This is my first post here and first time reaching out for parenting advice. Our son is an only child, and when he was little, was a great kid. He did very well in school and absolutely loved baseball. He loved going to baseball games, collecting baseball cards, and playing baseball. He was very good at little league and had the trophies to prove it. He was every parents' dream child and we had a good relationship. But that all changed when we moved to a new community over the summer between 8th grade and high school. In 9th grade he fell in with a bad crowd. He was a follower and not a leader, but he chose to follow losers who today are mostly either dead or in prison. Now I'm not talking boys will be boys mischief, a little drinking and smoking a little pot, I'm talking trouble with the law-the kind that can get you locked up. The first serious incident happened when he was 15. He and three of his loser buddies stole my wifes' brand new car and totalled it. This is where the friction also started between the wife and I. I was raised in a "spare the rod, spoil the child" household. If I seriously misbehaved I could count on a beating with Dad's belt. My wife on the other hand did not believe in hitting children. She was and always continues to be the "softie". This is something I have always chalked up to the strong mother-child bond. Back to the story- since this was his first serious episode my wife did not want to press charges. I disagreed and we fought over it but I eventually gave in. We had numerous trips to school and court over truancy. He would skip school and he and his buddies would hang out at our house drinking and doing whatever sort of drugs they were doing. He was openly defiant to ANY authority. I tried physically forcing him to attend school by taking him there personally every day. It didn't matter as he and his friends would just leave and hang out at our house. We tried to stop this by taking away his house key. However, we would come home from work to find evidence that someone was in the house. Turns out he had a copy made of the house key. So we had to change the locks. That still didn't stop him. He would break in through his 2nd floor bedroom window. Took us a while to figure out how he was getting in the house. He also stole money from us. He took $100 from his mothers purse one time. At 16 he was expelled from school for truancy. He got arrested when he was riding around in a car with a bunch of his friends and someone cut the driver off. His buddy chased the other driver and ran him off the road. The guy took down the license number and called the cops. Shortly thereafter the cops caught up with the kids and arrested them. My son was only a passenger, but alcohol and marijuana were found in the car. He also got arrested for shoplifting two times. The final straw broke when he and his friends stole a car and got caught when he was 17. The judge sentenced him to a group home for troubled teenaged boys. Well our son is attracted to losers like a moth to a flame. He and a couple of other boys snuck out of the home and were caught. They had a zero tolerance ploicy and he was kicked out and sent to juvenile hall until his 18th birthday. At 18 he came back to live with us despite my protests. My wife as I mentioned before is very soft-I would consider it enabling, and he took full advantage. The boy is a master manipulator and liar, and is very good at telling anyone exactly what he wants them to hear and make them believe it. He used his manipulative ways to pit my wife and I against each other. My personal philosophy is that at 18 you are an adult, and you either join the real world, join the military, or go to college. The military was out. The Army wouldn't take him, and in hindsight that's good since he probably would have ended up in Iraq. The wife and I came to a compromise when I agreed to let him move back in with us as long as he got a job and paid us for room and board. He quickly found a job painting houses, but he was also quickly up to his old tricks. When rent time came, he continuously sweet talked and made excuses to my wife to let the rent slide. "I'll pay you next week, because I need money now for.......", and of course, when next week came, the money didn't. His attitude didn't improve much either. He was defiant and disrespectful, maybe even moreso now that he was legally an adult. He also delveloped a huge sense of entitlement. He didn't think it was fair that he had to work and pay us for room and board. He thought that he could just sit around on our couch all day smoking pot and watching TV. He was home for less than a year before we finally kicked him out after he had a very heated fight with his mother. He drifted around for a bit, staying with friends and even with his aunt for a while. At 21 he landed a job as a prep cook at a resort. Part of the deal was the resort provided room and board for employees. My wife and I hoped that he would finally grow up and be able to make it on his own in the adult world. October came around and one day my wife approached me and told me that our son wanted to come stay with us for a while. Things slowed down at the resort and he was laid off for the winter. I was 110% against it. Been there, done that, and oh by the way, we kicked him out of the house two years earlier. He was an adult and he needed to take care of himself. My wife assured me that it was only temporary and his employer told him he would be hired back next summer when business picked up again. She also assured me that he knew he was expected to chip in around the house. If he couldn't pay for room and board, he could earn his keep by doing chores. Reluctantly I agreed and for the first few weeks things were okay, but soon after it was just like old times. This episode nearly ended with me divorcing my wife and walking out. As an adult, I had much less patience for his BS and really adopted more of a hard line approach with his unacceptable behavior. He would tell his mother that I am mean to him and treat him terribly. He caused my wife and I to fight constantly. He told both of us numerous times that we didn't love him, and when I told him I had a good mind to put him out, he told us that if we did he would kill himself. Of course that struck right to my wife in the short term. He was very successful at pitting my wife and I against each other, but the charade and lies would soon come to an end. Memorial day came and there was no talk about returning to work at the resort, so my wife confronted him and that's when he admitted that there was no job to go back to. He had been fired for smoking pot on the job. It blew up into a huge fight and we