people become acquainted and, as they proceed, start talking. Initially, conversations rarely progress beyond the standard questions posed and reliable answers proffered. If the elusive chemistry exists, the masks slip down and less polished selves may emerge. Then the real connection begins.
That “real connection” happened very few times in my online dating journey. We clicked and I could sense potential, the first rustling of distilled hope and longing against a background of increasingly mechanical introductions. A woman and I would talk and share, or, if we lived close enough (not always the case), actually meet and stroll through the city or a park. We would reveal jagged bits of biography to signal trust, a willingness to explore what our contact could become. Those bits, I discovered, could also be a warning: beware.
I recall one lingering summer afternoon picnic on a lake with a woman I’ll call the Swan. After stop-and-go contacts, the warmth of the encounter convinced me that we both had our hearts pointed in the same direction. To my shock, she leaned over and kissed me and I finally got the message. But later, standing in the parking lot, the Swan remarked, “I could bolt at any time.” I remembered but ignored this comment, so laden with prophecy.
And bolt she did. Call it a matter of timing, of circumstance, of appearance, or simply, “She’s just not that into you.” The exact recipe of the fatal brew does not matter; I’ve always thought that if there’s a will, there’s a way, and for one of us the will was not there. Our fitful migrations into each other’s lives left me feeling buoyant and then, always, bereft and abandoned. Similar possibilities flickered and ended—throttled by distance, hesitation, self-delusion, misunderstandings, the competition. I sketch some of those stories elsewhere. I had my share of stunned surprises staring at the final email, the last blunt conversation, the ceiling at midnight. And I caused my own share of disappointment and confusion.
Yet I found that heartbreak carries a functional value. I’ve hung around management consultants enough in my career to adapt their world view. I sometimes think in terms of costs and benefits, the bottom line, the so-what learned from a situation, moving from the current state to a future state. Could I ever find the ultimate MECE relationship, that is, “mutually exclusive and collectively exhaustive”? (MECE is a grouping principle that management consultants use to find solutions to client problems. Come to think of it, a durable relationship should, in fact, be mutually exclusive and collectively exhaustive, don’t you think?) Never one to know when to hold ’em and when to fold ’em, I would construct a flow chart of romance through project-management milestones, digressions, decision trees and quantitative analyses. That net-net value of heartbreak and experience emerged in response to questions that singles like to ask. Over the years, my dates were curious about what had worked and failed, my online experiences, my emotional engagement, what I was seeking. Did I date much? Did anything click?
Such questions are more than light banter at Starbucks. While I was once memorably called a “self-involved prick who just doesn’t get it,” I actually do have some basic insights into the dynamics of dating and the human condition. These kinds of questions are anything but casual time-killers; I’ve read enough Deborah Tannen books to know about rapport talk and the urge to connect. They aim to sound out my past and intentions, my goals, my hopes, my wariness and openness. After initial hesitation to talk about the past, I learned to combine honesty and discretion. When asked, I replied, “Yes, I had some things that looked promising. We really connected. But the timing wasn’t right. They just didn’t work out.”
But life went on in its maddening, hope-surging way. As I started chasing the Swan, I contacted