The dilemma I am a man in my late 50s. I am youthful and go to concerts, festivals and art exhibitions. I have been married for 34 years. My wife and I get along quite well. We share a sense of humour, talk often and holiday together. But there has been no sex between us for 15 years. I have always been a sensitive and feminine man. I like emotional movies, poetry, women’s clothes and so on. I like being surrounded by women and feel uncomfortable among men. Lately I have secretly been buying women’s clothes from online stores and have started using makeup when I am alone. This happens often, because I live in my employer’s apartment in another city during the week. I am almost always alone when I am not with my wife. I have no friends any more. I closed all my social media accounts years ago during a period of depression. I am confused about who I am. In which direction should I go? What about my marriage situation? I know I am getting older day by day and that time is running out.

Mariella replies You’re hopefully aware that it’s a pretty sad missive you’ve just dispatched to me. You’re at a terrifying but conversely pretty exciting crossroads and it will require a mammoth degree of forbearance if you take one path and enormous courage for the other. I’m no expert on the specifics when it comes to transvestite lifestyles, cross-dressing or issues of gender realignment, but I can tell a life half-lived when I see one. Everything you are describing sounds like an alternative way of living is not just beckoning but building to a reality that you need to explore for your own peace of mind.

At the moment it sounds as though you’re inhabiting a twilight zone between one life and another, and until you take decisive action, you’ll remain happy with neither. Encouraging you to take radical action is easy for me in my entirely unremarkable, safe, heterosexual, white, middle-class world. I’m not going to have to do any of the legwork or risk undoing many years of peaceful, convivial co-existence to step out into a world that I’m unfamiliar with and possibly ill-equipped to countenance – at the beginning at least.

Any radical lifestyle change requires courage to embrace, but happily you are at the perfect time of life for seismic shifts. The majority of people who divorce or come out do so in their 50s and while I’m not suggesting either is your destiny it seems the appropriate decade to confront the notable absences in your marriage and lack of fulfilment in your day-to-day existence. Until you test the boundaries of your desires, you’ll be perpetually dissatisfied and compromised – and that’s no way to live.

Right now, you’re existing with so much of who you really are shrouded in secrecy and your most compelling impulses hidden from the world. You and your wife sound like you have a fantastic friendship and that’s really important because you will need as much support as you can muster. Does that shared sense of humour mean you’d dare be honest with her about your experimenting? I have no idea how she might react, but I’m pretty sure that she is where you need to start when it comes to any attempt to express a more honest version of yourself. It sounds as though your partner is the one person who remains close to you, so trying to enlist her support and understanding is the obvious first move. She may well be your saviour in terms of urging you to find yourself. In an ideal world she might even join you on an experimental journey – but after 15 years of sexual abstinence that’s less likely.

Empathetic support would take quite a strong person and a robust relationship, so you need to be prepared for the opposite reaction. You of all people shouldn’t be surprised at the lies we all tell ourselves to avoid complication, embarrassment and confrontation. If you’re in agreement about approaching your wife first, you do need to be prepared for a less sympathetic hearing. There’s no telling what her reaction will be or what narratives she’s created around the nature of your relationship. You’re already leading semi-separate lives, so if this is an adventure she’s not happy to have a role in, the most likely solution would be separation. Logistically it may not be too complicated, as you’re already leading semi-divided lives, but don’t be deluded into thinking untangling emotions would therefore be simple.

Finally, there’s the online community you abandoned some years back. Usually in this column you’ll find me railing against the internet and the hold social media has on us. In your situation, however, I think it could be of great benefit. It certainly seems a good place to start connecting with people who’ve experienced similar desires and who can perhaps invite you in from the cold. It would also be good to see a therapist or counsellor who can give you dispassionate support while you negotiate what may turn out to be a huge and liberating life change! As I say often, in your 50s, you’ve got a whole part two to live, so it’s worth taking radical action to make sure you squeeze every drop out of the miracle of human existence.

If you have a dilemma, send a brief email to mariella.frostrup@observer.co.uk. Follow her on Twitter @mariellaf1

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