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The Art of Wooing: Observations and Tips from the Trenches

Do you find yourself sheepishly emailing friends to dissect ambiguous interactions with your crush or trying to decipher text messages for a clear sign of interest? Have you wondered if you’re being asked out on a date or just for coffee? Are you struggling to find ways to flirt that land you on the right side of the line between being adorable and being offensive? Welcome to wooing in the modern age!

Wooing is the slippery, occasionally delicious, but more often infuriating exercise between being attracted to someone and dating that person. Courtship has a long and storied history, with intricate rituals and passing fads, and the dictionary definition of wooing outlines a defined path towards marriage. But this is neither here nor there in the free-wheeling world of men and women today. As I have come to understand it, the real “art of wooing” in this day and age is not about manipulation or trickery. Instead, it involves mastering the art of communication, taking chances, and being real with other people…

Sometime between leaving college and realizing I’d become an adult, I found myself pursuing an elusive poet who came into my life as my kickboxing instructor and, like most people who are attracted to each other these days, we had no idea what to do. I survived the 18-month tumult, as I survive most of my life, with support from friends who weighed in with advice and shared their own experiences in this tricky task.

Looking back at the “email tale” culled from the back and forth, I was struck by the profound wisdom (in hindsight, of course) which had emerged about the current climate of today’s lovers-at-large. So, rather than trying to formulate a definitive set of guidelines for everyone, forcing the eventual outcome of the one-size-fits-all mentality – undoubtedly one-size-fits-none – I distilled the data into 10 themes, and a Unified Theory of Modern Wooing emerged.

In short, I contend that flirting began to meet its death on college campuses as the very real fear of sexual harassment and date rape collided with a crescendo of feminism in the wake of 1960s women’s lib and the Clarence Thomas backlash of the ‘80s. Men essentially developed verbal performance anxiety, and women became hair-trigger sensitive to innuendo that threatened their equal footing. Or so goes my theory.

Many of us, roughly between the ages of 20-45, were raised to believe that our American society was governed by new rules. But the truth is that when the social gender norms of the ‘50s were dissolved, they were never replaced with more flexible parameters. In 1945, when a housewife chose to go out wearing black fishnet stockings and fire engine red lipstick, she knew which message she was sending out AND she knew that men would receive that message undiluted. There was a consistency of communication.

Now, I watch everyone sending out mixed messages, trying to read minds and playing at a romantic game no longer governed by commonly acknowledged rules. And it doesn’t help that with marriage happening later, we woo with much more baggage than we would if we were honing in on a high school sweetheart. Many of us bring the patterns of past lovers and lessons learned into the expectations of our present passions.

Finally, if we factor in the breadth of diversity to which we are now exposed and from which we can potentially meet our match, I see real language and cultural barriers added that were not as common in days past. Given all of this, the only conclusion I can draw is that we need to throw out the rules as we know them, adapt our wooing on a case-by-case basis, and commit to communicating with each other one-on-one. Easier said than done, believe me, I know (she says as she’s currently struggling to broach the “Do you like me? Check yes, no, or maybe” question with a great guy sitting squarely somewhere between friend and flirt).

But I have found that keeping in mind the following three themes, seemingly the most obvious though requiring the most effort, will absolutely improve your ability to woo more effectively:

Read Between the Signs: If you are confused by the signs you are seeing, stop and ask directions. (Yes, this means you may risk being rejected, but at least you’ll know if it’s time to take that exit ramp.)

Baseline Vital Stats: Take frequent readings to establish a sense of baseline behavior before jumping to conclusions. What is standard flirting vs. being friendly for your object of affection? Calibrating properly means gathering lots of data (i.e. going out several times).

A La Mode: Love comes in many styles. Wooing as someone else leads to confusion when your real self shows up. To avoid disappointment, be yourself.

Individuality has long been a key ingredient for Americans. But as we emphasize our unique qualities, we render romantic generalizations more useless still. There are many kinds of lovers out there and wooing as though there are only two, namely “men” and “women,” seems overly simplistic to me. Most of us would like to be seen as more than the sum of our stereotypes.

My kickboxing poet was very different from the man who came before him. And, while it is impossible to avoid making any assumptions, I really got to know him by getting to know him. We must become comfortable with communication, from every angle. We must be willing to listen and to share. And, no doubt, if you pursue this path, your valiant wooing efforts will be a tale worth sharing with friends, if not the start of “happily ever after”…

Kaz Brecher is the author of “The Art of Wooing: An Email Tale of Modern Courtship,” which has been called to the “Griffin and Sabine” for the Sex in the City crowd. Brecher is a keen observer of human nature in the context of changing social psychology, and this unique mixed media book, unfolding through email exchange, has a growing following across the world. The book is available at