Someone at work that used to be my direct manager had a meeting with me to introduce themselves. They didn’t recognize me at all and I didn’t want to out myself by disclosing who I was, so I went along with it.
I don’t like lying, and when they asked about my work history I was honest even though it created immediate suspicion (how could we have not worked together given when I started working and my job experience?), and I just shrugged. It’s obviously a kind of deception to not out myself, and I don’t like that - but my instincts say it’s better in this context to not out myself.
Probably relevant to the context is that the boss is male, older, conservative, and an immigrant from a non-Western culture that is not open minded about these things.
I am pretty sure based on things they have said in the past that they wouldn’t be tolerant of a trans person.
Anyway, to my trans elders: how have you handled situations like this?
People who in theory know me quite well have failed to recognize me (at first, at least), and I’ll go along with re-meeting them. I think that’s fine: I’m a totally different person now from who I was in the past, notwithstanding that we have a shared history. I don’t think you owe it to anyone to “come clean” about having met them before: there’s nothing wrong with starting fresh, and if challenged later on you can say exactly the same thing: you’re a different person now.