A few months ago, I was working as a long-term substitute teacher at a school in upper Manhattan. Although I had no background in the subject I was called on to teach, I had confidence in my ability to keep my class engaged. The class was tough. The kids didn’t want to be there and had no interest in learning. When things truly got out of control, a mystery man appeared in my classroom. He didn’t introduce himself, but he reappeared numerous times to help me maintain order. Later on I learned his identity—the dean of students.

Ordinarily, I might have been miffed about having someone else come in to help me with my class. With this stranger, however, I didn’t mind a bit. He was a cute twenty-something with dark hair, green eyes, and a smile that made my heart melt a little (it is always better when a good looking man comes to your rescue). I had no idea who the stranger was, until I asked my students. I was surprised that the dean would take time out of his busy schedule of meetings and disciplining students, to come help me control my class, in fact I felt flattered.

Despite the out-of-control students, seeing the dean of students each day made the experience less onerous. During the nearly two weeks I spent at the school, I saw him at least once a day. Yet, we never did more than exchange the standard “how are you today?” or “how are your classes going?”

The countdown for my leaving began. I started to think about ways to say goodbye. Could I come up with an excuse to give him my number? Would he regard it as being unprofessional? Would it be crossing a line?

I finally came up with a game plan: On my last day, I would go to his office and thank him for all his help. And, I would suggest paying him back by buying him coffee or perhaps a drink.

As they say, the best laid plans. The night before my last day, I was told a permanent substitute had been found who actually knew the subject matter. My plan was foiled. I missed out on my chance of asking this guy out—or so I thought.

Time passed. With school winding down for the summer, my days as a substitute teacher came to an end. I decided to look for a fulltime job and after an interview in Soho, spent some time shopping around. As I was leaving to go back uptown to my apartment, I spotted him. He was coming up the stairs to the A train as I was going down. I smiled and he smiled back, probably thinking I was a stranger. He took a few steps and then turned around and said, “Hey, how are you doing?” He had remembered me! I had only been at the school for less than two weeks and my hair was much shorter. But, he remembered me!

It was my serendipitous moment, fate was giving me a second chance to ask him out. We chatted on the stairs of the subway about my time at his school and I asked how he was excited for the year to be over. I kept trying to think of a good way to propose meeting for a drink. I kept thinking: What if he has a girlfriend? or What if he says no?

My fear of rejection won out. I didn’t ask him out or give him my number. He smiled. I smiled. We said goodbye. What was he thinking? Was he also afraid to ask, regretting his own lack of courage?

My serendipitous moment passed. I was given a second chance and let the opportunity pass me by.

Will there be another encounter? One of chance or one I can somehow arrange? It’s a big city, but stranger things have happened. Those old clichés run through my mind—if it’s meant to be. Third time’s the charm.