When I was that age, the more my Mom pushed it, the more I resisted.
My late Dad on the other hand, just kicked back about the whole thing. Meaning he took a different tack on it. He just made sure we "knew" he was there for us no matter what and that we could talk to him whenever/however/about anything. He'd often stay up late at night just watching tv. Not for his sake, but for ours (me and my sibling). He KNEW that it was late at night, when things were mellow, that we would approach him with thoughts in our heads and ideas about life. So, he waited. And sure enough, we would come out of our rooms, sit down, not making it obvious... but we'd then open our mouths and broach topics or our "problems" with him. He'd listen. Not judge or lecture. But listen. Then we'd ask for his ideas. And he gave them to us, as mature peers. Honestly and laid-back like. Then we'd be happy, and feel close to him. It was a "bonding" that we had with him. And I miss that still, with him, even though I am all grown up. THAT is what wonderful memories are, that he created for us, with us in mind.
But the thing is, he KNEW our cues. He knew us. He understood us. He never forced himself on us, to talk about our life. We offered it to him. Openly, and trusting him. We knew, he'd always be there, not judging us or telling us how to "be". He took us for "who" we were, and who we were becoming. Of course, he'd look out for our safety and friends. He made sure our home was where we could bring our friends. And he even planned things for us at our home. Making our friends feel at home. Not judging even if they had mohawk hair or whatnot. My friends, even would talk with him as a "parent." So, we inevitably made good choices, about friends, our problems, our life, our interests or hobbies. He also 'accepted' us. THAT... is key, with a teen.
Let your son know, you know he is growing up. But that you are always there for him, as a soft place to fall... and no matter what. And guide him, as you accept his changing maturity and age. Take interest in his interests... see what floats his boat. Take walks with him, and talk. Letting him lead the talks. Not judging. Just trusting and being proud of him.
All the best,
Susan