I am not what you would call a risk taker. I cringe when I see someone bicycling without a helmet. I wait an hour before swimming after I eat. I've visited ski resorts in Colorado, Germany, and Switzerland, but I've never hit the slopes. I prefer to trudge safely along flat surfaces in snowshoes instead.

But when it comes to relationships, I'm like the sucker in the dunk tank at the county fair. Hit my heart hard enough, and I plunge right in.

When I met Dan, I didn't jump into the relationship, I took a running leap into it. He seemed like my guide into a bigger, braver world. He'd lit firecrackers in the streets of Paris with striking firemen. He'd drunk grog ladled from a hole in the ground in Budapest. He'd spent a night outside in Athens, being stalked by wild dogs. And when he told me he cried while watching elephants play drums in Thailand, I knew he must be sensitive, too.

Two months after our first kiss, we flew from San Francisco to New York City for a three-week summer vacation. In the beginning, it seemed like I'd landed a starring role in my own romantic comedy. We spent hours lying on the grass in Central Park, deciding which countries we'd live in. After dining on pasta one night, we stepped outside into a July downpour. We ran through the rain holding hands and took shelter under a doorway. While we waited for the rain to pass, I slipped out of my bra. Maybe I thought it made me seem sexy and adventurous. I think I just wanted my skin as close to his as possible.

In the following months and years, the romantic-comedy glow faded and doubts grew. Still, we moved in together, and although there was never a date attached, we planned on getting married. Our apartment life was comfortable, but small. We spent more time snuggled up on our boat of a couch than we spent out in the world. And while there was no place that I would have rather been, I could sense him drifting away.

"How much do you love me?" I asked one afternoon, trying to be cute, but also fishing shamelessly for reassurance. Dan was sitting at our kitchen table, as I stood in front of him with my hands in the air, measuring out our love. "Do you love me this much?" I asked, and stretched my arms wide. Dan looked at me, his big blue eyes sad and serious. He put his hands in the air, shoulder-width apart, like he was holding a heavy box. He looked tired. "I'm not sure I love you enough," he said.

My arms dropped to my sides, and I gasped for air. I felt naked and dumb, standing in front of him crying. He opened his arms wider. I gave in and sat on his lap. In that moment, I had nowhere else to go.

Thanks to my job as an editor at a travel magazine, I was soon able to take the tearful show that accompanied the collapse of our relationship on the road.

Shortly after our kitchen-table conversation in July, Dan and I agreed on a monthlong separation, and I took off for Copenhagen. There, I cried over a plate of salmon and a pack of cigarettes to my press escort, Signe—a gap-toothed Dane who had been a squatter in the 1980s. "Give it more time," she said. "Don't push so hard."

Signe had a proven ability to commit to a punk manifesto and poop in a bucket, so I was inclined to take her advice seriously. When Dan moved back in at the end of the month, I was a new, laid-back girlfriend, totally cool with however much, or little, he loved me. Unfortunately, this often sounded more like desperate pleas for Dan to stay and frantic backpedalling on my earlier desire to get engaged.

By November, we were measuring and weighing the size of our love again. Dan had other questions, too, like "How do you know it will work out in the future?" And I had my own refrain, "Why do you want to be with me now?"

The questions had become harder to answer, so later that month, I escaped to Istanbul. I stayed with a college friend, Bridget, and her Turkish fiancé, Talha, in their apartment overlooking the Bosporus. Bridget had moved to a foreign country so that she and Talha could be together. Dan and I couldn't even agree on a weeklong vacation. Things were not looking good. After I returned from Turkey, Dan kindly gave me two days to get over my jet lag, and then broke up with me.

