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Awkward Moments in Dating: The Coworker

December 1, 2017

Dating stories are usually interesting because something almost always goes wrong.  Even when the dating turns into a long-term relationship, something is going to go wrong at some point, and that makes a great story.

It’s been over twenty years since this incident with my coworker happened, but there are some things you don’t forget, no matter how long ago they occurred.  This dating story centers on an awkward breakup, and I still cringe a little when I think about it.  I’m not talking about stuff like “We’ve grown apart” or “It isn’t you, it’s me.”  In this case, a woman broke up with me because I said something stupid.

First of all, I probably shouldn’t have been going out with this woman at all.  I had just gotten out of college, and this woman and I worked together.  Even early in my career, I had a strict rule about dating women at work.  There’s a familiar saying, “Don’t defecate where you eat,” and defecation might be a crude way to describe dating (I don’t treat women like that, I promise), but I understood the sentiment.  Too many things can go wrong when you date somebody from work.

There were a couple reasons why I broke this rule.  First, she was a couple years older than I was, and she had a high position at the company/firm/corporation but wasn’t my boss.  This was the early 1990s, and sexual harassment was already a nation-wide social issue.  At the time, our company was aware that even women could abuse their authority, and so a dating situation like the one we were in would be frowned upon.  In other words, she wasn’t going to make an issue out of our dating if something went wrong.  She had more to lose than I did.

Plus, she had money.  It wasn’t just that her salary was higher than mine.  Her family had money.  She had gone to a prestigious university.  I had gone to a state school.  When we first met, she had looked down upon me (maybe not because of the state school; I simply didn’t carry myself with much authority).

Her opinion of me changed after I bailed her out of a bad situation at work.  She had made a careless mistake, I caught it and fixed it before anybody else found out, and I kept my mouth shut.  Professionally, that lack of self-promotion is my weakness.  I’m reasonably intelligent, but I lack ambition.  When I fix other people’s mistakes, I don’t care if anybody else knows about it.  I think she liked that quality, intelligence without the arrogance.  Plus, I looked pretty good in my 20s.  I wasn’t top ten material, but I was in the top half of my age bracket.  Some social awkwardness made me seem more unattractive than I really was, but I had my good moments.

Other guys disagreed with each other about how nice-looking this coworker was (I never participated in these conversations, but I overheard them at work).  She had a couple features that some men don’t care for but I find attractive.  Maybe she could tell I was mildly infatuated and that made me more attractive to her, especially after I had bailed her out.

Once she started talking to me on a regular basis, she caught on to my sense of humor.  She invited me into her lunch group which went out to really slow expensive restaurants, so the 5-7 of us (depending on the day) would always get back from lunch late.  I caused a stir within the group by suggesting that we get back to work on time since we were getting paid to work, and though it was controversial, the coworker took my side, and we changed our lunch habits.

Anyway, there was good chemistry and banter between the coworker and me.  With my monotone voice, others couldn’t tell our conversation was banter because my banter sounds like clinical reading.  Maybe that was another reason she didn’t mind dating me; nobody at work could tell we had banter.

Nobody at the company knew about us when we started dating.  Like I said, it would have been frowned upon.  Plus, a lot of her friends/peers probably would have thought I was socially beneath her, and I would have agreed with them.

I knew this relationship wasn’t going to last long.  Before I got married, I went into most relationships knowing that they wouldn’t last long.  I always expected the breakup to happen.  That probably caused the break-up to happen in some instances.  But not this time.

This time, the woman broke up with me because I said something stupid about her name.

And I’ll get to that in the next episode.


To be continued in… Awkward Moments in Dating: The Ugly Name !

From → Dysfunctileaks

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