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Hey @AcidMonster55
I can only speak from my experience as a trans person and not on the behalf of your friend. Unintentional transphobia does hurt, but honestly, you can tell when some made a genuine mistake and when someone is just trying to be a jerk. It’s harder when you’re at the start of transitioning because you’re already exceedingly insecure so when someone messes up it feeds that insecurity. But as time passes you start to feel like you and feel more confident within yourself.
I doubt your friend would have forgotten but I also doubt that they would hold it against you. If you do decide to apologise, try to make it genuine and short. People make mistakes. That doesn’t mean that the mistakes don’t cause unintended harm, but it does mean that everyone deserves grace. I can tell when people view me as me. That’s all that I want. I can forgive them if they mess up my name or my pronouns once in a while or ask me stupid questions.