How Taking The Biggest Risk Of My Life Led Me To Finding True Love—And Myself

The way I figure it, there are two types of bears: those that find happiness in comfort, stability, pleasure, and strong relationships, and then the poor folks like me.

Erin Westgate, an assistant professor of psychology at the University of Florida, defines people like me as “seekers of psychological richness.” According to a recent paper by the American Psychological Association, “A nontrivial number of people around the world report they would choose a psychologically rich life at the expense of a happy or meaningful life…[one that is characterized] by interesting experiences in which novelty and/or complexity are accompanied by profound changes in perspective.”

That’s all great and everything, but in 2012, as a single mom working seven days a week in a gym in Houston, Texas, my bear-like craving for “deep psychological richness” was in hibernation. I worked. I raised kids. Living hand-to-mouth tends to crush one’s natural curiosity, mostly because you’re too tired to have any.

Yet I was far from unhappy. Those years were characterized by the foundational relationships I had with friends and my kids. In fact, I was sitting in front of my computer one night with Joyce, one of my dearest, closest friends (all other names will be changed to protect privacy) when a sidebar ad popped up on Facebook touting a writing seminar in Italy. Hosting it was an idol of mine. I’ll call her Natha Greenberg.

“I’d dig out a kidney, put it in an ice chest, and sell it on the black market to go to that thing,” I told Joyce. “Imagine being able to study with someone like that.”

Never could I have imagined how 23 (mostly) one-syllable words would radically deconstruct my universe.

Joyce is the kind of friend that happens maybe once in a lifetime. She’s wise, kind, supportive, and apparently very cunning, because I had no idea she was passing the hat around to all my terrific students and even some of my Facebook friends, one of whom (you know who you are, know that I love you and must accept that your generosity has completely changed my life) floated me his air miles so I could go to Italy. About three weeks before the seminar, Joyce artlessly asked me if I had a current passport (I did), and then with a big smile told me what she, my friends, and my students had been up to.

I was floored. Moved to tears. Elated. No one had ever done anything like this for me before. After scrambling to find instructors to cover my classes, I packed a bag, brushed the mothballs off my passport, and to Italy I went.

It was me and about 30 other writers, mostly women, that met at Fiumicino Airport the first week in October. Monica, the organizer, chartered a bus to take us to an 80-acre organic farm in Ronciglione, a comune about 60 kilometers north of Rome. There, Natha Greenberg would impart her considerable wisdom on the art of writing, while I, her most adoring fan, bright of eye and bushy of tail, would sit rapturously at her feet, soaking up the knowledge. I’d been writing professionally for many years at that point and had even made a few bestsellers’ lists, but no matter where you are in the process, there’s always more to learn. I was ready.

The farm, Villa Lina, was a hodgepodge of beautiful old buildings, olive groves, ancient fountains, and wicker chairs shaded by arbors of grape vines. That such places existed in the world stirred my soul in ways I’d never imagined. It was euphoric, but also the most painful kind of awakening. I lived with two teenagers in a crowded apartment behind a mall. Until that moment, I didn’t realize I’d only been half alive.

Unlike Italy, Natha wasn’t winning hearts and minds. In addition to being dry, cold, and humorless, she placed a moratorium on two things of great importance to women traveling to Italy: drinking wine and speaking before 1 p.m. All breakfasts were conducted in monastic silence, with only the clinking of tableware on ceramic to break the monotony.

We met with Natha in the morning, split off into smaller writing groups in the afternoon, ate dinner, and then reconvened at night to read what we’d written. No one was to praise or censure anyone else’s writing, which was probably a good idea. In theory. But on the first day of class, Natha reduced a woman to tears for innocently taking pictures of a patch of sunflowers. “Why are you doing that?” Natha snapped at her. “It’s compulsive. You refuse to live in the moment. Instead, you keep trying to capture everything with your stupid camera.”

This woman was from Kentucky. No one had ever talked to her about “living in the moment.” She felt ashamed and struggled to hold back tears.

But we were all about to be treated to Natha’s special brand of “bitchy Buddhism” that week. At one point after group meditation, she said, “It’s impossible to silence the mind. Ever. I mean, have any of you experienced even a few seconds of true silence?”

Meekly, I raised my hand. As a Yoga instructor, I meditated a lot. I’m not saying it happened all the time, but it did happen.

Natha pursed her lips and gave me a slitty-eyed stare.

And yet, unbeknownst to Natha, mutiny was afoot. People were sick of her head games and done with her rules. You don’t invite women to Italy to the tune of several thousand dollars per person and then put the kibosh on wine. Maybe Natha’s disciples (and there were perhaps 10 of them) neglected to tell her that it was a shitty thing to do.

