Coming Out on Wall Street

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There are lots of pieces to unpack from my coming out story. To start, I need to dig up the old me from the late 1990s, and try to reconnect with her—it’s not only two decades ago, it’s also an unevolved version of me, before I started working on my shit in therapy. There are parts of the Amy back then that will seem familiar: I was a fiercely loyal colleague who mentored scores of women, and loved to laugh out loud and socialize. But I was also young, cocky, brash—and widely feared in my industry. I was consumed with and defined by money and power, like many on Wall Street, and was talented enough to be rewarded with a considerable amount of both.

The country’s mores on LGBTQ status and rights were a world of difference back then. The governing principle of then President Bill Clinton, a Democrat, was don’t ask, don’t tell. Being gay was something largely hidden, and rarely celebrated. There was no such thing as legalized gay marriage or health benefits for same sex partners, and identifying as LGBTQ was legal grounds for being fired in most states, and quietly acquiesced to in the rest. There was no consensus as to whether LGBTQ parents were fit to raise children—an issue that weighed into custody decisions in divorce proceedings, and blocked eligibility for potential adoptions.

Back then, I was co-head of a trading department at a white shoe firm, Morgan Stanley, where we were frequently reminded we worked for the best bank on the street. In the firm’s culture of elitism, credentials for advancement were unstated but understood: you should join the right country and yacht clubs, vacation and summer at the right places, attire yourself like the upper crust, be married (heterosexually of course) and produce children—preferably two.

There was just one Managing Director, Sally, in my division that I suspected was a lesbian: she had graduated from Smith and Harvard Business School, and had a short, gray bob and a wardrobe from the pages of a Talbots’ catalogue. No one questioned why she didn’t bring a spouse to office parties, or have kids in tow for the firm’s Apple Circus outings. Similar to office affairs, which ran rampant with our long work hours, or the extracurricular happenings with clients after hours, such things were not spoken of aloud. I often tried to engage with Sally on a personal level, because I found her fascinating and captivating, but she always kept it to business.

A big part of the job in sales and trading was entertaining clients. As a mother of a toddler, I cut back on nights out, but nights out were still essential: business and personal were closely comingled. Years later, when I first came out to a sorority sister, she said she knew—and it was because of what happened that night at Gramercy Tavern.

I had invited a department head at a bulge bracket bank, and a junior person on her team, to dinner around the holidays. Kristina arrived, elegantly dressed as always—turning heads as she sashayed in her Chanel suit over to the table, where she smiled and shook my hand, then settled in her seat and reached for the wine menu. Moments later, I felt something amiss and sat bolted upright! Kristina was seemingly absorbed in the menu, but her suede Manolo Blahnik shoe was gently touching my leg! In that era, the fashionable hemline was short, and my Tahari dress landed well above my knees. I continued perusing the wine menu, assuming it was an errant encounter.

We settled on an expensive bottle of red, and moments later, it happened again. By this point, her young colleague, Deborah, was into business talk on a deal we were valuing, and I was doing my best to focus and pay attention. Kristina was now pretending to be absorbed in the dinner menu—but her shoe was again rubbing along my pantyhose—this time more slowly, more deliberately, caressing up and down. I downed a glass of wine, smiled like I was listening to Deborah (I wasn’t), and glanced over at Kristina. She was taking in the restaurant, grinning broadly, now and then looking over at Deborah as if vaguely interested.

When it happened the third time I looked up, and this time Kristina was looking straight at me.  She alluringly smiled, asking, “What do you think, Amy?” playing on the asset valuation conversation Deborah was now having with herself. I downed another glass of wine. Then another. Even though long nights out drinking were a routine part of my job, by the main course I could feel my cheeks burning and the words coming out of my mouth sounding increasingly slurred. 

I excused myself to the bathroom after dessert. Me, the calm, cool, collected Wall Street trader had devolved into a fluttering mess! I was titillated: Kristina was an older, elegant, brilliant and powerful woman. I thought about what it would be like to kiss her—my first kiss with a woman. What would it feel like? Would her lips be softer? Would I know what to do—did Kristina already? I looked in the mirror at my petrified 33 year-old self, and said almost out loud: What am I doing?!   

It would be typical after dessert for the night to continue. At dinner, Deborah had mentioned a new posh bar that had opened nearby. I took a deep breath, walked slowly and as steadily as I could in my Ferragamo heels back to the table, but Kristina and Deborah were already at the door, retrieving their coats. Kristina said she had to get home: she and her husband and teenagers were catching an early flight to go skiing. I asked Deborah for a raincheck on the bar hopping—as a new mother—wanting to get home and get some sleep. For the entire ride home, my mind played through the what ifs, with a mélange of longing, regret and embarrassment.  

There had been other close calls before. Once on a trip to Chicago with a colleague, after dinner and excessive drinking at a swanky bar entertaining clients, when the cab stopped at her hotel to drop her first she turned to me and didn’t get out. And on a trip to Las Vegas for a competitor’s high yield conference, flying in for the night to meet up with a senior-level client who was the only woman there, and she asked me to come be her partner in crime.

These occasions with heterosexually married women came and went without incident, until the night I got off the elevator.