How life was different during the early Internet

AI for nostalgia's sake

Dear readers,

You know those people who cannot bear to throw anything away? Every menu from a tasty meal in an exotic location, every abstract painting created by a toddler hand, every moth-eaten old t-shirt from a team event decades ago. You go to their house and their shelves are piled with knick-knacks, their garage is a U-STOR-IT in disguise, their bedrooms hide enormous cabinets overflowing with STUFF.

This is me, except for digital stuff.

Yes, I am a digital hoarder of the S-Tier variety. Across a dozen or more computer upgrades since I was a teen, even before the era of broadband and cloud, I have faithfully and diligently copied all my files from one place to another: every high school and college essay, images of hot dudes from the internet, chat logs with my friends, past websites, in the hopes that one day, when I’m old and bored, I’ll have nothing better to do than relive the nostalgic glories of my Internet past.

Well, my friends, that day has come, ushered in by the herald known as “Claude.”

With the power of AI, all those dusty folders in my digital attic’s digital attic can now be evaluated and sorted and worked upon.

And work we have. I’ve been using AI for a variety of purposes (more to share in upcoming essays), but this issue is dedicated to 3 weekend restoration projects that took me on a trip down memory lane back into the Internet of my youth.

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AOL Instant Messenger and my 2004 chat logs

It started, as these things do, with a directory I’d been carrying around in Dropbox for 20+ years: Memories/Old files/AIM Logs/, which was conceived of on a random Tuesday 3:43am in the clutches of a deep spell of self-preservation and future nostalgia. (This small step, dear reader, is how I started my journey into becoming a digital hoarder, S tier status.)

I dumped all my AIM logs into 1,556 .htm files from 2002–2007, each one a logged AIM conversation with someone from high school or college. My screen name in most of them was JouLeZoo. (Like any self-respecting teen, I split myself across four identities.)

Recently, while trawling through my copious digital archives, I saw this little folder and became curious to read the chats again. But double-clicking a .htm file in 2026 gets you red Times New Roman on white, no styling, no way to navigate between dates. So I tasked my trusty AI helpers to help me build a little web app to flip through them. I figured: ten minutes, a static index, done.

Little was I to know, I was about to embark on the great art of digital restoration.

The process

v1 was a sidebar of buddies and a clicker for opening the chat. Worked! But looked like every dev tool from 2010. I decided to make it more “old school” and what’s when it got fun.

The XP/AIM aesthetic came back hard: Tahoma, yellow buddy list, blue Luna title bars with the red ✕, rounded windows. We added the iconic Windows XP “Bliss” wallpaper as inline SVG with the blue sky, clouds, rolling green hills embedded right in the CSS.

A fake XP taskbar materialized at the bottom with a Start button and a clock that ticks. Anyone over 30 should get a small, specific dopamine hit from this view.

A few rounds of feedback (the buddy list was painted yellow when it should’ve been white; dates read like 2004-11-20 instead of November 20, 2004). Then I remembered I had a separate stash of .doc files I’d manually saved because some conversations were too funny to lose. Dropbox’s “conflicted copy” bug had dutifully duplicated them nine times. We used macOS’s textutil to convert each one, deduped by md5, and slotted them in alongside the regular logs. The original red/blue speaker colors survived the trip from 2002.

Then came sharing. I wanted my friends to be able to laugh at this blast from the past. But even though this was dozens of years ago I wanted to maintain the privacy of each person’s conversation. So: one deployment, Gmail login, an access.js mapping each email → the buddies they’re allowed to see, server-side filtering of every request. From a friend’s POV the experience gets transposed: their screen name becomes the “account” and my screen names become their buddies, so it reads like AIM in 2005 from their seat.

I can also “act as” any friend to verify what they see; the auth bar turns red while I’m impersonating, which saved my dignity at least three times during testing.

Then I tried it on my phone. Complete disaster: fixed-300px grid, overflow: hidden on the body, and a missing <meta name=”viewport”> tag meaning Safari was pretending the page was 980px wide and shrinking everything. Gotta make it mobile-friendly in this day and age! After the fixes, the XP taskbar at the bottom doubles as a window-switcher where you can tap to flip between Buddy List and IM.

The Era

These AIM conversations captured a specific moment in time: the last gasp of communication that happened on the home computer. Texting existed but cost ten cents a pop, so it wasn’t really a thing. The iPhone wouldn’t launch until June 2007.