My roomie at the Shepherd’s Cottage was particularly irate. She also didn’t like staying in the cottage, which was from the 15th century and smelled like an old crypt. “I can’t stand Natha,” she told me for the hundredth time. “She treats people like garbage.”

My writers’ group was just as angry. “Natha is out of control,” Jennifer, a tiny tour-de-force from New Jersey, complained. “I can tell you as a professional psychotherapist that this woman badly needs someone to tell her the truth about herself.”

Jennifer wasn’t afraid to tell me the truth about myself. If she hadn’t, I wouldn’t be here. After discovering that I hadn’t dated in three years (breakups are ghastly, even if you are the one to initiate them), she leveled a gaze at me and said, “Why are you doing this to yourself? What are you hiding from?” And just like that, I realized it was true. I’d been hiding. I’d put that part of myself in a cage, locked the door, and thrown away the key. That night, I wrote a letter to myself, apologizing, promising I would never do it again. I cried a lot. But when I woke the next morning, something was different. I felt…lighter.

As I headed down the hill to our learning dojo, Natha came up beside me and said, “I heard you wrote one hell of a piece yesterday. I just wanted to say congratulations. Good work.” No writer hates compliments, but weren’t we forbidden to give any? Natha told us praise would keep us locked in a vicious cycle of approval seeking, that it would corrupt our authentic voices. Which may be true, but these were dabblers, mostly. They weren’t at “authentic voices” yet. These weren’t professional writers; they were women who entertained the notion of writing. No one here was fresh off the Algonquin Round Table.

Meanwhile, there were many furtive trips down to the comune of Ronciglione for drinks and laughter, neither of which was to be had back at the gulag. By Friday, Monica, the organizer, decided to stave off open rebellion by taking us on a day trip. We were going somewhere called Calcata. I’d never heard of it.

After lunch on that brilliantly blue October afternoon, our bus churned up a mountain and then emerged from a canopy of trees. At just that moment, light poured from a cloud break, illuminating a spectacular tree-covered valley below. In the middle of that valley rose a volcanic stump the color of an old medallion, and on top of that stump, huddled like a troop of crazy, multi-size mushrooms, were the terracotta roofs of a medieval village and the single crenellated turret of a castle.

My heart pounded. I’d never seen anything so awe-inspiring in my life. Here, Tiziano’s painted skies were on full display. The same light that illuminated the Renaissance poured down on this floating island of 60 artists out in the middle of nowhere. I couldn’t wait to get off the bus.

The climb up to the village looked short but steep. A cobblestone passageway led from the parking lot to a forbidding-looking medieval archway. There was another arch topped by a coat of arms, and then a cobblestone piazza with three crudely-carved stone thrones. A 15th century church stood with its doors invitingly ajar. There were a few locals, but the village was quiet, drowsing. I wandered alleyways that took me past art galleries, a Yoga studio, and restaurants that kept only weekend hours. Then, while everyone else went inside a tea shop for lunch, I stayed on the church steps, so deliriously happy it was like being reborn.

They say when you die, a highlight reel of your best moments flashes before your eyes. I knew this would be one of them. Me, tummy down on the church steps, the pine-scented breeze from the valley wafting over me, the sun on my face. I was nowhere and everywhere. Connected and alone.

And then, in a pleasurable, purely female way, the hair on the back of my neck stood up. I felt someone watching me.

It was a man wearing cargo shorts and a dark T-shirt, clearly not Italian. He walked past me, and I waited breathlessly for him to double back around. Somehow, I knew he would. “I’m John,” he told me as I made room for him on the steps. “You’re American, aren’t you?”

He was sexy and smart and un-self-consciously European. When a friend walked by, he bantered with him in flawless Italian. I was growing more flustered by the minute. Now that I’d given myself permission to actually feel again, entire galaxies were being violently brought to life inside me.

Having no idea what it cost to live in a village like Calcata, I asked him in my typically forthright way, “How on earth can you afford to live here?”

“Oh, I’m a jazz drummer,” he said breezily.

“Jazz drummer?” I replied. “Do you know a tenor saxophone player named Ellery Eskelin?”

A look of baffled surprise crossed John’s face. “Know him? I’m from Manhattan. I practically lived across the street from Ellery. I’m a big fan of his playing.”

I went a little lightheaded when I heard that.

Ellery is my brother.

I’d traveled halfway across the globe only to arrive in an obscure Italian village of barely 60 people to find an American who personally knew my brother. If that wasn’t a sign from the universe, what was?

