A confession: back in my early-20s, there was a guy who worked in my office who disappeared for a few weeks then returned as a woman who worked in my office. For narrative purposes I'll call her Helen (not her real name). In retrospect, apparently I was among the few who didn't know this was going to happen, but in my defense we rarely intersected professionally and didn't move in the same social circles, despite being about the same age and at similar points on our career arcs.
And also in my defense, in my early-20s I was largely oblivious to and indifferent about anything that didn't directly impact me personally. But that's a long story for another day.
Anyway, this was my first conscious experience with a transgendered individual. While it's certainly possible that I'd known transgendered people before without even realizing it -- see above re. obliviousness -- Helen was the first person I actually knew before she became, well, Helen. It didn't bother me at all that she made this change -- again see above re. obliviousness -- but one thing did strike me as odd: the way she acted.
When Helen still had the body of a man, she was almost stereotypically male: very loud, pushy, assertive, what modern Americans might call a "bro", the British a "lad". If the boys were going to a pub or to crash a party or to get drunk and walk noisily down the middle of the street singing rugby songs, she would be right in the middle of it. In the office she would talk over people in meetings, push to the front at presentations, and if a sexist email joke was doing the rounds (yes, we still did that back in those days), she'd be in on it.
And afterwards, when she returned to work with long hair and makeup and skirts... she behaved exactly the same. And I remember thinking to myself: why doesn't she act more like a woman? But I shrugged -- it wasn't my problem -- and got on with life.
Shortly after that, I left the company in question for a better opportunity and never really thought about Helen again. It was only about a decade later that it suddenly dawned on me: perhaps the problem wasn't with how Helen acted. Perhaps the problem was with how I expected men and women to act.