Maria: Everything you are saying is so much like my other friend. Her son is a charmer too, has convinced other parents that his parents are gone for the weekend and he needs places to stay, etc. Unfortunately, I think you have a long road ahead of you. I know that you said that you worked, but is it possible for one of you to change your situation - even if only for a few months, so that one of you is home all the time he is out of school. You can drive him to school and pick him up at the door, you can even get the school involved to not dismiss him except to you (ie. don't let him walk out the door without you, etc) and try some tough love discipline for a few months. Seriously, physically keeping him in your house and away from the bad influences for a little while so that you can work on his soul (and honestly, his BG management too). I get the not taking away the phone, but maybe he needs to backtrack to one with only a few pre-programmed numbers that are yours and that restricts his texting with his friends, etc. Ultimately, you may or may not be able to get control of this situation, unfortunately. Knowing all of this, I would have a conversation about smoking but leave it at that - I think you have bigger fish to fry right now and hopefully he can learn that smoking is awful on his own - he might not right away but eventually he probably will.