December 15, 2014
I mentioned once that I felt a bit like Carrie Bradshaw when I sat down to write my first ever dating column many years ago. Just as Carrie would have shopped for clothes on Sex and the City, I want to talk about how online dating is a bit like clothes shopping. (I know the analogy is slightly cringe-worthy, but bear with me for a minute.) 
When most of us go shopping, we fall in love with an article of clothing, say some black pin-striped pants that look like they’d sit perfectly on our waist, and then we look for our size. Sadly, it’s not there—what a disappointment. But that’s not how I shop. I’m very petite (a whopping 5’1), so I have to do the reverse; I blindly shop for my size and then decide if I like what I find. And sometimes I’ll even learn to love something in my size (I can think of a red dress offhand) because it fits so well, even though it’s not initially what I set out to buy.
Online dating is surprisingly similar. People have a tendency to look through the whole universe of people online for that perfect-looking garment, or person, who on the outside looks like a match made in heaven. But as you dig deeper, you learn that the fit just isn’t right for one reason or another—he wants children and you don’t, she is not yet divorced, he doesn’t feel the same way you do about higher education, etc. But you want to make it work so badly because you love what you see on the surface. I can’t tell you the number of times I loved a pair of pants at Banana Republic, and I tried on a “regular” (rather than “petite”—aka “short”), somehow hoping that the sizing would miraculously be a bit off and they would fit that day. Pants we can hem, but people we can’t.
Think about this for a moment: Search instead for people who fit the objective things you’re looking for (your size requirements, or your non-negotiables), then send an email to a wide range of people who fit those criteria. Try to keep the non-negotiable list short, perhaps to a handful of things you either can’t live with or can’t live without. Beyond that, cast a wide net. You never know until you try on the pants, or the person, whether it’ll be a good fit, so you might as well search through everything in your size and try some things on. Maybe the person who didn’t seem to be your type turns into the red dress. It’s a match you weren’t expecting. This method is much better than looking through people’s exterior qualities and then finding that nothing is your size. You’re more likely to get a better fit in the end.