We went for a walk along the wall that overlooked the valley. I felt things I hadn’t felt in a very long time. Everything beneath my skin seemed to vibrate when I stood next to him. But when you’ve met somebody in a country where you don’t live, by necessity, wooing moves at lightning speed. John was shy. Finally, I turned to him and asked, “Aren’t you going to kiss me?”

And he did. For about an hour. Right below us was the lush, whispering valley. I felt as though I were dreaming. This wasn’t me. It couldn’t be. I drove my kids to school in a blue Kia Rio. I ate brown rice and broccoli over the sink. Every Thursday, I furiously vacuumed the house before my writers’ group came over. I most certainly didn’t make out with sexy jazz drummers who spoke fluent Italian.

When I finally rejoined my group, I was sweaty, and it looked as though a rat had nested in my hair, bore young, and died. They’d been looking for me, which made me feel guilty, and yet, what could I say? Sorry, I was having a transcendental experience? I was busy rediscovering who I really am? Everybody probably thought I was an outrageous slut, but horse/barn/out. Too late now.

When John sauntered back to his house, his ex-girlfriend, Katarzyna, a Polish fashion designer, was sitting on the steps, smoking. “The Americans,” she said laconically. “They lost someone and now they are looking for her.”

“Looking for who?” John asked.

Through a veil of smoke, Katarzyna flicked her eyes at him. “The blondie.”

John visited me that night at Villa Lina. My roommate had absconded to less musty quarters in the palazzo, so we had the room all to ourselves. One of the writers downstairs in the Shepherd’s Cottage was reading an erotic romance I’d written titled Catwalk. Later, she said we provided the soundtrack.

The next morning after John left and I’d drifted around Villa Lina feeling the way a person does when she’s had a religious epiphany, Natha held her usual morning lecture where nothing was ever taught and nothing ever learned. I’d call it more of a freeform experience, half diatribe, half abstract theory about writing, life, Buddhism, adulthood. She gave us a writing prompt, which is a sentence to get you started on a writing assignment. The prompt was: My name is….

“I’m going to eviscerate her,” Jennifer, the psychotherapist, told us later. “I’m going to write the truth about who and what she is, and then I’m going to read it to everybody tonight after dinner.”

I exchanged uneasy glances with the two other members of our group. Sure, it sounded fun and exciting, but what was Natha going to do after she heard it? We joked about Jennifer needing a twenty-four-hour security detail. I say joked, but not really.

After dinner, everyone formed a circle to read their work. Natha sat across from me. One by one, each person read, and the reading was met with the usual awkward silence (remember: we were forbidden to comment, even after pieces of enormous pathos and vulnerability), and then it was on to the next person. The closer it got to Jennifer’s turn, the sweatier I became.

Finally, Jennifer took a deep breath and started: “My name is Natha Greenberg, and I am a miserable, self-loathing, rotting shell of a human being whose only happiness is making other people hate themselves as much as I hate myself…”

After the first sentence, I couldn’t hear much on account of the hysterical deafness, but the meaning was clear. Natha was a bully. Natha was power mad. Natha wrote brilliant how-to books on writing, but couldn’t actually write. Natha was controlling. Natha resented women.

Jennifer finished speaking and set her paper down. The silence was thunderous.

Never in my life had I heard truth spoken to power like that. Support or reject what Jennifer did, it took cojones the size of Christmas hams to do it. She will always have my admiration and respect.

Someone started crying. No one knew where to look or who to look at. A long wet fart in F major, loosed in a church upon an unsuspecting congregation, could not have had the effect Jennifer’s words did.

But Natha was perfectly calm. Calmly, she gathered her things, calmly arranged her sweater over her shoulders. She stood calmly and walked calmly, and then she stopped in front of me.

“I heard you had a visitor in your room last night,” she said crisply.

I blinked, unable to form words, gilling up at her, I imagine, like a mentally deficient goldfish just snatched from its bowl.

Leaning closer, she hissed, “Just so you know, there are no men on campus. Do you hear me? No men on campus!” And then she stomped out of the room as though I were the one who had injured her. Not Jennifer’s writing assignment. Me.

I never saw Natha again. We left the next day, and she didn’t see us off. I had a moment on the bus where I thought, “I could jump off right now and run away. No one would be able to find me,” but the hugely problematic thing about friends and kids is that you desperately love them. So, back to Houston I went, brimming with stories to tell my endlessly patient friend, Joyce, who helped me transition back to “real life.” It was not easy.

