Dear Aviva,
My wife and I were planning on sending our son to an out-of-town yeshiva for ninth grade this September. He has always been socially anxious and has trouble making friends. We thought that going away would help him refine himself. He was not thrilled with the idea when we registered him, but now he expresses that he really doesn’t want to go. We don’t know what to do, because we think that he would benefit from having to make friends but we don’t want to have to fight him so much. He’s starting to cry to us almost everyday. What’s your take?

-Freshie Father

Dear Freshie Father,
I am so happy that you are writing to me before he embarks on a mission that we can call “Set-Up For Failure.” Sorry to be so harsh. But not that sorry.
Just like you have to listen to your own signals when you are too tired, too overwhelmed, too thirsty, you have to listen to the signals that your son is sending. And it sounds like he is very good at communicating his protests (hey, crying is a form of communication. Albeit a wet form.) Your son is telling you something.
A ninth-grader crying everyday is not a good signal. I’m not saying that keeping him home will alleviate his anxiety, but I think that sending a kid off like this is akin to shoving him off a cliff. It goes without saying that you had the best of intentions when these “push-him-off-a-cliff” plans were made.
You saw that there is an issue of social anxiety, and so you wanted to help him along. I think you should continue to go with that. Instead of shoving him along, try coaxing him along. Let him be in an environment that includes things that are not anxiety-provoking. If you were him, wouldn’t you feel less anxious to make friends during first period if you didn’t just wake up to having to figure out the best way to say “good morning” to your stranger roommate, your dorm counselor, and the kid who just walked in on you in the bathroom?