AOL Chat Rooms and My Prom Date

Recently, I read an article about two dating gurus who met on Twitter and are now engaged. The woman mentioned she'd been dating online since she was 19—and I couldn’t help but smile. That number sounded familiar. Why? Because I started dating online at 17.

Yes, folks—that’s nearly 12 years of online dating before the Comedian and I made it official.
Back in the good ol' days of AOL chat rooms, dial-up tones, and screen names like ValenLatina, I was a curious, lovestruck teenager looking for connection in the most 2000s way possible.

The story starts with prom.

I had asked an old coworker I was crushing on to be my date. He said yes. I was thrilled. But I was also 17 and had yet to learn the lesson that confirming plans matters. Weeks went by with no follow-up, and when I finally got a hold of him—cue heartbreak—he had totally forgotten. He apologized and said he had to work.

I was devastated. This was senior prom. A rite of passage. And in my teen mind, the world had officially ended.

Naturally, I turned to the only place I knew for comfort: the AOL Orlando chat room.

After the obligatory “a/s/l?” intros, I started chatting. "Hey ValenLatina!" messages came flooding in. And then one conversation stuck.
He was a nice guy, about an hour away, and he patiently listened to my teenage sob story: dumped by a flaky prom date and scrambling for a plan B. After some back and forth, he said:

“I’ll take you to your prom.”

I couldn’t believe it. I had a date! But of course, I had to meet him first.

We decided on Old Town—if you're from the Kissimmee/Orlando area, you know that place.
We walked, we talked, and honestly… he was polite and sweet. Not quite fireworks, but hey, my online dating adventure had officially begun.

Prom came and went. He wasn’t really my type (and I was definitely not feeling a love story unfolding), but he showed up when I needed a date—and that mattered. My mom thought he was cute, which was... a bonus for her, I guess. 😅

That night didn’t end with a fairytale romance, but it did start my digital dating journey.
And I wouldn’t change a thing—well, maybe just my prom hair. That was a whole other tragedy.