I too am used to the close-knit community our local elementary school provided. Since I volunteered in my children's classroom a lot, I know most of the kids in my children's grades throughout elementary school. My older one is now in 10th Grade and I remember that feeling of isolation when he started middle school, when I hardly see any of the parents at school. I still volunteered at the middle school but those were grade-wide events, so I didn't gain any knowledge of the kids at all. I am like you in that I don't feel comfortable sending my children to friends' houses when I don't know the parents (at least would like to have met them, etc), and I still don't send my son to play with his friends at their houses until I learn more about the families from my son. I also see that many of his friends' parents would just drop them off at the curb when they come over. You have made extra efforts to meet your son's friends' parents by being outside when they drop their children off at your house. I realize it's just different parenting style and levels of supervision. I am comfortable with what I do and accepting what other people do. What seems important to me is knowing who my children hang out with, and knowing the kinds of kids they hang out with (whether they are academically strong kids, whether their parents set limits for them [whether they have limits on video game or computer time is a good indication of this for teenagers]). Over the years, I also found that my son tends to choose friends who are similar to him, in academics as well as in temperament, and fortunately I am quite comfortable with the way he is. Untimately, our kids will have to know how to choose friends on their own, so my protectiveness is increasingly being satisfied by seeing how my son picks friends/people to hang out with, knowing what they do when they are together, what they talk about, etc. I AM blessed that my son does talk to me about his friends and such, even though it's whenever HE wants to talk and not when it's most convenient for me to listen (so I try to be there when he wants to share). I don' know if this speaks to your concern or discomfort on the issue. I personally won't succumb to peer pressure to drop my son at a friend's house where I am not comfortable, where I don't know anything about his friend or his friend's family.