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Thread: When should I tell my girlfriend....

  1. #1
    Aspiring Member Amy R Lynn's Avatar
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    Lightbulb When should I tell my girlfriend....

    I'm certain this topic has been covered in here before, but I can't seem to be able to find a thread that addresses this. There are plenty of "How To" threads, but I think the "when" is pretty important too.

    I have been dating a girl for about a month now. I have done some internet research on the subject of when should I spill my feminine secret, but have not come up with very good sugesstions. I have seen in some posts that it would be best to tell her early on, and others have stated that its best to wait. I don't want to wait too long. I don't think it would be good to wait until we are engaged and suprise her with Amy. However, I don't want to tell her too soon and scare her off. I plan on having a heart to heart with her. I just need to time it right. I am fully prepared to accept the possibility that she may reject me, but its better than being divorced.

    I am aware that every situation will be different, but I would love to hear the communities sugesstions here. How do you know when the time is right to tell her about this?
    Last edited by Amy R Lynn; 07-13-2012 at 10:49 AM. Reason: removed irelevant parts.
    "Oh my God, I realized, it's not that we're screwed up; it's just that we've been trained to thnk so."
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  2. #2
    Silver Member prene's Avatar
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    This is a hard question.

    I have lost 95% of my girlfriends over this.

    I have always told them to early and to late in the relationship.

  3. #3
    Member Melissa Jill's Avatar
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    Probably about 2 weeks ago. She's either going to be accepting or not. Putting it off it just going to delay the inevitable whatever that may be.
    The ultimate woman is a man - House

  4. #4
    Aspiring Member ronda's Avatar
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    i think that most wait till they are sure that they in a serious relationship and that you can trust the person you are with not to out you to people that you can not afford to know such as some employers but do it as soon as you think it is important to let her know so she can make up her own mind that she can handle your cding.good luck Hugs Ronda
    hugs
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  5. #5
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    Only you can tell when the time is right. I can only tell you from my perspective...I'd been dating her for about a month, I felt compelled to tell her...though we've had tough times in the past...I'm now considered her girlfriend...18 years married this October. Good luck, but don't wait to long.

  6. #6
    Gold Member Alice B's Avatar
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    I have always said the sooner the better. If it is going to be a deal breaker it should be before emotions get too involved. If she proves to be accepting it will lead to a stronger bond. You have to be fair to her and yourself.

  7. #7
    Senior Age Member sissystephanie's Avatar
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    Amy, I told my late wife when I proposed to her! She did ask me some questions, mainly concerning how far I wanted to go with crossdressing as a female. I told her that I only wanted to wear feminine clothing, but did not want to actually become a female. I wanted to be her male!! she accepted that and we were married for almost 50 years before cancer took her.

    I have always believed in honesty, and felt then and still do that hiding something from the person who may become your wife is not proper. Unless of course it relates to a gift of some sort! The timing of telling her is totally up to you, but the longer you wait the harder it will be. I started crossdressing when I was 6 years old and met my wife to be when I was 9. So I did put it off for some years, but when I decided that she was the right one for me I told her! You are coreect, it is better to be rejected than to be divorced!! I say, tell her!!
    Stephanie

    Lady on the outside, but man underneath!

  8. #8
    Platinum Member Beverley Sims's Avatar
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    Get the relationship on a reasonably firm grounding and then tell her.
    Consider the worst case scenario and find the Right time, not necessarily on a dinner date or some romantic situation.
    Tell her before you both get too serious, you can test the water carefully by asking her views on alternative lifestyles.
    Try to be tactful and sympathetic towards her.
    I consider you have about a 20 percent success rate.
    If you wish to continue dressing, "You have to tell her".
    All the best in your relationship and keep researching the subject and take note of what others will advise you.

    To Prene. I don't think you have told them too early or too late. They did not want any part of it or did not understand.
    What about the other five percent?
    Work on your elegance,
    and beauty will follow.

  9. #9
    Member Kayla C's Avatar
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    You should tell her when you believe you are heading for a long-term relationship. But you should also brace yourself for the strong possibility you may lose her. Kelli is right - if she rejects you she is not the girl for you. But making a long-term commitment without her knowing is looking for grief down the road, especially if she discovers this on her own. As you'll see from other threads, it's usually the perceived hiding and deceit later on that creates problems, not the crossdressing itself.

  10. #10
    Member bridgetta's Avatar
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    immediatly.. also.. ask your self if she is the kind to understand or not..

  11. #11
    Just a girl on a trip cyndigurl45's Avatar
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    I had an unusual set of circumstances I had to tell one of my girlfriends I was a guy, we meet in a gay bar, I hung out there they were accepting as most gay bars are......

  12. #12
    Platinum Member kimdl93's Avatar
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    A month isn't very long. Have you known her for some time before you started dating? Have you learned anything about her attitudes towards transgendered people?

    I don't think its so much a question of days or weeks, but rather how well you know her and how serious you are about a long term relationship.

  13. #13
    Senior Member UNDERDRESSER's Avatar
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    Sigh.

    I'm in this situation now, or I hope I will be. I've been "seeing" this girl for 2 months now? We aren't...dating as such. She has issues to work through, but I know she likes me, and I'm prepared to give her as long as it takes. I KNOW, this one is going to be for the long haul, serious keeper.

    I'm working up my nerve to tell her soon. I think a decision point is approaching for her. Our conversations are almost painfully honest, subjects covered at this point, are ones you don't normally get into before physical intimacy, or at least when you are somewhere on the field if not yet having scored a home run, to use a common phrase.

