sounds like you've been very conscientious about expressing your concerns to him, and so far, he's responded with resistance, defensiveness, and counter-attack. I love that you phrased it "my concerns" rather than "his problem." This tells me you are already aware of the importance of using I-messages and taking personal responsibility in your communication -- and probably explains why you still have a good relationship with him. Good for you!
I agree that underage drinking is a serious concern, and you may indeed be right that he's depressed. I wonder if it might be time for a different approach.
Think of the current dynamic as a tug-of-war between the two of you. You shouldn't drink vs. I'll do what I want. While you are trying to pull him over into seeing things your way, the battle is about autonomy, not drinking. I'd be very surprised if he responded with, "Yeah, you're right Mom. I do turn into a monster when I drink. Thanks for bringing that to my attention. What should I do next?"
Getting him to see your side hasn't worked. Maybe it's time to drop the rope and stand next to him on his side, to see what it's like over there. To work together effectively as a team, it might help if you understood why drinking appeals to him.
I'm thinking you could say something like this:
Son, I've already told you I'm concerned about your drinking. What I haven't told you lately is that I know you are a smart kid with a very bright future, and I've seen you make lots of really good decisions for yourself. You must have decided that something makes drinking worth the risk to you. Clearly, that's not something that I or anyone else can decide for you, and even though I'm scared about what the consequences of this choice might be for you, I'm not going to try to convince you to change your mind. If you are open to it, I'd love to tell you about my concerns, so I feel like I'm doing a good job as your mom. I also would love to hear about your decision if you want to share it with me. I want to understand your perspective.
What's magical about this kind of approach is that it directs the spotlight of his attention away from resisting you, and onto self-examination. That's right where we want it to be. He may not open up all at once, of course. It might be a while before he trusts that you are truly not going to pick up that rope again and tell him he's wrong.
It's sort of like if our kids know we are not gonna question them constantly about their choices, they make them more carefully. When people are over my shoulder watching me work, I make a ton of mistakes because I am nervous. When they leave, I relax, and am far more likely to catch and correct my own mistakes.
Sound the fire alarm by respectfully sharing your concerns, and then get out of the way so he can put the fire out himself (by changing his behavior). If he asks you for help, then by all means, jump to his side.
We simply cannot reasonably expect to control our 16 year old's behavior anymore. Teenagers will inevitably experiment. They have to -- they need experiences in order to learn.
Parents can be the safe place where they can process that learning. We want them to see us as a resource to help them sort out their choices and the consequences. See if you can position yourself as a teammate, not an adversary. Let him have an opinion that is different than yours on this drinking issue. That doesn't mean you agree with him or endorse his behavior. It does mean that when he's not so busy fighting off your opinion, he has some time and energy to look at what drinking is doing to him.
I hope this is helpful.
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