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Taking a Risk to Get Your Money’s Worth

From the Apple Store to the local bodega, no retailer is safe from an editor with a haggling habit

I am not a wealthy man. But I’m no penny-pincher, either. With an upbringing somewhere between “comfortable” and “cushy,” I really can’t recall an instance when I didn’t get what I wanted—including the American Girl doll, Molly, that I desperately coveted as an eight year-old boy. Like most Americans, I learned the value of a dollar as a teenager, when I landed my first job as a receptionist at my local church, greeting visitors and answering phones for five bucks an hour. But I really learned it from my father.

Now, I would never call him cheap, but the man loves a deal. Much as Cher Horowitz viewed grades in Clueless, he sees sticker prices as a jumping-off point to start negotiations. Honestly though, who doesn’t? From ancient civilizations to modern metropoles, try to name a place without its own version of a public market—and the deal-making that goes down there. Commerce and bargaining go hand-in-hand, whether you’re hoity-toity or hoi polloi

My earliest memory of haggling—which Merriam-Webster defines as “to argue, especially over a price”—is as a college student, when my HP laptop fried just before senior year. The details are a bit hazy now, but I remember telling a customer service drone that I deserved a free replacement, not the discounted option company policy dictated. It didn’t matter that I had already bought a brand new MacBook—I wanted that free HP, damn it, even if it would sit untouched in my parents’ basement. Somehow, my arguments worked, and a free laptop arrived on my doorstep days later. To say the tech was swayed by my eloquence would be giving myself too much credit. It was more likely my sheer persistence, but still: I had argued especially over a price, and won. 

To the uninitiated, I will say there’s no feeling quite like getting what you want for less than what someone else decides it’s worth. Especially when you know you’re going to buy whatever it is anyway. Even so, I realize that when it comes to my passion for public deal-making, I’m in the minority. Take my boyfriend: like most people who fail to recognize the best things in life are half-off, he couldn’t be more embarrassed when I start negotiating in a crowded store. Recently, while buying a box of pasta at our local bodega, I noticed the sticker price—of three dollars and change—was much higher than the one I saw on the same product at Whole Foods. “Don’t,” my boyfriend said, noticing the gleam in my eye. But on principle, as we checked out, I couldn’t resist declaring to the cashier, “Three dollars for pasta? You know, Whole Foods sells this for $1.49.” I let my words linger for a moment, hoping they would prove to be that jumping-off point. “Three dollars for pasta,” the cashier confirmed, as my boyfriend pretended we were strangers. You can’t win ‘em all. 

I tend to have better luck with florists, which, when you spend as much time and money on flowers as I do, is really good for both my bottom line and what I like to refer to as my “practice”. Whether driving down the price of a planter’s box of paperwhites by twenty percent, or negotiating a free Yucca plant in exchange for a “defective” (read: over-watered, by me) Umbrella tree, I usually can—and will—talk an unsuspecting green thumb into parting with his foliage at a discount. Ironically, I’ve yet to succeed with what should be the easiest target of all: the flower vendor who sells stems from a stall inside my local subway station. Not long ago, eyeing a bucket of cut palm leaves priced at $10 each, I went in for the kill: “I’ll give you $7,” I said. “$10 each,” he answered. “$15 for two,” I offered. “$20 for two,” he replied. “Suit yourself,” I said, thwarted. “They’re just going to die down here anyway.” 

Surprisingly, I’ve found that haggling at big-box establishments, like the Apple Store, can be worth the stigma of being labeled the guy who haggles at big-box establishments like the Apple Store. On a recent visit, intent on buying my boyfriend an iMac for his birthday, I pondered how I could walk out with one for less than its $1,099 price tag. In a store full of Geniuses, I had to be smart. Using one of the machines on display, I Googled our desired model to find where else it was sold, and discovered its twin at Best Buy—for $100 less. Armed with this valuable information, I flagged down a passing employee, excited to get to work. “Best Buy is selling this model for $999. If you’re willing to match the price, I’ll walk out with one today,” I offered. He told me he’d have to confirm that Best Buy was selling the exact model, down to the serial number. “Of course,” I said, as I tapped the mouse of the Apple Store iMac, dramatically revealing its competitor’s bargain-basement price. “Please, see for yourself.” Cha-ching!

Has haggling saved me enough to put a down payment on a house? No. It likely hasn’t even saved me enough to pay this month’s rent (yet). But I have found it’s made me bolder, more assertive, and more confident. Which are priceless traits, especially when you consider that life is filled with all sorts of important negotiations, not all of them mere cash-for-goods. When you know you have nothing to lose and everything—or even a hundred bucks, here and there—to gain, not taking a risk simply isn’t getting your money’s worth.