Should Cinderella go to the ball?

Dolled up in Thailand

Incidentally I do have a step-mother and two step-sisters…

Christmas-time is fast approaching, and with it comes the looming spectre of the inevitable office Christmas party.

I’m still in a bit of a weird limbo at work; technically I work ‘as a guy’, but my team know about Jen, most of my department and, to be honest, it’s really not the best kept secret anymore. At the moment I’m happy to keep things this way, I don’t think I’m quite ready to take that first step into work in a skirt on a Monday morning.

Our Christmas party this year is going to be a fancier affair than I’ve been to in the past.  The venue states “No jeans, football shirts or trainers.” I wasn’t exactly planning on turning up in a Leeds United shirt, but my usual androgynous look revolves around girl’s jeans, hoodies and shoes-that-are-not-quite-trainers-but-are-kind-of-close.
So I’m guessing my usual attire is going to be a bit too casual for this particular event.

But in life I never got as far as being a smartly dressed guy.  In a shirt and trousers I feel (and quite possibly look) like a schoolboy… this won’t do at all.

On any other occasion if I was invited to a party like this, I’d say “Yay! Time to get all dolled up in a nice cocktail dress.” But the work Christmas party?  Now that’s a big step…

I’m all for pushing myself; my whole thing over the last few years has been about baby steps, lots of small steps toward my goal.  Sometimes I make a leap forward and, although they’ve been super scary at the time, so far they have all gone really well and left me feeling amazing.

So why is going to the office party different?  Why does this decision deserve a whole blog post to itself?

The problem in my mind is that although this would be an amazing step for me, I’m concerned about how other people will react when they see me again on Monday as a boy.  Would it in fact be a really misleading thing to do? Could it actually enhance that stereotype of only being a girl at the weekend?
Most importantly, will it be harder for people to take me seriously if I let them see me switch between gender roles?

Some of my colleagues have met me ‘as Jen’ and some have even been out clubbing with me.  They don’t have issues with how to treat me at work, in fact they say knowing about the trans thing makes them understand me a lot better.  One work-mate described it as “the missing piece of the jigsaw” and that “once it’s in place everything makes sense.”

Except those colleagues work with me every day.  At the party there will be people I’ve not run into at work yet.   Although maybe that’s a good thing?  I’d much rather people met me as Jen in a fun atmosphere with some drinks and dancing, rather than some official email from a senior manager informing them that “person X from department D would henceforth like to be known as person Y.”

I know a few people who have gone full-time at other work places. They’ve all done what appears to be the more traditional way, leaving as a guy and coming back 2 weeks later as a girl. I hope my more gradual approach is working by not only increasing my confidence, but also helping other people understand what I’m about.

Personally I think I’m ready, and I do need to be thinking about myself first and foremost. I know I’ll get such an amazing confidence boost out of this, it could completely alter my thinking about going full-time at work. Gosh I should go look at dresses online. What a great way this will be to end the year.

Hang on… have I just made a decision?!


5 thoughts on “Should Cinderella go to the ball?

  1. Jennifer Louise Carter

    Well Jen , it sounds to me like you HAVE made your mind up already, it is easy as a commentator to say this, but it seems to me that you are already a girl in your own mindset but you are worried about what other people will think, and how they will react, maybe you expect a confrontation?…not sure…anyway that’s entirely understandable, I would be the same…. in your position….maybe I wish I was! Anyhow you obviously do look and act very convincingly as a girl that is clear from your own experiences, …….and as for going full time at work you want to break people in gently ….. well I think you want to do that for yourself really….and I would be with you on that count, probably the way I would be as well. But just imagine….you could go to the Christmas party as Jen, and find that there was no turning back, you could go to work everyday as Jen… just might be the most natural thing for you to do….good luck , I hope you have a great party!! 🙂

  2. Lorry Brown

    This weekend was special for me. It finally gave me closure on something that’s been haunting me for over twenty years. That was the last time I went to a works christmas party. The dysphoria was doing quite well at that point. I was managing to keep a good lid on it, but all of a sudden, here I am in a formal party surrounded by all these ‘other halfs’ in their pretty dresses and makeup having so much fun dressed up for a night out.

    Of course I was dressed in a tuxedo .. Every time one of these ladies complimented me on looking so handsome, it was all I could do to fake a smile and thank them.

    That night was one of the worst of my life. I never attended another holiday party again. I couldn’t .. wouldn’t.. put myself through that again

    Since I transitioned, I’ve never had the opportunity to attend such an event until now (smaller (cheaper) companies that didn’t push the boat out at the holidays with a holiday bash.

    Needless to say, that I was smiling all night on Friday, just taking it in and loving every minute of it.

    I guess what I am trying to say Jen, is it took me over twenty years to make a new holiday party experience that I finally enjoyed. If they already know about you, then what better occasion to just go for it, dress up like a million dollars (and feel like a million dollars) and show them the beautiful woman that you are.

  3. Dean

    Do what makes you happy,don’t sell yourself short,you only live once and you should do whats best for you. If people can’t handle that then it’s their problem, not your’s. You are a beautiful person, be yourself.


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