To Tell Or Not To Tell, That Is The Question

By Amanda J.

Back in May 2024, towards the end of Kandi’s post The Fight of My Life: Me vs. Me, she talked about the loss of a dear friend, Jim, which moved me to include the following in the comment I left:

I have my own ‘Jim’ – a guy who I’ve known for four decades and who is now fighting his own health battles, battles which sadly he will lose sooner rather than later. He’s the brother I never had and I can talk to him about nearly anything and everything and when I feel the time is right, I will give him the final piece of the jigsaw that is me. I dread the day when I get the call to say that his suffering is over because that will truly create a void in my life that will be impossible to fill.

Sadly, the day I was dreading arrived this week.  ‘C’ was a friend of a friend who became a housemate back in my single days.  From that point on, we shared a love of music and he would always tip me off when one of our favourite bands was playing in our neck of the woods.  He shared my hopes that ‘tonight would be the night’ when we went out ‘on the pull’ and we commiserated with each other when returning home at the end of yet another unsuccessful evening.  He was with me the night I met Mrs A and by my side the day I married her.  We went through thick and thin together and whilst over the four decades we knew each other, there were extended periods when for one reason or another we didn’t see each other, the friendship persisted and became deeper over the past few years when we would meet weekly. 

Almost nothing was off limits during conversations between us.  As I said in that post, he was the brother I never had and I shared the highs and lows of my life with him, as he did with me.  And when, in the post, I said ‘when I feel the time is right, I will give him the final piece of the jigsaw that is me’ I meant it.

But, sadly, the time was never right.

I’m very proud of ‘Amanda’.  When I adopt her persona, I think I scrub up reasonably well and, more importantly, I like to think (or at least hope), that anyone that sees through the façade will understand that I’m doing my absolute best to respect what it means to be a woman.  Setting the inner woman free brings me unbridled happiness and whilst my male life as it is now is far more important to me than my brief forays into the feminine world, I often wonder how far, in a parallel universe without any of the responsibilities I have in this one, I would take this side of me, even daring to consider whether I would pass the point of no return. 

That would have been a pretty good starter for the conversation with C and in recent times there have been plenty of opportunities to spill the beans, so to speak.  In fact, I can think of several occasions over the past year or two when I have been talking to him and the thought of telling him crossed my mind.  But, as I said, the time was never quite right and those thoughts dissipated as quickly as they arrived.

My friendship with C was based on the fundamental premise that we’re both heterosexual males.  We talked about the things that guys talk about and, like me, C (who never married and went through life without a serious relationship) very much appreciated the sight of an attractive woman.  Conversations never strayed beyond that admiration but over the years of our friendship, I started to understand that our common interest had very different foundations.  How would he have reacted if, on spotting a woman he found attractive, I had admitted that my interest stemmed from a wish that I was her or wanted to put together an outfit similar to the one she was wearing?   At first almost certainly amusement but, as the realisation that I was serious set in, then what?  Would he have thereafter felt that he could no longer confide in me when he spotted or met someone he liked?

I have absolutely no doubt in my mind that had I disclosed, the friendship would have persisted and quickly returned to business as usual once more.  I don’t for one moment think C would have cut off all contact (although it can happen) but there may have been gentle ‘digs’ from time to time.

I guess the big question here is whether C would have truly understood.  Coincidentally, in one of our meetings a year or two ago, conversation briefly touched on trans issues and our mutual frustrations with the more insane elements of trans ideology.  Would my disclosure have made him feel that, despite what I professed to believe, I was no different to the bearded guy demanding to be called ‘ma’am’ or the purple haired disrupter demanding death to anyone who didn’t toe the line?  Of course, it would have been an opportunity for me to explain that they are a tiny minority and in no way represent the rest of us but would he have truly been convinced?

As I pause to take stock of what I’ve written so far, it strikes me that I’ve really just articulated problems that almost certainly didn’t exist.  C was sensible enough to realise that the knowledge that I have a feminine alter ego doesn’t change who I am and would quickly have understood that I was not to be tarred with the same brush as the extreme factions.  I don’t doubt that he would have listened with compassion as I explained my struggle to come to terms with all of this over the past half century and I would have had absolute confidence that he would not have betrayed my trust and tell mutual friends my secret.

But therein lies the issue.

As I said above, there were several occasions over the past year or two when it crossed my mind to tell him.  But at the forefront of my mind on each occasion was the simple fact that I knew his days were numbered.  And that in itself gave rise to several issues.

The fundamental question was why?  What would telling him have achieved?  Of course, it would have been an opportunity to share an important side of myself with my closest friend but was that really necessary for the friendship and, more importantly, would it have enhanced it?  Those questions in themselves give rise to many consequential issues but given that the friendship was already near-perfect, I can’t see any way in which him knowing my deepest secret would have benefitted either him or the friendship itself.

