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How do you educate ‘outsiders’ about issues?

As I was posting a comment about this on another diary, I thought that maybe this topic deserved some time of its own, rather than de-railing the topic in another thread.  One common question I've seen reading PHB is how do 'outsiders' request education and enlightenment about 'difficult issues'?  I've seen it asked in threads dealing with racism, homophobia, and transphobia.  A recent example would be the diary about transgendered people not being mentally disordered.  I agree and concede the argument.  However, (here comes the ignorant 'outsider' difficult question) If a transgender person is not disordered, then why should SRS surgery be considered theraputic?  If there is nothing wrong with a transperson, SRS is not 'fixing' something wrong . . . (and you see the slippery slope that leads to name-calling, offending both parties, and neither being learning anything or any other positive outcome.)  So,

  1. How do 'outsiders' ask these questions without being offensive?
  2. How do 'insiders' open the door so that these questions can be asked without getting insulted?

My thoughts after the jump.

I'm not sure that there is a way for an uninformed outsider to become informed without at some point being offensive.  You cannot replace 'old' ideas with new ones unless you acknowledge the old idea's existence and build away from it.  If the old opinion was negative, the educator has to neutralize the negative before presenting the positive information.

As far as insiders opening the door to awkward questions that are going to be asked, the only thing I can add is to be patient with the 'outsiders.'  It is fairly easy to tell when someone is trying to get your goat and goad you, and which questions are truly asked with a desire to understand. 

So that's my 2 cents worth.  What do you guys think?

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