You're not being mean, you're being a parent. It's not your job to be their friend when they are at risk of making bad decisions, it's your job to keep them safe and show them the path.

Yes, it was not good to threaten time with their father as a form of punishment, but let's look at what you did well there -- ultimately you got H to parent WITH you instead of letting D play one of you off against the other, and you got D to come home instead of sleeping over at friend's house. Would it be worth it to talk to friend's parents? I read a survey recently where 95% of the time, the other parents want you to say something if there is inappropriate behavior going on.

Finally, you didn't get into it with him yet again.

See? You've been thinking that he's living this happy care free life, but in fact he is miserable. He just told you as much.

Accuray

Married 18, Together 20, Now Divorced
M: 48, W: 50, D: 18, S: 16, D: 12
Bomb Dropped (EA, D): 7/13/11
Start Reconcile: 8/15/11
Bomb Dropped (EA, D): 5/1/2014 (Divorced)
In a New Relationship: 3/2015