What Was Your First Internet Date Like?

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Over at The Hairpin the other day, guest editor Christine Friar shared her first experience with online dating. Unsurprisingly, it was via MySpace. Even more unsurprisingly, it didn’t end in ~*tRuE lOvE*~.

What it did do was remind me of my own. I had just turned 15 and I’m not sure how we started talking, but I know AOL was involved. Possibly a chat room. You already see where this was going, right?

He was 19 and I didn’t find this creepy because he was OMG in a band, so we talked on the phone and made plans to go on a date. I wore a reeeeally cool sleeveless knit turtleneck and platform sneakers and he told me I looked pretty. We walked around in a circle around a park near my house and he talked about how ugly he was and how girls didn’t like him for about three hours straight and I think I probably said things like “No! You’re fine! That’s silly!” but actually he was pretty gross. This was before I knew how to end a date quickly (sneak out out of the bathroom window) so we just kept walking (and talking) in circles until I said my mom was making dinner and I had to go home. He tried to kiss me and I freaked out, so he apologized.

Later that night, I went online and had an email from him. No text; just a picture. Can you guess what it was?! Go ahead, guess. It took a long time to download because this was back in the day of dial-up, but slowly but surely, there it appeared. He had sent me a picture of his penis. I would like to think I yelled (“yelled”) at him, but in reality I just politely told him that he had been inappropriate and crossed the line. We never spoke again.

What was your first experience with dating on the internets? Was it as magical as mine? Please share in the comments!

Diana Vilibert is a freelance writer living in Brooklyn and on the internet. A/S/L?