I have never been a fan of storing my financial identity on a single device, especially one that I drop frequently and oftentimes forget in public restrooms. I now find myself being forced into the ‘cult’ of digital wallets, and I feel like I have taken another step into the realms of technology. This unique step towards modernity was taken not because of its potential benefits, but because of mild peer pressure.

I vividly remember being in line at a coffee shop last year and watched from the corner of my eye as the person ahead of me made their payment by simply waving their phone. No card required, no receipt was needed, and no waiting. Just a sudden swift tap was all that was required for them to leave the shop right after grabbing their drink.

On the other hand, I unfortunately had to go through my tedious ritual of payment, where I, more often than not, have to get my wallet out and extract a rather bent card to insert it into a machine, followed by waiting for my PIN prompt, entering that, waiting again, politely receiving the offers, and finally ignoring the receipt. The whole time there is a long line of annoyed customers waiting behind me to get served. I could see the impatience of the barista.

“You know, you can use your phone,’” my nephew said later in the week. From his perspective, I was still writing checks or doing something archaic like offering livestock. “It is faster and more secure.”

I didn’t believe either of those things, but the seed was planted.

Maybe I am the issue. Maybe my choice in payment methods is just a testament to my general reluctance to adopt change. So in a moment of weakness — or maybe elebaration depending on how you choose to view the circumstances – I decided to spend an afternoon setting up a digital wallet.

The process of verifying my identity was a bizarre. The proof involved taking pictures of my credit cards from ridiculous angles then capturing me performing a series of characters stunts that my password could ‘eat’ me, but too easily to break. When the process is finally complete, my phone is stuffed with ample details on my financial standing than my accountant.

Guess what, I’m ready. I’m modern, I’m convience. Checking my account, I realize my first successful contactless payment felt overly accomplishing.

Tapping my phone at the register gave me a profound sense of accomplishment head of the beep while paying at the bookstore. I remember walking away thinking, “This, I believes, is what progress feel like.” This is what efficiency must feel like. Efficient.

This honeymoon phase spanned around three days. I waited in line at the supermarket on the fourth day, my shopping cart stocked with a week’s groceries. As the cashier tallied my total, I had to remind myself why I avoided organic products in the first place – sticker shock.

Feeling confident, I held my phone to the payment terminal, eager to be greeted with the satisfying beep that indicates successful payment submission. I did not get a response. I attempted again, raising my phone closer to the terminal, thinking that it might work better.

I received nothing again. The cashier quipped, “Have you tried turning it the other way?” She had a huff that came with having to deal with impatience and ignorance. My phone began to look like it was performing an arcane ritual as I rotated it in countless directions, but the line grew longer and more people began to lose their cool.

I could sense my fellow queue mates glance at each other, judging me for my lack of technical abilities and etiquette. “You know, this Face ID isn’t working for me,” I admitted, but in reality my problem was way too broad. My phone’s screen also had the gall to ignore the payment terminal altogether, so there’s that.

“Are you in possession of a card?” the cashier questioned, revealing a slight smirk. Her patience was clearly running thin. So I found myself stuck in some of the worst situations money could get me in: waiting in line longer than any conventional paying method would have required, only to ultimately take out my wallet.

The smug card-on-file customer I envied was gone and been replaced with an even worse image – me. This same scenario has repeated itself with disheartening frequency. I sense when my digital wallet will fail me – when I need it most.

I can sense when I am the most pressed for time, the person behind me is getting angrier, and when I am with someone who oh so desperately wants to show off. My phone seems to suss out just the right time my confidence peaks to remind me of my place in the hierarchy. The logic behind these blunders is many, but are vastly vague.

Sometimes there’s the simple “connectivity issue” frustration. Then there are those times when the register states it is “not compatible” with my specific version of digital wallets. Other times my phone just needs to be restarted and I’m socked with a poorly timed solution when standing at a register with a line of people behind me.

Then there are businesses that pick and choose which digital wallets to accept, creating a payment “caste” system I do not understand and do not wish to learn. My phone claims it has NFC, which I have been told is a completely different thing from MST, and some terminals only accept one or the other. This is a HUGE issue during the transaction, but no normal person should be forced to think about this ever.

However, the most annoying failure mode is when everything seems to be working correctly. The most frustrating gaff, however, is when it looks like everything is functioning perfectly normally. The phone recognizes the terminal.

