Emily and I had been dating for a few months and everything was going great. Then she said, “I’d like to go to Venice and ride in a gondola.”

I winced. “It would be romantic,” she said.

Claiming that you don’t do clichéd, touristy things when traveling can sound pretentious and naïve, but in my case, it’s all about embarrassment. I’m afraid locals will judge me.

“What kind of loser rides the horse-drawn carriages?” New Yorkers say in Central Park. So I’ve never done that. I’ve never hopped on a cable car in San Francisco, never toured Buckingham Palace. I lived in Tokyo for years without climbing Mount Fuji.

Emily’s gondola remark was the first sign of anything suspect, so I pretended not to hear it—the way one pretends not to hear a partner who snores or says she dislikes sushi. I was still in denial that summer, when we decided to take a vacation.

“How about a street food tour of Southeast Asia?” I proposed. “You mean, a diarrhea tour of Southeast Asia?” Emily countered. To sell me on Italy she talked up gelato, and I quickly caved. On the flight to Rome, my mother’s voice echoed in my head: “Andrew. All your girlfriend wants to make her happy is for you to get in a gondola. What’s your problem?”

On the bus from the airport, Emily produced Rick Steves’ Italy, and I worried that Romans might sneer. At dinner, we dined among other Americans reading the same guidebook. (“Could you at least hide it?” I whispered.) In the morning, we visited the Colosseum, and before entering, Emily bought an espresso. As in, across the street from the Colosseum where they charge 10 euros a cup. “You know how much that is in dollars?” I muttered. Incredibly, we made it out of Rome without breaking up.

Next, we rented a car and drove to Umbria, where I was finally able to relax, probably because there were no boats around. In a gondola (the ski-lift kind), we ascended to the hill town of Todi, and blessed by a full moon and full plates of pasta, we kissed for the first time in 48 hours.

The tension returned on the drive to Venice. It was 260 miles; the closer we got, the more anxious I felt. At the Basilica di San Vitale, I prayed to a sixth-century mosaic of Christ that Emily would forget about the gondola.

No such miracle. That evening, we traded our car for a vaporetto, Venice’s iconic ferry, and as we zoomed along the Grand Canal, Emily stared out longingly at dozens of tourists riding in thin, black boats.

“Please?” she said. “They look so happy.”

She repeated some version of that, over and over, for three days. On the last, sweltering afternoon, I was flipping through Rick Steves’ Italy (to confirm how banal it was) when I found a description of a promising gelateria. The shop was on the other side of the jam-packed Rialto Bridge. “We’d be like salmon swimming up a stream of tourist sweat,” Emily protested.

Nevertheless, she endured the crowd and B.O., crossing the bridge and helping me search until, after an hour, I realized I had been holding our map upside down. We braved Rialto Bridge a second time and found the gelateria, not far from where we had started. By then Emily was exhausted, yet she was beaming.

“Why are you so happy?” I said, licking my cherry cone. “Because you look so happy,” she said. This is going to sound as trite as the ride on a gondola, but Emily’s happiness about my happiness made me want to make her even happier, and there was only one way. The place was teeming with men in striped shirts, so I approached the closest one.

We sat side by side on a red velvet love seat. Our slim, silver-haired gondolier snapped our photo (Emily’s request) and then steered us through a series of back canals. He didn’t sing (thank God), breaking the silence only once, to point out Marco Polo’s house. Does he mock tourists by saying any old house is Marco Polo’s? I stopped myself, and saw the question for what it was: a wall between me and my enjoyment of the ride with Emily. I reached for her hand, and surrendered to the stillness. Gliding through these quiet, hidden spaces, I felt at peace for the first time since we had arrived in Venice.

“Bliss,” Emily said.

Two years later, the gondola photo appeared on our wedding website. It shows us starting to fall in love, but also reminds me how far I’ve come. On our honeymoon, when Hawaiians draped leis around our necks, I barely flinched.

Illustration by Chris Lyons. This story appeared in the May/June 2011 issue.