But what if knowing my secret uncovered a side of him that I was similarly unaware of?  As I noted above, we shared frustrations about the more fringe elements of trans ideology but suppose that his opinions ran far deeper than he felt comfortable admitting?  Or suppose he found the idea of one of his closest friends dressing in women’s clothing funny?  Did I really want to take the risk that his reaction would not have been the positive and supportive one I hoped for, souring a friendship when he needed it more than ever?

In any case, as he fought the battle of, and for, his life, the focus had to be on him.  He was single minded in his concentration on a couple of projects that kept his mind off the ravages of the illness that was slowly killing him and I needed to be there to help him make those projects happen, not to derail them by moving attention onto me.  Perhaps knowing that one of his closest friends thought nothing of donning a dress, heels and makeup would have provided a welcome diversion but what if the disclosure had affected him deeply and caused him to take his eye off the ball as far as things that really mattered to him were concerned?

But a bigger issue is the burden of secrecy.  I know from my own experience that it’s emotionally exhausting having to constantly worry that I don’t do or say anything to give the game away to others.  But that is a choice that is mine to make; it is in my gift to decide whether or not to tell anyone I choose that I have a feminine alter ego.  Is it fair to transfer that burden onto someone else with the added proviso that whilst we have a choice regarding who and what we tell, they don’t?  We could argue with some justification that feeling someone is trustworthy enough for us to share our innermost secrets with them is the greatest accolade we can give, Maybe so under normal circumstances but is it right to add another burden onto someone, particularly when they have plenty of their own burdens to manage?

And then we have to think the unthinkable.  What if seeing photos I shared with him aroused emotions within him?  Conflicted emotions that suggested that he saw us as two distinct people, one his friend and the other, for want of a better word, a random woman who, if he hadn’t known the truth, he would have pursued?  Perhaps, in another life where things were different, we could have become life partners – our shared interests and values would have been a definite asset in that respect – but that is not the life we led and, once again, it boils down to the question of whether it would have been fair to risk putting him in that position in the twilight of his life, particularly when his illness and the strong drugs administered to him as a result were evidently starting to play tricks with his mind?

So even when opportunity presented an open goal, I listened to the little voice within me that urged me to think carefully by asking ‘are you sure?’ and kept schtum.  And as I look back on our friendship and reflect on all of the good times we had together, I am absolutely certain that I did the right thing.

At one time or another, I think that all of us who are to some extent closeted think about disclosing our secret to a trusted confidante.  Certainly in my case it became an obsession for a while.  Perhaps we see it as an opportunity for affirmation, a springboard from which we can form friendships in our feminine persona, a natural progression in our ‘journey’, a demonstration of our trust in the person we choose to confide in or an opportunity to show a photo in our finest while exclaiming ‘I bet you can’t guess who this is!’.  Or maybe we’re just wilting under the burden of the secret we’re carrying and ‘need’ to talk to someone else about it to maintain some semblance of our sanity.  All of those thoughts have crossed my mind at one time or another and I’m sure that there are many more ‘good’ reasons to underpin disclosure.  To be clear, I’m not talking about confessing to one’s spouse here as there are many layers to that particular issue, but just the choice of whether or not to tell non-family members.

I can only talk about my own experience but whenever I’ve considered telling someone about the side of me you all recognise as ‘Amanda’, I have always come to the conclusion that it is not something that anyone else needs to know.  I love the idea that Amanda can function as a ‘normal’ person in the real world.  I love the idea that she opens doors for me that would otherwise be firmly locked shut.  I love the idea that those I interact with take ‘her’ at face value and treat me not as a freak but just as they would treat any other person.  And I love the feeling of sheer bliss that comes with the emergence of the inner woman.  But as far as others are concerned, all of those rely on ‘Amanda’ being someone in her own right, not an extension of ‘him’.  Keeping my two worlds separate is more important to this side of my life than practically anything else.  And it was the plight of my closest friend that gave me that clarity of thought to understand that.

As I write this, two days have passed since C lost his fight and just over three weeks have passed since I last saw him.  Even then, he was too ill to receive visitors and we were only able to exchange a few words.  Words of reassurance that I would always be there for him and words that he acknowledged with a simple ‘I know’.   Those were the only words that mattered at that point and by association, the only words that really mattered throughout our friendship.  No other words were ever necessary and even if nature had not dealt him the cruellest of hands, would him knowing that I am a CDer really enhanced either of our lives?  I think not.

So, my dearest friend, the only thing left for me to say is rest in peace and thank you for everything.

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16 Responses

  1. I know so many have wrestled with that exact same question—whether to share this secret with someone they love before it’s too late. And the guilt that follows when you don’t… even when you know staying quiet was the right call. You honored your friend with love, presence, and loyalty—and sometimes, that’s more than enough.

