And for those who say their kids had never done x, y, or z? I grew up in a pretty relaxed home. My parents trusted me a great deal and were always frank and open. Because of this, I also knew that their opinions on issues were typically far more conservative than mine were. It did not "rub off" on any level. And, even though I knew I would not get "punished", I still did not tell my parents about sex, drinking, and drug use. I knew it would kill them and I did not want to do that to them. I knew I was going to be fine. And I was. And did not feel like I should bug my parents with it. To this day, my mom has no idea I have ever done some of the things I experimented with in HS.
1- i was always expected to do well... my parents thought highly of me, expected me to go to college, etc... i think this is major. Let your son know that he has the capacity *and* you expect him to achieve his goals. i'm not saying you expect him to be a doctor, lawyer, etc... but i think when kids see that we believe in them, they see beyond next week, kwim?
2- my mom (single mom, but my dad did this too from afar) supported all of my extra curricular activities. i was the motivator behind all of them, but she found a way to make it happen- music lessons, sports, doing an amazing semester away my junior year of high school, taking a year off after college to travel. talk about giving your kid confidence! it was awesome, i never felt held back. was i smoking pot this whole time? yup. was it out of control? no. and i knew when i had done a bit too much one week, and cut back. my life did not revolve around my occasional use, it was full of other things.
so, point is, all of those things you and your dh are doing to support him in finding other activities and reaching out- awesome. very cool, and very important.
3. my parents didn't do this, but instead of *you* telling your son all the potential issues with drugs- have him research it. you homeschool, right? make it a project. compare drugs, effects, consequences, history, etc... information sinks in more deeply when it's obtained through one's own efforts. certain things will stick with him. i'm not saying don't share your opinion; you say, 'no son, i think smoking is wrong and i don't want you to do it." he says, 'why?' and you say,'let's find out. what do you want to know? lets' do some research..." the books pp's have suggested to you are great.
4. finally, you mentioned something about an initiation or something your dh was going to do, the boy-manhood thing. i cannot say enough about this. super important. i am going to pm you wtih the information about a wilderness school i was involved with in Shasta, Ca with a man who does life-changing boys rights of passage. unbelievable.
i used to work with all the "screwed up" kids, the ones who got kicked out of school, started using in 4th grade etc... and i can say, not one of them came from a home like yours (meaning, theirs was severely dysfunctional and yours is not even close).