The terminal recognizes the phone. They exchange their digital niceties. And then, nothing.

No error message, no explanation, just two devices staring vacantly into each others eyes like two strangers at a party that have run out of conversation. “It usually works,” I find myself saying, which captures the entire essence of today’s modern technological experience. It works usually.

Except when it doesn’t. And you never know which time will be which. Having a digital wallet has brought a whole new level of anxiety into my life.

My concerns are no longer just about whether I have enough money. Now I have so many: Am I charged enough? Is my device’s payment system working?

Will my own device recognize my face? Is my battery level okay? Am I inadvertently worshipping the digital gods’ blood sacrifices?

Is Mercury in retrograde? I should really swap the digital wallet out for a physical credit card. But that would mean I have to carry around a bulky wallet everywhere.

Digital wallets should make life easier, but I just end up feeling much more vulnerable. I mainly use my card when I have to, but the indignity that comes with that is my true concern. I am expected to have an entire different payment strategy by now.

The cashiers always ask me questions like, “Oh, you don’t use your phone to pay?” I know these questions are innocent enough, but the subtext is clear: You either don’t know what you’re doing or are just too lazy to use your phone. Last month turned out to be a digital wallet catastrophe for myself. I visited a family owned restaurant where the net revenue is small enough for them to be cautious about card payments, Everything was fine until they updated their payment systems to allow for contactless payments.

“Now, you can make payment by tapping your card or phone”, the owner smilingly replied whilst handing me the receipt. Several patrons in the restaurant perked their heads up, ready to engage in a new old method of technology. This was the time when I could finally show my friends that I too belong to this technologically advanced society.

I confidently removed my phone, opened my wallet app and placed my phone near the terminal. By this time, a much larger group was present as they were intrigued with the new method of payment. Alas, nothing occurred.

Attempting to position the phone in a different way. Still no luck. “Perhaps if you wake up the screen”, one of the audience members suggested.

I could feel the blushing sensation creeping through my neck. The wallet app kept the terminal android uninterested. Another member of the audience asked “Is it charged?” quite insulting like he assumed that I hadn’t checked if my phone would run the app.

“Yes, I charged it,” I replied, feeling my voice slip. “It just… doesn’t always connect.”

It felt like hours, but I think it was less than a minute. Realizing nothing was going to change, I pulled out my physical card and completed the transaction the old fashioned which annoyed a few people in the audience.

The owner’s pride in his new system was slightly deflated. My reputation as a tech-savvy individual was blown to pieces. When they’re working, no one phones it in.

Everyone knows the irony of digital wallets. Rather a performance than an actual purchase. Technology is never kind and it turns you into an unwilling street performer, a real life, cautionary tale for those around you.

When they don’t work, everything goes to tatters. Despite all the humiliation I’ve had to go through, I still try to use my digital wallet. Some part of me wants to believe in the sheer convenience of it.

I’ve started to feel like those deeply invested in their horoscopes, so convinced by the tiny slivers of hope that signal to what they stand for the me feels like an even bigger joke. However, it’s also the awkward truth that when a digital wallet does work – when the tap registers, the payment goes through, and the delightful beep echoes – it is hard to deny that it is pleasing. It’s like we live in the future that we were promised to us in movies.

A world where payment systems are effortless and technology helps rather than makes everything difficult. These rare moments of interacting with technology is just frequent enough to keep me coming back, like a slot machine addict who believes that the next pull of the lever will give them a jackpot. This is where it gets interesting: modern technology is not meant to work all the time.

It only needs to function enough for us to keep believing that it should. With every functioning tap, we get closer to achieving the goal, and when it doesn’t work, it just becomes an unfortunate circumstance – seamless technology that has a few hiccups. Maybe I need to re-evaluate the whole situation.

Maybe I should take the stance that, like most technology, digital wallets are an imperfect tool that fail for no good reason, usually at the worst possible time. I should proudly walk around with my physical cards on the ready because the digital realm will always end up disappointing. But I know I won’t.

I will keep approaching each payment terminal with pointless optimism, phone in hand, prepared for the exciting beep of success or the all too common sting of public tech failure. Because in the end, that is what it means to live in the modern world: constantly stuck betwixt the convenience we’re offered and the issues we receive, one painful tap at a time.

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