How I met your mother

The Head of the Charles Regatta is a prestigious rowing event held annually on Boston’s Charles River. I’m not really into rowing. But all through college, I worked as a doorman/bellman/valet at a Boston hotel not far from the Charles. I remember standing in front of the hotel in my faux military doorman regalia as vanloads of people my age, pulling trailers with rowing sculls, rolled into town with smiles on their faces. My job at the hotel was actually kind of fun. But on Head of the Charles weekends, I always wished I were down on the banks of the Charles instead of carrying bags and parking cars.

On October 23, 1999, I finally got my shot.

I had traded my funny hat and white gloves for a post-college job at a technology company, and my weekends were now my own. Plus, one of my roommates, Andrea, worked at Boston University. So, in addition to being able to watch the Head of the Charles, I had a prime viewing location at the starting line—BU’s DeWolfe Boathouse.

When we arrived on the dock, I spotted some familiar faces. But there was also a girl with our group of friends whom I hadn’t seen before. She had an amazing smile. She looked cute in her perfect “late '90s fall in Boston” ensemble of a baggy sweater, jeans, and chunky black boots.

Her name was Christine, and she had just moved to Boston to take a job at an advertising agency and reunite with close friends from her time at Syracuse University.

I was immediately smitten.

I was too shy to ask her out on the dock, but through some careful working of mutual friend backchannels in the days that followed, I managed to secure a first date.

The night before our date, I went to the mall to buy some new clothes and shoes. As I was browsing at J.Crew, I ran into a work colleague with whom I had a bit of an office flirtation.

After we completed our respective purchases, we walked out of the store together, chatting as we stepped onto the down escalator. We were about a quarter of the way down when the J.Crew cashier ran out and exclaimed, “Miss! You forgot your credit card!” in our direction.

I made the split-second decision to run up the down escalator, grab the card, and heroically return it to my colleague.

At least, that’s how I saw it playing out in my head.

In reality, I took two steps up the escalator, tripped, and smashed my right hand on the edge of the metal escalator step. I did manage to stumble to my feet and grab the card, but my pride, my hand, and my romantic prospects with my coworker all took a pretty bad hit.

My colleague and I went our separate ways, and I continued on to shop for shoes. My hand hurt so badly that I couldn’t tie the shoes I was trying on. But I picked some out and brought them home. After a painful and sleepless night, I stumbled into the office the next day. I quickly discovered that my typing abilities weren’t any better than my shoe-tying abilities. I figured I’d better go down the street to the ER and get it checked out.

I arrived at my date with Christine with my new J.Crew sweater stretched over a hard cast that extended from my elbow to the tips of my index and middle fingers, both of which were enclosed in the cast.

I drove her from her apartment in Brookline to Boston’s North End in my brand-new, bright red Jeep Wrangler. Unfortunately, the Jeep had a manual transmission, and I could not grip the shift with a cast on my right arm and hand. As I navigated the busy streets of Boston, every shift required removing my left hand completely from the steering wheel, reaching across my entire body, shifting, and then quickly returning my hand to the wheel before I hit something.

The skepticism that appeared on Christine’s face with my vague explanation of where my new cast came from soon gave way to a look of genuine concern.

We somehow arrived intact in the North End, and the conversation flowed easily at our dinner at one of the neighborhood’s many amazing Italian restaurants.

But the first rule of dating in your 20s is that you don’t get serious with a jackass who runs up down escalators a week after you move to a new city.

It took me a year to get the second date.

But I did eventually get it.