Hey, StarsPony, welcome to PsychCentral (PC). "Interesting" situation you've got there. I think, were it mine, I'd wait a goodly amount of time to see if it will stick; I'd frustrate him just a little by not giving in and see if I could check in on him at "odd" times to see if he's sticking with his hard work of starting a new company or hanging out with the boys again? There's no hurry to get back into a bad situation is there? I'd make sure it was gonna stick and not have to just take his word for it; give him a lot longer to "practice" doing things well. I'd maybe even wait until he got his DUI's/Probation under control?