Why Last Night Sucked (For You)

As New York City’s premier expert on “fun,” people often ask me for advice on planning their weekends. My tips seldom amount to more than “Greasy food and orgasms!” which may or may not be helpful, I’m not sure. But since last night was Halloween, I think it’s time to give some serious thought to how to have fun.

Halloween is a tricky beast. Like Valentine’s Day or New Year’s, it’s a Holiday Where You’re Supposed To Have Fun. The pressure piled up on these poor, overtaxed calendar days means that they tend to collapse under the weight of expectation and party dresses. More than New Year’s—whose only real demand is “Drink!”—Halloween is supposed to be crazy, a requirement that troubles everyone besides art school students, whose tuition down payment grants four years’ access to an unlimited hoard of bonkers beans.

People who aren’t crazy on their own try to make up for it on October 31 by putting on stupid hats, drinking dumb things, and then whining into the next day’s brunch that, “this Halloween sucked.” Well buck up normals! The secret to a fun Halloween is the same one that makes one night stands worthwhile:

Low Expectations.

Unless your brother is an aspiring white masked psychopath, you will not have a Halloween like in the movies. Your costume will be worse than the one’s on television. It will either be uncomfortable, hard to understand, inappropriate for the weather, or too fragile to do any of the things you want to do. (All four of these problems can be yours if you’re dressed up as, say, a sexy placenta.) The party you wanted to attend will be cancelled, far away or (as a friend described a Lower East Side shindig she ended up at last night) sweaty.

Disappointment comes when you try to make your social life something it isn’t. Last week, were you the sort of person who likes waiting in line and spending lots of money? If the end of October hasn’t seen you transformed into a sweaty Jersey boy with skin the color of an autumn leaf, you probably don’t want to go to a haunted house any more than you usually like going to clubs. Are you generally too lazy to truck out to Brooklyn for a warehouse party that may or may not have free beer? Then you won’t enjoy doing it while dressed as a giraffe. Just because you’re dressed as someone fun doesn’t mean you actually are.

I understand myself well enough to know that at my core, I am as outgoing as a wilted fern. So last night, instead of filling my belly with jello shots and my face with cocaine, I cooked a quiet dinner at home. (Sauteed grouper! Scalloped potatoes! Kale! What could be more thrilling?) Afterwards, I occupied a friend’s sofa and watched the Yankee game while seven or eight of my buddies pregamed. As they debated when to go out—headed to a party in an abandoned Green Point Catholic school—the TV and I acted as an anchor, keeping us so tightly focused on baseball that by the time we left it was past midnight.

They skipped off to the L train, and I went to a party that, by midnight-thirty, was already winding down. My friends were at Arrow Bar, on A, a place with very loud music that is occasionally not awful. We watched the end of the game and tried hard to dance, finally decided that the music was too loud to do so, and went back up to the street. As though it was a casual suggestion, I floated the idea of going back to my place. We got beer, we got pizza, and we stayed up late enough to watch the clocks change.

This would have looked like a typical weekend, except that I was wearing a bathrobe and toting a towel. I think that’s the point. What’s wonderful about Halloween is that it’s a holiday for everyone—crazy Halloween is not. I wish it weren’t such a big deal; I wish there weren’t so much pressure to HAVE AN AWESOME TIME. I wish Halloween happened four times a year. The fun comes in walking streets you see every day, streets that have become stale, and seeing them covered in wacky drunks. Strangers are social, and everyone’s looking for fun. Disappointment comes when you overreach, and a safe bet is just to do what you always do, but with a wig on.