Perhaps you can find a time when just the 2 moms can go out for a nice coffee and talk as friends without kids. I try to keep my eye on what is happening in groups and will suggest that he give a shy or new kid a real chance. I admired it then and still do now, but sometimes it put me in a very awkward position. I do believe that family obligations should trump this at times, which might mean that your son sometimes has a playdate with a kid because you want to hang out with the mom, or because you don't want to hurt anyone's feelings. When I was growing up my mom was always a champion of the underdog. This worked great in early preschool, but now that the boys are in elementary school my son no longer wants to do those playdates. I'd feel proud for helping and being kind yet I didn't have anything in common with the other kid.