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In Search of the Perfect Night

You hear a knock at your door. It’s your friend Steve.

While it’s physically impossible, Steve seems to bound through the door before you even open it. “Excited” is an understatement: he’s psyched, and you couldn’t reach his level even if you tried.

Around two, you and Steve made plans to go out tonight. You spent the afternoon doing laundry, going to the grocery store, taking out the trash, and doing some light reading. Steve spent the afternoon plotting the perfect night.

This is not Steve’s first foray into the “perfect night” — far from it. Steve’s last plan failed, and so did the twenty-two before that. But Steve is not a quitter. He adheres to the “twenty-fourth time’s a charm” philosophy.

Steve really outdid himself this time. The amount of research he performed makes you question his sanity. He even prepared maps and charts. You buy into his madness. You question your sanity. His design does appear flawless, however.

“Tonight is going to be awesome,” he says with unbridled enthusiasm and a furrowed brow. “This is what we’ve been waiting for.”

The plan accounts for everything. Not a single second will be wasted. Not one beautiful girl will go unnoticed. All the hottest bars will be visited. You’re going to be in basements and on rooftops — at the same time. Somehow, there’s even a horse involved.

The night starts off well enough.

Pretty soon, Steve starts acting like a millionaire. Shots for everyone! Everyone includes you, though, so you’re okay with it. At least for now. Besides, everyone likes Steve. He buys them things. He talks to them. Your proximity to him gets you in contact with some pretty cool people.

Steve speaks only in the tongue of grandiosity, making lavish promises and telling of fantastical escapades. Another round of shots!

All of a sudden, Steve’s face turns white. He didn’t see a ghost. He’s out of money. “I don’t know how it happened, man!” You roll your eyes. It doesn’t take Sherlock Holmes to solve the case of Steve’s empty wallet. “You got it, right?”

Yes, you got it. And the drinks for that entire bachelorette party? Yeah, you got that, too. You’re a good friend.

To mitigate the financial impact of Steve’s prodigal activites, you start drinking Miller Lite (because something’s gotta give). You have to somehow offset the financial burden thrust upon you.

From there, the night gets progressively worse. Steve abandons his earlier design in favor of new, hastily planned ambitions. For instance, he decides that he doesn’t want to wait in line at West Bar, so you jaunt over to East Club.

East Club has a thirty-dollar cover, which you pay. And of course, you pay Steve’s cover, too. As soon as you get inside, someone spills an entire long island iced tea all over your trousers. Nobody could have anticipated that. What do you do? Take a taxi back to the apartment and change? Hang out under the hand drier in the bathroom for an hour?

Steve had convinced you that a perfect night was in store. Now, however, you realize something. Steve’s design was overly ambitious; his objectives were unattainable. What convinced you was the confident oratory of a passionate man. Besides, you didn’t have a plan of your own.

Steve made a valiant effort, but he didn’t — and couldn’t — account for everything that happens in a night. He didn’t account for long lines. He couldn’t account for the actions of others. Even an ostensibly airtight plan was bound to fail. The perfect night — or day, or weekend, or whatever — is simply not something that can be designed.

There’s a classic episode of How I Met Your Mother that captures this lesson. One New Year’s Eve, Ted decides that he’s going to plan an unforgettable evening. Most of the gang’s New Year’s Eves have been dry and underwhelming. But not this one. No, Ted rented a limo. He assembled a list of the top five parties in New York City. They’ll have to keep a tight schedule, but they can pull it off.

Quickly, however, the night devolves into chaos. Unanticipated events happen left and right. They lose people and find people—including a criminal bearing a strong resemblance to Moby. Ted loses his date. In the end, nobody makes it to all five parties. To the extent that anyone has an enjoyable evening, it’s without friends. The saving grace? A spur-of-the-moment champagne toast inside the limo while stuck in traffic.

Steve is Ted. And Barney. And you. And me.

Steve is also the head of the Department of the Interior. And a member of the County Zoning Board. And the Mayor.

Steve is a man — a good man, but a fallible man. Because of his very nature, Steve is incapable of planning the perfect night. No matter how many smart people he surrounds himself with, no matter how many Yelp reviews he consults, and no matter how many hours he spends at the drawing board, Steve can never plan the perfect night.

Yet, the perfect evening can happen. In fact, perfect evenings happen all the time. They happen in the absence of meticulously detailed design. They happen when you surround yourself by people you like. They happen when you let the night take you where it may. They happen spontaneously.

“To assume all the knowledge to be given to a single mind… is to assume the problem away and to disregard everything that is important and significant in the real world.” –F.A. Hayek

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