Ask Hannah!

Any advice on a first night out en femme?

Going out for the first time is a life-changing experience.  And I don’t say that lightly.  
I felt so many things my first real time out en femme.  I was scared beyond belief.  My nerves were a wreck, my legs trembled, I was jumpy, I was excited. 

Whenever I go out en femme, the first interaction with someone else really kind of sets the tone for the day.  It’s a positive experience it really starts me off in a good mood.  Luckily most times I go out en femme my first visit is for my makeover.  The two artists I see on a regular basis also make me feel welcome and beautiful. 

My first interaction on that crucial day couldn’t have gone better.  The cashier at the coffee shop was smiley and I felt a huge wave of relief.  I accomplished something!  I did it en femme!  I took my coffee and I felt like I was walking on air.  It was wonderful.  I spent the rest of the morning shopping and just soaking up the day.  

As wonderful as the day was, it almost skewed my expectations for the next time I went out.  My second outing was at a busy mall on a Saturday afternoon.  Most people were nice or at least indifferent, but I also noticed more…  confused looks, more stares, more suppressed smiles.  It was depressing, especially after my first time out.

When you go out for the first time, or the hundredth, you should prepare for everything.  This includes practical things, such as what you should have in your purse.

Before I go out, I always make sure my purse has:



-Finishing powder


That’s the fun stuff.  The reality is that I have a lot more in my purse than makeup.  I recommend every t-girl have the following in their purse:

-Cash.  This is pretty obvious but I use cash for everything when I go out.  If I want to get a coffee or need to pay for parking, I use cash.  I like cash because I don’t run the risk of turning over my credit card (with my male name) to a cashier.  I also bring my debit and credit card just in case.

-Proof of car insurance.  If you get into an accident or get pulled over, you’ll need to provide proof of insurance.  Simple enough but plan for the worst.

-Fully charged cell phone.  Pretty self-explanatory.  You’ll need it in case of emergency.  Any emergency.

-Roadside assistance information.  You need to know who to contact if you get a flat tire.  Sure, I can change a tire myself, but no way I am doing that in a dress or heels.

-Driver’s license.  Again, if you get pulled over…

-Spare car key.  If you’re not used to carrying a purse, you might forget to place your keys in it.  A spare key tucked in your purse saves a call to a locksmith.

-Medical insurance card.  Again, plan for the worst.

-A friend.  I don’t mean bring a friend with you, though shopping is a lot more fun if you do, but if you’re out to anyone in your life, drop them a message to let them know you’re stepping out.  It’s good to let someone know you’re out on the town in case you need help.

-I would also recommend downloading the Uber or Lyft app.  If you run into car troubles and need help, having this on your phone can be a lifesaver.  I have an app on my phone and I have multiple accounts associated with it.  One for my male life, one for Hannah.  I’ve used Uber as both genders and I’ve never had an issue.

There is a practical side to being who we are, such as the things listed above, but we can’t ignore the emotional and mental side either.  We can look amazing, but if we don’t feel amazing, then our confidence is shot, no matter how beautiful we are.  If we are so hung up on passing or blending in, then we may never feel ready to go out en femme.  It’s important to remember that not everyone likes us and not everyone will treat us with respect.  It will happen.  You’ll have moments and experiences that range from wonderful and affirming to humbling and humiliating.  Don’t let it dull your sparkle.

And above all, be safe.

Related reading

All Dressed Up and Nowhere to go

Just a Small Town T-Girl, Living in a Lonely World

It Will Never be Okay

Love, Hannah

Have a question for me?  Oh yes you do.  Ask me here!

4 thoughts on “Ask Hannah!

  1. Great advice. As an Uber driver , i can tell you i have had several crossdressers , trans in my car always delightful folks. Wish i could just drive them. Best wishes to a great experience.


    1. When I see comments like “It’s just who we are” I think it’s an over used phrase.

      To test this phrase, how does it sound when I say, “I rob banks to make money, but it’s just who I am.”

      Or, “I feel so much better after beating my wife, but it’s just who I am.”

      The use of such phrases appears to me to be making excuses for your likes, behaviors, needs, etc. I like the opposite approach, such as “own it!”


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