    I've thought about just burying this part of me, and just pretending. it would mean a total purge and shopping for expensive mens briefs. Don't think it would work. The subject of crossdressing was raised yesterday, I jokingly suggested wearing a skirt to work to be cooler, her response was jocular, and suggested I pass it off as a Summer kilt. etc


    The stress of holding this back from her is beginning to tell. I don't WANT to be dishonest with her.

    My view is tell her, in a controlled manner, in an appropriate setting. I have NO idea what her response will be, this is just my opinion.

  14. #14
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    Now! If you loose her over this then wait until you can get one that will accept it, life would be MUCH more easier! I know its hard to let some go....Amanda

  15. #15
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    In my opinion the best time is before you are dating. There are lots of open minded people that don't care. So its not worth investing months or years into a gamble of whether or not someone will accept you from waiting to tell.

  16. #16
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    Quote Originally Posted by Ayame View Post
    In my opinion the best time is before you are dating. There are lots of open minded people that don't care. So its not worth investing months or years into a gamble of whether or not someone will accept you from waiting to tell.


    Ayame, you said it the best! BTW I do know what it feels like to let a girlfriend go, but surely it would be worth the wait for one who is accepting? Would it not?

  17. #17
    ADMINISTRATOR Sandra's Avatar
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    Coming from a GG......Do not leave it until things get serious, if you do then she may feel that she cannot trust you and will probably question everything that you say to her.
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  18. #18
    Member max's Avatar
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    Tell her soon, that way if she doesn't really love YOU for YOU then you can start moving on.
    “Courage doesn't always roar. Sometimes courage is the quiet voice at the end of the day saying, "I will try again tomorrow.”

    Mary Anne Radmacher

  19. #19
    Member Engendered's Avatar
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    The sooner, the better. It will get much harder as time goes on. Good luck!

  20. #20
    Senior Member mikiSJ's Avatar
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    I would suggest you tell her as soon as you feel confident that she won't go running down the street telling everyone your "secret" and also as soon as you feel there is something there in the relationship. Each relationship is different, but it is up to you to screw up the courage to share your "secret". If this relationship fails because of your "secret", keep trying and trying and trying.

    My first marriage was on the rocks for a couple of years, but when I told her, that was the proverbial "straw". I was very up front during my next intense relation. She was accepting and the relationship failed because she was on the rebound from a failed marriage.

    I told my current wife the same night I proposed to her. I trusted her confidence, I trusted her "openness" and I suggested she talk with a counselor she had been seeing previously. The counselor was a very European Dutch man who gave her reading material and "acceptance" of her choice to marry me. That was 37 years ago and I still share part of her closet.

  21. #21
    Girl from the Eagles Nest reb.femme's Avatar
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    Quote Originally Posted by kimdl93 View Post
    A month isn't very long. Have you known her for some time before you started dating? Have you learned anything about her attitudes towards transgendered people?

    I don't think its so much a question of days or weeks, but rather how well you know her and how serious you are about a long term relationship.
    Hi Amy,

    I totally agree with the above.
    Posts have often mentioned sounding her out for TG/TS/CD feelings too, so why tell if she is heavily against? Maybe then, better to find a way out before anyone gets hurt.

    A little simplistic in short but surely this consideration must be weighed up first.
    Hopefully, if she is at least sympathetic, then you have a basis upon which to advance.

    Rebecca x


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  22. #22
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    I am an avid reader of Dan Savage's weekly sex advice column. He gives six months as a deadline for when you should disclose any potentially deal-breaking kinks. Basically, she needs to know you well enough to be willing to try it, but before any long term commitments are made. I don't have any experience using this guideline, but it seems well-reasoned.

    Also, I know that CDing isn't really a kink, but it's similar enough from the SO's perspective in this case.

  23. #23
    Ice queen Lorileah's Avatar
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    Quote Originally Posted by Sandra View Post
    Coming from a GG......Do not leave it until things get serious, if you do then she may feel that she cannot trust you and will probably question everything that you say to her.
    and there you have it. I have said many times that there is equity you build in a relationship. the longer the relationship the more equity. When you wait then you start to have things that you didn't before. Feelings get stronger and thus the hurt gets deeper. People resent it when you waste their time. They resent it even more when they believe they have a solid relationship with you. You want to see a hurt look? Wait until your GF thinks that everything is sunshine and roses, That you ride a white charger. Then tell her. Watch the look of confusion and then hurt. You are building trust. Think of trust as a huge wall (or tower) and you pull the lynchpin block out. If that wall is only two layers high, you are disapponted but you say, "hey that isn't much to rebuild" If that wall is 50 layers and you pull that brick, then you watch as everything you have worked for crumbles. Some will rebuild from this, some will rebuild better. Most will walk away shaking theitr heads and mumbling.

    Continuing the analogy, you tell her early in the building process, you can make sure that brick is in there solid. That if it is a problem you can either work around it or make it stronger.

    It may or may not be an issue but really wouldn't you want to know earlier so you can move on if needed?
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  24. #24
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    There is a point in every relationship where you go from dates, to dating. We all have a feel for when the change happened. That point where it's serious. That is when.

  25. #25
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    Always hard to give advice since there are some many variables at play.
    Also, there never seems to be a perfectly "right time" to share such an important personal and private part of your life.
    Regardless, please know that MANY if not all of us have gone through this at some time in our lives.
    It's takes a lot of courage and is scary.
    Fortunately, you have many friends here in cyberspace to help you along the way.

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