‘Should I tell my wife that I'm a crossdresser after more than 20 years together?'

Irish Times

2 days ago

Dear Roe,
Should I tell my wife I'm a crossdresser? I've kept this part of me secret since childhood and through our marriage. I really haven't had much opportunity to explore this part of myself but it has always been there. Over the past year or so, I've bought my own clothes, make-up and wig and taken some time when home alone to dress. More recently I've found some community with other crossdressers online, sharing photos and chatting. I've enjoyed this sense of connection and recognition. My wife and I are happy, we have three beautiful kids, good careers and share interests in the outdoors and travel. Our values and priorities are aligned and we make a good team. We also love each other very much and have been together for more than 20 years. But I'm pretty certain she would reject this side of me – I don't think she would accept me expressing myself through crossdressing, but more so because of the deceit. I should have told her about this – before we married and had kids, and before I took the next step of engaging online.
So my dilemma is: do I keep this secret? I don't think I can stop completely, but I've kept it secret for almost 40 years since childhood, so why not for another 40? On the other hand, I know my mental health is suffering from keeping secrets, and if there was acceptance at the other end of what would be a difficult process then I know I would be happier. But at what cost? Do I have the right to shatter my wife's image of me as a good husband, father and partner for something so selfish? Is it possible to stop or even keep it secret indefinitely? I'm worried if speaking this truth will open up a path to something else. I don't know what to do.
There's an emotional line running through your letter, underneath the question of whether to tell your wife about your crossdressing. It's something deeper, more painful: the fear that doing so will collapse the image she holds of you. You're afraid that being honest will somehow undo your role as a good husband, father, or man. Let's be very clear: it doesn't. This part of you doesn't cancel the rest of you. You are still good, still worthy, still lovable, still the same devoted partner and parent. That remains true, whatever comes next.
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You carry guilt for not telling her sooner – before marriage, children, private exploration – and that's understandable. But it's also understandable why you didn't. You chose secrecy not out of malice but out of fear, out of shame, out of a cultural world that tells men like you that femininity is weakness and gender play is deviance. Most of us were never given the tools to talk about this stuff in real time. You were trying to protect the life you were building. That doesn't make you malicious, that makes you human.
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You also feared that speaking this truth might start something you couldn't control, and that it would lead somewhere unknown. And that's probably true. Opening this door may indeed lead you to learn new things about yourself, your needs, your desires. But those discoveries aren't threats – they're invitations to a deeper, fuller and ultimately more sustainable self. Self-suppression has a cost, and you're already paying it: in mental health, in emotional loneliness, in the wear and tear of hiding. You've lived so much of your life for others. But your needs matter too. To feel truly loved, you have to be fully seen.
Let's pause here and say this clearly: crossdressing does not automatically say anything about your sexuality or gender identity. It means wearing clothing typically associated with another gender – something that's been heavily policed for men in particular. People crossdress for many reasons: comfort, play, expression, eroticism, identity, artistry or joy. It doesn't make you any less of a man, or any more of a woman. It simply means you're exploring a side of yourself that deserves compassion and space.
Crossdressing challenges an arbitrary gender binary – this rigid system that says men must act one way, dress one way, feel one way, and women another. It's a system that's deeply cultural, not natural, and it harms everyone by limiting how we get to be human. Crossdressing is well overdue destigmatisation. It's kind of pathetic and silly when you break it down. It's just clothes. If our patriarchal society wasn't so deeply threatened by gender fluidity, it wouldn't be an issue. And if the gender binary was really so natural and innate, we wouldn't have to police it to such ridiculous levels. You are not doing something shameful or unnatural, you are stepping into a fuller expression of your humanity.
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The fear that your wife might grieve or recoil isn't irrational. She may feel grief – not necessarily because you crossdress, but because she'll need to reorient her picture of your inner world. That's okay. That's part of real intimacy. None of us stay exactly who we were when we first fell in love. The people we marry will change. Long-term love makes room for evolution. Relationships thrive not by avoiding change but by meeting each other with honesty and care when change happens.
You fear ruining her and your children's image of you. But what if, instead of ruining it, you're giving her the gift of knowing you more truly? What if her image of you as a 'good man' becomes even richer – because it now includes courage, vulnerability, complexity and honesty? What if your experience of parenting becomes more meaningful because you're teaching your children how to love and respect everyone around them as they are; teaching them that just like you, their identities and realities deserve love and support; and teaching them that the world and human beings are so much more rich and beautiful and complicated than patriarchy's small, rigid boxes – and that that's gorgeous?
If she struggles with the secrecy, explain that you didn't hide this to deceive her, but to protect yourself
When you're considering whether to share something this personal with someone you love, especially after so many years of holding it in, it's not just about disclosure – it's about connection. About finally bringing a part of yourself out of the dark in the hope that your relationship can hold it. That kind of truth-telling takes courage, and it also benefits from preparation.
Before you talk to your wife, take time to reflect on what crossdressing means to you. Is it private? Creative? Sexual? Do you want her involvement or just her understanding? The clearer you are, the more safely you can guide the conversation. Frame it as an act of trust, not a confession. Something like, 'This has been part of me for a long time, and I've been scared to share it. But I trust you, and I want to be known more fully.' You're not detonating your marriage – you're opening a door to deeper connection.
Expect emotion. She may feel confused, hurt, even betrayed, not necessarily because of what you're sharing, but because it's new and unexpected. You've had a lifetime to make peace with this. She hasn't. Give her space, stay present, and don't confuse discomfort with rejection. She may have questions, and it could help to have resources to offer a gentle path to understanding – articles, stories or media that show this is a real, human experience lived by many in healthy, loving relationships.
Tell her what's not changing: your love, your role as partner and parent, your commitment to her. That reassurance matters. If she struggles with the secrecy, explain that you didn't hide this to deceive her, but to protect yourself from a world that told you this part of you wasn't acceptable. You're not asking her to bear the burden of that shame – you're asking her to help you put it down.
A couples therapist who is informed about gender identity, expression, and nontraditional relationship dynamics can be an invaluable guide.
Letting this part of you breathe may feel risky, but it's also a step towards being fully known. That's where deeper love begins. Good luck.
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