I spend a lot of time thinking about this because it’s essentially the situation I’ve been in for the last few years. So, I consider myself something of an authority on the topic as it applies to married crossdressers. But here, I’m aiming to reassess the usage of the phrase “don’t ask, don’t tell,” or more accurately, advocate for abandoning it altogether. You might wonder why I’m proposing this, and there are two reasons: one, DADT largely carries a negative connotation; and two, it’s often not a fully accurate description of the actual arrangement (in some, and I would argue most, cases).

 

Let’s start by addressing what DADT really connotes. The concept of “Don’t Ask, Don’t Tell” became part of the American vernacular during the Bill Clinton administration, when the military adopted the stance that it was acceptable for gays to serve in the armed forces, as long as it wasn’t talked about. In other words, no one is going to ask what your sexual orientation is, but just keep it yourself. While this was a huge step forward, with 30 years of hindsight, it seems old-fashioned and ultimately demoralizing to members of the LGBTQ+ community. For all intents and purposes, it’s saying, “We’re going to let you join the club, but we still think there’s something wrong with you.” Hence, the negative connotation.

 

As a crossdresser who told my wife, and honestly did a really poor job in doing so, the outcome I imagined from having the “talk,” and the reality of where we ultimately landed ended up being quite different. Though the words “don’t ask, don’t tell” were never spoken, the fact that she requested I not dress up around her was exactly how I internalized it. Since I had botched the initial conversations so badly, which led to several weeks of awkwardness, I took this as a “win” and figured this would be a satisfactory compromise. But the negative implications of DADT – a term I picked up from various crossdressing forums I frequented – only sustained the feelings of guilt and shame I had been trying so hard to shed. I would ask myself, “If there’s really nothing wrong with me wanting to dress like a woman, then why doesn’t she want to see it?” And therein lies the second issue with using DADT when describing crossdressing.

 

As mentioned, the words “don’t ask, don’t tell” were never uttered in our discussions. Though beyond the scope of this article, I’d be curious to trace the actual history of using it for CD relationships! Be that as it may, it certainly seems to have stuck. Not to get overly semantic, but if you take these words at face value, they imply that the topic at hand is NEVER brought out into the open. Going back to the military, they were essentially saying, upfront, “we don’t want to know.” According to Wikipedia: “The “Don’t Tell” stated that a member may be discharged for claiming to be a homosexual or bisexual or making a statement indicating a tendency towards or intent to engage in homosexual activities.” Here is where the analogy to a married crossdresser really starts to break down, because the above implies that by telling your partner about your crossdressing, you would be “discharged” from the marriage! Logically, simply by having the conversation, it’s already moved from “don’t tell” to “tell.” Even if you decide DADT applies moving forward, the knowledge lives on in the partner’s psyche – it can’t be “un-told.” 

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So, what am I proposing? Let’s assume that the words “don’t ask, don’t tell” haven’t yet been suggested as a compromise with your spouse or partner. How would you describe the reality of your partner’s needs going forward? What are they really asking of you? A popular saying that comes to mind for me is, “you do you.” Because of all the emotional baggage that being a male-to-female crossdresser can carry, it was a short leap for me to hear my wife say, “I still love you, but I don’t really want to see it,” as “I think you’re a sicko, so keep it to yourself,” i.e., “don’t ask, don’t tell.” But if we reframe it as “you do you,” then the meaning more easily becomes, “I love you and I understand this is something you need to do. I prefer not to be a part of it, though.”

 

By no means am I suggesting this is the right compromise for everyone. If your needs include transitioning, or presenting full time, then this obviously doesn’t help. But in that case, “don’t ask, don’t tell” will not cut it either! For those who don’t necessarily need to share everything with their partner, this can be a much healthier way to think about it. Or in my case, when I needed her “approval” in order to feel good about myself, I might’ve accepted that just because she didn’t want to participate doesn’t mean I wasn’t getting her support. I’ve often referred to how my wife and I cope with my crossdressing as the “Pink Floyd Solution.” I’m a huge fan. Their music connects with me right down to the core of who I am – and my wife can’t stand them! But she has never once suggested that I shouldn’t like them or listen to them… she just doesn’t want me to force her to listen!

