Poor Milo. He’s a sweet kid (often). He’s a bright kid (when he’s not calling himself dumb). A well-liked kid (though he possesses the social skills of a mud turtle). But he cannot find anyone to consistently play with at recess.

He started out this year—first grade—largely alone. The two boys he’d gravitated to in Kindergarten were in different classrooms, which, in elementary school terms, may as well be other galaxies.

Kids would say hi to Milo, ask him to play games, but he would snub them, too embarrassed to even acknowledge their offers. He preferred, instead, to hang out with the instructional assistant on recess duty—a tall, gentle man who tried to give Milo as much attention as he could while also monitoring the other children lest they knock themselves unconscious on the zipline.

Finally, a couple months into the year, Milo met a girl, Mary, who was sort of a shy outsider, too. They hit it off and Milo had a sidekick at last. Mary made sure her mom packed nut-free lunches so she could sit at Milo’s table. The two were together for every recess. They had playdates. They joined the same after school clubs.

Except recently, Milo reports, she’s been abandoning him. Running away with another girl when he approaches.

Milo’s gone back to milling around the instructional assistant at recess. He’s matter of fact about it all, but I can tell he’s hurt. Who wouldn’t be?

I explain to Milo that actually saying hello to someone who greets him, even a smile or a wave, will make his social life easier. Or that, I don’t know, agreeing when another kid invites him to play will make his recesses more enjoyable.

But I can only do so much. I can’t go onto the playground and make friends for him.

So I wait. And, in the circle of light cast by his reading lamp, we talk at night. Learning to be social is one of his struggles. It’s just who he is–a nice, reserved, ridiculously stubborn boy who, as he gets older, is going to have to deal with a mother who finds him prom dates and college roommates.