First of all, kudos on asking for advice, I know that that’s not easy to do, especially in situations like these. I don’t have kids so I can’t imagine what you must be feeling right now, but I work with kids like these every day at Our Place so I hope I can offer some ideas. Please pardon me if I seem blunt at times. Please correct me when I’m wrong.
Someone said above that in their opinion your kid isn’t going anymore, that he’s already a but further. Based on your description I would say that’s accurate. While there is what to be said about what people said above about trying to instill a love for yahadus is nice, but it has to be in context. It sounds from what you said that your son is angry about something and that is making him dislike judaism and by extension his family. The most important thing is unconditional love, as mentioned above by several people.
You ask a good question though, exactly how permissive do you have to be to be seen as loving unconditionally? The truth is that permissiveness and love are not mutually inclusive. For example, if a small child shoplifts and you reprimand him, do you not still love him? Permissiveness is not necessarily love, not is lack of permissiveness a lack of love. But back on point. I would say based on your description that it’s past the point of permission, so that’s a moot point. How do you show unconditional love for someone who does not appear to value that love? Good question.
First of all, accept who and what your son is. That does not mean you have to like it, that does not mean you have to approve of it (nor should you), but you should accept it. When you see your son now you need to see your son, not what you would have liked him to be, not who perhaps he might have been, you need to see and love what he is. That means that no matter how he looks, and who he is with, the smile on your face when you greet him is the same as it would be if he looked like the next bochur. I know that that’s hard to do, but that’s what he needs. You need to love him.
This is not meant as a criticism, it’s just instructional. Mussar has a time and a place, and it is only to be given if it will be readily accepted. It doesn’t sound like your son is interested in any, so don’t offer it. When you interact, leave it all off the table, and just treat him like you would if he were your standard run of the mill kid. The idea being that right now there’s something holding him back from embracing yahadus, and many times it’s common for kids to view their parents as the source of whatever is bothering him. Eventually that something will hopefully go away, and when it does he will be looking for a strong support system to fall back on. That strong support system will ideally be his family.
By doing this you are investing in his future. Support him and love him and he will eventually return. If he isn’t interested in going to yeshiva, don’t push it. Make a man out of him, help him learn a trade and get an honest paying job. There is no reason why he can’t be an upstanding member of society just because he doesn’t feel like being frum now. It will help in the long run if his life gets in order now.
About the wrong crowd though…that’s a tough one. There’s not much you can do about who he hangs out with, and forbidding it outright will just make him drift further away. I don’t know what he’s into, or what his friends are into. Many kids turn to the streets just to do what they want regardless of the consequences, but the fact that your son comes home at night is a very good thing. Please try to keep it that way.
You have quite a challenge ahead of you, and I wish you much hatzlacha. Just two questions, one may be a bit offensive but I don’t intend it that way. 1) Do you have any idea what might be causing such intense anger? 2) Is he on anything? Please be mochel me for the second question and feel free not to answer it.