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The Dating Files: The Playboy Dummy

April 1, 2010

During a bit of a dry spell last year, I met a guy who was funny and cute and witty. Jackpot! He asked me out for drinks and got my contact info so we could schedule. We chatted and bantered back and forth and slowly it became obvious he was avoiding telling me exactly what he does for a living.

I confronted. Reluctantly, he admitted. Playboy. He edits content for their website. Which is a nice way of saying, he helps make the internet just that much pornier.

However you may feel about soft-core porn, I’m sure you might be able to see why I was fairly uncomfortable with the idea of dating someone who looks at augmented and airbrushed bodies engaging in sex acts all day long.

So I asked him, tell me more about this porn job of yours. Maybe I’m picturing it as much worse than it is? He he shoots back, “Oh yes, it’s pretty much normal office life around here. Just everyday, run-of-the-mill, office boringness with the occasional morning meeting where we discuss double-anal.”

Oh, um what was the last part? Where you discuss what? Double-anal.


So I let him know, OK if this is ever going to work you’re going to have stay mum on your business life for now. Don’t throw stuff like that in my face and maybe eventually I’ll feel less threatened/terrified/grossed out/like calling the police.

So we go on our first date and have a great time! Lots of laughing and wittiness and flirting. The next day, I wake up to an email from him. Excited, I check it.

A request for a second date!

…and some attachments: Naked pictures of his ex-girlfriend. And himself. Doing… things.

I guess you can only stifle the perv for so long. There was no second date.

(P.S. I know this is posting on April Fool’s but it *did* actually happen. My life is just that weird.)

11 Comments leave one →
  1. April 1, 2010 8:23 am

    OK he sounded NORMAL up until the point where he sent you sex picks of himself and his ex.

    But… was it really an ex… you sure it wasn’t a photoshop job pulling your chain since you obviously had a problem with him working for Playboy?

  2. April 1, 2010 8:28 am

    That wasn’t an attachment, that was his email signature. Duh.

  3. April 1, 2010 9:13 am

    I am speechless. What the hell would possess him to attach those pictures?

  4. April 3, 2010 12:58 pm

    You know what’s weird? We talk about double anal in our work meetings, and I *don’t* work for Playboy.

    • April 5, 2010 8:26 am

      really? we keep it nice and clean with stuff like bong rips, keg-erators and Amsterdam’s red light district. you can see why i balk at double anal.

  5. April 5, 2010 6:29 pm

    Wow. That is special. Ugh.

    • April 6, 2010 11:09 am

      Met on Match, if you can believe it. I bet you can, seeing as it looks like you’re in the know on the Match-crazies.

  6. April 28, 2010 11:45 am

    Perv = Crazy
    People can only hide the crazy for four hours
    therefore, the perv can also only hide for about four hours

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