I don’t remember what did it – it might have been the “clean” foundation that spilled out all over my hands – but one day, I woke up and realized that everything I’d bought on Instagram had been bad. All the products that looked so great in the ads – so stylish, and so tailored to my exact requirements – turned out to be a letdown on delivery.

Take the one-piece bathing suit. Andie is a brand that was unknown to me until it burst on to my on feed like a middle-aged answer to Hot Girl Summer. It was even blurbed by magazines like Glamour and InStyle. After checking my measurements against the company’s fit guide and scrolling through 1,500 satisfied customer reviews, I decided to order their Amalfi style in my usual size.

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When the cherry-red tank was delivered, the compression fabric was so taut, the bra shelf drew up only to around my waist. I re-ordered the style in a “long torso” version, but when it arrived the neckline just barely bisected my nipples.

Faced with a $10 processing return fee plus shipping, I decided to give the suit to my little sister. At this point, I blamed myself. Everyone should know not to buy a women’s bathing suit from social media; they’re hard enough to shop for in person.

But anyone, I reasoned, should be able to buy plain cotton underwear online that fit. Oddobody’s organic cotton panties had looked so pure on screen. But when they arrived, the $21 bikinis sat high at the back, low in the front. I still wore the greying, pilling organic cotton underwear as they were comfortable, even as my boyfriend noted that they failed to do what a fig leaf did for Eve in the Bible.

Next, I acquired two pairs of sensible Smartwool underwear in black and white merino lace. They were touted in an ad for a local mountaineering company for the fabric’s natural breathability. Shortly after I started wearing them, I developed a rash in an embarrassing place. It looked so angry I called the doctor’s office.

“Hmm,” the receptionist said. “It could be shingles.”

The next step was to take a selfie of the afflicted area and load it on to the doctor’s FTP site. You would think one would be inured to doing everything online at this point, even one’s intimate medical care – but this felt like a new failing on society’s part, a sure sign that the center does not hold.

Sensing my discomfort, my fiance pre-emptively sent me a picture of his own backside to, as he put it, “normalize the experience”. (It helped.)

When I got the call to go in the clinic, the handsome resident on duty was nonplussed. “Contact dermatitis,” he said, and wrote me a prescription for a strong-looking steroid cream. “And never wear those underwear again.”

phone monster with many arms

Until a few years ago, I hardly ever shopped online. I’ve always loved the experience of discovery that comes from shopping in person. At one point, I even had a travel column for a newspaper where I reported on the retail scene in different cities around the world.

The pandemic changed all that. While others were stockpiling toilet paper and Clorox wipes, my first impulse was to buy underwear and socks. Instagram was happy to deliver.

According to the platform’s own data, nearly half of people who use Instagram shop weekly. “I was not an online shopper before the pandemic and it created a monster,” said an acquaintance. “I was just scrolling through my Instagram and in two minutes received four to five different ads for stuff I might consider buying.” I understood.

Maybe because I’m a writer, I assumed that what gets people shopping on Instagram is the stories it tells. There are the ads we watch for their own sake: take one Nordace video, which features a young woman packing a seemingly inexhaustible number of water bottles, chargers and lip balms into her work backpack for an upcoming trip, never mind that she looks too young to have any direct reports or a company credit card.

Anne Sutherland, a veteran marketer who runs her own branding and consulting company, New Thinking, offered another perspective. “I don’t see them as ads,” she said. “What I’m really responding to is the problem solving that is presented to me.”

Sutherland started shopping on Instagram a couple of years ago during pandemic lockdowns and sent me a screen cap of one of her recent purchases: a tiny, handheld ironing board that can be fitted to the back of an article of clothing as you iron so the garment doesn’t need to be taken off the hanger. I was enchanted. Instagram, she says, excels at fulfilling “unmet needs”.

The best encapsulation of this principle I’ve seen is a video in which two languid dogs are lying on the floor, presumably bored, as their owner checks in on them virtually from her office cubicle. (The problem: you got a pandemic puppy. The solution: the Furbo, a webcam that dispenses pet treats even when you’re not at home.)

Sutherland thinks Instagram’s other power lies in its removal of the obstacles that stand in our way as shoppers. Instagram has a point of sale system that is faster than any checkout and even most stores’ own websites. “The technology is supporting this seamless transaction, even for people who would normally probably be careful with their money.”

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I don’t remember when or why I gave my email address, home address and credit card number to Shop Pay, the in-app widget launched by Shopify, the e-commerce platform that underpins many of the fashion-forward businesses I transact with. (There are similar options for PayPal and Apple Pay.) But now, whenever I click as if to buy a product on someone’s Instagram page – say, to find out the cost of shipping – it auto-populates an order and, in some cases, even has my credit card number, so it’s close to one-click ordering.

In more than one case, a well-known company took my order and my payment and then ghosted me – which made me feel like a noob. Unlike me, Sutherland – for whom shopping is a form of research – doesn’t experience a sense of personal failure if her purchases don’t work out. “But I do have [a feeling] like, ‘What the hell, Anne? You don’t even know what you’re spending.’”

When I think of my biggest shopping regrets on Instagram, they were for the products that offered an identity just outside my own experience.

If a salesperson in a boutique told me I needed an Armani suit – which actually happened when I got my first editor-in-chief job at a magazine – I would see through it for what it was: an attempt to make a commission. I would then head for the nearest Cos.

phone monster vomiting words
Illustration: Edward Steed/The Guardian

But if someone younger or cooler pitches a new lifestyle product on Instagram – whether it’s a plum-colored silicone Bento box, or a new eyebrow gel – my normal defenses are down. That’s how I ended up with not just one, but two “alternative shampoos”, including a monogrammed bottle tailored to the pH level of the tap water in my city. Both failed to transform either my hair or my life.

In the end, neither Prose nor Newash managed to transform my hair or my life. In hindsight, the “normal” people with beautiful waves walking through SoHo in some of the ads must have been just models with good styling. Because it looked like content – candid, intimate confessions of the kind Instagram excels in – I had fallen for basic advertising.

Events culminated in my being taken in by career counseling offered by a “thought leadership” expert purported to help professional women. After I signed up for a free webinar about burnout, a consultant followed up and we talked for about 45 minutes on the phone one night – what I thought was an unusually long amount of time for advice I wasn’t paying for.

Then the knife turned, and she tried to sell me $10,000 worth of executive coaching classes.

Instagram is cluttered with ads for “mini MBAs” and other online classes at schools like Oxford and Yale offered through a company called GetSmarter; I initially took the webinar for one of them. When I explained that I had no intention or ability to pay for the full package, the salesperson doubled down. I knew she must just be following a script, but it felt like an awkward conversation given that the company’s value proposition was empathy and feminism.

She finally asked, as if playing her last card: “Why is it you don’t think you’re worth this?”

Worth it? What a question to ask anyone at this time in history. We’re all worth more than everything we’ve been dealing with over the last few years – more than a pandemic, rising inflation, social inequality. Worth more than the biggest workplace disruption in recent history, as our families and personal lives hang in there till we’re finally off that Zoom call, if ever.

But in the world of Instagram shopping, value isn’t the point. The money and time I’ve spent on orders and shipping and returns have shown that. It was only about the promise of an online shopping dream – a world you can access with the swipe of a finger, that remains perpetually just out of reach.

Jessica Johnson, a Canadian journalist, is a former editor-in-chief of The Walrus