I get a LOT of emails, messages, and questions about relationships and crossdressing related issues.
For the purpose of this article, I am going to use "crossdressing" and "crossdresser" as overall blanket terms that could include, but not limited to, other ways one can identify, such as transgender, nonbinary, and others.
You can read previous posts about this subject here:
This is me. Promise. Well, Maybe...
Coming Out, Part 1
Coming Out, Part 2
Coming Out, Part 3
Every single person in the world is different and has their own soul, their own heart, and their own dreams. Every relationship is also different. Different dynamics, different vibes, different communication methods and all that. When two people (again, individuals with their own heart and everything else) commit to each other, then what begins is a journey together that is intended to bring happiness, security, joy, and peace. Both people enter the relationship with dreams and expectations.
One of those expectations is that your partner is secure in their gender identity and sexuality. I don't think it's uncommon for people to be in a relationship and wonder what they would do if they found out if their partner was cheating. Something I think that is far less common is worrying if one's partner will realize (or admit) that they are a crossdresser. Because it's not a scenario most people think about, this revelation will likely catch someone completely off guard and completely unprepared if and when their husband of five years admits that they wear panties.
My previous articles get more in depth when it comes to this, so I am not going to discuss what could potentially happen when we come out to our partners, instead this article is about the realities of finding a partner that understands and accepts a partner that does not identify as cisgender. This article was inspired by a message I received a few months ago. The messenger had been reading my website, specifically posts about gender identity/gender presentation and marriage. I have an amazing wife, even apart from her support when it comes to who I am. I fell in love with her hard (and do so every day) and my infatuation with her had nothing to do with her perspective on one's gender identity.
The message asked me where I found my wife. I mean, I met her at work, so that's not necessarily an exciting story, but I believe what they really wanted to know is where I found someone who would be so supportive and understanding when it came to, well, who I am. Here's the thing, when I fell for her, I had no idea what her thoughts and perspective were when it came to gender identity. It wasn't part of WHY I fell for her. It's not like on our second date she told me she wanted to marry someone who had more dresses and stilettos than she ever would.

Here's the thing, when I fell for her, I had no idea what her thoughts and perspective were when it came to gender identity. It wasn't part of WHY I fell for her.
What I mean is that I don't think most people necessarily specifically seek out a life partner that crossdresses. When people think about the type of person they want to commit to, they usually want to find someone who is kind, emotionally stable, and on the same page as themselves when it comes to family, religion, and politics. (among other things). It's been a long, long time since I dated but when I was single I never met a girl who said she wanted to date a crossdresser.
Of course, I am speaking in some very general terms here. After all, there are others in the world who would love to be with someone who disregards gender norms and I don't want to exclude anyone here. My point here is that my wife (nor any of the other people I dated before her) did not intend (or expect) to be in a relationship with a crossdresser. I did not find someone who already understood and accepted someone like myself. I found someone who was, and is, kind, funny, smart, beautiful, and empathetic. All the traits I wanted to find in a person. She was everything I wanted in a partner. She still is.
Of course, the BIG unknown was there. At this point in my life I had acknowledged, accepted, and embraced my crossdressing. This part of me was, well, PART of me. I couldn't disregard or neglect this aspect of myself no more than I could NOT be autistic or right handed or tall. I knew that if I was going to commit to someone they would need to know about me. About all of me. I had been in relationships where I came out to them annnnnd it was requested that I never discuss my crossdressing or ever do it again. I had agreed that I would stop because, well, I was in a very lonely part of my life and I would have agreed to anything if it meant I wouldn't be alone. Additionally, I also thought I COULD stop.
We've all been there.
But by the time my wife and I started to date, I knew that I couldn't be in a relationship where I couldn't be who I was. Even though I found the perfect person for me, I knew that I would always want to, and always would, crossdress. I had to come out to her, and I did. For those of us who have had The Talk, we all know how it can go, and this conversation wasn't much different. A lot of questions about transitioning, sexuality, and everything else. It caught her off guard mainly because this revelation wasn't really on her bingo card. Again, more people are prepared for what they would do or feel if they found out if their partner was cheating on them as opposed to finding out their husband wore lingerie.
What I am saying is that my wife wasn't predisposed to accepting and understanding a partner who had a completely different gender identity and wardrobe than her friends' husbands. Like almost every part of a relationship, we learned how to make things work. We got to know each other, not only while we dated but also every day since. We talked. We talked a LOT. I went to therapy not because I wanted to understand WHO I was, but how to better communicate with her, not only about my crossdressing but also about everything else.
This is neither here nor there but my previous relationships weren't really, well, healthy for me and I wasn't really used to communicating my thoughts and feelings. Before I started to date my wife I had been in therapy (and still am) to learn how to be open and how to be emotionally available. I had to unlearn what my previous relationships "taught" me.
I suppose what I am saying is that I did not come out to my wife while we were dating and she was immediately on board and thrilled her boyfriend wore panties. Of course, I didn't expect her to have that reaction either. I knew that coming out was going to be a shock and she would go through a lot of thoughts and emotions and fears. LIke every aspect of a relationship, we needed to talk about this aspect of myself and understand how this would impact US.
