Because so many guys on Craigslist are so sexually unique, at least 50% of the women on Craigslist are pros. The big takeaway from my adventures through Craigslist personals is that internet dating in general is a zero-sum game. Dating, as any rational human will tell you, is a humiliating psychological battlefield that offers endless opportunities for failure.
The virtual Main Street where we find apartments and used cars also has a freewheeling dating scene; “freewheeling” not only in the sense of joyful abandon, but also freedom from the constraints of conventional morality, general propriety or truth.
Unfortunately, it also guarantees that you’ll eventually feel like a scumbag if you troll CL personals long enough.


My long odds are better when I have the chance to deploy my scintillating personality in a live setting while out with friends. Just like you’d do things with your friends on a night out that you’d never think of doing in your own home, the Craigslist personals allow one to do things that would result in a ban from conventional dating sites. The majority, however, will either attach a picture that has absolutely nothing to do with anything—a sunset, the ocean—or simply fail to include one, knowing that the type of man searching Craigslist prefers the allure of mystery to the distraction of actually knowing what a potential companion looks like. But it’s good to know that, if things go sideways, I can always get a quick fix via Craigslist. And unless you happen to look like the result of a union between Johnny Depp and the Old Spice Guy, starting an unsolicited conversation with a woman on the subway or elevator will almost certainly get you maced.


That’s because Craigslist, whether trying to sell old 8-tracks or the idea that someone is doable, is all about getting down to business. While that may sound totally awesome, dude, the reality is that casual sex gets old real quick once you pass 30, and enough of it will turn you into an emotional robot whose only hope of continued companionship rests in the seedy environs of Craigslist. But I can guarantee that the other half of your weirdo friendship coin can be found on Craigslist.



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