    1. Michelle, thank you for sharing your thoughts and support.

      There are many good reasons for sharing our secret with a neutral confidante but we do need to be careful. As I said in the post, telling a female acquaintance became an obsession of mine for a while, driven by the hope that it would lead to a girls’ outing. But the more I thought about it, the more I realised it carried a huge risk, not that my secret would be betrayed but that whoever I decided to tell would not be able to get past seeing me as ‘him in a dress’. And the plight of my now late friend cemented my doubt by leading me to consider who would actually benefit. We have friends in common so the burden of secrecy on his part would have been huge and even if he hadn’t been terminally ill, I would have been the only true beneficiary of the act of disclosure.

  2. Amanda,
    First of all I’m sorry you lost a very close and dear friend .

    I was never good at maths and equations didn’t make sense , sometimes life’s equation don’t always add up , there is never the right answer to some of the questions .
    Being full time I’ve obviously been through this scenario the difference being Teresa was no longer in hiding she was out to the World and all that dwell there but the question still persisted , did I need to tell and if so why ?

    I’m actually facing the dilemma at the moment , I have a very good GG friend who is losing her battle with cancer , I know more of her life but not all , she knows a little of my life but she’s aware of gaping holes in my story . She only knows me as Teresa but nothing of my male side , I never speak of a wife but openly talk about my children and grandchildren . The question is do I owe it to her before she departs this life and if so why , do I need to risk losing a good friend when she may need me the most and what would I gain ?

    Otherwise I’ve found that people you feel you’ve lost as friends eventually come round because they respect me for my committment . This is why I feel it’s harder for those who have to transition from one to the other to suit circumstances , it can mean others are making the rules for you rather than you being allowed to be totally honest with yourself .

    We can spend endless hours debating the rights and wrongs but it’s often wasted time because there is no definite right or wrong , we can never know how other people will react . We can only be who we wish to be when others are aware of us , you held back from your friend but the question is how much did you really know him , was he hiding something from you ? Sadly you’ll never know and perhaps it’s sad he didn’t know all about you .

    1. Teresa, thank you.

      As I put in the post, I last saw C around 3 weeks before he died. That was not out of choice and I would have sat with him every day if that was what he wanted. But at the time, his sister just explained that he didn’t want visitors. I saw his sister yesterday and she explained that it wasn’t just his friends that were shut out; she was given instructions not to tell any family members that he was nearing death too. I’m sure that some of them feel put out that they were denied the opportunity to say goodbye but the simple fact is that what time he had left belonged to him and much though we wanted things to be different, we had to respect that.

      So to my mind, the answer to your question about whether you owe it to your friend to give her more information about yourself is that you don’t unless she asks. There are few people in life who can derive benefit from knowing intimate facts about us and it sounds like she understands sufficient about your background to not wish to pry further. Equally, if she was to ask, then you would be doing her a disservice by not being honest.

      As regards your final paragraph, we talked a lot about various aspects of our lives so I almost certainly knew more about him than most. Of course, it’s highly doubtful that I knew the whole picture but I knew that I could have discussed my female side with him if I felt it appropriate and I believe that he similarly felt that there were no limitations the other way too. In the end, though, even if he had not been so ill, there would have been no tangible benefit from telling him. If he’d been female, then perhaps I would have a different view because even if the friendship is platonic, the male-female dynamic is very different to the male-male one. As I put in the response above, telling a female friend would have carried an ulterior motive which was obviously not relevant in C’s case. So I’m 100% comfortable with the decision I made and have no regrets.

  3. Amanda,
    I could face the same situation with my friend if she chooses to withdraw from life , her background is very sad so my thoughts are more supportive for her than my needs . I must admit her situation has made me wonder how would I deal with a life changing event especially as Teresa .

    I agree the dynamics are very different between male and female relationships , I’ve possibly reached an age where sexual needs have been repaced by the need for good friends . I guess we also reach an age where things remain unsaid , they serve no useful purpose .

  4. Amanda,
    I agree you made the right decision in this case.
    Now from a different point of view. I have a very few people that know I have a girly side. One woman and I have borrowed clothes from the other. And she “gifted” me a sequin top and some other items and I have introduced her to some makeup techniques.
    I don’t completely hide my ‘girl’ from the world and I don’t show the world my full girl either. I am in 4″ heels and I have my nails colored all the time, but my fiends have never ask if I am a crossdresser. Maybe they just assume it. I have never been asked at work either, even though I am in heels and have nails for over a decade and some has seen me at Halloween when I am completely dolled up. But I have no intention of tell anyone, why? What good would come of it?

