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Achievement (Almost) Unlocked: Redefining Dating Success

CaptureCaitlin and I were walking home. To one side of us, trees. The other, commuters desperate to return home and buses who vote liberal with their horns.

“It’s amazing to me how when I wasn’t dating, I didn’t care about being single. I didn’t think about it.” Caitlin had spent the better part of a year actively not dating. She didn’t put herself in situations to meet men, In the four months I’d known her I hadn’t witnessed her flirt, and while we discussed prior relationships, she never once alluded to anything in the present. “But now that I’m on OkCupid? Suddenly I feel like a failure.”

Funny, this topic had come up during my awkward-hello date with Russell, too. Sometimes it feels like the entire datingverse is buzzing with the same topics (dude, like right now I can’t turn around without someone telling me about/asking me about the 100 dates girl). Yes, it was meta of us, but Russell and I had wound up talking about dating – at least, the psychology of it – while on a date.

Which means I actually had an answer to Caitlin.

“Well, you’re an achiever, right?” Caitlin has two degrees from an Ivy League school, is tenacious enough to do things like move across the country alone, and like the best of cats always lands on her feet. I know she’s an achiever, but I wanted to make sure she knew.


“That’s why this dating is hard. People like you – and me – learned at a young age that if we put our mind to something and practiced like heck, we’d be able to be successful at anything. It worked for piano lessons and public speaking, for O Chem homework and even drinking games. So it stands to reason that when we put our mind to dating, we find an amazing human being who doesn’t break a date for a lame excuse, doesn’t stop calling, or generally doesn’t do other things that happen.”

“Makes sense,” Caitlin said, staring across the street at the homeless guys taking turns petting a tail-wagging Rottweiler.

“But dating is not that simple. So when we don’t see results after trying – or happen upon our limited definition of success – it feels ten times worse than when we were not trying. We’re achievers. It’s frustrating not to achieve.”

She didn’t feel better with this assessment. “I get it, but…where does that leave me?”

I think it leaves her – and me, and everyone else – with one clear option: to redefine what it means to go on a successful date. We don’t have to look at dating as a means to meeting a mate. We don’t even have to look at it as a learning experience. Why not look at dating as exactly what it is: meeting a new person, finding out a bit about them,trying to understand them. No expectations. Just whatever is happening in the here and now, accepting that for what it is, and not worrying about later.


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