The Fling

"My therapist thought it was time for me to trade in my tired, dysfunctional routine for something radical: casual dating."

A childish painting I made of Zach’s “shedding-allergen-factory” of a dog, and gave him as a parting gift.

Of all the feelings the tragedy of September 11th, 2001 could have evoked in me, I wasn’t prepared for this one: I was suddenly in the mood.

I was three weeks shy of 36, and had been recovering from a painful breakup with someone who’d cheated on me. For months, I’d had zero interest in dating and was reviled by the thought of being touched. Then, unspeakable tragedy not far from my East Village apartment sparked a rollercoaster ride through a series of overwhelming emotional states—terror, shock, rage, sorrow. What the hell was desire doing in there among them? 

Later that week I informed my shrink: “Now that the world is ending and I’ll probably never need it again, I managed to relocate my libido.”

“Yeah,” he said, shrugging, unfazed by my announcement. “That’s normal.” He proceeded to deliver a mini-dissertation on “post-disaster sex”—how humans are unconsciously hard-wired to try and propagate the species at times when extinction seems like a real threat. What an irrational impulse, I thought. When the world is utter hell, we feel driven to make more people so they, too, can be subjected to it?

When the evolutionary biology lesson was over, my shrink went back to being shrink-ish. “Lots of other people are probably feeling open now, too,” he said. “Go out and meet one of them.”

He was nudging me again, trying to get me to take the first steps toward moving on from my ex, as he’d been doing for a couple of months. My resistance immediately went up. “I’m sorry,” I said, “but I still don’t think I’m ready for a relationship.”

“No, no, I’m not saying you have to have a relationship,” he said. “I’m suggesting something lighter. Have a one-night-stand, or a fling. Just get laid.”

Oh, sure. A fling was a great idea in theory. We’d been talking about this in some of my sessions—that not every relationship had to be long-term. How, in-between longer relationships, you could have some shorter ones with people you had some chemistry with, who maybe weren’t your ideal long-term mate. Get some short-term needs met, then move on.

I had absolutely no idea how to do that. I mean, I knew how to choose men who weren’t relationship material. At that, I was a champ. Most of the boyfriends I’d been with in the nine years since my first marriage had ended were clearly much better candidates for one- or two-night stands than for the year or three I’d invested in them—guys either without jobs, or effectively married to their jobs…recent dumpees very much not over their exes…active addicts resisting recovery…a musician whose manager, it so happened, did a good portion of her “managing” between the sheets.

A fling was a great idea in theory. We’d been talking about this in some of my sessions—that not every relationship had to be long-term. How, in-between longer relationships, you could have some shorter ones with people you had some chemistry with, who maybe weren’t your ideal long-term mate. Get some short-term needs met, then move on. I had absolutely no idea how to do that.

Growing up I got the impression that there was only one flavor of relationship on the menu: permanent. Those relationships that didn’t go the final distance—even if they’d gone on for decades—were considered failures. There was no room for the possibility that a connection had just run its course—and that there existed shorter legitimate “courses” than forever-and-ever. Happily-ever-after was the primary goal.

When I found myself single at 26, after having been with only two men in my entire life—a high school boyfriend, and a college boyfriend, whom I married too young—I neglected to expand my perspective on dating and relationships. Despite very much needing some time to myself, I went back to looking for long-term love, and in all the wrong places. Regardless of whether or not a man was long-term relationship material, or vaguely suited for me in any number of ways—long before I could even know whether he actually was—I was auditioning for the role of the love of his life. I had no idea how to keep things light and unserious, not even in the very beginning.

How did you get just a little involved? Fall just a little in love? Care for someone only half-heartedly? Even more vexing, how could you stand someone caring only half-heartedly for you? I couldn’t bear that. And so, if you slept with me once, you were basically my boyfriend, no matter how many ways you hit me over the head with the information that you just weren’t that kind of guy.

Obviously this approach to dating and relationships wasn’t working out terribly well. My therapist thought it was time for me to trade in my tired, dysfunctional routine for something radical: casual dating. Maybe he was right.

~

I knew of a vigil that night in Union Square. I’d been meaning to attend. Existing for days in the same fragile emotional state as so many others, I felt the need to be both alone and among strangers—people I didn’t need to individually interact with, and many of them. This is one of my favorite things that New York City offers, the ability to lose yourself in a crowd, to let the din of others’ voices—their pulses and heartbeats—help your mind wander.

Maybe instead of putting on the same jeans and tee shirts I’d been wearing for days, I could pull myself together. It felt strange, that evening, applying makeup, tidying my long, unruly hair, choosing the more fitted jeans—efforts I’d foregone in the months since my breakup. Walking from my East Village tenement to Union Square, falling apart as I passed walls teeming with missing-persons photos, I became self-conscious about my mini-makeover. It felt like a sacrilege. I was hyper-aware of the blusher I’d applied to my cheeks, a blaring, Dusty Rose beacon of crass desperation.

Overcome with shame and grief, I aborted my half-hearted pick-up mission and was happy to disappear into the crowd. It was a big swarm of people, shoulder-to-shoulder—exactly what I needed. Someone handed me a candle. I waded through the sea of stunned but unusually friendly New Yorkers, and found myself near the statue of George Washington on a horse, where a demonstration was happening.

