If you encountered “shemale” in a search or media label, do not assume it is an appropriate way to address a date. GLAAD's transgender terminology guide lists the hyphenated form among defamatory terms. This page names the term to explain that issue, not to label members or suggest a category of people to pursue.
Separate finding a word from adopting it
Search results can contain language that a person would not use about themselves. Repeating a label because it appeared on a website does not establish that the person you are speaking to accepts it. Begin with their name and their own description.
When you mean a trans woman, say trans woman if that description is relevant and welcome. Often identity does not need to be mentioned at all: “I enjoyed meeting you” is a complete message without any category attached.
Do not turn a label into expectations about a body
A search term cannot tell you someone's anatomy, medical history, interests or preferences. Do not use it as a reason to ask intrusive questions at the start of a conversation. Being attracted to someone does not make their private details available for inspection.
Try an opening based on something they actually shared: “You mentioned enjoying photography. What do you like taking pictures of?” This shifts attention from an imagined category to a person who can choose how to respond.
Correct your wording without asking for approval of your intentions
If you have used the term and someone objects, acknowledge the specific mistake. “I used a disrespectful word. I will use the description you asked for” addresses the action. Avoid asking them to reassure you that you are a good person or debate what strangers elsewhere accept.
Changing the wording should include introductions and messages to other people, not only direct conversation. Do not circulate a screenshot of the correction as a story about your dating experience. The person's reply is not material for public discussion without permission.
Let the explanation end
You can learn better terminology without repeatedly bringing the offensive word into future conversations. Respect is demonstrated by the language you continue to use and the choices you honour, not by making someone listen to a long account of your learning process.
Source and scope
GLAAD: transgender terminology. The guide supplies the terminology classification; the conversational examples here are editorial suggestions, not claims about every person's reaction.