Yeah I have a Google Calendar event set to auto-email me every 3 months so I'm reminded to message all my friends in Hangouts and quiz them briefly on how they feel about trans people. Sometimes they pretend to be incredulous that I'm asking about it again, which signals that it's a topic they're at least uncomfortable about, if not outright in opposition to. I've discovered that most of my "friends" tend to get really upset about trans people after I've known them for a year. Just a sign of the times I guess.