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More than a decade ago, the brilliant, funny Tom Chiarella penned an article for Esquire called “The $20 Theory of the Universe.” He surmised that a well-placed $20 bill could offer far more than its paltry face value. To prove it, Chiarella greased palms all over New York City. Sometimes he was plainly rebuffed. But most of the time, he got what he wanted: a better seat at the show, an unpaid-for upgrade, a peek into cordoned-off places ubiquitously closed to the rule-following masses.

Inspired, we replicated Chiarella’s experiment, but with several new and untested variables. First and foremost, the Twin Cities setting (after all, it’s one thing to slip a twenty in Vegas; it’s entirely another to try it in St. Paul). Also, there’s the inflation issue. Chiarella worked his experiment in 2003, when $20 sang a significantly sweeter tune. The same bill today is a bit flat and nasal at $14.48. And then there was the last, possibly most significant variable of all: me. 

Now, I’ve never met Tom Chiarella, but my Google search tells me he looks like a man’s man. He’s got a salt-and-pepper goatee, fashionable-male eyeglasses and a taste for charcoal wool blazers. He looks like the kind of guy who could swagger up to a valet with $20 and end up getting his car waxed while he dines on a medium-rare steak. He looks like, I don’t know, a guy who writes for Esquire. I, on the other hand, am a wordy, nearsighted, 31-year-old woman with a nail-biting habit and penchant for sensible shoes. In essence, if I can make something happen with a $20 bill, anyone can.

In 2003, Chiarella left his readers with the dos and don’ts of flashing a twenty: Do have a specific request. Do use a $20 bill when you don’t want to wait. Don’t try to buy something that already has a price tag. Don’t attempt to grease the same person twice. And don’t be hesitant or apologetic.

With this advice ringing in my ears, I set out with a nice roll of twenties. I started small, cruising into Twin Cities Reptiles on University Avenue just a few minutes after 9 a.m. I slid a twenty toward the girl working the counter. I told her I wanted to be photographed with her most exotic snake. She slid it back to me but then waved me toward the snake cages. 

“Don’t tell anybody,” she said. “If we let everyone do this, we’d spend the whole day putting snakes on people.” She pulled a massive albino ball python out of its enclosure and draped the sleepy serpent around my shoulders. Then she spent a good five minutes carefully photographing me with my smartphone from different angles. “Do I look like Britney Spears?” I asked. “Oh, yes, definitely,” she said, with a confused shrug. It occurred to me that she was probably 12 years old when Britney Spears performed “I’m a Slave 4 U” with a Burmese python. Oh well.

As we walked back toward her counter, I nudged my folded twenty toward her again. “Buy yourself a nice lunch,” I said. She looked nervous and wary, but took the money. “A lunch,” she said. “Yes, I’ll get lunch, and then I’ll share it with my coworkers.”

I nearly hugged her, just for being so gosh-darn adorable, like a kitten wearing a top hat. Such a wonderfully Minnesotan thing to say. At the same time, it crystallized for me why this experiment might be doomed from the start. There’s a kind of rapt wholesomeness here, a bone-deep sense of fair play. People wanting favors with a $20 bill might, in Minnesota, be right in there with line-cutters and tax cheats — entirely antithetical to the culture of this place.  

I tried my trick again at the Minnesota School of Bartending just down the street. I asked the guy shuffling papers to teach me how to make a killer Singapore Sling and unceremoniously handed him a twenty. Without a moment’s hesitation, he plucked the bill from my hand and replied, “Sure thing.”  For the next 20 minutes, he walked me through bartending 101, showed me twice how to make the drink and then let me make one myself, waiting patiently while I delicately arranged the plastic cherry and orange slice on top. OK, that wasn’t so hard.

Then came my seemingly endless streak of bad luck. I tried to get a security guard at the Minneapolis Central Library to take me down to see the vault where the rarest and most expensive books are kept. “Yeah,” he guffawed to himself. “That’s going to happen.” I tried to convince a waitress at the Loring to give me a call the next time Scott Seekins came in. She literally backed away slowly, something I’d never actually seen in real life. I tried to convince one of the handlers at the Raptor Center to let me wear one of those thick falconer gloves and let a hawk or eagle perch on my hand. She looked at me with steely eyes and told me that volunteers “train for years before we let them handle the birds.”

Artful Living made me a reservation at the Saint Paul Hotel, and I stalked weirdly around the lobby until one of the desk clerks, a pretty, young thing, was finally alone. I placed my twenty at the edge of the counter and slid it her direction. I made eye contact and said, “If there’s anything you can do to get me a great room, I would really appreciate it.” She nodded earnestly, and I felt confident we had an understanding. She handed me the room keys then lifted my twenty with a puzzled expression. “Did you need change?” she asked. My shoulders slumped. “No, it’s for you,” I said, deflated. “You know, for your help getting the room.” “Oh, OK,” she said, giving me a bright smile. Sure enough, the room she gave me was nice. A nice, standard room.

Obviously, I was doing this all wrong.

I reread Chiarella’s article and immediately realized my flub-ups. He wrote that it’s usually a strikeout to ask somebody to do something that might get them fired (like, say, a security guard giving unauthorized tours of the vault at the Central Library). At the Raptor Center, I’d flashed my twenty in earshot of a volunteer, probably one of those earnest, rule-following folks who trained “for years” before he got to hold a hawk. At the Loring, I’d propositioned the waitress in front of my husband, which probably looked, in hindsight, like a creepy dare. And clearly, I was trying to be too sly at the Saint Paul Hotel if the clerk didn’t even get that I was trying to bribe my way into a better room.

Then, like a Lake Calhoun sunrise, the solution came to me. What I needed for this gig was a believable story. Yes, Minnesotans are generally good-citizen types, out voting early and snowblowing the neighbor’s drive. But there’s another side to good behavior: the socialized need to please. 

It reminded me of a story I read in women’s studies in college, of a woman who was being followed by a creepy guy to her building. Being female, being socialized from birth to be kind and helpful, she held the door open for the guy when he turned to go into her building instead of following her instincts and slamming the door in his creepy face. As a result, she was raped in the elevator of her building. Not to put too fine a point on it, but I needed to be that creepy rapist. I needed to exploit Minnesotans’ innate desire to be sweet and helpful.

At the Marquette Hotel, I again lurked around the lobby until my desk clerk was finally alone. When I got his attention, I had my story ready: “I’ve been in conference meetings all day, and my shoulders are just killing me. Is there any way to get into a room with a Jacuzzi tub?” I slipped a folded twenty under his mousepad, this time acting as more of a sweetener than an inducement on its own. With a whisper, he said, “Let me see what I can do.”

Five minutes later, I had the keys to a fantastic corner suite on an executive level with a deep soaking tub and access to the executive lounge with gratis drinks and hot popcorn shrimp. Score.

I tried my new strategy again at Bar La Grassa on a packed weekend night. It took awhile before the reservation-desk guy was alone, but again I had my story ready: “I told my husband I made reservations, and then I totally spaced. Can you help me out? I’m in a real jam here.” I gave him my best panicked look and again slipped a folded twenty under the side of the mousepad — so convenient!

The guy tried to hand the money back, saying, “I don’t want to take this, because I might not be able to get you in for another hour and a half.”

“No, take it,” I said. “Just for trying to help.”

“Alright, but like I said, it could be another hour and a half.”

The husband and I waited exactly two and a half minutes before the reservation guy motioned us to a great table by a window. “Right this way,” he said. 

Read this article as it appears in the magazine.

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