How do I tell a girl that I crossdress?

I crossdress and like to be feminine but I am attracted to women, but yet that seems to bother girls I date or ask out.

How can I approach them about it? should I hold back and keep it a secret, or should I just be up-front about it. I wonder if i should stop or if I should continue to do it since it makes me happy. What should I do?

Lauren Ostrowski, MA, LPC, NCC, BC-TMH, CCTP, CCH
Lauren Ostrowski, MA, LPC, NCC, BC-TMH, CCTP, CCH
I tailor my therapeutic approach to each client's strengths and goals

Thanks for asking this question. I think the most important part of what you mentioned was that you do it because it makes you happy. For that reason, I would encourage you to keep doing what makes you happy.

As far as telling girls or keeping it a secret, I don't really think that it's necessarily one or the other, at least not the first time that you meet. In other words, one part of your decision-making could be whether it is something that you always want to address in the first date, or perhaps something that you address after you've known each other for a couple of meetings. The answer to that question may also change depending on who you are dating. I would imagine that each person that you are with mainly due to a different decision this was when to disclose this. 

It sounds like this is an important part of you, so I would think that if you were going to date someone long-term, you would want them to know about the most important parts of you, including that.

I also encourage you to remember that if you meet someone who is not comfortable with this, that does not mean that there is anything wrong with what you are doing, but rather something that the other person is in some way deciding not to continue learning about or choosing to have someone they are dating like to cross-dress.

I'd also ask you to consider this: Are the people who you say this to expecting it? My guess is that the answer is probably not. Along with that, Are they going to have questions? I would imagine so.

Are you comfortable answering questions?

I wonder if you could figure out yourself or with friends (or perhaps even with a therapist) how you would answer these sorts of questions:

  • What exactly is cross-dressing?
  • Does that change the gender that you're attracted to?
  • What does it mean to you?
  • Why is it important to you?
  • And what you want your listening person to know about you related to cross-dressing.

There could even be ways that you can start the conversation by asking them to be open to listen to you and ask questions about what they are thinking before they make any quick decisions about you or the relationship.

I certainly hope that you find the right person for you. I imagine that having this conversation could be stressful, especially considering the idea that you have had some negative reactions in the past. Remember that talking this through with a therapist could be very helpful.

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