If you have never dated a trans woman, or successfully dated a trans woman, you may be nervous and have questions. That is okay.  It is normal to feel unsure in new situations.
The best thing you can do is do research first.  Trans women get tired of having to be a constant source of intel about being transgender.  Get the answers to your questions before you go on a date.
They are looking forward to a date, just as any other person would be.  Remember to treat this woman as you would treat any other woman.  Save intimate and personal questions for when you know this person better.
Here is a simple list of things you should do:

  • Make her feel comfortable. Ask her if she would like to meet you at the location of your date.  Respect her wishes about where and when she would like to meet you.  All women have learned that they must be wary and careful to make sure they are safe in a dating situation.  Trans women have to add an extra level of wariness, so respect that.
  • Do not make assumptions about this person based on any other experience with a transgender person. There is not a stereotype, and each person is different.
  • Check your motivation. Make sure this is a person you are interested in getting to know.
  • Respect her boundaries and ask before you touch. Do this with any woman, trans or not.
  • It is okay to ask questions when you are not sure, but make sure you ask her permission first. Say something like, “I am not sure how to ask about your experience. Are you comfortable talking about it?”  Respect her answer.  Some are very comfortable and proud of the journey they have made, and others are not there yet.
  • Be thoughtful, kind, and considerate.
  • Make sure you are prepared to deal with trans phobia. It is a real thing.  You should be prepared to stand up to it even if you are not with a trans woman.
  • Give some thought to things you may have in common. Have things to talk about that do not center around her gender change.
  • This one is important. Most trans women do not consider it a compliment to hear some version of  “You look great.  I would never know you were trans if you had not told me.”  Keep it simple.  Just tell them that they look beautiful without any qualifiers.

So, now you have an idea of the things you should do and a few that you should not do.  It is not that complicated.  Trans women are women.  They enjoy most of the same things that other women do.   They are looking to meet people who see them as more than their transition between genders.
Relax.  If you have been on a date before, then this should not be much different.  Treat this person with the same respect and care that you would treat any person.  Focus on getting to know her as a person and be willing to share about yourself as well.
If the relationship continues and is moving toward intimacy, make sure you know what your partner is comfortable with and what makes them uncomfortable.  Respect the journey they have been on to be living openly as a woman.
Have a good time.  Get to know one another.  Laugh and enjoy each other’s company.  This may not be a forever relationship, but that does not mean it can’t be a fun evening.

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