Coming out to our partners isn't always a dealbreaker. I didn't think I would hear her slam the door and she would walk out of my life after I told her. I was prepared for the shock and the fear and her questions. I was prepared for the weird tension in the following days. I was prepared for her privately thinking if she wanted to be with someone who wasn't as, well, normal when it came to their wardrobe. I had a fairly good idea what she was afraid of and what was unspoken. I knew I couldn't MAKE her understand who I was or MAKE her accept this part of me, but I knew I could be patient and honest and empathetic to how she was reacting to this.
So, what changed? How did we go from that to where we are now?

We made this work not because my wife was already accepting of having a crossdressing husband, but because we were both honest and transparent.
It's quite boring but it took work. Communication. Patience. A commitment to understand this. It took honesty and transparency. I believe that when it comes to relationships it's not always the crossdressing itself that is the problem, but rather the problems that are RELATED to crossdressing. What I mean (and this is a huge oversimplification) is that it might not be an issue that one's husband wears high heels but it's that he spent $300 on five pairs when that money was meant to pay the cell phone bill. It's not necessarily a problem that one's husband wears lingerie, but the problem is that it feels like he is only initiating sex so he CAN wear lingerie. Intimacy is no longer about two people expressing their love but now it's all about him having an opportunity/excuse to wear a negligee.
I fail more than I succeed. I am not an expert on anything. Although I am blessed beyond my wildest imagination when it comes to who I am spending my life with, it's not because I did everything right in our relationship. But I will say that I feel I did more things right than not when it came to coming out and the days and years that followed. There were times when I wasn't always listening to my wife's feelings when it came to my crossdressing and that caused problems, but through therapy I learned how to be a better listener and I became better at acknowledging how she was impacted by who I was. She and I both knew that this is who I was and I couldn't ignore this aspect of myself, but we both knew I could be more considerate and receptive to how she felt.
The other major thing I did right was telling her before the relationship required any significant commitment. We had The Talk before I proposed. We had The Talk before our first apartment. I wanted her to know this about me so she could decide if the relationship would continue without the stress of breaking a lease or an engagement.
As crossdressers, our journey isn't easy. Relationships take work. Our partners change. We ourselves change. Relationships change. The only thing that can and should remain consistent and reliable is being open and honest with ourselves and our partners.
I understand wanting to find a partner who already understands and accepts someone who crossdresses is, well, appealing and would save a lot of time lol, but I don't know if that's the right expectation. Over the first few days of meeting my wife I knew she was everything I wanted to find in a person with the exception of not knowing her perspective on boys who wore girl clothes. I knew that this was probably not something she had ever considered when it came to a potential partner. I knew that if I asked her in those early days of friendship it probably would have weirded her out. When we started to date I knew that we would need to have The Talk but it didn't need to come just yet. Honestly I wanted both of us to learn if we were compatible with each other first. Her being accepting of me was crucial for me, but it wasn't the only thing I needed from a relationship. I wanted to find someone who was kind, smart, funny, and beautiful as well. I didn't want to settle for someone who accepted my crossdressing but wasn't someone I was compatible with in other aspects. If I set out to find someone who accepted my crossdressing and this was the first, and biggest characteristic in a potential partner, then it's possible I would have found a partner, but doing that would by default make other things, such as compatibility, less important.
We made this work not because my wife was already accepting of having a crossdressing husband, but because we were both honest and transparent. We made this work because of who we are and how we communicate with each other. We communicate the way we do because I took responsibility for my gender identity and went to therapy to learn how to be open with my emotions.
I knew a long term relationship was going to take work and would require two people to be on the same page on values and what was important in a relationship. I knew that relationships would include two people supporting each other in life and two people doing mundane household chores. If two people can't replace a leaky sink faucet without wanting to kill the other, it really doesn't matter if they are accepting of your crossdressing. Sure, they may be supportive of what you wear, but if every other aspect of your relationship is broken, does their acceptance really matter?
I suppose this could be summarized by saying that I knew that my future partner would need to be aware of, and at least tolerant of my crossdressing. But I also knew that there were other things I wanted to find in a partner, such as someone who was kind and intelligent. I mean, when we date people we are doing so with the intention of finding THE ONE, right? And THE ONE needs to be (almost) EVERYTHING we want in a partner. I found someone who made me realize that I could fall in love with someone for the rest of my life. We started as friends. We developed trust. We dated and got to know each other on new levels... such as this aspect of myself. It was the first test of our relationship and if that friendship, trust, and love wasn't there it would have been hard to have an open and honest conversation about my gender identity.
In retrospect, this all makes sense. A relationship is built on love and respect. It has to be. When challenges surface (and they will in a relationship), then two people will face them together with the love and respect that they have for each other. If the love and respect isn't there, it makes facing a challenge (such as one's gender identity) very difficult. It's hard to have the energy and motivation to stand by someone, to put in the effort to understand someone, if there's no love.
Love, Hannah
1 comment
Hannah, that was a beautiful essay and you are so right in how deal with who you are. I am comfortable and confident in who I am, but my relationship with my wife is not very good. She has never tolerated my feminine side. I have done the opposite of how you handled your situation.
The most important thing you said is that “it’s hard to have the energy and motivation to stand by someone, to put in the effort to stand someone, if there is no love” I think that is more important then making mistakes in telling your loved one about this difficult event in their lives.
You insight is always well thought out and gives me a lot to think about. Thank you so much.
Hugs Julie