Here For Laughs

The Family Computer: Windows 3.1 & The Forbidden Machine

The first computer I clearly remember having was a Gateway desktop with a giant CRT monitor, running Windows 98. It felt like a beast of a machine at the time, and even though I didn’t fully understand what I had at my fingertips, it became the start of my journey into the digital world.

But before that, there were others—computers running Windows 3.1 and Windows 95. I was too young to know whether the Windows 3.1 machine was upgraded to 95, but I do know one thing: in the beginning, I wasn’t even allowed on it. At the time, I didn’t understand why, but looking back, it makes perfect sense—Windows 3.1 was basically command-line. My parents called it the “family computer,” which meant they used it more than anyone else.

Eventually, my time came.

JumpStart & My First Clicks

At first, my access was limited. I had to sit on my mom’s lap to use it, and my gateway into computers wasn’t through coding, the internet, or productivity—it was through JumpStart Pre-K.

And let me tell you, that game was legendary.

I don’t remember much about the actual games, but what I do remember is a talking dog. A very specific dog. I can still see it in my mind, moving its mouth, guiding me through activities. That dog was the greatest thing ever. Eventually, I worked my way through JumpStart Kindergarten, 1st Grade, and 2nd Grade before moving on to other games, but JumpStart was my first real interactive experience with a computer.

The Gateway Era & Early Internet Shenanigans

By the time we had the Gateway desktop with Windows 98, I had full access. This was the era of dial-up internet, when you’d hear the iconic screech of the modem connecting, and if someone picked up the phone—goodbye internet.

This was also the time when the internet was still the Wild West.

I remember discovering Rotten.com, a website that was basically an unfiltered look at the worst humanity had to offer. I’m talking real-life gore, shocking images, and things that made you regret clicking—but for some reason, we kept going back. That era of the internet was filled with stuff that would never fly today.

Then there were the infamous internet shock videos. If you know, you know.

• Two Girls, One Cup – A moment that defined the “do not click” era of the internet.

• Lemon Party – If you were ever told to “Google it,” you learned a harsh lesson.

• Meatspin – “You spin me right round, baby, right round…”

• Goatse – The original internet trap.

• Ebaumsworld & Newgrounds – The home of flash games, ridiculous videos, and everything unfiltered.

• Albino Black Sheep – The birthplace of many viral videos before YouTube took over.

This was back when YouTube didn’t exist, social media wasn’t really a thing, and people got their content from random websites and message boards.

The Games That Defined My Childhood

Before I got into real gaming, I had a few go-to titles that made that bulky Gateway feel magical:

• JumpStart Series – The first step into education.

• Oregon Trail – The game that made dysentery a household word.

• RollerCoaster Tycoon – The first time I truly felt like a god of my own world.

• Doom & Duke Nukem – The game we all know and love.

Eventually, I moved on to The Sims, Age of Empires, and Unreal Tournament, but it all started with that Gateway and those chunky Windows 98 menus.

Looking Back at My First Computer

That massive CRT monitor, the clunky keyboard, and the fact that the computer was probably slower than a modern smartphone didn’t matter. At the time, it was my portal to another world. Whether it was games, the early internet, or discovering what a computer could actually do, it was the foundation for everything that came after.

Today, we carry more computing power in our pockets than that Gateway ever had, but there was something special about those early days. The internet wasn’t as polished or censored, computers felt like a privilege, and you had to actually work for your entertainment—whether it was waiting for a webpage to load or begging your parents to get off the phone so you could connect to AOL.

And honestly? I wouldn’t trade that experience for anything.

What Was Your First Computer?

Now it’s your turn! Drop a comment below:

1. What was your first computer?

2. What were your first games or programs?

3. Do you remember the first websites you visited?

4. What’s your favorite memory of the early internet?

Let’s take a trip down memory lane together!