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I cast a wide net in my searches, looking up posts by straight or bisexual women between the ages of 18 and 35 who lived anywhere in Chicagoland — a large metropolitan area that's home to close to five million females.Most of the women wanted something very specific they couldn't find in their normal lives: Someone to help play out a particular fantasy, someone vastly older than them or someone of another race.

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A woman wrote in response to my sweet "cuddling first" ad saying she was in town for only a couple of months, and that she was frustrated she couldn't find a relationship.Very few of the women who were advertising seemed to be looking for anything I would consider a "normal encounter." Nevertheless, I tailored each response to whatever they were looking for.I typically wrote two or three paragraph replies and matched the tone of their own messages, then attached a couple of tasteful photos of myself.It goes without saying that the content of this article is not intended for children or those made uncomfortable by such topics.But if you're interested, read on for the story of my seven days on Craigslist's Casual Encounters — my failures, near misses, discoveries, insights and successes.

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