 

I owe a debt of gratitude to The Fox and The Phoenix podcast for a recent episode that also took a deep dive into DADT. Though I had been mulling over this concept for several weeks, that episode really helped crystalize my thoughts on the subject. I highly recommend checking it out if you haven’t done so yet.

 

So, I’ll leave you with this thought: as a community, let’s agree to stop using an outdated reference to a demeaning policy when talking about our relationships. Whatever you call it, “you do you,” “it’s your thing,” or something equally empowering, let’s choose positivity. Who’s with me?

 

“I believe, this is heaven to no one else but me. And I’ll defend it long as I can be left here to linger in silence, if I choose to, would you try to understand?”

Sarah McLachlan, “Elsewhere”

En Femme Style

 

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Alexis "Lexi" Moon

40-something, married "baby" trans. Been crossdressing since age 5, but just this year finally accepted that my obsession with dressing in women's clothes is ultimately driven by the fact that I'm happier presenting as a woman. Still trying to figure out what that means, but just trying to enjoy the ride for now! I'm also a guitarist/singer/songwriter.

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Mysti Strachan
6 months ago

Thank you for sharing. My wife is supportive as she has always known I dressed since early in our relationship development, but I am still working up to my first dress session in her presence. I guess I’m fearful of revealing my full feminine side; despite her encouragement.

Raquel Smith
Active Member
6 months ago

Lexi, Yes, by definition, once the cat’s out of the bag …. But for those of us who are in a relationship where our SO has seen signs of our crossdressing, but have never had The Talk, DADT is the actual situation. Is it stressful knowing, or at least believing in our hearts, that if we told, the relationship might be discharged. Yet, our SOs, might be equally worried about their own reaction, so they don’t ask, they don’t dig deeper. My wife knows enough that she could ask, but doesn’t, or at least, hasn’t. It’s much more than “you… Read more »

Raquel Smith
Active Member
5 months ago

Lexi,
I wrote a 2-part article about my own personal situation. Check out https://www.crossdresserheaven.com/does-she-know-part-1/.

I don’t have any answers, but she has voiced her opinion of crossdressing on more than one occasion. Let’s just say, I don’t think Raquel would be accepted.

Bree Heath
Duchess
Active Member
5 months ago

Thanks for the great article Lexi. I told my wife of over 20 years just last year in September. She says she had no idea I was crossdressing. We did a lot of asking and telling since then but she has only seen pictures of Bree and she is fine with that. I have been out fully en femme twice since then with her knowledge. 6 months and our new relationship is still evolving. I think the image of her husband and protector was a little tarnished by the knowledge. People as a rule are seldom exactly as they appear… Read more »

Marie Chandler
Baroness
Trusted Member
5 months ago

Very well written and thoughtful article. It’s pieces like this that keep me coming back to CDH! I hadn’t given DADT much thought, as it relates to CDing, but you make a great case for leaving it behind in favor of the much more supportive “You Do You”. My wife is accepting of my CDing and willing to see me dressed and even dress up with me on occasion, which I cherish, but I also realize that there is nothing about my dressing that is physically attractive to her and I totally get it. If she enjoyed dressing as a… Read more »

Last edited 5 months ago by Marie Chandler
Amiliah Rougeheart
5 months ago

Thank you for sharing, my experience was similar to yours even though my ex wife met me knowing I am bisexual, born as a hermaphroditic androgynous male and that I actively crossdressed in fact I was in shredded women’s cackies and a woman’s graphic t at the time we met, but when I expressed that I wanted to start doing so again publicly she enforced what I call the deep closet policy similarly to the DADT and YDY policies but as you expressed she wanted nothing to do with it, she agreed to stop throwing out my women’s clothing while… Read more »

Cheryl Ann (Cassie) Sanders
Active Member

Brilliant, simply, brilliant. Quibble with some of it; but that is minor compared to my general admiration for those who make the effort to live an examined life … and to write so well about what one finds.

It seems to me that this admirable trait is more common among crossdressers than others; maybe a corollary benefit of crossdressing?

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