The Upside of a Destination Wedding: Tales of a Serial Wedding Guest

Not many people would think the cure to a broken heart is attending a friend’s wedding. But when it involves a wine-filled adventure to an exotic locale, it's worth a try, right?


The invite came in the summer of 2013. A friend was marrying the man she’d met a few years before in an East Village cheese shop. Despite their cultural and religious differences—her father was a pastor in Phoenix; his family was Jewish and lived in Israel—their initial rendezvous over discounted Gruyere had been auspicious. They’d fallen in love, moved in together, and she’d begun to learn Hebrew. The wedding would take place in the hills of Jerusalem, in August. “I know it’s expensive and a long trip,” she told me. “No pressure to come. But you’re invited and it would be amazing if you did.”

That spring had brought the end of my own relationship with a man who lived in Seattle. I’d fallen for him quickly and deeply, and we had maintained our long-distance relationship for nearly a year, but by May it was no longer working. While no one was to blame, I was heartbroken in a way I’d forgotten I knew how to be. Prone to tears at a moment's notice is not a great way to attend someone's wedding, but I decided that a trip to Israel might help me feel better rather than worse. I decided to do it empowered-single-lady-style, on my own. I’d book a nice hotel in Tel Aviv, sit poolside and relax, go on long walks, go to the wedding, of course, and hire a driver to take me to Jerusalem on a day trip. No sense taking a 12-hour flight to Israel if I wasn’t going to see Jerusalem.

After I bought my plane ticket, though, Laura got in touch. She was a friend of the bride from Arizona, single, like me, and considering making the trip. Though I’d met her only once before at a boozy brunch, that seemed enough of a guarantee that we could team up. “Let’s share a room,” I agreed. We could sit by the pool together! But she had other ideas. “I don’t know how you feel about renting a car and driving to different towns,” she began, and I was forced to confess I hadn’t driven in years. “You can navigate!” she said. “I can handle that,” I said, fingers crossed.

We met at the airport in Tel Aviv, her flight arriving a few hours before mine. There she was, patiently waiting, her guidebooks and organized itineraries spread out in front of her. I hadn’t spent much time figuring out what I wanted to do in Israel; I’d been focused on getting away from a me that felt small and sad, stuck in the past rather than free to imagine the possibilities of the future. I only knew that I wanted to be somewhere else. And here we were. We checked into our hotel, and the adventure began. Laura was courageous, opinionated, and no-nonsense. It quickly became clear that plenty of wine and good food would keep us in harmonious alignment. By day we toured Tel Aviv; each night we dined out luxuriously and found ourselves having a wonderful time, even more so because we were together. I shared the story of my breakup, and she revealed her own past heartbreaks lurking underneath that capable exterior.

The wedding took place halfway through our stay, at a picturesque farm so high in the mountains that I became dizzy from the altitude, the heat, and, probably, dehydration from my wine-drinking the night before. As I watched my friend marry her husband under the shade of a tree, I pressed a cold compress to my neck, willing myself not to faint. I was so proud she had found this person she loved and committed to him, and him to her. Later we sat with the couple outside the little villa where they’d stay for the night. “That’s where David fought Goliath,” said the bride, pointing down below, and I thought, Where am I, and how in the world did I get here?

Our last evening in Tel Aviv, before we picked up the rental car and began our planned drive to the top of the country and then down to Jerusalem, we decided to return to a restaurant that had become a favorite. As we sat and ordered wine, a group of guys asked us to join them. “You can join us,” I said boldly, and they did. Something then happened that has never happened to me in a (lengthy) history of American bar-going. One by one, a circuit of other men approached and tried to win our interest. “You should not like him, you should like me!” said one. Another announced he had a boat, as apparent incentive.

I stuck with the boatless guy who had been talking to me from the beginning, and his friend to Laura. We went with them to another bar, and by the end of the evening, this man and I were kissing, and then I was going home with him. I woke up in the morning fully clothed, both of us having fallen asleep just hours before on his bed. He looked over at me. “Want to get married?” he asked. “We should probably get married.” I laughed, and even though I knew he was kidding—he was kidding, right?—I felt just a little bit pleased. The world seemed infinitely bigger than it had days ago.

I made my way back to Laura, and we picked up our rental car. She drove, and as promised, I tried to navigate us out of Tel Aviv, my mood dimming each time the GPS app cheerily proclaimed “Recalibrating!” It took us nearly an hour to reach the highway, which should have been 10 minutes away. At one point, near tears, I suggested we return the car. I was a failure; I could not even be depended upon to read the map, and how could anyone expect me to read signs in Hebrew? Laura wouldn't let me give up. “We’re going to do this,” she said. “Let’s just try again.”

Our trip to Haifa was cut short, but we reached the wineries of Zihron Y’akov, and then, as the sun set, our hotel in Jerusalem. Over the next days we toured the ancient city, and when we checked out of our hotel on our last day in Israel found our way to the Dead Sea, where we took a brief dip in its buoyant waters and ran into the parents of the bride doing the same. By the time we were heading to the airport, where we again got lost trying to fill the car up with gas, I was exhausted, but it was a satisfied exhaustion. I’d realized that even if I messed up the first 47 times, I could do this — in travel, in relationships, in life. After all, I’d journeyed on my own to an unfamiliar country, drank in countless delicious, beautiful things, made a life-long friend, and been proposed to by a stranger. The me who had felt small and sad a week ago was now someone for whom the world seemed bright with possibility. Maybe on the next trip I’d re-learn how to drive.

Jenn Doll’s memoir Save the Date: The Occasional Mortifications of a Serial Wedding Guest will be out in May from Riverhead Books.