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Over at SexyTypewriter, there is a discussion about the best way to tell someone that you don’t want a second date.  “See you soon” is probably not that way. “I could stop thinking about you” has the advantage of being honest, and the writer describes that awkward end-of-date feeling of “oh god…so many expectations and ways this could go wrong….oh god.”

I’ve done a lot of internet dating, and early on I was very optimistic about people.  I looked for the good in everyone, I thought of ways to make things work, I talked myself into being attracted (hey, why not?), and I enjoyed the act of meeting new people for its own sake. Most people were not The Man Who Would Not Break Eye Contact or Gropey McTicklefight, most people were just disheveled nerds like me, and while I didn’t make many lasting connections I did have a lot of fun nights out of the house and discovered a lot of cool pockets of Chicago when I was new in town.

While I was very willing to go on first dates and meet people, I was pretty picky about who I spent further time with.  I’m an introvert at heart and while I love friends and a good time and conversation sometimes often I find myself asking the question “Will this be a better time than screenwriting/finishing this novel I’m reading/playing CIV/being in a completely silent room full of silence?”

I also had numbers and our sexist dating culture going for me.  I was a woman with a nice smile and huge…tracts of land… and an ability to be entertaining and keep a conversation going, so I just had to sit and look pretty and wait for people to write to me and then accept or reject them.  I didn’t have to work at finding people to date, they came to me.  So there was an unbalance in some of those interactions from the start – I might think “Hey, this guy seems nice and I’m free tonight, why not?” while the guy might be overjoyed at finally getting a response after weeks of getting no response and think “She must really like me to write back at all, this is so on!”

What I’m saying is that there were a lot of perfectly fine first dates that did not lead to a second date.  At 25, did I handle this in a straightforward, cool, honest, mannerly way?  No.

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