The First Date

The camera pans to find two genetically blessed individuals leaning in for an all-consuming conversation. What are we watching, you might ask? It is none other than the moment every single woman simultaneously craves and dreads- the first date. Granted, experiencing a rom-com level first date is even more elusive than the date itself. However, when you’ve been dating as long as I have, you come across a few stand-out initial connections that make you wonder how they didn’t lead to deep, fulfilling relationships.

I met Mr. Wall Street while standing in front of the Copley Sheraton. I had a friend visiting from out of town and having said goodbye for the night, was waiting in the bitter cold for an Uber to take me home. While I watched my driver get lost for the third time on my phone’s navigational map of the surrounding streets, I saw a handsome man with newly graying hair and a confident stride approach me. Without any attempt at an introduction, he asked me what it would take for me to cancel my Uber and grab a drink with him.


Although I was becoming increasingly annoyed with my driver’s incapability of finding Dalton Street, I was also aware that Monday evenings are not incredibly convenient for impromptu dates. Naturally I asked the most important deciding question for whether I would accept a $5 cancellation fee for my ride: where are you planning on taking me? His answer? The Lenox. I decided that a free glass of the most expensive Chardonnay I could find on the menu was worth staying out late and risking a poor Uber rating.

Two expensive- and delicious- glasses later and I found myself intrigued by this stranger. He was a venture capitalist in town from NYC on business and I was no match for his wit and sense of humor. I found myself captivated by his stories and gradually opened up with my own. We decided to head to Mini Bar for more drinks and a little dancing. One gin and tonic later and I was looking into Mr. Wall Street’s eyes while rhythmically moving amongst a crowd of people packed into a Boston-sized space. A young man beside us confided that he had a crush on a girl he came to the bar with. Mr. Wall Street began giving him relationship advice, proclaiming that he and I were out celebrating our one year anniversary. I found this rouse enthralling and played along, pretending- if only for a moment- to be a part of his fantasy.

We ended the evening with a goodbye kiss on the empty streets of Boston. He asked for my number, but we both knew we would never see each other again. He was only in town for a few days and how often do relationships stem from a chance encounter and whirlwind evening. With 4:00AM fast approaching, I requested an Uber and relished in the post-date glow. Which leads to the question- how does chemistry transform into a relationship?

mybigfatgreekweddingI can’t help but think about another 2000s classic- My Big Fat Greek Wedding. When Toula first spots Ian in her family’s restaurant, she is eccentrically smitten. Her awkwardly adorable fumbles do not deter Ian from asking her out on a date and the two end up conversing over dinner a few scenes later. The connection between Toula and Ian is undeniable and leads to a series of dates that culminate in a proposal. Setting aside the ensuing culture shock of meeting a mob of loud relatives, Ian is smitten with Toula and vows to spend his life with her.

So, what sets a date laden with chemistry apart from one that cultivates a long-lasting relationship? I suppose if we knew the answer to that question, the first date would become the vestigial organ of romantic relationships.


In the case of Mr. Wall Street, I have a sneaking suspicion he was actually Mr. Married. While gossiping about my adventures the next day, a sympathetic friend pointed out that the likelihood of a handsome, successful man living in a NYC brownstone as a bachelor was one in a million. Upon further reflection, my friend was probably right.

With Love,


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