ended up kicking him out of the house again. This time good fortune seemed to be on his side. While he was living with us, he met a girl at a party and they started dating. When we kicked him out he moved in with his girlfriend and her roommates. Eventually they got their own apartment. It could have been he was just growing out of his "bad patch" or maybe his new girlfriend did what we could never do, but he seemed like he was really turning his life around. She was motivated and had goals and that was probably good for him. He soon had a full time job (where he worked until just yesterday) and did very well. He was promoted to a supervisory position. They got married and in 2007 they purchased a home. I remember at their wedding reception feeling something I hadn't felt in years-pride in my child. They were even trying to start a family and his mother was super excited over the thoughts of becoming a grandmoter. Well it all came tumbling down starting last October. He stopped by our house one day while I was on a business trip and told his mother that he and his wife were separated. She moved in with her cousin and he was living in their house. Form that point on it was like things just picked up where they left off nearly ten years ago when we kicked him out of our house. At first it started with the visits, and we were happy. What parent doesn't want to see their kids more often? But the visits became like three or more times a week, often just showing up. Next came the borrowing of money. We knew things were tight because they had a big mortgage and his soon-to-be ex was not giving him anything. She told him she didn't want anything to do with the house anymore. Of course at first, borrowed money was returned promptly. When he couldn't pay us back I made a deal that he could work his debt off by donig chores for us. He painted our house to work of debt. But even that came to an end. He would start making all sorts of excuses why he couldn't come over, and even when he promised to come over, he would be a no show. I would get angry because we would sit around all day on a Saturday waiting for him and he would not even bother to call. As of the $100 he borrowed two weeks ago, he now owes us over $500. I am angry because he always seems to have money for pot and alcohol and buying clothes for his new girlfirend, yet two weeks ago he calls and asks to borrow $100 because his lights are going to be shut off. His mortgage hasn't been paid since his ex-wife moved out, and at this point he's nearly $20,000 behind. When he was married, they ran up a bunch of credit card debt. Last summer he took out a loan in his name to buy his wife a car because her credit was maxed out. When they split, she took the car and said she would pay the loan. Last month she bought a new car and dropped the other one off with our son, and surprise! she hadn't made the payment in two months. A couple of months ago our son started dating a 20 year old that he met on a popular social media site. Seems to fit perfectly because he's acting more like a 20 year old kid than a 30 year old man. All these two do is party together. While married he did like the partying, but we never paid it much mind since he was keeping his life together, but since his split with the ex, it seemed like he was drinking pretty much all the time. But wait, there's more. His new 20 year old play thing lived nearly two hours away. She doesn't own a car and shared an apartment near her job with roommates. Their lease was up and she was looking for a new apartment when they had the bright idea that she would move in with #1 son. Since she has no car, she quit her job and moved in with our son. So now he's supporting her, both of them living in a foreclosed house. Any effort to try and give them advice was met with defiance. She landed a job offer soon after moving in with him but didn't want to stop smoking pot long enough to pass the drug test, so of course the job offer fell through and she's made no effort to find employment since. Two nights ago he calls during dinner and asks if we could do him a favor and drive his girlfirend to her uncle's house. When we asked why, he told us that he had to go to rehab. Apparently he showed up wasted for work and they told him to go to rehab or be fired. When my wife asked why he couldn't drive her, he admitted that his car had been repossessed and he was hiding his ex-wife's car so that the repo men would not find it. Apparently he and his new girlfirend are both hooked on prescription pain killers. He admitted to us that's where all his money has gone. Yesterday he calls his mother and for whatever reason, he decided not to go to rehab, so now he's out of a job. Eventually the bank is going to take his house, so soon he and his girlfriend will be homeless. Today is his 31st birthday and it seems like things in his life are worse than ever. My wife is absolutely shattered over this. When she's not crying she is staring blankly into space. She says she wants to do something for him. I on the other hand, while very concerned, am angry and disgusted. I told her that there is no way he is coming to live with us, even on a temporary basis. I am also not willing to give him a single cent to get out of this latest fix. Personally I have a good mind to tell him that we want him out of our lives and don't call us unless you get your life together. My loser alcoholic uncle was living with my elderly grandparents when he was in his 50's and I will not tolerate that with my kid. He's a grown man for crying out loud. But part of me worries that this is the wrong thing to do. Prescription pain killer addiction is the first step to heroin addiction. I guess part of it is that deep beneath my tough love exterior, I feel guilty about cutting off ties with him. Part of my strong feelings come from holding the past against him. I understand that addiction is a disease and bad things happen to good people, and if this was the first rough patch in his life I would be more compassionate and willing to do whatever I could to help, but I just can't stop thinking about all the BS, lies, and stealing from his teen years and the two times he lived with us as an adult that ended with him getting kicked out. I am also concerned that this latest episode could end my marriage. God forbid, if he overdosed or killed himself it would just destroy his mother. I also feel a bit selfish because I want my house for myself. It's just been the wife and I and the dog for nearly a decade and I DON'T want a roommate, I want my peace, quiet, and privacy. Is it tough love or am I being an uncaring jerk? Is there a way I can help our son without enabling him?