I know this post was started almost a year ago, but I am having a very similar issue right now. My son, 30, has been in jail for over a month now awaiting trial. He has gone from desperate to understanding to outraged and everything in-between. The emotional roller coaster is killing me. I almost caved in yesterday, I was on the website to pay the bail, but backed out. He has been causing heartache in the family since I can remember. Has been arrested 6 or 7 times now. Along the way I just wanted to help him, but I know my help was mostly just enabling him, and on top of everything I am feeling guilty about that too. I ask myself "what if I practiced tough love 10 years ago", etc, etc. He has learned to manipulate people like a pro. I don't know if he knows how to tell the truth and sometimes I think he believes his own stories. He has exhausted each and every family member (and friend) and I am the only one left that is talking to him. I have spent almost $500 on phone calls and commissary so far. This is after I promised myself I wouldn't spend another dime. Everyone loves my son and sees the potential in him, except him. He is an alcoholic and drug addict. He has two daughters, one that will never know him if he doesn't get clean. This is all so sad and depressing to me. I just want to see him do good. He has no where to go but a homeless shelter at this point. I never thought this would be in store for me when I had kids, it is the most heartbreaking thing to experience. Knowing that his choices are Clean and Sober, Dead, or In-Jail, haunts me every night. He thinks I am bailing him out, and I don't know how to tell him I am not. His trial date is 8/17. Please help.