First — this continues to be an amazing, intelligent, thoughtful and smart discussion — kol hakavod to YWN for hosting and managing this board — I imagine so helpful to so many people.
I did want to respond to something WOW had written earlier.
I can only go by my own experience — but telling your son that anything goyish is dangerous schmutz is about the worst way to approach this — he knows that’s not true and makes you untrustworthy and then irrelevant.
By now he’s figured out that most goyim arent shickers; the best secular writers and moviemakers convey the challenges and complexities of life (especially what he’s experiencing) with insight and profundity; the canon of Western music, from Bach to Bebop to the Beatles to Broadway, reaches into the human soul in ways nothing else can.
I would suggest that you need to find a way to not paint this in black and white but give him the space to find ways to explore and incorporate the best of mainstream culture into his Judaism and not create a situation where one is set against the other forcing him to make a choice you won’t like. While I know this is not your Hashkafa, it may be the process by which he finds a Judaism that’s comfortable for him rather then breaking with everything.
I hope this is helpful