Existing for days in the same fragile emotional state as so many others, I felt the need to be both alone and among strangers—people I didn’t need to individually interact with, and many of them. This is one of my favorite things that New York City offers, the ability to lose yourself in a crowd, to let the din of others’ voices—their pulses and heartbeats—help your mind wander.

Hoping to climb up onto the low stone wall surrounding the statue for a better view, I bobbed and weaved until I reached it, and then looked up. Right above me was a cute young guy with dark hair, ice-blue eyes, and one of those khaki photojournalist-in-the-field kind of vests. He had a professional-looking Nikon pressed to his face, the lens pointing down at me. As I smiled nervously, he let go of the camera, leaving it to rest on the strap around his neck, and extended a hand to lift me.

“Who are you shooting for?” I asked awkwardly once I was standing next to him – assuming that like me, he worked in the press. It was also the most neutral, non-pick-up-ish thing I could think of to say.

He laughed. “No,” he said, “it’s just a hobby. I’m Zach, by the way.”

We started talking—mostly about the attacks, and the aftermath, and how scared and sad we were. The conversation was warm and friendly, and it didn’t end until he walked me home. At my door, he kissed me. It was the first bright moment in months of personal darkness. I had no idea where it would lead, but I went to bed that night feeling lighter and more hopeful. Who knew that in the wake of such devastation, it was possible to connect with another human?

~

Zach called the next day to invite me to an exhibition hockey game at Madison Square Garden. He was a hockey and skating coach, he explained, a one-time NHL hopeful whose chances were ruined by a torn ACL mid-try-outs. Before the game, over Thai food, we exchanged more details of our lives.

Easy-going and comfortable as it was, a laundry list of obvious incompatibilities came to light. For instance, he was six years younger, almost 30 to my almost 36 (our birthdays were a day apart), which in and of itself wasn’t necessarily a problem, but in the eight years since college, he hadn’t established any kind of settled life. In the warmer months of the year— when he wasn’t working twelve or more hours a day, six days a week—he traveled the country in his van, taking photographs, accompanied solely by his shedding Shepherd mix—the kind of dog I happen to be deathly allergic to. He also sometimes coached baseball, and had little interest in the arts, other than nature photography.

I, on the other hand—at the time, a freelance arts journalist— had failed gym in ninth grade and was known to some in college as The Girl Who Slept Through Game Six of the 1986 World Series, head down on the table, snoring, in a bar filled with cheering Mets fans.

We had a nice rapport, but in other ways, were a complete mismatch. Perfect.

“I found my fling.” I announced to my shrink at my next session. I told him all about Zach and he gave his blessing.

Then the thing that always happened after my first night with someone inevitably happened. An invisible cement began seeping out of me, eventually filling all the gaps between us until I no longer knew where he ended and I began. This time the concrete set faster than usual.

In a matter of days, without any discussion, we were essentially cohabitating, alternating between his place and mine. Most of our relationship was spent sleeping together – literally sleeping, his shedding-allergen-factory snoring at our feet. Sure, there was some sex, but there wasn’t a lot of time for that. Because of Zach’s long coaching hours, most nights we’d meet up for a late, quick dinner, and then turn in soon afterward, so he could start the next day at 5 a.m.

I think it was all that slumbering that got me. Unlike most men I’d been with, Zach would wrap himself tightly around me, cradling me affectionately non-stop through the darkness until his alarm went off in the wee hours of the morning. Night after night, he lulled and comforted me in a way I clearly needed during that scary time in the world. In my oxytocin- (and Benedryl-) addled state, I slept more soundly than ever. I got hooked on it, and on him.

Over Thai food, we exchanged more details of our lives. Easy-going and comfortable as it was, a laundry list of obvious incompatibilities came to light. For instance, he was six years younger, almost 30 to my almost 36 (our birthdays were a day apart), which in and of itself wasn’t necessarily a problem, but in the eight years since college, he hadn’t established any kind of settled life.

But quick dinners followed by six hours of shut-eye didn’t afford all that much getting to know each other. And so it wasn’t until Zach invited me to his mother’s house in New Hampshire for Christmas, and we faced a pair of seven-hour rides alone together in his van, that more obvious details of our mismatch emerged.

Take the return trip from New Hampshire, when “Let it Be” came on the radio and I started singing along.

“Who is that?” he interrupted.

I stared at him. “You’re kidding, right?” It was only one of the most popular songs of the twentieth century.

He nodded blankly.

“It’s…the Beatles?” I couldn’t believe he didn’t know that.

“Oh,” he said, after thinking for a second. “I think my step-mother likes them.”

This was a fellow Gen-Xer, a man born in 1970. “Seriously? That’s your only reference to the Beatles? What kind of music do you like?”

“Oh, no,” he answered matter-of-factly, shaking his head, “I don’t like music.”

