Halloween Encounter with a Colleague

By Paula Gaikowski

Last week, while working online with my colleague, a cheerful woman in her 60’s, our conversation took a delightful turn toward Halloween. Little did I know that this discussion would lead to an unforgettable connection and a dash of personal revelation.

As we chatted, my colleague shared stories of her past Halloweens, particularly huge Halloween parties featuring crossdressing contests and drag shows that she attended. In response, I chuckled and mentioned my plans for Halloween were dressing up as a woman. She couldn’t hide her excitement and urged me, “Please get some pictures!”

With a mix of apprehension and a desire to connect, I confessed that I had already taken some snapshots during a costume try-on session the previous weekend. I didn’t mention that I am typically trying on costumes every weekend of the year.

In a brave move, I shared my screen, revealing my three en femme costume choices. One featured me in black pants and a matching top, another in a flowing skirt and sweater with funky boots and the third in a sleek pencil skirt, a black sweater, modest heels and an air of confidence.

Her reaction was the epitome of positivity and support. She not only complimented the outfits, but also candidly told me which one she preferred. It was heartwarming to witness such acceptance and our ensuing conversation was filled with laughter and camaraderie.

After this impromptu and encouraging chat, I couldn’t help but wonder how my revelation might affect our professional relationship. The following Monday as we met online again, her very first question was, “How was your weekend? How did the party go?”

I beamed and told her it went splendidly, though I had opted for a different outfit – a teal skirt suit that had long been a favorite. 

She couldn’t contain her curiosity and asked to see a picture. I obliged and shared details about my days presenting as a woman. I shared a few anecdotes about going out and about as a woman, how I found it exciting and fun to cross boundaries and see life from a different perspective.

 

In sharing these tales, I subtly dropped hints about my identity, though I hadn’t explicitly mentioned being transgender. However, the descriptive narrative I told was thinly veiled by the cover of Halloween. She was probably expecting a caricature of a woman, the man in a dress prank. My accomplished femulation probably extinguished any doubts about this being my first time to the rodeo.

The conversation was filled with positivity and praise.

“I think it’s great that you did this.”

  

The feeling of validation was nothing short of exhilarating. It was as though I had found a new friend who appreciated and celebrated this part of me that I’ve kept hidden for decades.

Reflecting on this memorable encounter, I can’t help but smile. It’s incredible how a simple conversation about Halloween can lead to profound connections and understanding. 

While the Good Ship Lollipop might not be everyone’s preferred mode of transport, it’s a wonderful feeling to sail on it, embraced by acceptance and camaraderie. 

Who knew that discussing Halloween costumes could lead to such a heartwarming connection in the midst of the corporate world?

Wearing St. John