Your First Email Address Was Embarrassing and That Was Fine

The email address was sk8rboi_69@hotmail.com.

I didn't skateboard. I had tried exactly once, in Tyler Durgin's driveway, and ended up with a scraped palm and a bruised tailbone. I didn't know what 69 meant. Not really. I knew it was a number that older kids thought was funny, which was enough. I was twelve years old, sitting in front of a beige Compaq Presario, and Hotmail was asking me to decide who I was going to be on the internet.

I had never been asked to name myself before. This was new territory.

The Agony of "Already Taken"

Here's something nobody warns you about when you're twelve and trying to create your first email account: every good name is already taken. You type in something you think is pretty clever - let's say cooldude - and the screen comes back with that soul-crushing little message. This username is already taken. Try adding numbers or letters.

So you try cooldude1. Taken. cooldude99. Taken. cooldude420. You don't know what 420 means either, but taken. You are learning, in real time, that you are not as unique as you thought. There are apparently hundreds, maybe thousands of cool dudes out there, and every single one of them got to Hotmail before you did.

You were twelve, and a website was telling you that your identity was already claimed. Welcome to the internet.

This is the moment where the underscores start. The desperate, flailing addition of underscores and numbers that turns a clean name into something that looks like a password. cool_dude_742. You don't want 742. Nobody wants 742. But the alternative is to go back to the drawing board and admit that cooldude was never going to work, and you've already invested emotionally.

So you pick something else entirely. Something edgier. Something that says, "I'm not just a cool dude. I'm a cool dude with layers." That's how you end up with sk8rboi_69. Or xXsurferdude_42Xx. Or darkangel_2001. Or, God help you, lilpimp_13.

You were branding yourself. You just didn't know the word for it yet.

The Holy Trinity of Free Email

In the late '90s, your choice of email provider said something about you, though none of us could articulate exactly what.

AOL was its own universe, of course. If you had AOL, you didn't just have email - you had a screen name, which was somehow even more high-stakes. Your screen name was what showed up in AIM, in chat rooms, on your buddy list. It followed you everywhere inside that walled garden. Picking a bad one was a social catastrophe that could take months to undo, because changing it meant telling everyone your new one, and then they'd ask why you changed it, and then you'd have to admit that SoccerStar2233 no longer reflected your personal brand because you quit soccer in October.

Hotmail, though. Hotmail was the people's email. It was free, it was easy, and it had the word "hot" right there in the name, which honestly might have influenced some choices. You could sign up without a parent's credit card, without a CD-ROM, without permission. Just you and a computer and a decision that would haunt you for years.

What You Thought Was Cool

The beautiful thing about a 12-year-old's email address is that it's a time capsule of what that kid thought was cool. Not what was actually cool. Not what adults thought was cool. What a specific child, in a specific year, with a specific set of influences, believed coolness looked like.

And the influences were so transparent. You could reverse-engineer an entire kid's personality from five characters and some numbers.

A kid who watched too much TRL had something like surferchick or sk8punk. A kid deep into The Matrix went with neo_ something. The wrestling fans were out there with stonecold316 and therock99. The kids who read too much fantasy had darkwolf or shadowblade. And then there were the kids - mostly boys, let's be honest - who reached for some vaguely tough or flirtatious word they'd heard on a Limp Bizkit album and just ran with it, consequences unknown.

Your email address was the first lie you told the internet about yourself. It was also, somehow, the most honest thing you ever said.

Because here's the thing. That email address wasn't really a lie. It was an aspiration. When I typed sk8rboi into that Hotmail registration form, I wasn't trying to deceive anyone into thinking I could kickflip. I was trying on an identity the way you try on a jacket at the mall. Seeing how it felt. Seeing if the world would buy it. The internet was the first place where you could be someone other than the kid who got picked last in gym, and the price of admission was just a username and a password and a security question about your first pet's name.

The Slow Embarrassment

The problem with naming yourself at twelve is that you don't stay twelve. You grow. You change. And your email address stays exactly the same, following you around like a tattoo you got on spring break.

At fourteen, sk8rboi_69 starts to feel a little young. At sixteen, you're putting it on your first job application at Blockbuster and suddenly realizing that a hiring manager might have questions. At eighteen, you're applying to colleges and you need to type your email on the Common App, and the full weight of your choices hits you like a freight train.

This is the moment you finally make a new email. A mature email. First name, last name, maybe a dot in between. Gmail, probably, because by then Gmail exists and it feels like adulthood. Clean. Professional. Boring. Everything sk8rboi_69 was not.

But that old Hotmail account doesn't die. It just sits there, in some server farm somewhere, holding all your forwarded chain emails and your Neopets account confirmations and one truly unhinged email you sent to your crush at 1 AM that you will think about on random Tuesday nights for the rest of your life.

The First Act of Becoming

What I didn't understand then - what none of us understood - was that picking an email address was practice. It was the first time most of us had to answer the question who do you want to be? and commit to it in writing. Before the internet, your name was your name. Your parents picked it. You were stuck with it. But a screen name? That was yours. You chose it. You could be anyone.

And who did you choose to be? A skater. A surfer. A dark angel. A cool dude. Someone tougher, cooler, more interesting than the kid sitting in the computer chair in cargo shorts and a Billabong shirt they bought at Pac Sun. Someone with an edge. Someone with a number that might mean something dangerous.

The identity wasn't real. But the desire behind it was. Every dumb email address was a kid reaching for a version of themselves that didn't exist yet. Sometimes it never would. I never became a skater. But I became someone who understood the impulse to reinvent yourself with nothing but a text field and the courage to hit "Create Account."

That's not nothing.

Somewhere, on a decommissioned Hotmail server, sk8rboi_69 is still waiting for a reply from his crush. He's not going to get one. But you have to admire his confidence.