> What's so wrong with asking someone in an elevator? I'm all ears.

If the request makes them uncomfortable, the closed nature of the space makes it difficult for them to make a polite exit. The same applies to other locations where someone is temporarily unable to leave.

This also isn't really so much about dating or gender. Equally inappropriate would be uninvited political or religious commentary, bleak comedy, reference to recent very sad topics (violence, disease, natural disaster, abuse scandal,) or other topics with an unusual likelihood of creating distress.

The general idea is, just wait for the elevator to open, and ask once they have stepped outside; thirty seconds isn't going to kill you.

There's nothing insulting about having a mental illness. However, having such blatant disregard for others' feelings and established societal norms can land you in jail. While you may be incapable of empathy on your own, therapy can help you find ways to make the effects of empathy beneficial to you (usually by some form of quantification of results based on emulation of empathy).