#15) On Heartbreak

A series of stories on true, devastating heartbreak

This week we’re going to try something new. We’re going to tackle one of the tougher topics in this series—experiencing true, devastating heartbreak—and stay with it for the next few weeks. As I unpack the story of Tara, I will do my best to leave some tools and lessons learned, which I hope can be helpful in your own healing, present or future. Or at the very least, let you know that you are not alone!

Ironically, my broken heart did not come from my two long-term relationships, or other meaningful dating relationships. Rather, it came from a woman with whom I imagined all the possibilities of what I wanted in a relationship—a nuance we will be exploring. We’re going to start with a story I wrote at the time for myself, Four Sundays, as part of my healing process, when I thought it was over with Tara. As I penned this story, the hurt was still fresh and raw. 

While Four Sundays is not a complete story of what occurred, it will convey the agony and brokenness I felt at the time. Even re-reading it a decade later, I can still connect with my utter anguish, as I thought, finally—this is it! She has arrived!—only to have it all slip away, slowly and painfully, and being helpless to stop it.

Four Sundays was a story I wrote while working with Esther Cohen, my editor at the time, for a fun book about my experiences as a woman on Wall Street. We met each week on the Upper West Side to review my writing progress and chew the fat. The first time I met Tara, I told Esther all about her, pulling out my phone to show her Tara’s photo on her company’s website. Weeks later, at one of my weekly meetings, Tara snuck out of work and cabbed up to meet me and say hello to Esther. Tara was, as you’ll see in the story you are about to read, beautiful and glamorous, and swept into the restaurant as we were finishing our work over lunch. She greeted Esther, then she and I walked out into the sunlight, down Columbus Avenue, hand in hand, her in a designer dress and heels, and me in jeans and a casual top, both in our aviators, imagining a life together as a lesbian power couple in the city.

A few blocks down, Tara wrapped her arms around me, kissed me goodbye, and hailed a cab back down to work. By the time I got back to Westchester, she had closed the door of her office and called me in a panic! I pulled over in a CVS parking lot before picking up my kids at school, as she shared her anxiety, wondering out loud if she could go through with it. As she was commuting home that evening, she texted it was just a bad moment—she had it all under control. This rollercoaster of ups and downs, which you are about to read about, became our familiar pattern. Esther, who was my only friend to meet Tara, helped me pour my feelings onto the page as a path to cope with the pain.

Tara stayed in my life for years, which we will explore in coming stories. Despite how much she had hurt me, I cared for her so deeply that when she fell apart after walking away from us, broken heart and all, I hurt along with her. Our lives criss-crossed again and again, and each time I held out hope that this time would be different, but it never was. It was just an occasion to repeat our patterns, and break my heart into pieces again.

Writing Four Sundays helped me start to make sense of it all—at least in my head. My heart would take years more to get there. I held on tightly, hoping she was who I imagined her to be. That optimistic side of me you have been reading about saw her potential, and wanted to believe it, and once again it worked to my detriment. It took me years of therapy, and then tools from a famous astrologer, to finally align my head and heart and completely move on.

Given a chance to do it all over again, would I? Absolutely, yes! I am still a believer that all these experiences, happy or horrid, are part of a life well lived. And with that, we’ll start back a decade ago at the beginning, picking up from last week’s story, just days after the premature death of a colleague made me question what was missing in my life, and discovering it was focusing on love as I was about to leave for a conference.

Four Sundays

We started on the elevator. Again, a woman propositioning me on a hotel elevator.

I noticed her across the ballroom, at breakfast: glamorous in a designer dress and five-inch YSL heels. She took the seat next to mine at dinner. Then as the group reconvened at the hotel bar. I was flattered as this gorgeous, accomplished, Ivy-educated woman praised me and my organization, demurely hanging on my every word. When I paid my tab, Tara excused herself and followed me to the elevator. 

