My friend Big Steve recently asked me to contribute to a fund-raising charity of his. Now, this isn’t United Negro College Fund or Anti Defamation Legue. This is a VERY important charity.

You see, Big Steve works at my local college. In the computer lab. Where he helps students with their educational attempts etc. And if you are in the computer lab it is 76% likely that you have only seen a picture of a naked woman. ‘Cause, let’s face it… the only people in there are sweatypalmed socially awkward kids with unfortunate hair and skin and chapped lips that look like scales from a giant fish.

Well one of these kids also has Asperger’s Syndrome. And not to mock the afflicted but he is so socially awkward that he once peed his pants when a girl told him that his new haircut looked “cute”. Needless to say he’s a 19 year old virgin. And Steve wants to help him rectify that.

By going on Craigslist. And getting a hooker.

Now, I’m all for this. At least, in THEORY. Because #1, I believe in legalized prostitution and also de-stigmatizing it. And #2 the kid NEEDS it.

He’s failing a class because he keeps drifting off and daydreaming about living a life where he’s able to talk to girls and trick them into coming to his house and making out in the basement like anyone his age would do!!!

But that is not the case.

The thing is I’m only for this in THEORY because I can see this going completely Nixon and him either chickening out or …. well… guys know. I don’t need to explain. and then he’d get freaked out.

So, with tax-time swiftly approaching….. is buying a hooker for a 19 year-old Apserger’s kid a deductible expense?