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  • Topic: How I should tell my girlfriend ?!?!

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    • April 26, 2009 4:02 PM BST
    • How I should tell my girlfriend ?!?!

      I'm the classic transvestite and recently divorced. I have been dating a beautiful girl that I have totally fallin in love with. Knowing I should tell her before our relationship goes further, I'm am too shy although I have dated her years ago and I believe she has suspicions of my femme self.
      What's a gurl to do ??
    • April 26, 2009 5:53 PM BST
    • How I should tell my girlfriend ?!?!

      The one thing you want to do here is be as honest as possible. It might not always turn out the way you want it to but hope for the best and expect the worst. When I told my girlfriend her jaw dropped and a couple weeks later she broke up with me. BUT when I told my EX girlfriend (whom still wants to be with me) she was completely cool and comfortable with it. She now wants to help me find new wigs, clothes and do my makeup. It all depends on the girl but you #1 should never have to seperate yourself from yourself (if that makes sense) and #2 should be able to find someone who isn't all up tight about it and can accept you for you! Don't worry, things will work out!
    • April 29, 2009 9:05 PM BST
    • How I should tell my girlfriend ?!?!

      Hi Julia,
      How to tell your girlfriend - wow that's a challenge. It sure has been rough for me, since I didn't know exactly what I was when I first started talking about it with my wife, whom I had dated many years earlier as well. I think the main thing that's caused me trouble is exactly that - my wife knew me as a different person. Changing that perception later can be a major challenge. Your girlfriend could be attracted to you for who you *were* not who you *are* now. I'll get back to that later.

      I'd get together privately to talk about this. It's not really appropriate in a public place, like a restaurant. Plan for an hour or more just for this, depending on how long your story is that you've chosen to share.

      I'm a bit of a wordy person, as you all can see (lol!) so I'd tell the whole story. Make sure you include that it started before puberty (that's if you have at least a few early childhood stories) which will help her to understand it's not just something that came from hormones. Tell her the whole story, top to bottom. At the end, tell her where you'd like to go with it - how you imagine yourself in 5 or 10 years. If telling it makes you impassioned about it, that's a good thing - she needs to see where you heart really is.

      Be prepared with answers for things she might bring up like, "I'm not attracted to women", or "I'm not bisexual", or "All I'm hearing is about what you want - what about me? I want a man in my life, not another woman", or "Are you planning on cutting off your privates?"

      Getting back to how you have changed since she knew you last: once you see her reaction then you'll be able to understand where the relationship is going. If she 'concedes' and let's you be who you are now, then that's a bad sign she might not allow for additional changes in her mind. Another thing she might do is say, "It's ok, but let's keep it a private thing just between you and me." That's a huge red flag for me, since that pretty much places your decisions in her hands.

      You and I both know that's inevitable as you grow into who you are and express yourself more. She needs to whole heartedly accept you for who you are *now*, and in addition, be willing to accept who you might *become* in the future. And, she needs to allow you to do that publicly. You might not want to now, but things might change for you and you want to allow for that now while you still can without as much heart-ache.

      I sincerely hope the best for you. Let us know how things turn out.

    • May 9, 2009 9:15 AM BST
    • How I should tell my girlfriend ?!?!

      hi, i was in the same situation as you until recently, you need to be honest because if you let it get too serious you will break her heart, i told my girlfriend about a week ago and she understands i even borrow her clothes, so be honest if not for her sake then for your own.
    • November 10, 2009 11:32 PM GMT
    • How I should tell my girlfriend ?!?!

      I agree with everyone else about honesty and the need to tell your significant other before things get too far.   Tiffany
      This post was edited by Tiffany Monroe at February 2, 2012 7:10 PM GMT
    • November 10, 2009 11:38 PM GMT
    • How I should tell my girlfriend ?!?!


      Like everyone has said honesty up front makes things easier in the long run. When I told my girlfriend I liked to wear women's clothes she was stunned to say the least. She asked questions, I answered the best I could. We've now been married for 28 years.

    • November 11, 2009 10:25 AM GMT
    • How I should tell my girlfriend ?!?!

      Echoing all advice and much luck to you Julia, but I really liked Princess Tiffany's analogy. I'm definitely going to use that in about... a month. =)
    • November 11, 2009 1:36 PM GMT
    • How I should tell my girlfriend ?!?!

      What an excellent analogy Princess Tiffany. A tom girl, how perfect. Julia, the gal who originally posted, hasn't been here since the day after she posted the question. She said she was a transvestite and I can see Tiffany's tom girl idea being the perfect way to introduce a CD/TV's feminine side to a woman. However I think the gal needs to be prepared to answer whether or not she intends to go further with this "activity". I'm not saying she needs to volunteer the information, just be prepared with an answer should the question arise.
      That is where the "honesty" everyone agrees with comes in.

      Another twist on this is here at TW we so often think of everything as male-to-female, but think of this in a female-to-male scenario. A gal who is the tom boy telling her boyfriend she likes being the guy. I'm sure that has a lot of minds scrambling for an answer.

    • November 12, 2009 9:56 PM GMT
    • How I should tell my girlfriend ?!?!

      Marsha Ann,

      You are exactly right. In both cases the inevitable question came up about how much further I wanted to go with my "activity." I believe the exact question both of them asked was "Do you want to have a sex change operation?" A girl definitely needs to be prepared for the follow up questions but figuring out how to broach the topic in the first place is half the battle! They both did appreciate my honesty and I was lucky that it worked out both times.

    • April 27, 2009 7:35 AM BST
    • How I should tell my girlfriend ?!?!

      Jenny is right. Honesty and as soon as practical. It will hurt less now than in 5 years if it goes badly. You will not be able to change what you are inside. I would recommend that you understand about yourself before you try to explain it to another. Check out There is no "one size fits all" type of transgendered person.
    • April 27, 2009 1:42 PM BST
    • How I should tell my girlfriend ?!?!

      Honesty is the only thing to do here. It's unfair to her if she chooses to be with you without knowing about who you truly are. Plus, do you really want to spend your future hiding your femme self away from her? I believe it's better to come clean now, and hope for the best, than to keep it hidden. If she has suspicions anyway but hasn't reacted badly, then that's a pretty good sign, but if you care for her she deserves your honesty.


      Nikki x

    • April 27, 2009 2:58 PM BST
    • How I should tell my girlfriend ?!?!

      Hi Julia-

      The fact that you're asking the question shows that you're a caring person. Jenny, Wendy and Nikki are absolutely right, you need to tell her about your "real" self before things go much further in your relationship, that is if you care about her feelings and want to spare both of you pain and heartache later.

      However, I noticed the title of your post was how to tell her, not if you should. That's something else entirely and all depends on her and you and how far your relationship has progressed and how much of your own personal lives and feelings you have already shared. All I can say from personal experience is to go slowly and move at a pace that is comfortable for her. Watch her reactions, ask her if she has questions and answer them honestly. If you have pictures of yourself (tasteful and modest ones), don't just whip them out but have them handy. Some girls have images of flamboyant drag queens or Jerry Springer episodes in their heads when they hear the term crossdresser or transvestite and a nice pic or two can dispell that.

      More than anything, Julia, honesty and truthfulness are the most important elements of the conversation. Certainly you don't want to spend your life hiding who you really are and she does not want a partner who is less than honest with her. Good luck, girl, let us know how things go, if you don't mind.

      Hugs...Joni Marie

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