Casual Catastrophe: learning to stay away from craigslist's casual encounters

The process of posting in Casual Encounters is, like everything on Craigslist, very easy.  But the place is infested with relentless bots hawking cam sites, scammers who are certain you have drugs or money which they can extort, and aggressive homosexuals who, despite my listing under m4w, have difficulty being convinced of the unflappable equation: my penis + another man = never. I promise. Unless it’s a doctor, but even then quite reluctantly and with great fear I would get an inexplicable rogue boner.


The trick to successful Casual Encountering is niche marketing. If you list “Boy wants girl to fuck,” you open the floodgates to all the aforementioned undesirables and then some. But throw in “Skinny guy with tats wants a BBW with a pierced clit” and you narrow the field. Post “Skinny guy looking for red head with one arm and a tattoo of Mr. T on her labia” and eventually you’ll get your girl.


I’d been exploiting variations of this niche marketing charade until I got to a variation of “Young guy wants to fuck older woman.” It seemed like a no-brainer.  And I didn't expect it to cause much trouble.


I’d been with older women before and had few complaints (Note: Older = 10 years). They compensate for waning and sagging beauty with skillful navigation of my body coupled with leniency in my exploration of theirs. Not to mention they have a much better sense of when the show is over: It’s a true luxury to have the woman expedite the split after what should clearly be a one banger.


My ad didn't take long to attract Pam.  We didn’t get too specific in the initial correspondence, but she seemed to know the score at the age of 41. We exchanged pics. She was solidly do-able; a cheerful, lively face atop a body kept in shape through genes rather than the getting-old-freaking-out-exercises-too-much variety.


We set up a meeting at a dive bar about halfway between our houses. I picked it: A true shit hole people went to specifically not to see or be seen.  I left my house with zero urgency.



When I’d set out on this mission, the best case scenario would have been a pre-9/11 Maureen Dowd. Worst case would be Ms. Reeves, my elementary school art teacher; a shrill, bitter woman better suited for maritime swabbing than critiquing childrens' brushstrokes - and whose halitosis remains undefeated.


Judging by Pam’s picture – and one is quite the idiot to judge by an internet picture – Pamela would be closer to Maureen, but likely sans Pulitzer.


Characteristically late, I scanned the bar. The woman in the picture wasn't there. But one seated by the pool table was certainly smiling shyly and waving. I'd been duped by the oldest trick in the internet dating book, the dastardly “Picture from a decade ago-a-rooni.”


Instinct told me to jump out the window, run bloodied to my car and drive home or just drive. But manners prevailed and I walked over, smiling.


When I was close, it was clear this wasn't a creature in which to insert one’s penis. This was a woman responsible for the extra good potato salad at a church gathering. This was a woman to remind you that horseplay was strictly forbidden. This was a woman whom you would neglect to include the word ‘vagina’ if asked to list her organs.


A post menopausal frump-hump had risen where her lap used to be. Her breasts nearly touched the hump when seated and were classed in the asexual National Geographic genre. Her smile sent shock waves of wrinkles to the far corners of her face, and revealed the weathered landscape in her mouth; a mix of browns and yellows and crags and crannies that could serve as the ‘before’ picture in a dentist’s office.


We jumped into standard “Hi, how are you’s” and jokes about punctuality. She was drinking wine and smoking extra long cigarettes. I went the scotch route, and as she sipped, I drained glass after glass - once again subscribing to the perpetually damning hope that a good buzz would somehow yield the solution to the mess.


But it soon became clear that Pam wasn’t truly behind the idea of a casual encounter, anyway. She came clean about her age: 49. She spoke about her troubled highschool senior son. She talked about the inconvenience of not having a man around - I don’t remember what happened to him, or if she told me.


When I finally asked her what she wanted out of this meeting, she said, as if from a prepared statement, “I just want somebody to come over and help out, you know, clean up the yard while I cook some steaks. Maybe just help rearrange the furniture while I cook some steaks.”


She had quite a few of these; stereotypical male chores to be performed while she cooked steaks. For a while the steak-n-chores date was a punchline in this story. But the more I have reexamined this fossilized method of socializing, the more it has grown on me. It’s at least a decent alternative to another Goddamn tapas date.


But at the time it sounded alien and stupid. I felt bad I’d gotten her into this mess. It was my fault and we were both already worse for it; this lonely older woman and this lonely younger man together in this shit bar with the ominous potential of having to address the prospect of uniting our genitals.  Why would I ever consider putting two people through this?  Especially when I was one of them?


We were in gross violation of vital social order, victims of the internet’s all too common side effect of putting two people face-to-face who were never meant to be. We weren’t just bad chemistry. We were bleach, ammonia and lemur shit swirling together in a cracked beaker resting on a wobbly Bunsen burner in a Tanzanian munitions dump.


And before it could go on any longer, I found the courage to lie. Nothing fancy. I just needed to go get my cell phone from my car.


As I drove home reveling in the unpleasantness of my brief date with Pam, I swore off casual encounters for good. I would stick to normal dating. No more of this deviant shit. The status quo. Find a pretty girl in my generation. One who had seen and heard the same things I had. One who I knew what was coming.  And maybe one who needed something moved. Something heavy like a couch. Or maybe a lawn mowing or a tree trimmed. And maybe she could cook steak.


It took an Atacama Desert-like dry spell and a cruel bout of Adderall-induced insomnia to discover the secret to succeeding on Craigslist Casual Encounters. While the morally superior may say that no real ‘success’ could come from this, the morally superior are a bunch of suckers.

Besides, morality wouldn't keep me from resorting to another Casual Encounter hook-up; Pam would.

Ask any sleaze ball who has ever tried it. If they’re man or woman enough to admit it, they’ll tell you the process of casual encountering is not so casual.

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