i struggle a little with playdates, which seem to be the main way for kids to 'socialize' (another concept i find odd) these days.
my kids mostly had playdates with other kids in the neighborhood. they weren't planned out, they just happened organically. as did the socialization.
but they did have friends in school and baseball and from the barn who didn't live right there, so sometimes they'd go to their friends' houses or vice versa. but for the most part they played with THOSE friends at school or baseball or at the barn.
if there's no one in shouting distance for your kid to play with, then yeah, you've got to set up these playdates, i suppose. but it'll be hard to do since your happy medium is really pretty narrow, isn't it? if they're not besties you worry, but if their friendship becomes 'too intense' you move to shut that down.
it's hard to see how your naturally diffident child (which is not a bad thing) is going to learn to navigate human relationships under these circumstances.
i wish you'd spend more time learning about and learning to accept your son's personality just as he is instead of trying to manipulate the environment to conform to some ideal that's never really defined.
your intensity is probably troubling to the parents of the other kids. i think your best bet is to stop trying so hard, and just let your son make friends at his own pace. when they invite him, or when he likes another kid enough to ask for him to be invited to your place, that's the time to set something up.
and then let it unfold how it unfolds. every playdate doesn't work out. not every kid with whom yours spends an afternoon is destined to be a best friend. that's okay.
breathe.
trust your kid, just a little.
khairete
S.