I mentioned last week in another blog post that I used to be a street musician when I was studying abroad in Sydney. I did it not because I was desperate for money. I did it because I loved to play my guitar and sing. I loved writing songs. Playing on the street seemed fun and felt a bit dangerous at the same time. I had a blast doing it. At the time I met some interesting characters, and it was fun to draw a crowd and get them to sing along. I looked like a street rat, with my purple hair, oversized flannel, ratty jeans and guitar in a cardboard box. But I was really just an American student who lived in a comfy dorm room in the suburbs.

There was one night in particular that stands out as particularly fun and dangerous. It was a Saturday night, and I was sitting out on my milk crate I’d absconded from behind the coffee kiosk at Circular Quay, in front of that duty free shop on George Street that had that awesome sloped overhang that helped to amplify my voice.

I was taking a break, drinking a bit of water, when two guys walked up. They looked to be in their 50s.

“Will you play for me?” the one in the black leather sport coat asked.

I strummed out the intro to Closer to Fine by the Indigo Girls. It was one of my favorite songs to play because I could belt out the choruses, and I could whistle the flute solo. The whistling made me feel like I was super impressive.

Half way into the second verse, Black Leather Jacket tossed a $50 bill into my hat. I stopped playing and gaped at him. “Whoa, you put too much money in there. I can’t take that.”

“Take it,” Black Leather Jacket said.

His friend, Curly Hair With Turtleneck Sweater leaned in “He’s a millionaire. It means nothing to him. Take it.”

A millionaire. Yeah, whatever.

“Finish the song,” Black Leather Jacket said. I picked up where I left off while the face on the $50 bill, some past Prime Minister, stared at me while I sang. “That was beautiful, thank you,” Black Leather Jacket said. And then they walked back toward the bridge, and they probably got harassed by Richard, the other street musician who played there. His MO was to block the sidewalk until people gave him money. Classless.

I played some more, talked to people, watched small coins accumulate in my hat. Some guy threw 10 cents in my hat and called me dreadful. I stopped playing, handed him the 10 cents back and told him that insults cost more than that. Black Leather Jacket returned to me, alone. I played a bit more and he hung out and watched. Then he said “I have a bet with my friends. Will you come out with us so I can win?” A bet. Oh really? I nervously strummed my guitar. “I’ll cover whatever you would have made tonight.” It was a slow night, he’d already more than doubled what I would have made.

“We’re just at Jackson’s,” he pointed up George Street. “It’s in public, you can leave anytime. I just want to win my bet,” he laughed.

If he’s a millionaire, why is winning a bet so important?

I looked down the street. Pedestrian traffic was low for a Saturday night. I was thinking of heading home anyway. “OK, I’ll go with you. But just so you can win your bet.”

I packed up my guitar, my hat, my change. He carried my milk crate back to the coffee kiosk. We walked by Richard, he raised his eyebrows at me.

“This guy is a jackass,” Black Leather Jacket nodded at Richard. “Can you believe he wouldn’t let me pass until I gave him money? You’re way more talented than he is. I told him I gave all my money to you.” I am sure that pissed off Richard. He already warned me about cutting into his take.

A few blocks up from Circular Quay we walked into Jacksons on George. His friends cheered at the sight of me walking in beside him. Curly Hair With Turtleneck Sweater threw a $50 bill at him. Black Leather Jacket moved to tuck it into my woven straw bag I flung over my arm. I blocked his hand, but he dropped it in there anyway. "You won this, you should have it."

I declined the offer of a beer, they joked around with each other and I felt out of place.

“I’m starving,” Black Leather Jacket said to me. “Want to go across the street and have dinner with me?”

I was kind of hungry. “Sure,” I said. I figured if it gets weird I can always leave, right? Just stick to the public places.

Across the street was the Regency Hotel. I knew it was a five star restaurant. I strolled in with my guitar in a cardboard box under my arm, my purple hair and my baggy flannel shirt. We strolled by the concierge desk in the grand lobby to the restaurant to the right. The hostess looked me up and down. I smiled at her. I was pretty ballsy when I was 20.

He ordered us a bottle of pinot noir. I never did get the taste for wine, I drank half a glass to be polite. They didn’t have anything vegetarian on the menu, I was one at the time, so he had something made for me.

And then the most extraordinary thing happened. We had an awesome conversation at dinner. We talked about music, about traveling, about how he’d closed a $10 million deal with the government of China that day. Which I still kind of think was bullshit. I’ve googled him here and there since that night, and I never was able to find a picture of him with that name. But really, you never know. He told me it was to finance a large apartment complex that was basically like its own village. There would be highrise buildings with shops and restaurants on the bottom floor. It was the level of detail that made me think maybe it wasn’t bullshit. But you never know. At any rate, it didn’t matter to me. It’s not like I was going to marry this guy, or even see him again.

We sat at dinner for hours, just talking. He asked me to go to a club with him. Again, public place, if it gets weird I can leave. We went to put my guitar in his hotel room. When we got to his room there was a note slipped under the door. I caught a glimpse when he opened it. “How’s it going? –Graeme.” I recognized that Graeme was Curly Hair With Turtleneck. Great, I wonder what else they bet on.

He sat on the bed. “Will you play for me?”

I pulled my guitar out of my case, and strummed a few chords. I played a Suzanne Vega song I had told him about at dinner, The Queen and the Soldier. He was leaning against the headboard and I sat at the foot of the bed. When I looked up from my guitar I saw he had dozed off. I looked at my watch, it was 2:30. The last bus home was due to leave at 3:05. I needed to leave then to walk to the Queen Victoria Building to catch that bus.

I didn’t want to wake him, so I started to write him a note. But he had been so nice to me, I didn’t think a note would suffice. I gently shook his arm.

“I have to leave, I have to catch my bus.”

“Let me have my driver take you.”

That was an interesting idea. If he had a driver, maybe all the stuff about being a millionaire and the Chinese government deal wasn’t bullshit.

“No, it’s OK. You’ve been so nice to me. I’ll just take the bus. But I have to leave now. Thank you for dinner and for tonight.”

I kissed him on the cheek, then made my way onto George Street. I pulled my flannel tighter to fight the chill in the air, and made my way to the bus stop at the Queen Victoria Building.

BJ Knapp is the author of Beside the Music, available for purchase here. Please sign up for the Backstage with BJ Knapp mailing list to get updates on events, signings, dog pictures and so much more.

BJ Knapp is the author of Beside the Music, available for purchase here. Please sign up for the Backstage with BJ Knapp mailing list to get updates on events, signings, dog pictures and so much more.