    1. Cali, thank you. It’s one of those paradoxes – we’re more than just our clothes and yet our clothes can define who we are. In your case, I’m sure that those who know you are totally comfortable that your nails and heels are just a part of who you are and further insight is unnecessary. I also have to admire you for having found your presentation niche so to speak (although I know that the primary driver for the heels is comfort following injury). Ultimately, what I think many of us fear is the shock factor of revealing our hidden side; I know from my albeit limited experience that hardly anyone either notices or cares about guys presenting as women these days and even friends would soon get used to the idea. But it’s the point of disclosure where things can go wrong and one only has to look at forums to find examples, albeit rare, where the desired outcome has not happened.

  5. Hi Amanda and thank you for this insightful and heart wrenching post. I feel your pain of losing a close friend it is hard to take and even harder to accept. I told my wife not that long ago that I only have two close friends left both are people I worked with. My very close friend from high school passed away 2 years ago and I still miss him terribly.

    I think you made the right decision my friend. At that stage you really had no reason to. My heartfelt condolences go out to you Amanda.

    Love,
    Trish ❤️🤗

    1. Trish, thank you for your kind words and support. I’m very much of the view that we should remember the happy times of life rather than dwelling on death but this loss has hit hard, not least as I have no siblings and, as I said in the post, C was a guy I could talk to about pretty well anything including the frustrations in life. More than anything, though, losing friends at our age is a reminder of our own mortality, something we can no longer dismiss as being too far away to worry about.

      I’m also sorry to hear that you have been through similar.

  6. Amanda, thank you for sharing and I’m so sorry for your loss. As always, I love to read your thoughtful posts, even on more serious or sobering topics like this. I have longed to share my girl side with someone close. But don’t know if I’ll ever tell any of them about my trans identity. I think that day will still have to come as I really want to live full time eventually instead of the occasional crossdressing in in my alone time. How would I tell and how would it affect those closest to me? I cannot imagine but I really don’t think the reaction would be good. I appreciate the stories and wisdom that is shared here and the insights that could help inspire other girls how to go about it. I think there’s still a lot of life ahead in which to figure this out. But you never know and I really would rather not come out yet and reveal this side of me if it would break up friendships and family ties. Thank you Amanda, I always feel uplifted after reading what you share, even on more serious subjects like this and I wish there was anything I could say or do to help you out in a time of sadness like this.

    1. Elizabeth, thank you for your kind words of support.

      I think it’s important to draw a distinction between telling someone about a facet of our personality and telling someone that we’re making permanent changes to the way we live. People can choose to accept or reject either scenario but, as far as living full time is concerned, that risk is unavoidable and goes with the territory. It’s also a necessary risk to take to have any chance of maintaining relationships with those who it turns out are accepting. There are different dynamics at play as far as occasional CDing is concerned and if I can’t explain why a seemingly normal guy has this persistent but transient need to transform into the best version of a woman possible, it’s going to be very difficult for me to satisfy others’ curiosity in that respect. And that can then lead people to the default view that it’s a fetish. The irony is that despite it having far more far reaching consequences, gaining understanding about a permanent transition is easier than convincing people that recreational CDing does not have a sexual undercurrent.

      I think you’re approaching your own situation in the right way and you’ll know in your heart when the time is right to share who you are with others.

  7. Amanda,
    That is a very interesting observation , when we transition and live full time but we still have sexual needs but living as a woman has to to be built on trust . That is possibly suggesting men are all predators , all they think about is sex which of course isn’t true but is there that expectation ?
    Personally I would suggest age does have a bearing for me but interestingly I am now experiencing from a female perspective how men react to women .
    Also your point was clearly evident at my social meetings where CDing did heighten sexual interest but saying that it also caused confusion to some who had fully transitioned .

    Our path certainly doesn’t flow in a straight line there are many twists and turns .

  8. Amanda, I am so sorry to hear about your loss. I have struggled with who to tell and when. Like you I am proud of my feminine side but is telling someone about this lifestyle when my wife opposes it the right thing to do. I am getting more confident in who I am as a gender-fluid individual. Perhaps I will tell more of my friends. Thank you for sharing, I love your insights.

    1. Julie, thank you for your kind words. It’s a difficult call to make; telling someone is consequential and there is always a risk involved. Equally though, bottling everything up is not healthy and sometimes we just need someone to sit down and listen. For me, a big factor in not confiding in C was simply that he was male and the confession could have been read as me saying I had less in common with him that he thought. Confiding in a female naturally has the opposite effect and could facilitate a closer friendship than is normally the case with the male-female dynamic.

  9. Amanda,

    Many different situations require CD’s to subjugate their dressing life in favor of higher priority real life issues. Your friend, and his well-being, took priority over everything else which is as it should be. Perfect way to approach that situation.

    I’m sorry to hear about C but you certainly have many good memories of him to keep you company.

    All the best,
    Fiona

    1. Fiona, thank you. I have no regrets about the decision I made and I can’t help wondering whether, had I decided to confide, I would now by looking back and feeling that it was the wrong thing to do. I like to think that most of humanity is accepting of the choices we make but you just never know.

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