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Eight Windows Challenge

Twenty years ago I was an awkward nerd with poor social skills (as opposed to now where I’m a weird but fun nerd), and I desperately wanted the company of women, but I had no way of getting any: I was terrified of small talk with women, and my only social outlet was Dungeons and Dragons. What I was good at with women, though, was online chatting. Until I was issued: The Challenge.

Way back then, I was on one of the first services that had chat rooms: Compuserve.  I figured practice chatting online with women in a controlled environment, would help me learn how to talk to them. What I discovered pretty quickly was that it was hard to find women to chat with. Mostly it was hundreds of guys talking about whether the enterprise or the millennium falcon was faster. I found that if I wanted to chat with a real woman, the only I could do this was by going to the lesbian chat rooms and pretending to *be* one.

Now I realize that today this seems obvious, but back then nobody was doing it, and it was like I had invented fire.  I’d come up with a persona, start chatting and within a few minutes of hanging out – poink – you’d get a private window remarking how funny something I said was and a few minutes after that, boom – text sex. I know this sounds sort of sad and desperate but I was so lonely, and while my D&D buddies were nice company if you wanted to fight demons it’s not the same.

Soon, though, women started to catch on that guys were prowling these boards, which meant that I had to up my game, which wasn’t easy, because women are sensitive and smarter than guys. My sister Judy was intrigued and figured a feminine perspective would be useful so she started helping me. Yeah. she's my sister, but I assure you that there is nothing dirty about me chatting with women online and my little sis helping me! We did all sorts of crazy stuff together. We both viewed it as sort of a fun intellectual exercise!

She got me to stop using lines men that think women say like “who here likes kittens”. But Judy also kept goading me to push the envelope, which eventually led to “the challenge”:

One night I had just hosted a game of D&D, and Judy remarked how easy it was for me to talk in character as the Barkeep or the Dragon, etc. And I said, “Well, as a seasoned game master, maintaining any number of active characters is child’s play” And Judy said “well that’s easy when it’s just your nerdy friends. Real people aren’t fooled as easily.” You don't mean people, you mean lesbians, and yes they are. Watch me.

From there it was a descent straight into Nerd Hubris, specifically: how many open windows of chats could I run at once, each one with a different persona? Two were simple: In this window I’m an ex-librarian from New Jersey…and in *this* window I’m a female cop with a kid from south Philadelphia who’s divorced who missed my guy,  you know how it is ladies, but lately has been considering ‘what it might be like’.

Judy made me do more and more simultaneous windows. I was a Hispanic child care provider, a divorced mom who had discovered herself in a yoga retreat and one that really worked well – a bi-curious married housewife using her hubby’s computer who was ‘scared’, etc. I jumped from window to window, juggling chat windows, all with Judy yelling “No – you have a dog in this one! Talk about your kid! No, no kid in this one, you're fifty years old, they’re in college! FOCUS.”

Five windows. Six Windows. I was reaching the breaking point. I tried using the amazing Kreskin chess trick, where you take the chat from window 7 and use it to reply to the chats from window 8 – essentially making two windows chat with each other, but Judy saw through that fast.

Then – for one brief, shining moment, I touched heaven. There arranged on my screen were eight windows, each one with a lesbian (or a guy pretending to be one, sure) texting from a different part of the country, the screen all lit up with one-handed typing errors. I had done it! But I couldn’t hold it and soon things started falling apart. I couldn’t type fast enough. Eventually one of them got pissed, then got the moderator who checked my profile – I wasn’t smart enough to remove my smiling face from the profile – and I got banned from Compuserve. 

I learned something from my little nerd experiment. That the safe controlled world I lived in was sterile, and devoid of the terror and uncertainty of the real world. So now, instead, I made BIG mistakes in the REAL world, and bomb spectacularly in real life with real women. And its so much more satisfying.