It’s tricky dressing like a girl when you live next door to your parents.
Our elder has some advice and encouragement for a man whose fiancé is fine with it—but doesn’t know how to tell mom and dad.
Hi, I am currently engaged to a wonderful woman. I have the issue of feeling like a girl and wanting to dress up as such. My fiancé is fine with it and enjoys it but with her being the only one knowing it makes it inconvenient because I can rarely dress up since I live next door to my parents and they ask for me to come over a lot when I do dress up. I need advice on admitting that I feel like a girl on the inside and like dressing up as one to be who I really am. I’m just terrified of what she might think. Any advice is great. Thanks in advance!
First let me tell you I am impressed that you were so upfront with your fiancé! So many men would have hidden this desire and then been found out later, with unfortunate results. And your fiancé must be an amazing woman. I’m proud of you both.
Regarding your parents, a couple of things occur to me. First, sooner or later they are going to have to deal with this. It sounds like you are unlikely to change. And you seem to have the full support and love of the woman you love. I know this is hard, but just tell them. Maybe you and your fiancé together. Something along the line of, “Mom, ever since I was little I felt like a girl inside and I’ve been dressing like a girl when I get a chance. So next time you ask me over, I may be wearing a dress instead of jeans.” She will be shocked, of course, but she will get over it. And if she does not get over it, it is her problem and not yours. That may sound harsh, but if your mom loves you, she will come to accept that this is just a part of you and move on.
The first time your mom sees you dressed up, make it subtle, perhaps a unisex look with makeup. Nothing too startling for her.
Once you are married you may also want to consider finding another place to live. A married couple needs space and time of their own, and having parents literally next door may be too much.
Finally, as you get more accustomed to being ‘out’ in this way, you will want to consider how many of your friends should know. I think it would be great if you could show up at a dinner party dressed as a woman one time, a man the next time. In my opinion, you should not have to hide this part of yourself. You will get some shocked looks and some resistance, but I think you’ll also find some people very curious and maybe even envious. People today are so much more accepting of different lifestyles than they used to be.
I hope this is useful.