Great prompt to go back over one's timeline, thanks!
My main exposure to ideas about gender was being involved/on the fringes of feminist/ queer/performance art events where diverse gender expression seemed exciting and creative.
Actual 24/7 trans people seemed weird and sad though. I remember being introduced to a cross-dressing colleague in the 90s wearing his leather boots and badly fitting blouse, and it was incredibly awkward. I think they were introduced as, this is Frank, he's transitioning to be a woman, so make sure you call him Veronica...
Read bits and pieces of Gender Trouble in the 90s, and was interested in the general mashup of gender identity. I was frustrated with the constraints of femininity, so a flexible understanding of gender appeared to be advantageous.
Attended an event with Annie Sprinkle where she showed a film featuring her transmale lover - first time I'd seen a constructed penis. It wasn't for me but I found Annie compelling and impressive, and they seemed to have a nice relationship.
Read and watched Tales of The City, with lovely Mrs Madrigal as house mother. It just seemed bad taste to refer to her past life as a man - if you even clocked that.
Felt a certain protectiveness towards trans women. One stopped me in the street to ask directions to a well-known gender clinic in my city (I worked for the NHS) and I felt oddly flattered they'd chosen to approach me, that I'd appeared safe to them. They seemed vulnerable and I was worried for them. This was in the period where you had to live as a woman for X years before you could get hormones/surgery, which seemed like a trial by fire.
Fast forward to the mid 2010s, and it started feeling problematic. Male friends on the music scene would turn up in bad drag with a new female name, and the assumption was that nobody should laugh or question it and that they were effectively the same as me now (albeit none of the men would "date" them). I felt huge social pressure especially from male friends to accept them without question, that it would be small-minded not to, which irritated me. I was never rude, but the conflation of transwomen with women made me feel as if I was at the bottom of some hierarchy. They had male advantage, but were weaponising femininity too.
However I was sort of sitting on the fence, until the houndings began, of women who didn't toe the line. Seeing women, including quite well-known figures in my local arts and music scene, isolated, othered and monstered as terfs was intimidating, depressing and obnoxious. And it's still going on.