The best parenting advice I ever read was in one of those bestseller title-bait books they put at the front of the grocery store. I have no idea why I had time to kill at the grocery store, but I did, so I flipped open the section with numbered tips for parents of teenagers. The one I remember is 'don't ask questions'. Seems counter-intuitive. Don't ask questions! But at 16, if your kid wants to talk to you about his day, about girls/boys, about his friends, he will. If he doesn't, he won't. Let your teenager start the conversations, or else he will associate being around you with being forced to air subjects he'd rather not, and eventually he'll stop talking to you altogether. My relationship with my parents is trash, and this is part of why. It's great advice. Additionally, it can serve as a simple warning system. If you continually force your kid to have vapid conversations about homework and his weekend and whatever, you may fail to notice if he withdraws. If, on the other hand, you let your kid initiate all non-quotidian conversations that you have, you'll notice very quickly if something is wrong, because you won't hear from him. Anyway, backing off is an underrated parenting tactic. Doesn't fit all situations, but most of the time it's the right move.