Super Fun AND Super Serious

I tend to look at gender in two very different ways.

Gender identity and gender presentation is super fun.

Gender identity and gender presentation are super serious things.

And yes these perspectives and opinions do seemingly contradict each other.

I get emails quite often from people who are in the early days of acknowledging that their gender isn’t as black and white (or as blue and pink) as they thought it was.

And this realization is quite vexing and frightening to them. It’s normal for this acceptance to cause a lot of overthinking, self-analysis, and anxiety.

What does this mean? What should I do? What am I? Who am I?

These questions are normal. And expected. And honestly? Likely unanswerable at this part of one’s journey.

When I get an email from someone who is clearly overwhelmed and confused by their realization that they don’t always want to wear trousers or the color blue or what have you, they are usually very lost. It’s not unlike waking up in a land that is completely new and you have no idea how to navigate this world.

I am asked questions in these emails about identity and labels and like I mentioned earlier, these questions are likely unanswerable at this point. The sender doesn’t have the answers and I don’t either.

I feel honored that I am asked a question that is so personal. I am grateful for the trust that this person is putting into me. They are likely at one of the most life-changing moments in their life.

It’s a new world, baby.

So, what do I tell the person who is asking questions that don’t have an answer (yet)?

I tell them to have fun.

Buy that dress. Sleep in that nightgown. Wear that cute bra and panty set.

This response is a little surprising for some, I think. And I don’t mean to come off as discounting their very serious questions. My thinking is that they have accepted that there is more to them than they ever imagined. I feel that they have started to become who they are and although the path ahead will not always be easy, it will be filled with pretty clothes and moments that make them happier than they ever imagined.

Essentially I am suggesting that they stop fighting these feelings, and, well, give it to them.

Buy that dress. Sleep in that nightgown. Wear that cute bra and panty set.

And then? See where this goes. Try not to overthink. Try not to overanalyze. One step at a time. Slip into those stilettos and see how it feels. Does it feel right? Do they make you happy?

You don’t have to completely cannonball into the pool of femme presentation. I am not suggesting that someone has to empty their bank account and buy a wig and breast forms and makeup because honestly those aspects of presentation aren’t right for everyone.

Start small and see where this goes. Baby steps, baby.

I tell them not to get too in the weeds with labels. It’s not for someone else to decide if you are a crossdresser or non-binary or agender or transgender or anything else. Besides, the word you identify with will likely change and evolve over time.

I feel this response is a little unexpected to them. It’s a seemingly casual response to a question that is Very Big and Very Serious. But I feel discovering yourself and acknowledging who you are is, well, I think it’s a lot of fun. It’s an adventure.

Burdening yourself with labels and what all of this means and where this is all going will overwhelm someone. And I know I overthink all the time and I sound a little hypocritical here but overanalyzing our identity will, well, take away the natural realization of who we are.

We don’t have to figure this side of us out right away. We have our whole lives ahead of us to do that. For now, enjoy the journey. Take in the sights. Take your time.

On the flip side, I’ll get emails from people who are full steam ahead. Usually these emails are a little jarring, equivalent to a car going from zero to a zillion miles an hour. Most of these messages are along the lines of “I’ve always wanted to try crossdressing and now I want to be a full-time girl!”.

No exaggeration.

It’s not unlike someone saying “I’ve always wanted to eat pasta so I am packing my suitcase and moving to Italy!”

Girl, slooooow down.

You want to try crossdressing? Okay, cool. Buy a pair of panties. Paint your nails. Go from there. Making the jump from never wearing “girl clothes” to living full time is incredibly hasty.

To further the travel metaphor a bit, when I was in high school I wanted more than anything to live in downtown Chicago. It just seemed COOL. And then I went to Chicago. And although Chicago is amazing and beautiful I realized that…. mm, maybe living in the heart of a bustling metropolis isn’t for me. I was glad I figured that out before I did anything.

Anyway, when someone messages me about wanting to take estrogen and living full-time I tell them that they should seek out a therapist that specializes in gender and to talk to their doctor.

And honestly? I think it’s the last thing they expect me to say.

To be clear, I don’t mean to kill their enthusiasm. Not at all. BUT transitioning is likely the biggest decision someone can make in their lives and it’s one that I feel needs the guidance and care that medical and psychiatric professionals should be guiding you through.

Besides, if you’ve never “tried” crossdressing how on earth do you know that you want to medically/legally change your gender or gender presentation? What if you don’t like it? What if the first time you slip into a dress you realize that MAYBE femme presentation isn’t for you? AND! what if this IS all about clothes? AND! gender presentation and gender identity doesn’t always mean one has to, well, choose a gender. I mean, I don’t feel I need to pick a gender to live as for the rest of my life. I’m bi-gender, I’m good with whatever.

Sometimes I get a little pushback from people who tell me they want to be a girl. Like, why so serious? Isn’t it fun to wear dresses and makeup? To be clear, yes, it is. But be realistic. Being a girl isn’t just about clothes. You don’t have to transition to wear a skirt. If someone is going to transition, I feel it should be for reasons that are more than just wanting a certain wardrobe.

I suppose I could summarize my perspective like this: discovering who you are should be fun. Deciding on a major life change should be taken seriously.

Love, Hannah

4 thoughts on “Super Fun AND Super Serious

  1. Way back in 2008 on my fiftieth birthday I decided that I needed to seriously address this “thing”. All my life I had been cross dressing but firmly in private, in the closet. I realised that I couldn’t control it, and that I wasn’t going to grow out of it, so I had to deal with it.
    I also made the decision to only address the next question, so that started with do I want to go out? Then gua do I want to join a group, and do I need help, I ended up where I am. But by just taking one baby step at a time I knew what I was doing and avoided the pink fog!


  2. To those hell bent on going from zero to 60, ”… under the sun, that the race is not to the swift, not the battle to the strong, neither yet bread to the wise, nor yet riches to (wo)men of understanding, nor yet favour to men of skill; but time and chance happeneth to them all.”


  3. Dear Hannah, Thank you for sharing these two opposite sides to the same story. I find myself somewhere pretty much in the middle and am very thankful for that. My greater environment, meaning the German society as a western constitutional democracy and the large city of Frankfurt that I live in provide for a safe place to go out en femme without being harassed, arrested, or killed. My wife approves of my dressing and she also benefits from my feminine traits. I know, between society at large and my wife there are still a number of more or less close people that have yet to learn about Franziska. On the other side, I am thrilled to be able to enjoy my feminine side (of and on, as I see fit), far away from any grappling about transitioning or not. I love your blog, Hannah, and I stop by regularly. Love, Franzi


  4. I am one of those girls who has to “grab some crumbs of time” as I have a non-supportive wife. Before her retirement I had the opportunity to be en femme a la June Cleaver for day, several days a week. Now? Fortunately, we sleep apart for medical reason and she is a late riser. Yes, I am able to sleep in bra, panty and nightgown or slip, and, then in the morning don a dress. I get about three hours each morning to peck away on a keyboard attire as much as I am able.


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