The Kind-Hearted Smart Aleck

I'd say roughly once a month I read an article which is titled something along the lines of, "What not to say to someone who is transgender" or "Ten questions you should never ask a transgender person." Now, granted, some of these comments and questions are so insensitive and ridiculous, even Ben Carson opened his eyes for a change to roll them. However, some questions which were mentioned came across as genuine and like the person simply wanted to learn more about the other and to understand them better. So, where do we draw the line between asking a transgender individual a question to learn more about him or her and yet do so in a way that doesn't leave them feeling uncomfortable? Is there a way? As my long-time readers should know by now, I'm rather progressive on most issues. The large circle of people I regularly associate with are quite diverse in terms of: Gender (well, duh), age, race, religious beliefs, political affiliation, orientation, etc...

I love my family and I love old people (okay, VERY mature people - I'll be nice), but there are times I have to sit back and wonder, "Is 95% of what you talk about related to health problems?" A couple months ago, I met up with some older friends of mine at a pub. One of them had been going through a lot on the health-front, so I asked him how that was all going. I'll never forget his response. He said, "The one thing you should never ask an old person is, 'How are you feeling?," because you'll never hear the end of it!" Sadly, in some cases at least, that seems to be fairly accurate. Unfortunately, if I were to follow this man's advice, how on earth would I start the conversation? It's just habit anymore to ask any person, regardless of age, "How's it going?" or "What's up?" After hearing this man's before-mentioned response to such a question, while continually hearing about some family members...