1. Don’t use the word Tranny. Seriously, don’t.
While it is a slang word that some in the LGBT community use, it is widely considered disparaging within the trans community. Same goes for ladyboy, shemale, and he-she.
2. Do Treat her like a lady.
It’s important that you treat your transgender date like you would any cisgender partner, with all of the respect you would want accorded to your sister or mother. Your T-girl has likely been through the wringer in the course of her life, so showing her respect will pay dividends.
3. Don’t ask about her surgeries.
You wouldn’t sit across a dinner table with a cisgender woman and ask her about her vagina or inquire abut her tits, yet a surprising number of men feel like this is appropriate conversation when having a date with a transexual woman.
4. Don’t ask her what her old or “real” name used to be.
Her name is her name, therefore asking questions about her previous name is merely bringing the conversation around to what was likely a difficult experience for her. Appearing to fixate on her transgender attributes is not the way to have a successful date.
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5. Do ask her about her hobbies and interests.
Like anyone else, your date has interests beyond sex and her transition. Showing interest in getting to know what excites her (outside of the bedroom) is a good way to forge a connection.
6. Don’t compliment her on how passable or feminine she looks.
We get it, this really is meant as a compliment, but a trans woman being told she could pass objectifies her and carries implications that she is trying to fool people. Being a trans woman is about being a woman, even if the woman she is looks mannish.
7. Do compliment her general appearance.
You look beautiful in that dress or you have such lovely eyes, hair, etc. are all perfectly acceptable compliments.
8. Don’t appear to fetishize her trans status.
You may have gotten off by some exciting tranny porn at one point, but bringing it up will have her heading for the door, having determined that you are a tranny chaser. If you really want the experience you have viewed on a porno, hire a professional.