Facebook had just been invented at Harvard in February 2004 and was still gated to specific college networks. MySpace, Friendster, and LiveJournal were the social internet. Gmail was an invite-only beta (the Google IPO was August 2004.) We pirated music on Kazaa and LimeWire and Bittorrent and sent each other songs via AIM file transfer.

For most of the people in my buddy list, the buddy list itself was the social network: a literal list of friends, in a window on your computer, where you could watch each of them come home from class by the green icon turning on. The “away message” was the status update before that was a phrase. The profile was the bio. AIM hit its all-time peak around 2006 (somewhere around 36 million American users) and was about to fall off a cliff once everyone got smartphones and being reachable became an ambient flat-state condition rather than an event. These logs are from the last era when “ARE YOU THERE” was a normal question to type at 1 AM.

What it actually looked like in there

• The away message was the social network (Jan 2005): “wow, you are FAST with the away message reading”

• Disambiguation that lands in 2026 (Jan 2005): “wow, and i mean ‘WOW’ as in ‘IMPRESSIVE’, not ‘WORLD OF WARCRAFT IN ALL CAPS’”

• The eternal Googler problem (Feb 2005): “it’s just SO HARD to find reasonable results for a search like ‘google caltrain shuttle’ since EVERYTHING ON THE WEB talks about google”

• Peak intern energy: “i was planning on making a new headphone purchase for my internship, since ‘desk headphones’ are very different from ‘exercise headphones’”

• Proto-parasocial creator-fan email, before that was a word (Dec 2005): “i emailed her once just to say i really enjoyed her blog… and she emailed back a ‘thanks! i’m always surprised people actually read my blog’”

• Recruitment, 2005 style — broadcast over away message: <X’s> away message read “WANTED: <Y> to Microsoft”

• Tribal coding tastes (June 2007): “i have a linux box at google, but it’s not letting me run php5, and google tech support has no idea why (as you can imagine, php is practically a swear word at google -- we don’t use it ever)”

• The moment JSON started eating XML’s lunch (July 2007): “Is there any reason we don’t use more JSON around here for AJAX?”

• The junior-dev cope (Nov 2004): “despite the fact that i’ve been doing my tasks at a snails-pace that to me seems realllllly slow, i’m actually Perfectly On Task! On Track! On Time!!”

• The specific cruelties of Frontend Hell (spring 2007): “in ie6 they calculate the width of the content area incorrectly” / “isn’t there something weird where input elements can’t be styled in safari?” / “i hate how firefox doubles the padding of all inputs”

• Peak finals-week energy (Jan 2006): “efficiency-robot-from-now-on-that-is-not-distracted-by-anything-and-does-not-think-about-anything-but-work-not-even-chocolate-ramen”

• The week poker night went digital: “so poker night has been replaced by VIRTUAL poker night, which basically consists of World Of Warcraft”

• A productive Saturday plan: “how’s about i bring over my desktop again (i.e. ‘move in’) and play WoW at your place… while you be productive and get work done!” (Reader, I married him).

• Apple-watcher snark on iPod shuffle launch day (Jan 2005): “in case your iPod mini was just TOO BIG and you thought the limited user interface of the iPod (and on/off switch is sooo passé) was too complicated…”

• The universal library crush (May 2005): “actually, there’s this short cute asian girl in the library i was hoping to see there tonight”

• 2005 China take that has aged like burnt bacon: “the Yahoo and Google of China may well end up being… Yahoo and Google”

• And of course: “1337!!! 1337Z0RX!!!”

the life of a designer / front-end engineer in 2006

If you have a Dropbox folder somewhere with the contents of your early twenties in it, I highly recommend asking your favorite LLM to help you go back in.

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My Website From the Age of Pure Internet Joy

A few weeks ago I spent an afternoon getting back online my website Tyro Tinge. My best friend Marie and I made it in high school between the ages of 16 and 18. Actually, we made eight different versions, because I could think of no better way to spend evenings, weekends and holidays than repeatedly redesigning this thing. (Yes, such is the life of an Early Internet nerd.)

Tyro Tinge was ostensibly the home of our digital illustration collection, which featured fan art and original characters done in Photoshop and Painter and Prismacolors, alongside a message board, print shop, an epic fantasy Marie was writing years before she became a famous author. There was even a tutorial section we named gyro minge, because it seemed important to us at the time that every part of the site had to rhyme with -inge.

