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How do you feel out potential allies? I've been wanting to come out to my sister, but I don't want to do for now if her reaction isn't going to be positive. We have never talked about gender or sexuality in the same room, so I know nothing about her views on the matter. I also feel like I can't just randomly bring up the issue, because I think she would connect the dots.
Cis people rarely connect the dots, fwiw. They might after you come out and be like "oooooh, that's why you asked me about trans people."
You can talk about trumps executive order defining male/female (badly) at conception, see how she feels about it. Joke about how it defined everyone as a woman or non-binary.
It would somewhat weird to bring up american politics with her, but I think your idea of bringing up some adjacent contemporary topic to be great. Thanks!
If you haven't heard her be obsessed with trans people, then she probably won't connect the dots unless she's trans or like a really good.
Some cis people are incredibly oblivious.
This comment I have written underneath doesn't add anything, I just wanted to share my experience in regards to cis obliviousness in the past days.
A week ago I started going out with a a lot more feminine appearance. I was in a waiting room with my sister, because we needed some documents signed. They called us up by saying "it's the two girls' turn now". They said it from some meters distance, so they probably couldn't see me properly, but it still felt great to be gendered properly in a public setting. It turned out we couldn't go in together, so I let my sister go first and then I went in after she was done.
Later she told me that while she was in the office she explicitly referred to me as her brother to "correct" them.
I have also been asking her a lot about hair care, skin care and depilation. However, three days ago I asked her what shop she goes to buy cosmetics, and we then had this exchange:
Not recent, but my mom was impressively oblivious. Like, she asked us to guess if our sister's baby would be a boy or girl and I said "idk, maybe we'll find out in [insert my own age] years" and the next time I visited I mentioned I rather not be referred to as "uncle" and that I'd prefer "aunt" to that and somehow she still didn't take a hint. Also things like growing my hair out, using hair clips, scrunchies, regularly painting my toe nails, and growing small boobs also went without notice.
TBF, I suspect her cis wife picked up that I might be trans long nearly 2 years before I came out (because she explicitly asked me if I was a trans woman nearly two years before after we had a couple of trans guests over at their house for Christmas). But even she commented after I came out that I "suddenly" had boobs. My stepmom has not really been transphobic like my mom though and she tries to avoid that topic in front of my mom.