07/02/2012 09:32 am ET | Updated Sep 01, 2012

Fearless Dating 101: Lessons From A Substitute Teacher

I found myself suddenly single and dating at the age of 32 after the abrupt demise of a 16-year relationship. As I had never read "The Rules," been around many single people, or even dated a man before (do the math... they were boys when I was last dating!), I had no prior conceptions of what it meant to date. This turned out to be a blessing.

I looked to what background knowledge I did possess in order to facilitate my dating adventures. Years before, while I was finishing my teacher certification program, I had worked as a substitute teacher. Subbing is very different from running your own classroom, especially as a new educator. As a full-fledged teacher, you know you're there for the long haul. The stakes are high and the pressure is higher. You need to get it right. In contrast, as a substitute, you are only there for the day. The expectations are low, which gives you the freedom and flexibility to experiment without the fear that a misstep will cause a precipitous drop in test scores or cause a mass riot amongst the students. I approached subbing as a continuation of my education. I went into each class not concerned about it being a "good" day or "bad," but only with the anticipation of walking out with a lesson that would ultimately make me a better teacher once I had my own classroom.

I decided to address dating the same way I had approached those anonymous classes as a substitute teacher. Instead of putting pressure on myself to find a relationship, I enjoyed each date for what it was: a lesson. I had no expectations of each encounter, apart from it adding to my ever-growing library of relationship knowledge and skills. It did not matter if we hit it off or suffered from endless awkward silences. There were messages to be found in both.

I learned how to tell if a man is insecure, regardless of the cloaks he uses to hide his fears. I asked pointed questions, listening carefully to the answers and learning about relationships in the process. I heard stories of why a man had never married or what caused his marriage to collapse. I saw patterns and profiles and filed them away for future reference. I learned how to show affection without smothering, how to communicate excitement without overwhelming. After coming out of a marriage that was characterized by deception that I had been unaware of, I used the dates to tune my internal lie detector. I practiced checking for inconsistencies in stories and reality and found a balance between turning a blind eye (my mistake in the past) and snooping (something that repulsed me).

Just like substitute teaching is a time for "trying on" different age groups and subjects, dating was a time of exploration for me as well. I dated architects and artists, introverted engineers and charismatic performers. I saw young men and older, taller and shorter, richer and poorer. I had no "ideal" composed in my head; I accepted each man as he was, even if he was only in my life for a 30-minute latte. I learned to appreciate different views and different types of intelligence. I began to look beneath the initial outward veneer that we all display to the world. As I grew more tolerant of others, I also learned to soften towards myself.

I did not master teaching after just a few substitute assignments (in fact, after 10 years of teaching, I am still learning more every day), but I did improve with each stint in the classroom. Again, I took that approach with me into the dating realm. I signed up for after exhausting the possibilities in my local gym. And I dated. A lot. I often went out every day of the week, mostly for coffee or a walk in the park, opening myself to new lessons and new experiences. I could practice without fear, knowing that I had a new date the next day if I inadvertently made a fatal error with the current one. I practiced and grew more confident and more knowledgeable with every date.

I did not find love that winter of Match Madness. I did not learn to fully trust or to completely open my heart. Those lessons came later. What I did learn that winter was the value in approaching life as a perpetual student; being willing to listen and learn. I realized the joy in the moment that arises when I let go of expectations and instead look for the good in what is. I still have no idea what "The Rules" advise, but I recommend approaching dating with curiosity and a willing spirit. You just might be surprised at what you learn.

For more by Lisa Arends, click here. Or visit her websites Lessons From The End Of A Marriage and Action Potential Wellness.

For more on becoming fearless, click here.