Illustrations by Seymour Chwast

Queen-Size Simmons Hamlet Pillow-Top Mattress at Sleepy’s
Retail Price:$1,499 plus tax and $89 shipping.
Method: “War of Attrition.”
Over the course of an hour, I gradually wore down the salesman’s defenses. I’d find a bed, lay down on it, ask the price, then get up and walk away without a word. He finally blew up: “Are you going to buy a bed or just play with me?” By the time I was ready to negotiate in earnest, he was simply happy to have me gone.
RESULT: $910, tax included, free shipping.

Ermenegildo Zegna Suede-and-Calf Sneakers at Saks Fifth Avenue
Retail Price:$325
Method: “Soft Plea.”
After trying on the shoes and walking around, I expressed interest to the salesman, then casually inquired about possible reductions: “Are these going to be on sale shortly?” He said no, so I discreetly asked whether there were any discounts he could apply.
RESULT: Failure. I even brought up the spirit of Thanksgiving. “No dice,” said the salesman.

All-Access Membership at Union Square Equinox Fitness Club
Retail Price:$645 initiation fee plus $170 monthly dues.
Method: “Growing Uninterest.”
Played it super-eager on the gym tour but grew testy once the Equinox rep brought up fees. “For this price, it doesn’t seem worth it. I mean, you don’t even have a dry sauna!” RESULT: Initiation fee magically dropped to just $95. (“Oh, I just got an e-mail from my supervisor,” said the rep.) The monthly dues remain the same, but I’m offered five free guest passes and 25 percent off at Kenneth Cole.

Mint-Condition Door Store Dining Table Off Craigslist
Retail Price:$500 at store; Craigslist seller wanted $190.
Method: “To and Fro.”
Over the course of an hour, we batted numbers back and forth over e-mail like a pair of commodity traders.
RESULT: I opened the bidding at $150. She came back with $180. I volleyed $160. We settled on $170, plus her boyfriend helped me carry it downstairs and put it into the car.

Basic Time Warner Cable
Retail Price:$13 a month plus $43 installation charge.
Method: “Cable Guy.”
Taking a cue from Matthew Broderick’s 1996 opus, I waited until the cable guy was installing my Internet and asked him, “Any chance you can hook me up with free cable?”
RESULT: “Yeah, I can do that. No problem.”
“You won’t stalk me like Jim Carrey, will you?”
“Ha-ha man, I just watched that shit the other night.”
“Twenty dollars okay?”
“Sure.”
Snip, snip. “Enjoy your cable.”

Eames Lounge Chair and Ottoman by Herman Miller at Design Within Reach
Retail Price:$3,599
Method: “Team Player.”
I appeared with a notebook in hand, asked dozens of questions about the chair, and talked about how I was furnishing my new Soho penthouse, basically playing the part of their dream customer. I only inquired about the price toward the end. “Is there something we can do about the price?”—emphasizing the plural, like we were buying the chair together. RESULT: “I actually have a $300 discount in the system that I can apply to this.”

Street Knish at Fifth Ave. and 54th St.
Retail Price:$2
Method: “You can’t do any better for that knish?”
“Hey, man, that’s the price. My supplier dictates.”
“I’ll give you $1.50.”
“What, are you crazy? This is Fifth Avenue.”
“C’mon, man, tough times.”
“Okay, $1.50 it is.”
“Here’s $2. Keep the change.”

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Annual Savings:$2,028
(The renegotiated prices plus the free Internet.)

Related:

• Archive: “Cover Story”
• Table of Contents: Nov 10, 2008 issue of New York | Subscribe!