I’ve always been the fun-loving, consummate girls’ girl. As social chair of my sorority, and twenty-five years later, as head of a national women’s organization, I’ve amassed and treasured countless female friendships and connections. But, here’s the rub: I’m a lesbian public figure. This creates the potential for confusing situations, especially since I’m a very passionate woman. I’ve managed by adopting a switch for my sexuality, which is safely set to “off” for work.

As the elevator doors closed, Tara leered and coquettishly proposed, “Are you watching SNL?” She’s inviting me to her room! Before I could fully process her words, reflexively, I replied, “Sorry, I’m too tired.” I stayed on, wondering.

A decade earlier, I’d been on an elevator with another high-powered, married woman. Back when I worked on Wall Street, where we didn’t bother with switches. I’d gotten off the elevator, stayed up all night making love, then embarked on my first lesbian relationship. Our relationship ended in 2006, the last time I’d uttered “I love you.”

 Before the elevator, Tara and I had discovered we lived a few towns apart. Our kids competed in sports. She lamented because of her long hours in the fashion industry, she didn’t have friends at home. We agreed to meet on Sundays.

The “what if’s” played in my mind until Sunday, when I walked into Tara’s gym and saw her, transformed from elegant to adorable. She wore black capri tights and a T-shirt; her red-brown hair pulled back in a ponytail, revealing her soft-brown eyes. Her arms were crossed over her lean body, and she tapped her foot, restlessly waiting. Upon seeing me, she radiantly smiled. The breath left my body. We embraced, as if it had been years.

We spent the afternoon immersed in conversation: her struggles as a woman boss; her dejected stay-at-home husband; her perpetually anxious children. Periodically, she’d inject her Pollyanna lightness, flirtatiously smirking at me, “Who are you, anyway?” I wanted to melt. Then, she was back to serious, her eyes welling with tears. “I’ve never had anyone take care of me.” I was falling for this powerhouse-by-day, vulnerable-by-night woman, recognizing my own struggles of a decade prior when I gathered the strength to leave my marriage and find happiness. Tara brightened and winked: “I’ve been telling my friends about this amazing woman who is changing the world.” 

We departed and shortly after, she messaged me, “I might be obsessed with you.” Tara was putting me on a pedestal. Which became all the more evident on the second Sunday, when she acted insecure and deferential. I longed for the possibility of two do-it-all women finding reciprocal love. So I messaged a reassurance, perhaps prematurely, “You're extraordinary. You’re everything. But married.”

I didn’t hear from Tara all week. I felt silly and exposed—I almost canceled! But I braved it and arrived on Sunday to find Tara pacing in the Starbucks parking lot. She grabbed my arm, “We’re going for a walk!”  

We headed for the Long Island Sound. As the wind swept the fall leaves aimlessly skyward, I was elated to be on even ground with Tara, as she professed, “I’m happily married, I’m straight.” Uninterrupted, she continued, “But I wake in the middle of the night, every night, thinking about you.” Intermittently, she pleadingly asked, “What is this?” I patiently listened until we were steps from our cars, when finally, I responded. “I think we’re in love.” Tara halted and grabbed my arm to avoid collapse.

We hugged a long goodbye, drove away, and moments later, she messaged, “I knew the first night at dinner. I wanted to kiss you today.  When?”

So began our roller-coaster of love.

At first, she was elated. “I’ve never met anyone like you!” I was despondent. The guilt!  I‘m breaking up her family! I set one ground rule:  no sex until we figure things out. Tara implored, “I’m a hot mess to have you be my first. Spanish—all passion!” I craved Tara, too. Spent hours each day fantasizing about making love to her: our bodies pressed together, moving in tandem, an endless stream of orgasms. With chemistry so explosive, I was certain our lovemaking would be all-consuming. But first, Tara needed to understand why she had come to me. A process of self-exploration, which started right away. Within days, Tara phoned me from her corner office, crying, “I’ve been half living my life!” I desperately wanted to help—her struggles so familiar—but I knew only Tara could rescue herself. 