To understand restoration, we have to remember what the Early Internet was like in that era.

This was the year 2000, before Facebook (2004), YouTube (2005), Twitter, Tumblr, or the iPhone. The biggest sites were AOL and Yahoo (actual portals, where the homepage was a curated directory of human-edited links plus a weather widget plus a stock ticker). People got news from those portals, or from blogs they’d bookmarked, or from Slashdot if they were nerds; there was no algorithm pushing news to you.

People like us made personal, bespoke websites using GeoCities and Angelfire, in HTML we typed ourselves, in tables nested five layers deep if we wanted fancy layouts. We got music from Napster, then Kazaa, then Limewire, then BitTorrent, ripping MP3s and playing them in Winamp (”it really whips the llama’s ass!”), burning the special mixes onto CD-Rs for the car.

Back then, you announced your existence with a hit counter and a “Best Viewed In Internet Explorer 6” badge. You talked to your friends on AIM with away messages that were almost always cryptic song lyrics. Blogging was DIY: if you wanted one, you downloaded CGI software like Greymatter or Movable Type and figured out how to install it on your shared-hosting account the way you figured out everything back then, which is by reading someone else’s FAQ or ‘how-to’ and a whole lot of trial and error.

I still had my old files from this website, faithfully copied from computer to computer. Restoring this was a perfect task for today’s vibe coding era.

First, the images: the originals were optimized for 1024×768 monitors and 56k modems, which means on a 4K screen they looked fuzzy or tiny. So I ran 1,572 of them through Real-ESRGAN, one AI model for the digital pieces, a different one for the scanned colored-pencil drawings (since the first model kept erasing the paper grain that reminded you these were real pieces made with my oh-so-prized Prismacolor collection because that shit was quality and expensive!)

Second, the markup: twenty-plus years of web-standards drift had broken a lot of things, from fancy Internet Explorer-only CSS that left whole pages rendering as blank canvases to hard-coded subdomain URLs that no longer resolved. There were framesets whose relative paths assumed a directory structure that didn’t survive the flattening and a 2002-era CGI message board whose admin password was sitting plaintext in a passwd.txt. AI shines in the thankless task of translating between standards and APIs, so I was grateful to my AI helpers for making this part a breeze.

Third, the eras switcher: I wanted to compress time and be able to access every past version of the site, so I created a floating toolbar with a dropdown that lets me easily visit each version. You can pop from v1: Forest & Fairies (June 2000) to v8: Nothing Gold Can Stay (~2002) in a single click and watch what nearly three years of obsessive teenage redesigning actually looks like.

The embarrassing part is seeing what I sounded like back then. Some excerpts:

Welcome, all ye happy travellers, to the quirky site of Tyro Tinge~ ^_^ Once here you will find utter randomness and chaos galore, as you can already tell from the oddball titles of the site’s sections.

Tyro Tinge is best viewed in Internet Explorer v6.0+, in 1024x768 screen resolution. Other formats may result in abnormally organized tables and cluttery strangeness.

we are busy students who like to procrastinate on assignments long enough to keep ourselves in a perpetual state of stress

Please do not take it personally...we’re just trying to accommodate our utter laaaaaziness~ @_@;;;

The design choices are also deeply cringe. Striped or over-the-top backgrounds on absolutely everything. JavaScript hover-scroll arrows whose speed you couldn’t change. Line-heights cranked down to illegibility because cramped felt socool back then. Sparkles. God, so, so so many sparkles, on everything, like I was some kind of next-gen Charles Dickens being paid-by-the-sparkle. As someone who was later inducted into the Dieter Rams way of design, I can only shrug and blame it on the poor taste of youth.

At the same time, I’m proud of that girl. She was an early fangirl before Tumblr made fangirls a real subculture. She had a blog in 2002, decades before traditional media died. She built a message board so her readers could write back. She invented a language of rhyming nonsense for the joy of how the words sounded.

What I want most to remember about that era is this: all my free time was spent on creating. My parents rolled their eyes and asked why I didn’t spend my time doing more worthwhile, college-resume-polishing work. There wasn’t any achievement in building websites back then; the Internet was still a fairly niche hobby in my suburban community.

