Anthony Esolen wrote an interesting article for the Catholic Education Resource Center about an all-boys camp he attended the summer before he entered eighth grade.
It occurs to me, finally, that everything I have heard for thirty years now about how we all want men and boys to express their feelings has been a bald lie. The last thing we want is that men and boys express their feelings. They may, if they wish, express feelings of weakness: They may cry, if they like, or be afraid, or look to their mothers for comfort.
They may not, however, show anger or indignation; they may not exult; they may not be proud of their masculinity. As for their need, emotional more than intellectual but surely both, to work with other boys or with men at something they can take pride in -- and their fear of humiliation or embarrassment before their more articulate sisters -- well, those on the left sneer and those on the right cough and look the other way.
That is a cruelty and callousness I at least was spared.
Is he right about the bald lie?
Cherchez le telos! Look for the end sought. Why are boys taught to express their feelings?
If it's because it helps people who relate to others through feelings -- call them PWRTOTFers (pronounced "chicks") -- relate to them, then yes, expressing feelings that makes it more difficult for PWRTOTFers relate to them will be discouraged.
If it's for some greater good of society proposed by some social theory, then yes, expressing feelings that society finds inconvenient will be discouraged.
If it's for both the personal and the common good, to help both the boy and his community thrive, then -- well, yes, even then, means of expression that are inconsistent with these goods will be discouraged, and feelings that can interfere with thriving will be, not discouraged (you feel what you feel, after all), but shown for what they are.
So maybe the answer is yes: To say you want boys to express their feelings is either a wicked lie, if the truth is that you want them to have only acceptable feelings, or a somewhat lazy approximation of the truth, if the truth is that you want them to own without being owned by their feelings.