Coworker Date Disaster

So here’s my dating horror story:

I was asked out by a coworker who was several years my senior. We had worked together for over a year and he seemed nice enough, so I agreed though I was a little hesitant with the age difference.

We made plans for dinner a few days later.

It had been a while since I had dated, so I took extra time getting ready. I picked out a dress that said ‘interested’, but not that interested and dug out heels that I rarely wear for the occasion. Though we weren’t going anywhere fancy, I wanted to look nice.

I was more than a little shocked when he arrived to pick me up. The car he was driving was old, dirty and sounded like it was in serious need of a major overhaul. I was sorely temped to feign illness and forget the whole thing, but reminded myself it wasn’t nice to judge.

It was possible he couldn’t afford anything nicer. So I swallowed my pride and answered the door.

That Was A Mistake
“Oh Dear God” I thought to myself when I got a good look at him.

He was way under-dressed in jeans and a stained polo shirt that looked like it was on it’s last leg. He was never this poorly dressed at work.

Maybe I was just lucky to see this side of him I guess. Well it was too late to turn back, so I climbed into his car trying to avoid getting dirt on my dress.

A Barrage of Weird Dating Questions Followed
The twenty minute drive to the restaurant was full of awkward questions about my likes and dislikes as if he had never met me before that day. I answered each one with as much patience as I could muster.

I even tried to initiate normal conversation, but he just kept asking me strange questions, like how many guys I’d dated and what I like to do for fun. Okay, what I like to do for fun is a reasonable question, but the rest were just weird.

Things Went From Bad To Worse As…
Half way to our destination he almost ran a stop sign. I screamed in a reflexive and undignified manner as he slammed on the breaks to prevent us from crashing through a fence and into a pasture full of cattle.

The rest of the way to the restaurant was driven in complete silence.

At The Restaurant
At the restaurant we were seated and ordered our meal. I had eaten at that restaurant before, so I knew the food would be good.

Our conversation went a little smoother as we talked about work and general topics.

But Things Went From Worse To Horrible…
As we were waiting for the bill, my dating horror story kicked into full gear. He started telling me about how he had moved to the area to get away from his ex-girlfriend. She had strung him along for over fifteen years and finally dumped him for another guy. He also proceeded to tell me about his heart problems and how he couldn’t have sex.

I was so embarrassed.
But even so, I was feeling sorry for him.

The drive back to my house was uneventful and mostly silent. He dropped me off in my driveway, then left.

He never asked me out again – for which I was truly grateful.

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