There wasn’t a whole lot more talking the rest of the way. There was never a lot of talking, actually. We didn’t have a whole lot in common to discuss! Did I take this as a sign, three months into my “fling,” that I should be grateful for the sweet time we’d had in the wake of the terrorist attacks, cut my losses, and move on? No, I did not. Instead I adopted a new strategy: I would culturize Zach. I took him to dance performances, and to hear friends play music. I got him to sit—granted, baffled—through a Richard Foreman play at the St. Marks Church.

Order the books…

I found ways to work with other clear incompatibilities, too. For example: each week Zach, an expert skier, ritually spent his one day off from coaching on the slopes. I, who never got over the time I fell off a descending chair lift at age 12, was “welcome to join” him, a familiar refrain from other non-committal men I’d dated. I ignored the part of my brain concerned with the lack of a proper invitation in “welcome to join” and became a regular in beginner school at Hunter.

When he wasn’t skiing, Zach was practicing his flight skills in a tiny rented Cessna out of Teterboro. Lucky me, I was “welcome” there, too. And so I logged several flight hours in the passenger seat, my head thrown backward into the only position that precluded projectile vomiting.

Once winter and hockey season ended, it came time for Zach to spend half his year in his van with no one but his dog. Before we met, he’d set his sights on Alaska, and once he was no longer coaching, he got to work planning his trip. He once again informed me I was free to tag along for the next six months. But of course, I couldn’t just pick up and leave my life.

Or could I? I mean, wasn’t that what laptops were for?! I could line up some travel assignments—maybe something about the virtues of domestic road trips in vans, in the wake of 9/11…

I think it was all that slumbering that got me. Unlike most men I’d been with, Zach would wrap himself tightly around me, cradling me affectionately non-stop through the darkness until his alarm went off in the wee hours of the morning. Night after night, he lulled and comforted me in a way I clearly needed during that scary time in the world.

But Zach clearly hadn’t expected me to take him up on that “invitation.” When I considered it out loud, he pulled away, clamming up, taking impromptu day trips without me. He started calling me “Dude,” (there was no colder shower for me) and ending our phone conversations with “Take care,” as if I were someone he spoke to occasionally, not a partner with whom he was essentially cohabitating. We started talking about ending things, both of us unsure. Our differences were glaring. But we liked each other. Zach was wrong for me in every way but an important one: he was the kindest, warmest person I’d ever dated.

“What do I do here?” I begged my shrink. “Do I try to make this work with Zach? Could I make this work?” I even brought Zach in for a session with me, and then he went for a separate session, on his own. After that, I posed the question to my therapist once more.

“Please, tell me what to do…”

“Sari,” he answered, throwing up his hands, “if the guy was wearing a sandwich board that read, ‘I’M UNAVAILABLE,’ in all caps, it couldn’t be more obvious. This is not about you. Give it up. This was supposed to be a fling, remember?”

~ 

Zach and I broke up that June.

But then the first anniversary of 9/11 rolled around. Terrified and mournful again, I was happy when Zach reached out. We got together. And then, in a matter of days, we were cemented to each other once again. True to form, instead of just getting the little consoling I needed at a difficult moment and moving on, I held on for dear life, trying once again to make a complete meal out of what was merely meant to be a side-dish.

It wasn’t terribly satisfying. When Zach and I had gotten together the year before, our connection had benefited from newness and ignorance—from not yet really knowing each other, or how poorly matched we were. Now we knew we didn’t have much of a foundation to build on. We knew we were doomed as a couple. We were bored with each other, but comfortable and cowardly.

“What do I do here?” I begged my shrink. “Sari,” he answered, throwing up his hands, “if the guy was wearing a sandwich board that read, ‘I’M UNAVAILABLE,’ in all caps, it couldn’t be more obvious. This is not about you. Give it up. This was supposed to be a fling, remember?”

We trudged on together like that for five months until one afternoon, Zach blankly asked, “Do you think my playing spin-the-bottle last night constitutes cheating on you?” Instantly my mind flashed to Elizabeth Perkins in the final scene of “Big,” when she turns around to glance one last time at full-grown Tom Hanks, only to see a little boy in a man’s suit. I now knew without question that I had to move on.

We had a long, weird debate again about whether we should break up, even though we both knew we should. As part of his argument for letting go, Zach said, “You know, I’m kind of tired of being the better athlete in the relationship,” at which point I burst out laughing. Everything that was wrong with our now almost two-year relationship suddenly came rushing forward, and was impossible to unsee. It was time to say goodbye, for real.

~

A few months later, in October, 2003, I met my husband, Brian, through an online dating site. We married a little less than two years later. So, I never did learn to have a fling. It’s okay. I’ll be perfectly fine going through the rest of life without knowing how to do that. Flings are fine for other people, but I’m pretty sure they’re not for me. There are other more worthwhile learning curves for me to tackle.

I long ago gained enough distance from my relationship with Zach to look back with fondness, and also to laugh at how cluelessly I operated. These days I feel nothing but gratitude toward him. Each year around the anniversary of 9/11, I recall the hope and comfort he surprised me with when it felt like the world was ending, and I silently thank him.

---

A version of this essay appears in my memoir, And You May Find Yourself…Confessions of a Late-Blooming Gen-X Weirdo. But it’s something of a New York story, so I’ve re-shared it here, in the Goodbye to All That section.