Hi Barbara,
I was wondering how to deal with the following situation: my son has a friend, "Sam." They are 13 and have been friends since they were 6. Sam has been here countless times, as he is also in the neighborhood. Overall, he is a nice boy, but can sometimes get a bit wild when a group is together fooling around. Over the past 6 yrs. I have had to ask him twice to not break toys. This past weekend, my son had his group of friends over. I specifically asked the group (directed to him) to not be destructive.
Two days later, I found that a baby doll of my daughters was written on and a wooden dowel was pierced through its plastic/rubber head! My son was upset, told me it was Sam and that he had asked him to stop.
I do not know how to proceed with this. Do I speak with him? His parents? Even though it is an old toy not played with any longer, I am disturbed that he would disrespect a friend's property, that is was so deliberately violent and he didn't heed my or my son's requests. Please advise. Thank you.

Hi Jane,
I don't blame you for being upset -- that's a pretty blatant and destructive act. There are two pieces to deal with.
Let's take your son first. Chances are this friendship is on a downhill slide; at this age, boys tend to form new friendship groups, anyway, and it sounds like your son is pretty unhappy with Sam -- perhaps there are other behaviors you don't even know about. So while you don't want to specifically tell him, "I don't want you to be friends with Sam anymore," (that almost always backfires), it is important to validate your son's judgement, along the lines of, "Yeah, you're right, that was upsetting." Could he tell Sam he didn't like what happened? At 13, boys tend to talk about their feelings, certainly more than they did at 10, and he might be comfortable saying: "I didn't like that, Sam."
Also talk about what he could if there's a next time. Could he find some excuse to leave his friends for the moment (help him brainstorm that) and get the adult in charge? This is easier to do at his own house, but he could also do it elsewhere so that the adult can intervene while the behavior is happening. So if it's your house, what would you say? Remind Sam of the rules of the house (which you had mentioned when he first arrived), tell him you're disappointed he would destroy one of your daughter's toys, and it's time for him to go home. When the parents come to get him, tell them what happened: Sam got destructive with your daughter's toy. That puts them in the loop.
After the fact is trickier. I asked Arlington (MA) parenting consultant Linda Braun to weigh in on this. She's a professor emeritus at Wheelock College, the former director of Families First Parenting Programs, and someone whose advice always makes sense to me. Here's what she said:
"She could call the parents and tell them what happened, but I usually prefer to speak with the perpetrator first. So if this boy will be coming by again in the near future, she should take him aside and tell him that she needs to speak with him. Say you were disappointed to learn what he did last time he was there. Be very specific about the maiming of the doll. Then, if she is up to it, she could try to find out why: was he angry? was he trying to entertain the other kids? If he opens up, she can be understanding, but make clear that it is not okay to destroy others' property. Otherwise she can just say if anything like that happens again, she will call his parents and (if she wants) he will not be able to come to their home for a period of time. (She decides what period). Alternatively, if his response is defiant and/or she feels a need to share this with the parents now, she could tell him that she will be calling his parents to tell them what happened."
Should you call the parents anyway? More than likely, if he's doing destructive things at your house, it's happening at home, too. If this were my son, I'd want to know. Share your concern in a non-judgmental way: "I wanted to tell you because we were kind of upset by this."