Ask Hannah!

With Halloween coming just around the corner my wife and her sister would like to go as Charlie’s Angels.  They bought me this cute green dress to wear. My question is what heels do you think are the most comfortable to wear for longer periods of time? My wife does not know anything about my crossdressing and maybe this is also a good time to hint to her that I really enjoy it.  What do you think?

Every foot is different so I can’t say definitively what heel is right for you.  I choose my heels for the day (or night) based on how much walking I am going to be doing and what outfit I am wearing.  As much as I want to wear my six-inch rose gold stilettos, I know it’s not the best idea if I am walking outside on slippery, icy sidewalks during a Minnesota December.

If I am doing a lot of walking or standing I tend to select a lower heel.  Again, sky-high stilettos are my jam, but let’s face it, your feet (and eventually your legs and back) will start to hurt before too long.  On the other hand, I have tall heels that I can and do wear for hours and hours at a time without any sort of discomfort.  Again, every foot (and heel) is different.  

I recommend picking out the heels you WANT to wear, the heels that work with WHAT you are going to wear and practice wearing and walking in them for a few hours.  Practice going up and down steps.  Think of it as test driving your heels.    

As for using Halloween as a way to come out to your wife, every relationship (like every stiletto) is different.  How one person comes out to their partner isn’t necessarily how someone else should.  What I do know is that coming out to your partner will irreversibly and significantly impact your relationship FOREVER.  Coming out to my wife while we were dating is still up there among the most important and life altering conversations we have ever had.  And that conversation still continues (on some level) to this very day.  Coming out to your partner is something that can only be done once.  Regardless of how well you know your partner (or anyone else you may come out to) you really have no way of knowing how they will react.  They may be angry, hurt, confused, excited, relieved, or emotional. 

It’s important to treat coming out (and any potential reaction) with the appropriate gravitas.   Casually mentioning that you enjoy crossdressing, or hinting at it, might be appropriate for some relationships.  It wouldn’t have been the right method for when I came out to my wife.  Yes, perhaps if I had casually mentioned it to her after only a couple of weeks of dating that would be different.  But by the time I came out to her we had known each other for a long time, we dated passionately and deeply and intensely.  We spoke of getting engaged and moving in with each other.  I should have come out to her before we had conversations about our future.  By the time two people are married they have made serious and important commitments to one another.  Coming out after getting married is waaaay more serious than coming out while dating.  Treat the conversation as serious as it deserves to be.  Again, coming out to anyone will likely bring up a lot of emotions and conversations so please consider the weight that this revelation will likely have.

Love, Hannah

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

2 thoughts on “Ask Hannah!

  1. All – my experience was even more delicate. She found out by looking at my AirnB reservation after 30 years of marrige – god an she stayed with me!

    for both of us, i wish i had told her much much sooner

    hug to all

    Liked by 1 person

    1. I seriously lucked out! I told my wife before we even started dating. It took about 15 more years before I realized that I was transgender, and another two before wanting to transition, but I’m thankful she’s been by my side through all of it.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s