Julia mentioned your post to me last night at dinner. What she said brought to mind my experience as an intersession aide at Harriet Eddy MS, so I was interested to see what you had written. Having read it, I wonder if you are conflating “respect” and “obedience”. The students’ “idea of masculinity and authority” that you describe seems to involve fear and the implicit threat of violence (illustrated, for example, by the “greeting” given to your group by the tour guide at the jail.)

The relation between that and a relative inability to bond with men may be that even in white suburbia, many boys are raised to think that being “manly” is evaluated primarily in physical terms, particularly the ability to inflict and withstand pain, and to impose one’s will via force or intimidation. Those who operate in that mode are generally uncomfortable with those of us who opt out of it, and that discomfort tends to impede the formation of friendships.

In the case of your students, their disobedience flows from their perception that you are not a threat. I think this is not so much a lack of respect as a lack of maturity, and without exposure to and experience with different behaviors and points of view they will remain emotionally and intellectually immature. It is, of course, important for you to understand your intentions; for your students, however, it is your actions that carry weight, and you may never know how and when those actions will lead to a positive result for any given individual.

I know this has gotten windy, so I’ll close by quoting another windy sort – Shakespeare’s Polonius :
“This above all: to thine own self be true,
And it must follow, as the night the day,
Thou canst not then be false to any man.”
(Hamlet Act 1, scene 3, 78–80)