Dear Kristen,

My son is becoming very good friends with a little boy down the street. The trouble is, this little boy is a bit of a trouble-maker. It’s obvious he doesn’t get a lot of supervision at home and his parents seemed checked out. He has already taught my son some bad words and I don’t really like the influence he’s having. What do I do? I can’t exactly forbid the friendship, can I?
— Elise

I feel your pain. It sounds like you could be talking about one of the older boys on my street who occasionally comes by asking for my son. I have struggled over the past two years trying to dissuade a friendship.
When I was a kid, one of my best friends lived down the street from me. Her parents were free-thinking hippies, and one night at the beginning of our friendship my mom let me spend the night there. The house was full of incense and, ahem, some other smokey smells. The dad spent the evening in a daze, painting a picture of a topless woman under a rainbow. The mom let us watch an adult romantic comedy with a racy shower scene. My friend’s teenage sister arrived home drunk out of her mind, and the mom cursed her out in front of me. I ended up going home and relaying the whole story to my mom, who promptly decided I would never be allowed back at this girl’s house. She could play at our house, but I was not to play at hers. I was devastated, and it created a very awkward dynamic with this other family.
Now, as I parent, I find myself facing the same dilemma. We have a street full of young children, and fortunately many of them have parents who are great people and even close friends. But then there are some other kids, whose homes seem a bit more questionable, whose parents seem a bit too lenient, whose supervision of my own children I might question just a bit. I’m not really ready to let my kids play at a house where I have no idea what goes on. But the invitations have started coming, and he’s asking more and more. “Why can’t I go to his house, mom?”
For me, though, I think a reputation as the “strict parent” and some temporary resentment from my son is worth the alternative: having him exposed to things at a home where there is a lack of supervision. Now, I don’t know if this boy has negligent parents. But for me, that’s the clincher. Idon’t know, one way or the other. And I readily admit that my years as a therapist, delving into the childhoods of hurting adults has made me very, very guarded. I’m okay with that.
I don’t want to put naïve trust in people I don’t know to supervise my kids. There is a lot of garbage out there – especially as kids have more and more freedoms with cell phones and internet access. Do I know that the neighbors have passwords on their computers? Do I know if they check on their kids periodically? Do I know if they have unlocked guns in their home? If I don’t know the answers to these questions, I’m probably not going to let them play there.
Now, to your question about forbidding a friendship: no, I don’t think you can forbid a friendship unless there have been some obvious circumstances between your kids that question the safety of your child (or another child). If you forbid a friendship, your child will be frustrated with you, and it may create tension with the other family. What we have decided, as a family, is that our house will be an open door. This sometimes means that certain kids play at my house even though my son isn’t allowed at theirs. It isn’t always comfortable answering why, and sometimes it is a drag to have more kids to watch at my house without the ability to send them off for someone else to monitor a reciprocal playdate.  But for me, it’s a part of the sacrifice of parenting that I’m willing to make. And when kids are in my home that I have a bit of question about, I keep a close eye out and reinforce the rules we have set up in our own home. Having established these rules allows my son to be friends with whomever he chooses, because I don’t have to worry about unsupervised influence. I don’t allow for the opportunity.
Tell me: How do you handle this as a parent? What do you say to your child when they ask why they can play at one friend’s house, but not another? How do you respond when a parent invites your child over to a playdate, but you don’t want them to go? What to you say to a child who plays frequently at your own house, who asks why your child can’t play at theirs?