Where are you drawing the line?

I heard a story the other day whose message is echoed in an article I read a few minutes ago.  The story is about a rabbi who moved to Baltimore in the early part of the 20th century.  Someone questioned him about his yarmulke which he wore sticking out of the back of his hat which was not the rabbi's practice all the years and was not the practice of the group to which he belonged.

The rabbi answered - when I came to America I knew that I'd face struggles with my yetzer hara over matters of religious observance.  So now, even if the yetzer hara should win, what would he accomplish? That I would move my yarmulke back under my hat ...

In other words, getting back to the topic of the three previous posts, what issues in chinuch do we want to deal with? To a great extent, we can choose which ones.  As an example, if children attend schools with peers who have lavish parties for their bar (or bas) mitzva or peers who include sports activities in their bar mitzva celebration, their parents will have to contend with issues such as: will we do the same as the others? is it right to make our son different than his peers? should we compromise on how we would like to celebrate a bar mitzva? and so on.  But if the children attend schools where the schools set the rules on where a bar mitzva can be held and what is acceptable, and that is the school you choose, then how to celebrate is a non-issue.

As Emuna Braverman wrote in her Aish article called "The Makeup Wars": "Once we choose a school whose values we embrace then we have to allow our children to be in step with their peers – obviously within reason. At the same time that we were having this struggle with our daughter [about make-up], a friend of ours (whose daughter was clearly at a different school) was struggling with her over whether she could sleep out in the woods with her boyfriend. Suddenly makeup didn’t seem like such a big deal! We have to choose an environment that matches our values and then work within its parameters."

Which is why I think R' Twerski's unqualified call to warn our children about drugs because "drugs are everywhere, even in our Torah institutions" and "we live in a society that is awash in drug use" is misplaced.  Would he also say we should tell all teenagers in frum schools and yeshivos about what can happen if a boyfriend-girlfriend relationship goes too far? About out-of-wedlock babies? After all, by his reasoning in every school "there are marginal youngsters" ... Or would he agree that talks about sexual relationships are out of place in yeshivos?