Ask a Health Coach: “I’m a man who likes to occasionally dress up in my wife’s lingerie. But lately, I’ve had strong desires to dress like a woman all the time.”

collage makeup


“I’m a man who likes to occasionally dress up in my wife’s lingerie. She’s usually happy to play along. But lately, I’ve had strong desires to dress like a woman all the time. How should I approach this with her? I don’t want to do it behind her back.” – Wants To Wear Makeup


First, WTWM, I’d like to acknowledge the courage it takes to come out, especially to your wife. It’s great that you feel safe enough to consider discussing it with her, and I’m excited for you to start this new part of your journey!


What is gender and what about the biological sex we were born with?

This is a massively complex topic many have worked for years to simplify. I encourage you to check out The Gender Book. It’s a wonderfully illustrated book that breaks everything down very simply. You have the option of viewing some of the pages for free on the website, downloading the full e-book or buying a hard copy. It presents some excellent education on the difference between biological sex, gender identity and gender presentation. I recommend all my readers check this out – it’s an incredible resource that challenges many of the standard societal ideas we have about gender, and many of these ideas are limiting and even dangerous. WTWM, you’ll want to explore this and understand what this means for you. Is this just a way you want to express yourself through dress? Are you finding you want to be a woman? This book will help you answer many questions – and those your wife will likely have, so have it with you when you talk to her.


Who are you?

No doubt, your wife may have some questions or big feelings when you talk to her. It’s very important that she understands no matter how you dress, you’re still the person she fell in love with and wanted to spend the rest of her life with. Things will be different as you explore this part of yourself, but who you are to her doesn’t have to change. Make sure she understands this.


Difficult Conversation 101

This is an extremely sensitive topic to explore with your spouse. Though you’ve surely imagined every possible reaction, you have no idea what will happen until you actually talk to her about it. Fear of the unknown can make it so hard to speak up!*

Reid Mihalko, sex and relationship expert and founder of has a fantastic guide for facilitating scary or difficult conversations. You can even download some free worksheets! I’ve personally used this guide multiple times and it truly does make a complicated, tangled-up problem much easier to articulate to your loved one. It works in two parts: prepping your difficult conversation (understanding what it is you truly want to say) and organizing your difficult conversation (figuring out how to say it). Check it out HERE!


WTWM, I hope this helps. I hope you’re able to have an open, transparent conversation with your wife and I hope she’s not only supportive of who you are but wants to share in this part of your life. Wishing you much happiness in this part of your journey!


*Note: I do not recommend anyone ever come out to someone with whom they do not feel safe. If you suspect they might react abusively, follow your instincts and stay safe. But if you do feel safe sharing something like sexual orientation or gender identity, this is a big conversation and an important one.





Keep sending your wonderful questions! You can submit anonymously below. If you’d like to set up a complimentary consultation with me, let me know – I’d love to talk with you!





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