The Office Dating Game

Somewhere in the early 2000s, I ran the IT Department for a modestly sized marketing firm in southeast MI. When I say that I ran the IT Department, a more honest assessment would be that I was the most senior IT person in a modestly sized department. As such, I was responsible for all of the technical issues that would come up on a daily basis, in addition to all of the behind the scenes work that goes into making the servers run and the email arrive.

Being a small company, everyone knew everyone else; and everyone had an opinion of everyone else. It was easy to pick out which employees got along, and which did not. For nearly every employee, you could find a nemesis; a polar opposite. Almost everyone had their arch-rival; mine was Don1.

Don was everything that was wrong with white collar society. He was a smarmy, over-educated but under-intelligent, sycophantic bastard, and I detested him. When he quit to follow his wife to another state for her job, I (somewhat) silently cheered. When I heard months later that he divorced his wife because she was cheating on him, I did a small Irish jig in the main conference room. When he came back to work for us again, it was all I could do not to leap from my ninth-story window. He would take every available opportunity to make my life miserable, and I would do the same to him. Then, one day the ultimate revenge fell into my lap…

On a fine, sunny day in late September, a few months after his return to the company, the anti-Jer wandered into my office carrying his computer in his hands. Already, I was enraged. What is he doing with this computer in his hands? He’s not allowed to disconnect his computer. He’s not allowed to carry it around the building. As he dumps it unceremoniously onto the corner of my desk, he says brusquely, “It’s running slowly, I need it back by tomorrow”, and walks quickly from my office.

This is exactly why I keep my office door locked.

Knowing that he won this round, I opted not to fight the inevitable, and I booted up his system. Just as I thought, tons of installed software and extra crap is being loaded on startup, slowing everything down. In a gesture of defiance, I decide to baseload his system and load user rights management on it. In preparation, I started copying his user directory to the server. While waiting for the copy to complete, I called a friend and spoke to him briefly about plans that evening. It was during this conversation that sweet, sweet revenge came a-knocking.

“You have to come down here right now and look at this!” I exclaimed.

“What is it?” Gary asked.

“Just come look…”, I said, before disconnecting the conversation.

Moments later, I was showing Gary what has passed before my eyes just a few minutes before. A directory named “Personals” with subdirectories for “Adult Friend Finder”, “Yahoo Personals”, “eHarmony”, and several other dating sites. Inside of each directory was a series of pictures of Don, a Word document containing his advertisement blurb, and, most importantly, his log of conversations with people from each site. It was a veritable goldmine of usable information…but what to do with it?

We called our friend Ron, the only other smoker, and invited him out for a cigarette, where we related to him what we had found. It was Ron who put to bed our ideas of turning Don in or blackmailing him in favor of something much more fun. Starting a relationship with him. We agreed to go out for drinks that night to formulate a plan of attack.

The next day, I returned Don’s computer to him, and I couldn’t even find it in myself to respond to his barbs because I was too excited about what the day had in store. I hustled back to my office and got right to work.

First, I searched the web for images of a woman. Specifically, I needed to find a very pretty brunette (Don’s preference) with photos that did not look professional, and more importantly, I had to be able to get several clothed pictures of her and at least one revealing photo. I found what I was looking for on some young woman’s vanity site.

I then created an account on one of his less popular free dating sites. I created a profile that matched his “ideals” nearly precisely, gave an address that was in a neighborhood near-but-not-too-near to his, uploaded one of my pictures, and entered “Elizabeth’s” ad.

Gary, Ron, and I had spent most of the evening trying to figure out what to say, and had ultimately come up with a masterpiece that extolled the virtues of shorter men, the love of movies, the lack of desire to travel, and an adoration of hockey. The adoration of hockey nearly ruined us several times, as there was not a hockey fan among our number. Later, once things got going, we recruited Allen as our hockey expert.

Our plan was to wait a few days, then message Don as if we had just run across his ad, but things were hastened when he replied to our ad that same day. During work hours no less! I quickly printed off his message, grabbed Gary and Ron, and we left to go smoke. Over our smoke break, we read his message several times and formulated a response. When I got back to my office, I sent it off, and thus began our beautiful relationship.

