New Zealand is bloody expensive and dripping with wealth. I don’t know the specific facts on income in New Zealand relative to the rest of the world, but I do know that somebody forgot to welcome the people on that island—North and South alike—to join everyone else in the world’s current financial crisis. The median weekly rent for a three-bedroom house in Auckland is 19.047 percent more expensive than it was this time a year ago, at which point it was more expensive than the year before that. A bar in New Zealand was offering Long Island Iced Tea (U.S. $3.50 in Central America) on special…for U.S. $16.34! That’s crazy. I figured that couldn’t be the right price, or else it must be a pitcher’s worth of the lethal brew, so I tested it out: I ordered one, and sure enough, that bastard at the bar handed me the cocktail on the rocks and invited me to deal him the full sixteen and change. Ain’t nothin’ “special” about that.

In many places, it’s necessary to spend to have fun, and New Zealand is one of these places. But on my trip, I also knew to remain wise. Everybody we traveled with knew that Hobbiton and the movie set where they filmed The Lord of the Rings trilogy are tourist traps, way overpriced, but in Queenstown, one shan’t skip out on the Milford Sound cruise just because he or she is pinching pennies.

Auckland reminded me of Boston, except a little cleaner, more modern, and without the seedy side. The buildings are glossy and reflective, windows freshly cleaned without streaks. Distinguished people rush about in business suits, sunsets drip from the sky at the waterfront, minimal buggage. The harbor teems with yachts, and locals pack into corner wine bars from happy hour into the evening.

Even the destitute are of a sophisticated ilk, a relief from the street hustlers of my first five months of travel. Our first night in Auckland, Ivana and I wandered down Queen Street, and—true story—we passed a guy cradling a cello, playing symphonies for spare change. A cello. He must have had a hundred and fifty dollars in coins strewn in his case.

I watched him as we passed, an idea sparking in my head. I had thus far kept my gambling problem under strict supervision—declining offers to join local poker games and avoiding strategically placed casinos—but I needed to scratch my swelling competitive itch.

“We could go play pool,” I suggested to Ivana.

She pulled her gaze away from a happy couple walking with their children. “Pool? Billiards?”

“Yes, pool, billiards.”

We were walking away from the city and approaching the waterfront.

Ivana’s slim shoulders raised and dropped in a shrug. “Okay.”

“But let’s bet something.” It was hard to keep the excitement from my voice.

“Okay. Massages?” she asked.

I grinned. “I like where your head’s at, babe, but I’m good for a massage win or lose.”

“Right. I will remind you that you said that.”

“Here’s what I was thinking. We’ll play two out of three, and the loser has to go downtown and play the harmonica on the street for a half hour.”

We neared the waterfront at this point, the faint sound of waves lapping against a barnacle serenading us. “The harmonica?” Ivana asked. “You can’t play the harmonica.”

“Exactly. You can’t either.”

“I don’t understand.”

We gathered around the pool table at our hostel. The room was mostly empty. I laughed as Ivana continued to invent Slovak rules. I beat her two out of three, despite a variety of silly errors. Don’t call it a hustle—I’m not a shark—but I may or may not have underestimated a little on how many times I’d played before. She went upstairs to download harmonica tips for beginners, but I told her I would give her a month, until we got to Christchurch, our final destination, to practice.

Well, that plan fell through. For one, she only found forty-five minutes to practice during the month, and she spent those forty-five minutes developing bad habits that made her sound even worse. Two, Christchurch was a broken town, literally, still reeling from a series of devastating earthquakes—one of them among the strongest ever recorded in an urban area—in the eighteen months prior to our arrival. Any tall buildings that hadn’t already fallen were condemned and in the process of being demolished. The earthquake the year before our arrival killed 185 people from twenty different countries. Everyone lost so much; it would have been classless for me to demand that we perform our mockery in that city.

So we waited until our flight landed in Melbourne. She found a set of stairs on the busy corner of Elizabeth and La Trobe and made good on the bet, puffing a half hour’s worth of unmelodic tunes for the masses.

Now, I want you to picture this girl: this bashful, innocent Slovak girl, sitting on a concrete step among hundreds of passing pedestrians in a foreign land, with a baseball cap full of change set in front of her crossed legs. She hesitated at first. She smiled sweetly. Her head ducked to face the ground so no one could see her flushed face. She breathed lightly, whispered discords barely reaching my ears. Every now and then she peered out from behind the sunny blonde hair covering her face to see whether anyone was watching. At that point, she hadn’t blown into a harmonica more than sixty minutes in her life, and the sum of her knowledge consisted of a Google search for “harmonica for beginners.”

And then, inspiration struck.

She must have thought something along the lines of, Screw it, let’s seize the day, bitches, because she upped the tempo. She raised her head to face the crowd at the corner waiting to cross the street—men in pin-striped suits, a few weary travelers in safari outfits. Evening had begun to set around us, and the streetlights washed her with fluorescent light. She made eye contact with those waiting to cross the street, if only for a moment at a time. She tried to string notes together to make a tune. And she couldn’t. She was awful, a sad contrast to her dulcet singing voice, and she knew it. But she played on with confidence, blowing grating notes out of that little piece of metal. At her best, she sounded like a slowly unfolding ironing board, and at her worst, a finback whale trapped in a Norwegian gill net. Ladies gazed and smirked; businessmen wrinkled their brows in confusion. This was new to Ivana, being the center of attention, but she bought into it completely. Abashed, just this side of horrified, her face glowed red.

Per our agreement, this continued for half an hour, but more fun, I was up to my own antics, our preset deal having been that she had to act as if she didn’t know me. She couldn’t stop playing for a half hour, no matter what I did. We had only two rules: I couldn’t touch her, and I couldn’t take my pants off.

I strode by every couple or three minutes, tossed in a few coins, and made requests with the straightest face I could muster.

“Play some ‘Amazing Grace,’ please.

“’Piano Man?’”

Of course, she knew exactly zero songs. She tried “Hey Jude” ten times in a row. I struck an annoyed pose and raised my voice. “Ugh, you just played that one! And why do you keep playing in G minor? How ’bout a little F flat?” How ’bout I had no idea what I was saying, and her nerves couldn’t keep her from laughing while she was playing. Every time she laughed, wheezing notes bubbled out of the harmonica in quick, breathy bursts.

I stood there, staring. This was so bad, the only explanation to the public was that she had been hired to keep pigeons away.

I followed all of this with an interpretive dance, my hands and feet flailing in a mix between a rain-dance and an Irish jig. The way Ivana fought hard not to smile filled me up on the inside. After that, I tossed a twenty into her hat and pulled out change.

“This is brutal. But getting better.” I walked away. I came back with a note scrawled in blue ink on a wrinkled piece of paper and set it next to her for the crowd to read: THE QUICKER I RAISE MONEY FOR DINNER, THE QUICKER YOU DON’T HAVE TO HEAR THIS HARMONICA ANYMORE.

She played and played, zipping nonsensically up and down that harmonica. As her prescribed time drew to its end, I calmly took the instrument from her, set it against my lips, and started violently blowing and sucking in and out of it as if I had just come to the surface after three minutes underwater. A full sixty seconds I did this, and a full sixty seconds Ivana looked down at her shoes. Outside the two of us, nobody was amused.

Ivana faced a trying task that night, and I was surprised—nay proud—that she’d gone through with settling her debt. She’d braved the streets of Melbourne to raise exactly zero dollars and zero cents. The only thing left to do was to celebrate over sushi.