Cross-Dressing and Encouragement

I have dressed like a woman twice in my life.  That is two times too many.

The first time was for a grade.  My 7th grade advanced English class (or nerd class as I liked to call it) decided to put on a production of The Wizard of Oz.  Using the word “production” is a little bit of a stretch.  There were no sets made or props or anything else that required a great deal of work or committment.  And we didn’t perform it in front of thousands; the other 7th-graders served as the audience.  This was a good thing.  If more people saw it then more people would have mental scars that are incapable of fully healing.  I already have too much guilt on my hands; I don’t need anymore.

For some reason we were made to do the play with boys playing girl parts and girls playing boy parts.  Which meant that the boys in the play would have to wear women’s clothing.  Which meant that I would have to wear women’s clothing.  I thought about arguing with the teacher, but she looked a little bit like a man in women’s clothing herself.  A big man.  And her shoulders made her look like she could have played linebacker for the Chicago Bears alongside Dick Butkus.  You simply don’t argue with a teacher who possesses the ability to rip you in half.

I was picked to play Glenda the Good Witch.  Of the characters I could have been picked to play, she was probably the best because she had fewer scenes than the other female characters. Plus, I was really beautiful in the long, blonde wig.  Just kidding.  I looked like a  cross between Brad Garrett and Lady Gaga.   It was terrible.

I can blame someone else for my first foray into cross-dressing, but the second time was all my fault.  A few years ago I worked for a company that had an annual Halloween Costume Contest.  There were plenty of prizes to be won in a variety of categories.  Scariest, Best Theme, Funniest, etc.  I didn’t really plan to participate and then I had an idea.  What could be funnier than a 6’7” man in drag?  Answer: nothing.  The only problem was that I had this thought at about 9pm the night before Halloween. 

My wife and I scrambled.  We found a dress that would sort of fit me in my mother-in-law’s closet.  We found a tiara.  We found army boots to wear.  Why army boots?  Why not?!?  The next morning, I awoke early and Kristy went to work on me to make me the best looking man/woman I could be.  She painted my nails, fixed my make-up, helped me on with my garb, and fixed my hair. 

Even though she prepared me to look like a woman, I wasn’t prepared to look like a woman.  At least not on the drive to work.  The looks I received from my fellow motorists were all pretty much the same.  They looked horrified and slightly amused.  I got honked at, waved at, and winked at.  It was my most awkward drive to work ever.

Upon making it to work, I sat in my car for a few minutes and took more than several deep breaths.  All of my nervousness vanished when I went inside.

I was greeted by a standing ovation.  Literally.  It started slowly with the people near my desk standing and cheering.  And then more people stood to see what the commotion was about and started cheering.  And then more.  It wasn’t long before I had over 200 people cheering, and clapping, and chanting my name. 

It felt great, but it would have felt better if it didn’t take me dressing up like a woman for this to happen. 

One of the worst things about the world we live in is the constant criticism that we hear.  Another of the worst things is the constant criticism we give out.  The lack of encouragement is terribly discouraging.  And it is something so many of us desperately need.  Really, all of us need encouragement whether we choose to admit it or not.

Encouraging words are inexpensive gifts that mean more to the recipient than cheap knickknacks ever will.  In this season of giving, I encourage you to encourage others.  Lift someone up.  Be a cheerleader.  Don’t wait until those you love are dead to say good things about them.  Tell them while it will still do them some good.

I appreciated the standing ovation that I received.  I would have appreciated it more if I didn’t have to wear a bra to get it.

Those things hurt. 

(Men–have you ever dressed up like a woman?  Women–have you ever helped you husband with his make-up?  When have you felt most encouraged?  Let us know!)


6 thoughts on “Cross-Dressing and Encouragement

  1. Matt, have you ever been called Pastor Doubtfire? 😉

    That was a good read, my friend. We all need encouragement, and I appreciate all that you have given me online. Humbled to be included in your blogroll. Since I started blogging in earnest it has been a wild ride. Excited to see what else the Lord has in store.

    To answer your question:

    No, I’ve never dressed up as a woman, but back before we had children I let my wife practice doing sculptured nails on me. Don’t tell anybody! 😉

    • I’ve nver been called that–but I’m sure I’ve been called worse. I don’t know how long you have been blogging in earnest–I just started a couple of months ago writing every week-day. Before that it was once or twice a month. I’ve really enjoyed it–keep on keeping on.

  2. Amazing post!! You are so very right. I feel most encouraged when I feel totally overwhelmed and unequipped to do a job and someone tells me how great I am doing and how I am the perfect person to do this job. It gives me the strength to keep on trucking. I think that many of us don’t love our jobs simply because we don’t receive enough encouragement and support. I feel like I could work for 15 hours straight if I knew that what I was doing made a difference and was appreciated. It’s hard to spend half of your life somewhere where people don’t appreciate you. (Do I sound bitter!? I don’t mean to. Okay, maybe a little.)

    • I’ve been in those places before–you work and work and work and it goes almost completely unnoticed. And when it is noticed is seems terribly insincere. You’re right–true encouragement makes a tremendous difference.

      • I think insincere encouragement makes things way worse. It just shows that people are trying to placate you with pretty words while you toil away. (Yes….still bitter). I have had jobs where you are appreciated, encouraged, and given support when you need it…and those are the jobs that don’t feel like work. Even if you leave bone tired, you feel like you were part of a team and did something important. I don’t think we need to have a pat on the back every 5 minutes just to do our jobs, but it makes a world of difference to receive it when it’s most needed. This isn’t just an issue in the workplace. We forget to thank and encourage our spouses, significant others, friends, and family members all the time. I got a nice pat on the back this morning from a co-worker….I am thinking that is God’s way of saying….”stop griping on Matt’s blog, people appreciate you!” 😀

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