It was apparent, right off, that Don was as full of himself as we had always believed. It was hard to ignore or, worse, applaud some of his ridiculously self-aggrandizing statements. When he talked about how much he wasn’t “hard on the eyes” or how important it was that he keep his body “rock hard”, it would stump us. How would an actual woman respond to such stupidity? More to the point, how stupid must we make “Elizabeth” sound that she wouldn’t laugh at such idiocy? Nevertheless, we plugged on; it would be worth it.

We began to run into an issue when he wanted to meet with Liz. We had made her an ER nurse at a hospital that was local enough to seem reasonable while being far enough to dissuade him from trying to surprise her at work. The ER concept was a godsend, allowing us to schedule dates with Don then cancel the day before or the day of due to work several times. Between the crazy ER nurse hours and her long drive to work, it was easy to paint a picture of her as someone that was just very busy at the moment and unable to make schedules work out. Fortunately, she had a promotion coming soon that would reduce her hours dramatically. Until then, Don had to make due with an increasingly sexual text-based relationship.

Why text based? On three or four separate occasions, we communicated with him by phone using my friend’s girlfriend, Lisa, as our proxy. This proved to be unnerving to all of us, because Lisa laughed when she was nervous, and she was not good at extemporaneous speaking. She would just freeze while we fed her something to say. Fortunately, Don was not the sharpest pencil in the box, and chalked up her lack of ability to communicate to general nervousness. The upside to Lisa, however, was that she had a sexy phone voice. When he started talking a little dirty to her, she took off on her own and, in no time, was getting phone-sex-operator nasty with the dwarven geek. We had to keep voice conversation minimal, because even a chud like Don would notice her inability to do anything but phone sex with any degree of normalcy sooner or later.

By the end of October, Don was getting restless. We had put him off as long as we could, but his interest seemed to be waning due to the lack of physical or even vocal contact. Things had gone as far as they could go; or so we thought.

In retrospect, a few less beers consumed by each of us would have probably made our thought process a bit more clear. Had Allen not bought several rounds of shots (he was a regular in our group now), we would have probably rethought our brilliant finale. As it turned out, we got just drunk enough that our brilliance knew no bounds. We decided to meet him for lunch on Halloween. It began as a simple enough plan; plan to meet him at the Mongolian barbecue, show up before he does, take a picture of him getting stood up, and drop off a printout of all of the emails and the picture on his desk later on. It was fantastic.

Then it got better.

I made a joke about showing up and saying “Hi” to him. That turned into me showing up in a wig, which ultimately transformed into me showing up in full drag and introducing myself to him as Liz. That, ultimately, was the downfall of the experiment.

On that fateful day, I called in sick to work so that Don wouldn’t see me in my pretty blue dress. We had set lunch for noon, so Gary, Ron, and Allen had all arrived at 11:30 so they could get seats overlooking the fun. At 12:15 I entered the restaurant.

To say that Don had a puzzled look on his face when he saw me walk through the door would have been an understatement. I must have looked quite a sight, and I relished in his demeanor change as his glance moved down from my long black hair haphazardly stuffed under a platinum Marilyn Monroe wig (the only we had available), past my goatee covered face, along my tattooed and hairy arms, below my wide hips, and across my hairy legs, coming to a rest upon my work boots. His confusion slowly dissolved into amusement, then was quickly replaced by shock as I approached his table. Horror overtook his features as I stopped across from him and said “Don? I’m Liz!” in my rather masculine voice.

There were many ways to react to this. Really level people would realize what had happened, see the humor, and laugh it off. Most people would get very angry and storm off, plotting revenge. There is a third option; extreme aggression. This is not an option that we had taken into account. When Don leapt to his feet, my assumption was that it was to rush from the building. When he cocked his fist and swung at me, I was taken completely off guard. I ducked and punched him. He lost his balance and fell to the ground.

It was madness. Rather than get arrested in full drag, I chose to sprint for the door before Don could regain his feet. I would live to fight another day.

The epilogue to this epic battle is that, for the next two months, work was a very uncomfortable place. At no point was our little joke ever brought up…and his dating foibles became similarly off limits. In December, I quit to pursue a better option, but I would like to think that Don still thinks twice before he dates on the Internet from work. And the moral that you can take with you from this story? Maybe, just maybe, you should be nice to your IT people.


1 All names changed, because some of these people might want to work in this town again.