I'm in the same position as you. I am 30 and my daughters are 13 and 10. I feel as if I'm able to balance the parent/friend thing very well. You have to understand that they are going to do things they shouldn't regardless of how strict or lenient you are. It's part of being a kid. I don't think there's a kid in this world that hasn't done something they knew would piss their parents off. My daughter tells me plenty of things that she knows I'm not going to be too happy about.. and I like the fact that she feels she can talk to me & confide in me. I don't ever want them to be afraid of what I'll think or say. The fact that your son confides in you knowing he will get in trouble shows you raised an honest kid who knows when he does wrong he gets what he deserves and knows that you're doing what's best for him. Sounds like you're doing a pretty good job balancing the parent/friend thing yourself. Who knows why exactly kids do what they do.. maybe b/c they do and then think.. not think and then do?!