For example, I have a few strictly lesbian acquaintances IRL who have been really confused and kind of distressed about being attracted to specific men, only for those “men” to later turn out to be trans women.
Back in highschool, I dated an outspoken lesbian who rather bluntly told me that she wanted to date me as an experiment to see if she was bi... She was the first person IRL that I came out to as a transwoman.
We eventually broke up because I was in no mental state to be a relationship (cyclical anxiety and depression is not a fun time) and I was also realizing that I'm ace, so uh... compatibility issues. But we remained really good friends. In hindsight, I really needed an assertive extroverted friend to drag me around to things I wanted to do, but was too afraid or defeatist to do. She knew just how hard to push.
...I lost contact with her after highschool when she shipped out with the national guard. One of the biggest regrets of my life.