The Single Guy vs the Last Day of School

The following tale is based on actual events which occurred a number of years ago. This is the final part of a trilogy of stories about the Teacher. Part one is here, part two is here

Seven simple words. String them together and throw in a question mark at the end for good measure. How hard could that be? “Would you like to have dinner sometime?”

But in the days leading up to the end of the school year, I had a hard time making those words fall from my lips. I was constantly looking for the right moment to ask that simple question of the Teacher. Faced with a deadline, I began wondering if the opportunity would ever present itself. When the last day of school arrived, I realized that I couldn’t wait around for the opportunity to just appear and be seized at random. I would have to create the opportunity.

Creating an opportunity like this wasn’t about scripting and plotting and arranging for things to be just right. This simply called for me to be a little more assertive than usual. Honestly, it meant showing the ability to be just a little bit assertive, since assertiveness is not exactly one of my most overwhelming personality traits.

Last Day of SchoolThe day progressed as any normal final school day of the year should progress. In other words, it was kind of chaotic. During the previous day, I was informed that it would be a dress-up day. The students would be encouraged to dress nice for the end of the year awards assembly and the teachers were expected to look their best as well. Unlike my short career with the bank, I had not been expected to wear a tie as a counselor. But I knew I could rock a tie when the occasion called for it. Maybe this “dress-up” situation would play to my favor.

As it would turn out, no amount of nice clothes would help me out. I came close to asking the Teacher out at the end of the abbreviated school day. But just as the question was about to leave my mouth, the Teacher’s aide walked back into the classroom. But it wasn’t necessarily the end of the day for me. I had some work to do, so I knew there would be another opportunity. I would simply wait for the end of the retirement party that the school’s faculty and staff were putting on for one of their own.

As I waited, I had a chance to talk to a fellow counselor. I had noticed this other counselor talking to the Teacher from time to time, so I thought that she might know more about the Teacher than I did. And she did. It was in this conversation that I learned just how unavailable the Teacher really was.

“I’ve seen you talking to the Teacher, would you say you know her pretty well?” I asked. “Are you friends?”

“More acquaintances, really” said my coworker, “I’d say I know her partner better than I know her.”

It took a second, but it dawned on me exactly what she meant. “You don’t mean business partner, by any chance?” I asked, knowing my hopes had been dashed.


“So I shouldn’t ask her out…”

The counselor frowned slightly. “I wouldn’t.”

Chasing AmyI was glad that I had not had the opportunity to put my foot in my mouth by asking the Teacher out. It could have led to some pretty severe awkwardness. However, I do wish I had discovered the information that she was a lesbian some time prior to the last day of school, before I allowed myself to become so taken with her. I got over it. It helped that I didn’t work at her school again until after she had moved to another school herself.

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