It's not as bad an idea as you think, but I'd stay away from self help type stuff and think more along the lines of storytelling and novels. Think graphic novels.

17 year old boys are not going to be reading Medium articles about relationships. They're here, but theyre predominantly in niche stuff.

Also, with any kind of teenager, the best way to teach them stuff is the piggyback method. If you try to talk to them directly about intimate things without them having had specifically asked, they'll typically tune out and feel preached at. Then you're looking at some sullenness and loss of street cred.

They're not stupid.

Without already having an established relationship with them where you've cultivated trust, to them you're just going to be yet another annoying know-it-all adult riding their ass.

So you slip it in, in the between times. Like that last article I wrote, a young man who stumbles on that learns that if you don't wake up at the same time or go to bed around time time , then leaving "love" notes is a good way to keep in touch and combat feelings of loneliness.

From Serendipity, a young man will learn that when women talk about wanting vulnerability, they don't mean dumping all your angst on them, as a stranger in the street, they mean being present in the moment so that women can interact with you. Even moments of annoyance can spark a fun and flirty interaction. The performative masks aren't doing young men any favors because they're inadvertently signalling that they want to be left alone.

Being 40 isn't what makes you uncool. Elon Musk is in his 50s and Andrew Tate is just a few years younger than you but still more than twice the age a teenage boy. They're both perceived as cool because they're living their own narratives and not someone else's.

In the end, no one wants to have to live their life by someone else's leave. You know what I mean? People want to be free and unmolested to make their own decision and choices. We all want that.