I’ve Gone Through At Least Seven Wallets Since Last Year. Are They the Worst Or Am I?


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“I don’t know if you can rate your wallets on a scale of worst to best because they all represent different features and personas of the worst that wallets can be.” — my friend Cougar

A woman unwittingly dropped her wallet on the sidewalk on 14th street and kept walking. I saw it happen, so I picked up the wallet and inspected it. Nice leather. Spacious but compact. A button snap for security. Perfect.

Then I considered the contents of my left butt pocket. A mess of cards and a wad of cash kinda-sorta stuffed into a sharp-edged money clip monogrammed with the message “To my Jim Duggan” (not my name), “Love, S. Reynolds” (not a real person). The wallet I’d been using for months before that? A rubber band.

Maybe, I thought, I’ll return her cards and cash, but keep the wallet for myself. I was due — desperate — for an upgrade.


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“Who the hell is Jim Duggan?” — my coworker Keri

At the office, Keri had spied me taking the money clip out of my pocket, the money clip Sunny gifted me. (Sunny is the person I’m dating. We don’t like “girlfriend/boyfriend” or “partner” or “significant other.” So we eschew titles and instead settle for “person I’m dating” or another phrase that’s equally clunky, reductive, and vague.)

Anyway, Sunny and I love to wrestle. And not sexy-flirty wrestle. Like, actually wrestle. One time we tackled each other on the sidewalk, much to the concern of two passing teenagers on hover boards. Wrestling with Sunny is a lot of fun because she is as strong if not stronger than I am. She is tall and tough like a power forward, and when she reads this I promise she will take it as a compliment.

“We fit so well together,” Sunny once noticed when we were cuddling in bed.

“That’s because we have the same body,” I said.

Sunny is also intelligent and beautiful and creative and funny and as fearless as I’d like to be, but that’s not important to this story. What is important is that she loves roughhousing, kicking over chairs, and yelling in an accent reminiscent of the guys on Buckwild. So it was no surprise when one of her coworkers gave her a nickname and, with it, an alter-ego.

Sunny became Sunshine Reynolds, a fictitious wrestler who wears a hard hat and a tool belt and is prone to disqualification for pummeling opponents with a hammer. Sunshine reminded me of actual former pro wrestler “Hacksaw” Jim Duggan, who romped around draped in American flag and patriotically bashed people’s faces with a two-by-four. Naturally, in the weird make-believe world of our relationship (another word we avoid but haven’t gotten around to replacing), she was Reynolds, I was Duggan, and they became the most feared tag team in the entire wrestling world.

Sunny thoughtfully gifted me the money clip after noticing that my previous wallets had included a dilapidated nylon situation, a series of rubber bands, and an assortment of plastic bags.

“To my Jim Duggan,” read the engraving. “Love, S. Reynolds.”

So sweet, so funny, so personal. All of it, yes. Except the first time I used it, the money clip’s sharp edge lacerated and irreversibly ruined the black band on my newly-refilled MetroCard, which the MTA has not — and might not ever — replace. Her thoughtful gift has cost me $35.


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“Not only were you a prisoner to this terrible wallet, but a grown man who has likely made many good wallet choices in the past was going through the same experience.” — Cougar

“I always thought the funniest thing was how it looked without anything in it,” Cougar recalls. “If you walked by it on the street no one would think twice to pick it up. It kind of reminds me of those blue Ikea bags everyone carries around.”

He’s talking about my Allett brand wallet. My dad loves his and gave me one when I started college.

For a while, the Allett was great. It featured two sets of interior pockets for cards and two other sections for cash. The parachute-like material offered a lightweight body and allowed the pockets to expand and accommodate my card-hoarding tendencies. But there was a downside.

You had to always keep an exact amount of cards in it to make sure everything didn’t fall out, and you also had to take out all your cards to grab the one you needed,” Cougar recalls in a weirdly vivid way. “And as time went on it stretched and you would have to add new cards to keep the structure stable. A fruitless and never-ending cycle.”