That’s why I get nostalgic looking back at Tyro Tinge. At that point in my life, there was no audience to optimize for, no metric to hit, no outcome to build towards. Just a fascination with art and fandom and an absolutely magical new technology, the pouring of hundreds and hundreds of hours into making something for sheer and simple joy of creation.

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(fluff)Friends during the nascent days of social gaming

Some weekends ago I cracked open a Photoshop file from 2007, dusted off some PHP, translated a bunch of ActionScript, and brought (fluff)Friends back to life as a gift for my husband.

Mike and I built (fluff)Friends one weekend in 2007 on the brand-new Facebook developer platform. It blew up practically overnight.

To explain why a tiny app where you adopt a cartoon panda instantly created millions of fans, you have to remember what the Facebook platform was back then.

You could write a few hundred lines of PHP and have real people, lots of them, mostly young folks, trying your thing by lunchtime.

I was a designer-engineer at Facebook back then (this wasn’t yet a meme) and I worked on the platform’s initial launch. We had an internal hackathon to build some stuff on the platform. Someone built a quiz app, someone build rock paper scissors, and I built a pet adoption app full of cute creatures I used to doodle for fun.

Remember that this was pre-Candy Crush, pre-Zynga, pre-mobile-anything. The iPhone had launched five months earlier, the App Store didn’t exist yet, and developer platforms as a concept was novel. (Apple was, at the time, telling people to write web apps for their new phone)

The Facebook platform took off. Tens of millions of people who had never installed a piece of software in their lives were suddenly doing so, daily, in their browser, because it was so easy to do so.

(fluff)Friends was our entry. Built in PHP, MySQL, a folder of Flash files, we launched it into the world and it caught fire.

Here’s how it worked: you’d adopt a creature — a panda, a flying giraffe, a turtle, a tofu cube with a tiny smile, a monkey called a Munkii. You’d name it. You’d give it a saying. (“pet me.” “i miss my mom.” “i contain multitudes.”) You’d share your link, and your friends would come pet it. The more love it got, the better its mood. That was v1.

A few weeks later we added munny, a virtual currency you earned by petting friends and spent it on habitats, clothing, and decorative items for your fluff. Then, a few weeks after that came the upgrade that changed everything: the FluffEditor. It was a drag-and-drop canvas where you could place habitats, props, and accessories around your creature, built in actionscript. Suddenly the game wasn’t just about adopting a thing. It was about expressing yourself with your pet.

People got unbelievably creative. They built comic book scenes. They built shrines. They built dioramas of their actual relationships. I spent every weekend after that drawing new props in Photoshop (this was pre-Figma, pre-Sketch) and then sitting in front of the app on Monday morning watching what people made with them.

The Facebook team had favorites too, and we printed our fluffs on t-shirts. For years afterwards my friend Jared would tell me, unprompted, how much he loved his Tottle shirt.

While it was a hackathon project for me, Mike took it much further. He quit his job and ran it full time. He made plush stuffies of the creatures and sold them. He built a racing game spinoff that became its own hit. He shipped subscription-based virtual goods years before the rest of the games industry would discover it.

The fluffs eventually went to sleep as the Facebook platform evolved (though I still have a few of those plushies sitting on my shelves.) Until now, when Claude and I spent a weekend re-rendering every creature at 4x with fresh transparent backgrounds. We translated the ActionScript animation logic into modern TypeScript. We rebuilt the Facebook 2007 chrome from memory and a few screenshots — sage frame, white canvas, that old shade of blue. We swapped MySQL for SQLite-on-the-edge, cookie sessions for Google sign-in, and a college-apartment hosting bill for the modern stack.

The creatures look exactly like they did in 2007, only sharper. Petting still gives munny. Munny still buys habitats. You can tell your fluff what to say. You can share your profile and friends can come pet it.

None of this would survive a roadmap review these days. And yet.

I think a lot about the difference between things we make to scale and things we make to make. (fluff)Friends was made to make. Mike and I sat on the floor of my apartment with a Flash IDE open and giggled at the creatures we were drawing. A few weeks later, millions of people were giggling too. We didn’t do market analysis or have a roadmap. We had a weekend and a feeling.

Every new platform has its early adopters, and every early adopter remembers the fun of the raw, wild days. It’s a feeling I’m still chasing.

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