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The Antisocial Network: How the 90s Internet Died Like Diaryland

Before Facebook or Twitter, there was Diaryland. But it’s creator just wasn’t a Zuckerberg and it faded into oblivion.
Image: ayomide!/Flickr

Before Tumblr, before Wordpress, and around the time LiveJournal was just a twinkle in an emo teen's eye, there was Diaryland, a blog site overseen by a cartoon cat named 'Constable Whiskers.'

Andrew Smales, a self-taught programmer from Canada, built Diaryland in 1999 for people to accomplish a paradox: write their diaries in public. The site gained attention fast. With 2.2 million users at its height, it was poised to draw a massive sum of venture capital. But its founder seemed to lack the cutthroat gene that would go on to make so many other social media tycoons rich.


In response to a Salon profile published in 1999, which called the site "ingenious", Smales said, "I just like making little things." After that, Smales never became a Zuckerberg and Diaryland faded into total obscurity.

At age 16, I was one of the first users to sign up for Diaryland. I used it to catalogue crushes, name-drop serious writers ("my trembling collection of Ibsen plays"), ruminate on body jewelry ("I have been thinking long and hard about this, and…I am going to get my toungue [sic] pierced."), and most achingly, my own terrible poetry ("you fold your napkin on your head/and recite the Kuma Sutra").

My diary died around the time I graduated from high school, but I was reminded of it when I received an email from Smales's mailing list, "Eggpost" last year, and found that it had been hiding online all along, a virtual time capsule of my own angsty writing.

The email also made the announcement that Smales was launching his new venture,, a clearing house for gift ideas that the grown-up diarist might like—plaid shirts, Edison bulbs and space pens.

Smales had also set up a Diaryland Twitter account that deadpanned about its own mediocrity in 90s fashion to all of its 88 followers:

But the site so many used to frequent, fading away from the popular conscience, seemed to predict so much about the future of the internet: the oversharing, the self-obsession. It even had a cat mascot. So what happened to Diaryland?


I learned that while the site is not exactly thriving, it isn't quite dead. It creaks on from its headquarters in Smales's home in Toronto.

Smales said that although he's not officially planning a comeback, Diaryland still signs up a user or two each day. He claims he'll probably maintain the site unless "zero users" sign up who help pay the costs to keep the servers running. Smales requires new users to pay a one-time $2 activation fee to prove they're not a spammer.

Though others have expressed interest in bringing Diaryland into Web 2.0, Smales has declined. A thirteen-year-old kid recently contacted him about revitalization. "He was literally younger than the site," he said. "It's crazy. I was like, oof! Life is weird. He basically wanted to change it into Twitter."

I asked Smales if there were anything he would have changed about how he conducted the business side of Diaryland back when the site was at its peak.

"There are definitely a million things I would have done differently," he said. "There were sites that ended up making tons of money, money that I probably would have taken, but I never would have even asked for. I saw sites that didn't have any users, but maybe went to business school or were pushy or something, and then they would get millions of dollars. Looking back, I would have pushed a lot better."

Part of the reason why Diaryland died was that Smales could never figure out how to translate the site's pool of users into actual profit.


While he kept track of the cities that users claimed to be from, it was more for his own interest, and never turned into ad sales or data mining. For Smales, early Diaryland seemed more like the local indie rock scene he was a part of in the Toronto area.

"There was a different feel to it back then, sort of a 90s feel," said Smales. "It was a smaller community where everyone kind of knew who everyone was even if you didn't know the person."

Smales's grunge ethos in the eventual Zuckerbergian landscape of user commodification in social media sites, reflects the optimism of the 90s internet: trying to establish a place separate from uniformity and corporate interests.

Even now, Diaryland is still adamantly DIY, more in tune with creating your own space without ads or compromise, which in turn means dwindling profits and an undefined marketability.

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But only part of the blame for Diaryland's decline can be pinned on Smales's 90s sensibility and lack of a business plan. Diaryland failed because it misrecognized what Web 2.0 would become, and how it would render the diary obsolete.

Dear Diary is dead. Welcome to Dear Data

In our Facebook present, click-tracking and adware portray who we are more precisely than a diary entry ruminating on what band or boy we're into on any given day. Now, we write in our diaries every time we book a flight, order take-out, use an emoji of a hot vampire, or stream pixelated episodes of The Bachelorette.

These movements become the entries of our days, our data doubles; entries that we do not see, but are kept safe for us to be carefully tracked by advertisers and marketers, risk assessors, credit rating agencies, and insurers. Our true desires are revealed far more easily by what we click than what we write. Dear Diary is dead. Welcome to Dear Data.

And in 10 years? Though he was hesitant to pinpoint it, Smales did suggest that nostalgia could have its place.

"People are being more nostalgic about the early web," he said, "and part of me feels like maybe in five or 10 years that might be a thing. I think it's probably too early now, but if somebody revived LiveJournal, I could see old web making a comeback. It happens for a lot of things, like right now all the bands I listened to as a teenager are reuniting because everyone is nostalgic."

Maybe Smales will be right. For me and others, Diaryland evokes nostalgia for an earlier, seemingly simpler version of a pre-data mining internet where our stories of ourselves were something other than X-rays of our consumption habits, where oversharing was voluntary, and online surveillance was a sci-fi story, not our reality. As Kimya Dawson of The Moldy Peaches recently tweeted, "Fuggit. I'm going back to Diaryland."