heard from her so she must be done with me and, thus, I’m done with her.” I know I should not care, but how do you stop these thoughts in your head? And we separated 4.5 months ago and he moved out 2.5 months ago. I stopped the begging and pleading 1.5 months ago. When is it too late?