As magic as my time with John was, I never lost sight of the fact that he was a jazz drummer living in Italy, and I was a … well, whatever I was in Texas. I had no expectations. And yet, he kept calling and we kept talking. What a remarkable thing it was to be able to deepen our friendship every day, despite the seven-hour time difference. He told me he was coming to New York to renew his passport in February. Did I want to meet him there?

When you’re a person who defines happiness as “interesting experiences in which novelty and/or complexity are accompanied by profound changes in perspective,” you don’t say no to these opportunities. Three days before I was about to get on that plane, John called. “We are not having a long-distance relationship!” he barked. “I hate long-distance relationships. I tried it, it didn’t work, and dammit, we aren’t having one.”

I was hurt. Of course I was hurt. But my reaction to life’s slings and arrows is always in inverse proportion to how badly they sting. So, I said nothing. With a maturity that surprised me, I accepted John’s terms, went to New York City, stayed in his uncle’s art studio on 8th Avenue, had a romantic, sexy, marvelous week, and left more in love with John than ever.

A nontrivial number of people around the world report they would choose a psychologically rich life at the expense of a happy or meaningful life, the American Psychological Association reports. For people like me, that means accepting a rather large amount of risk.

No way was I going to let John see my tears, which fell silently as my bus sped toward the airport. No way would I let him know how much I loved him. His aunt had been scandalized when he left me alone for a few hours to have dinner with a friend, but I knew John was just as jealous of his freedom as I was: leave the gate open, and we’ll stay in the pasture. Close it, and we’ll keep charging the fence.

A few days later, much to my surprise, John called me. The news wasn’t good. “They confiscated my passport,” he said. “I have no way of getting back to Italy.”

Due to some stupid technicality, he was stuck. My heart hurt for him. His home wasn’t here, it was in Calcata. What would he do? I called the next day to get an update, but he didn’t answer. I called the day after that, and once again, no reply. He was ghosting me. It was over.

The great thing about being over 40 is the emotional self-control. I was heartbroken, but it never affected my daily life. I taught classes, trained clients, raised kids, and no one knew (except Joyce) how sad I was. John didn’t call, and I didn’t call John. But I did keep my promise not to put myself in a cage. I dated. A lot. I dated the way a woman dates when she’s been living on an island or in a nunnery, although my kids knew nothing about it.

Three months later, having coffee with a hot Canadian hockey player, I got a call from John. I didn’t pick up, of course, but for the rest of the date, I was thinking about John a lot more than the hockey player. John called again the next day, and this time, I did answer. Talking to him made me happy. Yes, he was back in Italy. Yes, he missed me. Yes, he wanted to give this long-distance thing with me a try.

If you are contemplating a long-distance relationship, speaking once a day, no matter what may happen to prevent it—rain or shine, death or disaster—it’s the key to a successful union. Each day at 6:45 p.m. (1:45 a.m. for John), we video-chatted, me in the gym parking lot, him in his apartment in Calcata. I’d train clients for their air miles and then come visit a few times a year, magical visits that made it harder and harder for me to return to my life at home. My heart was torn in two. I loved my job, my friends, my family. But my son was 18 and about to move into his dad’s much nicer and far bigger house. My 13-year-old daughter would surely follow. All I could do was wait.

In May of 2014, one-and-a-half years after we first met, John called and asked me and my daughter to move to Italy. I’d never suggested it, hinted at it, or slyly referenced the possibility. A commitment that big had to come from him. John was a lifelong bachelor who’d never had kids. He was a jazz drummer, which is not a profession that naturally lends itself to long-term relationships. But I knew, as he knew, that it was a now or never deal. You can’t keep dating long-distance forever.

Love makes that easier, by the way. I mean real love, not the schmaltzy Top 40 stuff you hear about on the radio. You have to be capable of it. Not everyone is. You have to keep saying yes to it, whether you’re feeling loving that day or not. You have to be fun, flexible, and forgiving, and above all, respectful. I didn’t understand how essential this was to my happiness. To love a man I deeply respect is a new experience for me.

Nine years we’ve been together so far. Nine years and a thousand lifetimes.

All this to say that no matter where you are in life, no matter how flat or unimaginative things may seem, all that can change tomorrow. If a poor, single mother can fly halfway across the world and find love, you can find love, too—and probably a lot closer to home. It comes with risks, of course. The best things in life usually do.

But if you are the same kind of bear that I am, one that prefers a life with mystery, heartbreak, confusion, despair, elation, and terror instead of a “traditionally happy” one, I beg you to honor that. Know thyself. Figure it out.

Because all you get is this one life. Do you really want to waste it?