This might be a weird question, but I just passed the anniversary of my biggest milestone, so I wanted to ask you:

In your “journey” (I know you hate that word) as Hannah, what would you say have been your biggest milestones? I have a few that I would happily share in a comment, but I’ll keep this brief… so what are some of the key moments that have defined who Hannah is today?

Congratulations on your milestone!

This is a really good question.  Thank you for asking it.

I thought about this for a while and I think this comes down to four key instances.

If I look at who I am as a journey (and yes, I totes hate that word but dammit if it isn’t an appropriate one), then my journey started when I was very young with trying on my mom’s heels, being fascinated my lipstick, dying to try on lingerie, buying my first dress, and so on.  I remember progressively going from underdressing to sleeping in a nightgown to learning makeup.  All this time I was discovering who I am, and how I wanted to look and what felt right.  As we learn makeup and build our wardrobe, we learn what we like and what looks suit us.  In many ways, my first real wig was the end of one part of my journey but also the start of another.  It was the final part of moving on from identifying as a crossdresser to realizing that all of this was more than just clothes.  It was about identity.  I didn’t know it at the time, but I should have realized at that moment that I was transgender.

I remember looking into the mirror for who knows how long the first time I was in full makeup, a dress, and a wig.  I didn’t look like me, and I was a far cry for what I look l like today, but at that moment I had never felt more beautiful.  I realized I had wanted to look and feel beautiful for my entire life.  It was one of the happiest moments I can remember.

The second instance was about a year after that.  After dressing fully at home and plucking up the courage to go out at night, I was ready to step out during the day.  I planned a day where I would wake up early and go into Minneapolis to buy a coffee at a cafe.  That was the plan.  That was the dream.  It was something I did almost every day in male mode, but this, this was something new.

This was significant in many ways as it was the first time I was interacting with the “real world”.  I had been out at night a few times to a LGBTQ+ nightclub, but this was my first time at a normal, everyday place and being seen by others outside of the LGBTQ+ community.  I had fears of people laughing at me, pointing at me, being harassed, and worse.  Thankfully nothing like that happened.  I was so ecstatic from the non-eventful reactions from others that my confidence shot way up.  No one cared.  Sure, they knew I was trans, but I don’t think anyone really gave me a second thought and if they did, I didn’t notice.  Although I had planned on only getting a coffee, I ended up going to two malls, a few other stores, and out to lunch.  This experience gave me the confidence to go out again.  And again.  And again.

The third milestone was the first meeting of the MN T-Girls.  I had been attending a trans support group off and on for a few months and it was a wonderful group with incredible girls.  But I didn’t really fit in.  The group was mainly attended by girls who were or had transitioned and many of the meetings involved conversations about hormones, surgery, and the legal process of legally changing your name and gender.  It was an important and necessary group for our community and I am glad it existed.

But my journey (ugh) was something different.  I had no plan or wish to live full-time or transition.  The group wasn’t for me.  So at the suggestion of my wife, I started to create a group for girls like me who weren’t necessarily looking to transition, and girls who just wanted to make friends and hit the mall.  Yes, it’s a little shallow, but my thought was that I can’t be the only one who wants to look cute and wander around a mall looking for heels.

Thankfully and surprisingly, I learned that I wasn’t.  Not by a long shot.  Today the group has close to 300 members and has been going strong (well, on hiatus under the shelter-in-place orders) for over six years.  But the group had it’s humble beginnings.  Our first meeting was in a coffee shop with about a half-dozen attendees.  Having others show up was huge.  If they hadn’t, I probably would have ended it right there.   But that day was the start of something I am very proud of.

Finally, modeling for Glamour Boutique and En Femme has been incredibly significant to me.  Doing my makeup, finding the right wig, and creating my look has been a humbling process.  I cannot tell you how many times I looked in the mirror and wanted to give up.  There are countless days where I spend an hour doing my makeup and seeing a boy in the mirror.  I have felt fat, felt ugly, felt too tall, too… male.  There have been days, there are still days, and there will always be days where I feel this way.  It happens.

But modeling has helped me feel beautiful.  I know it’s shallow.  I really know this.  But being considered pretty enough to model clothes and represent a business is incredibly affirming to me.  When I feel ugly or male, and I do a lot, it’s helpful to look at photos from a shoot or to look at the clothes I will be modeling next.

As I look back on all of these moments, I realize that all of them boosted my confidence in some way.  Whether it was how I looked or being able to create something.  Going out into the real world requires a lot of confidence, but a positive (or at least not a negative experience) can also boost your confidence.  I can do this.  I AM doing this.  I think when I present as male I take my confidence for granted.  I could look in the mirror and shrug and tell myself that this is just how I look.

But being en femme is a different story.  Looking male in a dress can crush my self-esteem.  A bad makeup day can be devastating.  Someone staring at me (in a rude way) can destroy me.  Although I can strut through hell with my head held high, I am faking it most of the time because I know that someone pointing at me or a bad wig day can reduce me to shambles.  It can often take an $80 makeover and a new dress to make me feel beautiful, but all it takes is a suppressed smile or a mean comment on Twitter to ruin my day.  Or week.

Anyway, that ended up getting depressing.  🙂

I loved this question and I would love to hear about everyone else’s milestones in the comments.

Love, Hannah

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