From first hand POV and not that long ago...the personal info he gives you, hating himself etc. is manipulation...he knows how to tug at your heart strings. The 40 bucks, been there is he a pill guy bc they always want 20 or 40 for some reason...the other things about being open about meetings, that is so you think he is trying and that he is still in the "using" you stage...as soon as you start saying no, sticking your ground and making boundaries, you will see the real him. Thank goodness you are not in debt and I am sorry to be the one to say this but, run like heii and be glad you don't have a baby involved. If I had a nickel for every time I heard this story I could trump the Donald...the best thing you can do is give him space, take a break and watch him when you are not enabling to see what his actions prove, words won't take back the years of stress, money, heartache, possible diseases and even high behavior that you are about to embark upon. If he is getting better it will show, if he wants to talk great, why must we jump on this ride and be so closely involved when someone is going through a whirlwind...love him from a safe distance...I didn't suggest no contact, but I don't suggest intimate contact either...just my experience...