I secretly dress up as a woman. Should I leave my wife?

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Dear Rachel,

I am a 66 year old married man, my wife is 67 and we haven’t had sex in over 10 years. Even when I try to hug her, she pushes me away. When I was younger, I would often secretly dress up as a woman; it’s something I tried to stop many times, but never could. Over the past two years, I occasionally went out alone for a night and dressed completely as a woman in public.

At first I kept to myself, but over the last few times I’ve become friends with a guy I met at a bar. He is fully aware of my situation and likes to treat me as a woman. In fact, the last time we met, we spent the night together at his hotel and made love. My dilemma is: I think I’m falling in love with him and he asked me to live with him, but I don’t want to hurt my wife. My choice is a loveless marriage or being with someone who really likes me. Please help.

– Anon

Dear Anon

The ultimate happiness of writing this column is that you discover the deep truth of the old Yorkshire adage that there is no such thing as strange as folk. Valued Telegraph readers prove to be anything but Disgusteds of Tunbridge Wells! When you undress it, you ask permission to leave your wife. The main problem for me here is not your transvestism or possible onset of bisexuality later in life. It is your fear of dumping your steady partner for a man. Essentially, it comes down to your obligations to yourself – your self-care, as we say now – and your marriage vows and duties to your wife. All you are asking is how to solve the dilemma that can arise at any time in a committed relationship, something that requires sacrifice and compromise from both parties.

Tessa Grazzini, a relationship therapist, says this: “Ultimately, your decision should be a reflection of your true self and what you believe will bring you the most peace and fulfillment in the long run. You deserve happiness and to be the best version of yourself. It is important to make choices that align with your own values ​​and understanding of yourself. People who love you will support you in this. Each step in this process is potentially challenging and can evoke a wide range of emotions, but you deserve to live authentically and be satisfied with your life choices.”

Well, yes. I agree with Tessa. But the reason you’re writing this is because it’s hard to break up. It destroys something and can break someone irrevocably. Marian O’Connor, also an advisor, says your letter raises many questions. “Changing what you wear usually doesn’t change your sexuality,” she emphasizes. “Have you been sexually attracted to men all your life, or were these feelings suppressed before this encounter in a bar? Second, what do you mean by falling in love? It seems you hardly know the man. Are you just recovering from the intoxicating feeling of finally being ‘known’? You were able to be open and honest about your cross-dressing, something you have never been able to do with your wife.

“Third, your marriage. Before you decide to leave, be open and honest with your wife about your cross-dressing, about your frustration at being sexually rejected for so long. You’re tiptoeing around, full of secret resentment, and instead of trying to have a difficult conversation, it seems you’d rather run away into the arms of another man. A grim abandonment is cowardly and will hurt your wife much more than an honest but painful conversation.”

My own advice would be to do what you do next for yourself because it’s good for you, not for some random guy you met in a bar, and it’s time you put you and your wife out of your misery. Let me know. And remember this, as a wise man once said to me, “the longer a bad marriage lasts, the harder it is to end it.”


Dear Rachel,

I am a 41 year old single woman living alone. I’m the only single person in my friendship group. I find myself being left out of many social events by my coupled friends. After a recent event was discussed in my presence without an invitation or any clear understanding of how painful it was for me, I challenged my friends and tried to explain that I felt forgotten, especially now that I had celebrated the weddings and the babies . I asked my friends to be more conscious in the future. Instead, I have been accused of turning one social event into a negative event about myself and of having negative thoughts about my friends and their families. Am I being unreasonable if I feel even more hurt by this lack of understanding?

– Single woman

Dear single woman,

For selfish reasons, I’m really glad you contacted me. Your question will resonate far beyond being alone. The fact that you have brought up a sore area around your ‘friendship group’ (another expression that postdates my formative years), an issue that concerns relationships rather than sex, is, I must confess, welcome because sometimes I can get enough of people snickering about my ‘sex column’ and even Private eye has called me a ‘sexpert’, which my husband finds hilarious. So thank you and I hope more readers will send in these relationship questions in the wake. Our daily relationships with our friends, family and colleagues, in my opinion, take up much more space and time than our sex lives and I would like this column to reflect that.

Right. I cleared my throat and this is what I thought in response. First of all, I completely understand. Like you, the tip of my pointed nose twitches with displeasure when I find out I’m not being asked to something I think I ‘should’ be invited to. No matter how many times you tell yourself: ‘not everyone can be asked to do everything’, a small, insecure part of you does mind. You have the opposite reaction of Liz Truss when the late Queen died on her watch, which was: ‘Why not me? Why not now?” if you’re being overlooked for a particular occasion. That’s natural.

This feeling of being left out is one of our first experiences with rejection. That’s why teachers beg parents to invite the entire class to birthday parties. The cruelty of comforting a child who has been ‘left out’ is unbearable (I even become homicidal if one of my own children is ever belittled), but as we grow older we must learn to deal with constant rejection on all fronts (there there is even talk of a podcast called My therapist ghosted me).

It sounds like you’re in a vicious circle. Your friends are aware that you want to be involved, and instead of making them want to see you, it does the opposite by making you seem needy and whiny. My approach would be to step away for a while and then have them drink coffee one by one – and not bring it up. Talk about them, not you. See what happens. It’s always nice to be asked, but think about buying presents, getting dressed, traveling – isn’t the invitation itself the best part?

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