After the guy was done processing my transcript request form, he asked me if there was anything else he could help me with. I told him about getting mail as “Ms.” and asked if they “accidentally” had me as female in their system. He looked, turned bright red, and told me they did.
Then he asks, “you're not a girl are you?”
I found this question fairly ridiculous considering he was asking a dude with a beard if he was a girl. I think the whole “Ms.” thing threw him off so much that he didn't really think about what he was asking – I don't think the trans thing even crossed his mind.
If he has asked if I was a transguy or if I had been born female/assigned female at birth, I wouldn't have said no – but I live and navigate the world as male and am not a girl. Simple as that. It's not my problem if he didn't connect the dots!
I have gained a lot more confidence in dealing with situations in which “the trans thing” comes up – whether it be administration at my old college, flying and TSA body scans, or running into someone from my past. I am always matter-of-fact about it and up front – there is no reason not to be, and a little education and awareness go a long way.