After two months of sobbing in bars, bookstores, and subways in the Bay Area, I flew to Chile. Professionally, I was there to review a lodge in Patagonia. Personally, I hoped to unload my broken heart at the tip of South America. Andreas, a kind-looking older man in rumpled Dockers, picked me up at the airport. He introduced himself as "a student of English," but it seemed he had recently begun his lessons, and I spoke no Spanish, so we sat in silence. After about a half hour, Andreas put on a CD. The lyrics were sappy, but tears welled up in my eyes. Oh god, it was Phil Collins. I had traveled for 29 hours to the other end of the earth for a cathartic experience, and I got Phil Collins. I stared out the passenger window, trying to hide the flow of tears and snot. By the time Phil sang, "And you coming back to me is against all odds, and that's what I've got to face," I was crying uncontrollably. Were all my vacations, as another poignant pop act, the Go-Go's, once sang, "meant to be spent alone"?

That summer, I scheduled what I hoped was the last stop on my Heartbreak Grand Tour, a yoga retreat in the beachside town of Tulum, Mexico. I didn't have a leisurely year to rediscover myself; I was down to seven final days to get over it. Deep stretching and long walks along the Caribbean Sea were not going to be enough. So when I heard about the day trip to a cenote, an underground pool that the Mayans once believed was an expressway to the underworld, I signed up.

On the day of the excursion, I followed our dreamily handsome guide, Josh, out of the sunlight, through an opening in the dusty ground, and down wooden steps stained black with mildew. A domed cave, dripping with stalactites that looked like massive cathedral candles, opened up before us. Josh pointed out a diving platform, jutting from the stairs. "If anyone wants to skip some steps, you can jump off here," he said. "Hell no," I muttered.

When we reached the bottom, I spied two giant inner tubes leaning against the wall and grabbed one before anyone else could take it.

As I bobbed in the mystical pool securely wrapped in my rubber tube's embrace, Josh explained that this cave was one chamber in a network of thousands of underground arteries. "When the skies were barren, the Maya would offer a human sacrifice to Chak, the god of rain and fertility. Stripped naked, the sacrifice was painted blue, like a fallen piece of sky. The High Priest would then cut out her beating, bloody heart and toss her body into the water," he said.

"Sounds like a bad breakup," I thought.

After Josh's story, three women in our group climbed to the platform and, each with a joyous yelp, slid through the air and into the water. They all popped up radiating happiness.

Then a strange thing happened. I found myself paddling toward the water's edge, leaving the tube's supportive hug, and, most mystifying of all, climbing the stairs.

I walked out to the landing. The water below had an ethereal color, as if it was lit by a hidden flame. If I wanted to avoid getting bruised on impact, I couldn't jump. I had to simply step off. I'd like to say that beauty called to me, seduced me, and lured me over the edge. But when I looked down, all I could think was "That's a 45-foot drop. What the hell am I doing up here?"

At 35, I thought I'd be standing at an altar in front of my friends and family about to take the plunge into marriage, not standing in front of a group of strangers, my shaking legs silhouetted by two small floodlights. This jump that had seemed like a fun two-second ride had somehow turned into a big, meaningful moment.

I'd spent all this time being upset with Dan for not taking a leap of faith with me, but I was the one who was afraid of the unknown now. I knew what our life on our comfy couch looked like, but without him, the future was a big, black emptiness.

"Just let go," I repeated to myself. "Just let go. Maybe you are braver than you thought." In the last few months, I had danced in an underground blues club in Copenhagen while a singer named Reverend Shine Snake Oil shouted at me to sweat for him. I had hiked along a rocky, windswept shore to a gray glacier in Patagonia. I had laid my bare ass on a marble table in front of twenty-some strangers and let a round Turkish woman scrub me clean. Maybe I was the kind of person who could free-fall into a Mexican cenote. And with that last thought, my feet left the platform.

The air rushed by me, the water grabbed me, pulled me down, and then pushed me back up. I had stepped out into a dark abyss, and the worst thing that happened was my bathing suit went up my butt.

Maybe it was the adrenaline rush, but when we emerged from the cave and into the cloudless day, I felt lighter. Maybe the mantra that motivated me to walk into the air had helped me stop clinging to something that was no longer there. And maybe, for now, I was okay with traveling through the world on my own. recommended