He’s right. At one point, my wallet contained an astounding 34 items, including a bevy of expired insurance cards and gift certificates; public transit cards for Atlanta, Chicago, San Francisco, D.C., and Amsterdam (which I visited in 2011); some fraternity phone directories circa pledging, 2008; a business card to a baby clothing store, which I wish I don’t remember visiting; and, rather irresponsibly, a slip of paper featuring the number of both my checking and my savings account.

The Allett had reached critical mass, and grossly so. The useless cards were jammed so tightly into the pockets that they were busting through the material, like the Hulk, mid-rampage. But if you took one single card out, dozens more would come spilling after.

I tossed the Allett. My dad, meanwhile, still has his and offers to buy me a new one whenever I go home.


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“How many bad decisions did this person have to make to get here?’” — Cougar

My former roommate, Blook, gave me the following pros and cons for the wallet I carried this fall:

The pros: “Tight seal, waterproof, compact, low cost.”

And then the cons: “It was a plastic bag.”

“It ripped easily,” Blook continued. “I felt bad packing lunches for work because I felt like I was stealing your wallet. It was hard to sift through all your bills and Subway gift cards. And lastly, it was a plastic bag.”

“And not even a zip-lock, right?!” Cougar (correctly) recalls. “If I’m not mistaken, you used the one that you have to match up the ridges, right? It’s like the people who paint themselves up as the Statue of Liberty in Times Square. You think, ‘How many bad decisions did this person have to make to get here?’”

At first, my poor judgment and stinginess masqueraded as creative resourcefulness. After my previous wallets proved defective or simply too embarrassing to carry, I dumped my belongings into a sandwich bag, and what began as an act of desperation quickly evolved into a gambit of defiant pragmatism, the ultimate statement of function over fashion.

Except then one day the bottom gave out and scattered all my cash and approximately 34 cards onto the subway platform.

“Do not go onto the tracks for any reason,” warned the voice on the eerily timely subway PA.

I considered what would’ve happened if any of my stuff had fallen to tracks, imagined risking electrocution trying to recover a discount coupon for acne cream. I wasn’t about to become a statistic for the sake of a punch card for a Chinatown message parlor where I was nine visits away from a free foot rub. Yes, I’d walked right into several bad decisions, but at least I’d averted death.


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“I think you need a pouch with a button or some sort of latch. And no joke, I think you need a women’s wallet.” — Cougar

There were other wallets I’d tried and retired over the last several months, including the seemingly superb option from Doc Marten’s, whose zipper broke within two days of purchase. Same thing with the replacement one I exchanged for it.

My sister was generous enough to give me a stainless steel money clip for the holidays, but it proved far too thin for a man who insists on carrying discount cards to every pharmacy chain in America. (Thanks, Jess! And sorry!)

I’d searched, too, spending days scouring Soho only to discover that only two breeds of wallets exist there. The first is a $30 canvas-and-Velcro combo meant for a chain connected to the jeans of a wannabe skater who’s about to start a fight club behind the alley of his middle school. The second is a sleek $200 leather kind for the slimy Meatpacking club promoter who resembles a bootleg Cristiano Ronaldo.

Internet shopping would seem like a logical option, but my irrational and inconvenient fear of online commerce deserves an essay of its own.

Throughout this saga I’ve been indecisive, hapless, neurotic, stubborn, irresponsible, and disgusting. But in this moment, I was lucky, standing on 14th street with a stranger’s wallet — the perfect wallet — in my hands. I really did think about keeping it. And then I ran an entire block and tapped the woman on the shoulder.

“You dropped this,” I said.

She looked surprised. Then relieved.

“Thank you,” she said, her eyes noticeably misty. It was clear that in returning her wallet I’d also done something to restore her faith in humanity. Without a MetroCard, I walked home. And when I got there, thought to myself, hmm…I wonder what kind of wallet that was.


Ben Kassoy is the Editor-in-chief of DoSomething.org, the coauthor of eight books, and a former online columnist for Glamour and Details. He’s written for the websites of GQ, Women’s Health, Teen Vogue, Human Parts, and others.


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