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Long ago, I dated two different women, both named Karen. They were about as diametrically opposed as two Karen’s dating me could have been. The first Karen was older, a divorcee with twin five year-old boys. The second Karen was younger and about as sweet as she could be; as innocent and lovely a girl as I had ever met.

The first Karen, I upset massively, ruining a New Year’s Eve party, and basically picking the worst night of the year to break up with someone.

As for the second Karen?  Well, I ended that relationship, too. I think on a fundamental level, I didn’t think I deserved someone as good as her. I simply wasn’t ready and was afraid of what a relationship with her meant. So, I broke her heart. It’s been seventeen years and I still feel terrible about it. For some reason she popped into my head the other day during a class. I was flippant about the end when I for some reason mentioned it to the class. It did tie into the discussion at the time, if only because I tied it in. Still, I feel terrible for having hurt someone so fundamentally pure and good.

If you run into the second Karen sometime, tell her Keith is deeply sorry and she was indeed too good for me.

If you run into the first Karen, tell her “hi,” but don’t mention me. I shouldn’t have been going out with her in the first place.


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  • […] and set me up with a very generous, wonderful, caring and beautiful woman whose heart I ended up breaking. I could be cruelly unfunny in those days. There are many stories I forgot, many I would later […]

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