Baby, I was born this way

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Now that we’ve covered my first woman and first time, next we’re going to explore other chapters of my life, and pull back the layers a bit on sexual identity and Generation X—a generation sandwiched between three raucous generations, and seems largely ignored. I was put up for partner at Morgan Stanley at age 35, which would have made me one of the youngest at the firm, and we’ll come back to that story. First we’ll skip forward to 2002, when I was about to come out on Wall Street, and to me that meant telling my best friend Arleen. I was incredibly nervous about doing so! 

Ever since we parted ways years before, Arleen and a former colleague from Amroc Investments, Mike Meagher, had been beckoning me back. I first met Mike over beers, while interviewing him for Amroc. He dressed and looked like any uptight investment banker from Lehman Brothers, and unbeknownst to me, he was gay. As we’ve discussed, such things were not spoken of aloud, but Arleen clued me in one day, showing me an article about Mike’s partner in a design magazine. Years later, Mike co-founded The Seaport Group, and brought Arleen along. We used to say the people in our industry were just one, big, dysfunctional family, so going to work with Arleen and Mike felt like coming home. 

Arleen, like almost everyone else on Wall Street at the time, was a Republican. Whenever the New York Post ran a story about Bill Clinton’s latest alleged mistress or some other supposed Democratic scandal, Arleen would gleefully cut out the article, print out a copy of my photo from the Seaport website, scotch tape it on, and have it waiting on my desk when I arrived. She was also Irish Catholic—not exactly the most hospitable to LGBTQ people: it would be another 14 years before New York City’s Saint Patrick’s Day Parade allowed our community to be represented at their event. One Friday afternoon, I finally gathered up my nerve as Arleen was rushing out to catch the bus back to Staten Island, to ask her if we could speak privately on Monday.

Monday came after what felt like a two month long weekend of waiting. When our morning meeting ended, Arleen and I stayed behind while the others shuffled out, after which she shut the door and admonished, “Okay, out with it!” I blushed, started to explain, “Well…umm…,” stopped short, started again, paused, looked at her, looked away, looked at my shoes, looked at her, and finally proclaimed, “Arleen I’m gay!” Arleen’s posture was as if the air had deflated from a giant balloon: she exhaled a big long breath, placed her hand over her heart, regained her composure, and as her face lightened, half yelled, “You scared me! I thought it was something bad!” Then, after catching her breath for a moment, Arleen chastised me for ruining the movie she saw on a date over the weekend, saying all she could do was worry that something was actually wrong! “I was worried sick!”

As I mentioned in last week’s story, there is no such thing as a well-kept secret on Wall Street, and before the day ended, Randy Wooster, who ran a competing firm, called Arleen and asked, “Is anyone there straight?” which Arleen happily reported to me after she hung up the phone.  Seaport’s COO was also gay. Then it was over, and yesterday’s news—poof! Turned out no one cared all that much, and the stress I had put on myself, conjuring up the unimaginable such as my BFF thinking less of me, turned out to be a total waste of energy and time.

Even as I made progress in feeling comfortable being out, over the next two decades as our country was becoming increasingly supportive of LGBTQ rights, Generation X remained stubbornly stuck. If you believe Lady Gaga that we were “born this way,” you’d be hard pressed to explain why a recent poll found that fewer than 4% of Gen Xers identify as “LGBT,” while nearly 1 in 10 Millennials, and 1 in 6 from Generation Z identify that way. More so, in the decade since Lady Gaga’s song, with the passage of gay marriage and a vast shift towards acceptance, Millennial LGBT identification shot up by more than 50%, while Gen X basically stayed the same! Who are these Gen X women that are gay or bisexual, but continue to identify as straight?

A decade ago was my first true heartbreak with a woman. I met Tara at a conference, but this time demurred and stayed on the elevator. She was glamorous, heterosexually married, and repeatedly pleaded with me to be her “first”—luring me with the fact that she was “Spanish. All passion!” I recognized her struggles and journey from my own, and told her we should wait until after she left her husband. In the ensuing months, we fell in love. Tara worked as a senior executive in the fashion industry, where coming out was becoming zeitgeist:  J. Crew boss Jenna Lyons had just gone public about her first relationship with a woman. I emailed Tara when the story broke, extolling, “WE should be next!”

But she couldn’t do it. Catholic guilt —“I am baking cookies and wondering if this is the last Christmas together as an intact family?”—and she was petrified of what her family would think. Arleen dismissed Tara using their shared religion as a crutch: “What a martyr!” Tara stayed in a marriage where, as she had once put it, she was only half living her life. Then I had the gut-wrenching experience of seeing her inner struggle devolve into physical manifestations. It tore me apart, and I stayed waiting with an open heart and false hopes for years.

In my stories, you will also meet women who did end up being in relationships with women, but stayed in the closet because of religion, ethnicity, or family politics and beliefs. Some had gathered the courage to leave with the help of a “catalyst girlfriend,” a term coined by LCSW Joanne Fleisher, meaning an LGBTQ woman who becomes the impetus for her to live as her authentic self. I know many lesbians whose coming out story involved this kind of relationship, whether it stuck and they got married, or more often it simply helped carry them to the other side.

The closest I came to becoming a catalyst girlfriend was with Tara, who you will be reading more about in my stories. More often, I have been like a gateway girl (my term this time) for questioning women, meaning an alluring choice for their first sexual experience. This is a pretty shitty role to play, but one I seem to keep playing. Remember, this isn’t a “Dear Abby” how-to newsletter, it’s my real misadventures!

More recently, I dated Sophia, an exotic woman who was from a prominent family in a country that is still backwards on LGBTQ rights. She was at the lower end of Gen X—14 years my junior—gorgeous, and had been heterosexually married with children. She told me I was her first, although I’m not sure this was the case because she was fantastic in bed—or it might have been that our bodies just fit together (we’ll be exploring this notion in future stories).

Despite living in liberal Westchester County, Sophia felt tremendous shame about her attraction to women. More than once, she canceled dates because she couldn’t process her feelings. One time, just hours before we were set to meet for dinner, as I was racing to walk Shep and Arleen (yes, my dog named after my BFF), she texted that while driving home from work, she was sweating and having heart palpitations and couldn’t make it. Could we reschedule? Please grant her understanding. It’s amazing what I will put up with for great sex!

We had a romantic weekend away, and after visiting a local museum, stopped off at a farm stand to buy cheese and crackers, a bottle of wine, and freshly-picked blueberries—her favorite dessert—before spending the next several hours in bed. We took a break for dinner at the hotel restaurant, and after our main course, the waitress asked if we wanted dessert. While I was scanning the menu, without missing a beat, Sophia announced, “We’re having dessert upstairs.” I forgot to mention that part of the exotic was her slight language barrier. The waitress blushed, and placed her hand by her mouth to hide the giggles. Sophia couldn’t see this because her back was to the kitchen door, but one by one all the waiters and waitresses, and I assume some kitchen staff, paraded by our table to check us out. I grinned at each as they passed, even half waved in acknowledgment, paid the check, took Sophia’s hand and whispered, “Time for dessert.” 

Glass half-full person that I am, I had such hope and optimism that with the passage of gay marriage, mainstreaming of LGBTQ characters in entertainment, and general acceptance of our community, Generation X would finally be able to more fully embrace that baby, we were born this way, but we have not. While Generation Z has progressed to gender fluidity being an afterthought, we are stuck in some strange time warp. And boy oh boy, do I have stories to tell!