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People who say dating was fun either don't remember or are simply wrong. When I plunged back into it, four years ago and freshly divorced, I was stunned by how hard it all was—knowing what to say, where to go, what to order off the menu, whether I was having a good time. Decisions I could make hundreds of times a day without thinking were suddenly excruciatingly difficult, freighted with the weight of the world, with the possibility of affecting my destiny. This was not—how do I put it?—fun. So I radically revised my approach to the enterprise: I began to use the world's most awkward social situation to practice the art of being me.

Successful dating—defined as anything better than an evening of Seinfeld reruns—required soul-searching and habit-breaking. I had to come clean with myself and admit the stakes were high. Time to discard the casual stance (I don't care what happens... I'm not nervous... I do this all the time) that was more armor than authentic feeling. I recognized the importance of seeking love and also that the chances of finding it were unbelievably slim. Such low probability was oddly comforting: I had the long shot's permission to run the race my way.

Like many women I know, I had always been more concerned with being liked than with liking. What would happen if I stopped arranging my behavior around attracting the other person? I changed the way I dressed for a date—still choosing clothes that looked good but not more revealing or frilly than I would normally wear. I tried not to fill the pauses in the conversation, thinking instead, This is uncomfortable—for both of us. I fully answered questions about my work (I write about community and race and identity and...thrift shopping!) and my interests (I garden and dabble in masonry and...thrift shop!), including those parts that I imagined might not appeal to my dinner partner.

I also reconsidered the way I looked at my dates. It's hard to see a person accurately when there's even a sliver of a chance that he might turn out to be the person with whom you share children and utility bills and a bed for years on end. What you want so often blocks what's actually there. And what's there on the table between you is two luggage racks full of baggage—a Samsonite sundae piled high with hopes, dreams, disappointments, losses, and long-held ways of understanding the world. We're all products of a particular time and place, family and religion, history and culture, coincidence and physical attributes. To listen with openness and say what you mean across that mass takes concentration and presence of mind. No time left to worry about whether you should have worn the Manolos.

"Thinking of us as colleagues and not adversaries helped me relax"

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