Tara, the problem solver, assured me she had a plan, “It’s linear: fix home; get into therapy; be brave; disentangle.” But within days, wild gyrations began: “Don’t wait for me, Amy.” Then, apologizing and professing, “You’re my first true love.” Then back down,  “He’s broken. But he’d do anything for me.”   

Our relationship was becoming morbidly lopsided. Tara was gaining an understanding of her life and I was feeling lost and helpless. I’d wake up in the middle of the night, gasping for air: I’m losing her! 

But, I stayed close-by. Tara said I was her “catalyst.” Her life coach termed it, “Nourishment for the soul.” Tara’s progress made me hopeful, and when I objected to the gyrations, she’d respond with vulnerability. She was letting me down. She was upset with herself. I was so important—not just to her, but to women’s progress: “I’ll put you on a pedestal if I want to!” 

The fourth Sunday was the ‘perfect walk’ (Tara’s term) on a secluded trail. We luxuriated in planning our future together, Tara flirting, “I want to spend a week in bed with you.” We bantered about coming out: New York City’s new lesbian power couple. Then we stopped and embraced. Tara gently stroked my hair, “Those eyes!  Can I kiss you?” My body awash in desire: to kiss her mouth, her neck, softly breathe into her ear, wrap my arms around her and feel her exhale. But, our rule! Instead, we indulged in a mechanical kiss—our first, our last.   

She drove home and told her husband. For years, he’d been jealous, certain she was cheating. After his tirade, Tara messaged me, seeming frightened. I barely slept for days, worrying about her. Then, I became concerned myself. My sister was incensed, “She put your life in danger!” 

I wanted to believe her confession was our beginning. I loved her so very much. But my omniscient best friend, Arleen, assured me, “It’s over. He’ll be watching her like a hawk!” There was never another Sunday.

I finally saw the husband while Tara was on a business trip. I sat with parents in the bleachers, cheering for our kids. He stood apart, rabidly chomping gum and nervously running his hand through his white-gray hair. His tall, lanky body was in constant, agitated motion as he berated his cowering player. Tara’s other child stood by his side, shoulders stooped.

Any remnants of my guilt evaporated: He’s a bully! Tara was ashamed that I knew. What did it say of her that she stayed so long? I comforted and reassured her. But, days later, Tara was pulling away, “He’s trying.” 

Now, the gyrations were taking a toll: I started losing faith. Sensing this, Tara phoned and lasciviously propositioned, “I’m going to be your best.” Tara knew this because I wasn’t her first! Initially, I was titillated. Then I felt betrayed. Do I really know Tara?     

When I pressed for understanding, Tara retreated. “I’m blowing it. You’ll be the one who got away.” She said she needed a break as she left for a five-day spa trip with clients. Then, I stopped offering my comfort and support. Those poor children! How could she leave them with that awful bully, knowing? Days later, she was off to Detroit, and I realized: That’s how she stays with him! 

Having lost my unequivocal love, Tara shifted. She was cold and professional, doling out the hurt on our final call: she had been sleeping with her husband all along; she couldn’t say she loved me—it would feel like cheating; she was “not in a position to discuss” whether she had entered psychotherapy. Then, the finale: “I want to work on my marriage.” I didn’t object. I felt numb with anger. I spoke to myself, collected myself. It’s time to move on! Broken hearted, betrayed, but with my dignity.

Fast-forward to a recent dinner at Casa Lever with a former mentor from Morgan Stanley. She asks, “What worries you most, Amy?” For her, it’s the economies in Europe. I’m embarrassed to share my truth:  I worry most about love. 

Before Tara, my life had been happy, fulfilled, inspired. I arrived on Sundays ready and willing to explore a lifetime together.  Now I wonder if my broken heart will open again.

As for Tara, words from Madame Bovary come to mind: “It seemed quite inconceivable that this calm life of hers could really be the happiness of which she used to dream.”