The night I learned tip #23 the hard way at Mac's Club Deuce.

Happy Frieze week! Exhausted yet? I hope not, we’ve got a lot more hobnobbing ahead of us. Speaking of which, through this month’s auctions, openings, parties, and dinners, I’ve started to reflect on my time reporting on this whole art-world social scene. Over the course of writing more than 80 Wet Paint gossip columns dedicated to peeling back the curtain on, blowing the lid off, or otherwise poking fun at the art world, I’ve picked up on a few sage lessons from mucking through these trenches.

What follows is an assortiment of tips, tricks, insights, and other knowledge painfully acquired. I can’t give away all of my secrets, but here are a few words to the wise I’ll share with you today. (Nota bene: I extralegally refuse to be blamed if any of these don’t work for you—sorry!)

#1

Line too long for a party at the Whitney? Go to the entrance on the West Side Highway, they’ll probably let you in if you ask nicely enough.

#2

The rich and powerful are like horses. The second they smell fear, they get agitated. Proceed with confidence and calm and you’re in for a smooth ride.

#3

Los Angeles galleries don’t know how to throw parties in New York. No one here wants to go all the way to the Boom Boom Room just to wait in line.

#4

That said, New York galleries really know how to throw a party in Los Angeles. The best way to make people happy is just to go to the Chateau.

#5

When a gallerist tells you what they’re “asking” for a piece, it’s usually not the same as what they’ll sell it to you for, depending who you are.

#6

Though it goes against everything I know from Southern hospitality, it is acceptable to skip the opening and go straight to the gallery dinner if work runs late. But hitting both is always remembered and appreciated.

#7

You can tell you’ve really pissed off a gallery when they open an email with “Thank you for your continued interest in our program.” The venom is in the word “continued.”

#8

A table for lunch at 3 Guys is often a tougher clinch than one at Sant Ambroeus—and often more high-profile.

#9

In a perfect world, I would not be writing the art-world gossip column. Art handlers would be. They know all your dirty secrets. Be nice, or pay the price.

#10

Parlaying your way into Paul’s Casablanca is chess, not checkers. Use the right opening gambit with the doorman followed by a smart sequence of pawn moves (a smile, a wave, a look of overpowering respect), and he may just let you get past the list.

#11

If you’re an art-world gossip columnist—or, likely, one of the many people that an art-world gossip columnist runs into on a semi-nightly basis—you’re going to become disillusioned and maybe bitter about the excess of it all about once a quarter. Taking a few days off helps. Whining about it doesn’t.

#12

Be good to your employees. Some of my most incendiary scoops have come from disgruntled employees who feel disregarded or undermined.

#13

It is only acceptable to wear one item of art-world merch at a time. Remove the Ballroom Marfa baseball cap, sir, you’re already wearing a Sky High Farms sweatshirt.

#14

The best drinkers in the art world are art advisors. If you think I’m talking about you, yes I am.

#15

The auction crews are like frat houses, if you’re going to get in deep with one, pick ‘em and stick to ‘em—Montagues and Capulets don’t mix for a reason.

#16

Obviously, your professional role in the art world is its own currency, but it’s pretty rude to ask straight up what someone does for a living. I’ve found that “So are you an artist?” is the most polite way to ask someone what they do in the art industry, because everyone would love to believe they could be one.

#17

On that note, it’s always “Good to see you” and never “Good to meet you.” You’re dealing with a lot of fragile egos and people like to be memorable.

#18

The hierarchy for respected mediums is as follows: sculpture, painting, drawing, photography, NFTs. I will not be taking any questions.

#19

The best name for a gallery I’ve ever heard is Guided by Invoices.

#20

Resist the urge to post a selfie in the bathroom at the Odeon every time you go—it gets a bit redundant.

#21

If you’re going to a dinner in Miami Beach you will not make it to the party in the city of Miami. Unless your transfer is by boat or chopper, Collins Ave traffic after 9 pm is enough to melt your makeup and dull your buzz.

#22

Art Basel Miami Beach may very well be the worst week of your year, masquerading as a fun romp in the sun. Make a point to carve out time for at least one truly fun thing, whether it be dinner at Joe’s Stone Crab, or, as I’ve enjoyed for the past few years, a morning jet ski session with some of your favorite art world friends. Keeping morale up is a high priority through all the stress and chaos and Collins Ave traffic.

#23

Don’t wear open-toed shoes to Mac’s Club Deuce. Just trust me. If you do, enjoy contracting trench foot.

#24

Can’t find the address for the afterparty? Try to find someone wearing a blue blazer and a fresh pair of New Balances. Chances are, they’re going to the same place as you.

#25

Reliably the best place for a pit stop during a gallery crawl through Chelsea is David Zwirner. The staff there is refreshingly unfussy about using their bathrooms.

#26

Studio visits: If invited, you don’t have to say yes, but if you do say yes, come prepared. Be ready to listen, but don’t feel required to offer artist therapy. Always ask what an artist wants out of the visit. Never promise anything.

#27

No bar has been able to replace the special place that the Rusty Knot holds in all of our hearts.

#28

Even though it seems awfully romantic to take the Hamptons Jitney, the train will get you out East far faster.

#29

The term “light bites” is actually code for “underwhelming sliders.” Eat before.

#30

No matter how sick of the Dimes Square scene you are, don’t underestimate its staying power. So long as the drinks are still getting poured at Clandestino, the artists and all-knowing art handlers will come.

#31

Never turn down an invitation to go to Palazzo Chupi. It is one of the more stunning venues I’ve ever laid eyes on.

#32

You can get an unflattering BFA photo removed from the website if you know who to ask, and ask nicely enough.

#33

It’s true that nothing good ever happens after 2 am. Head home while you’re still having fun and before people get catty, handsy, or otherwise unsavory.

#34

We seriously need a new word for “rainmaker.” If everyone is a rainmaker, no one is.

#35