How to Pick Up Women or Write Like You Do

Anyone can be nice, but sincerity is a gift.

I discovered this many years ago when I was a single. Too introverted to be the pick-up artist yet too horny not to try, I discovered a fool-proof method to start conversations with ladies: ask about their shoes.

I commented to a lady on the bus about her pink suede loafers, and got her phone number. I got a date when a woman spotted me staring at her shiny green heels. "Sorry, not to be rude," I said, "but I couldn't help but notice your shoes. They're really cool."

This comment was able to complete three objectives without coming off as craven. First, I got a response -- always. Second, I was able to flatter them; noticing the shoes shows one's attention to detail. Third, I got a boner. I mean telephone number.

And if I didn't get phone numbers from all these women, I was able to gain their interest. But there was a caveat: I had to mean it. I really had to think they had cool shoes. Women can spot false flattery a mile away, at least in those of us who are not sociopaths.

If I were to ask some comely lass about her Nikes, she would think, "That pathetic horndog." Or she would just say it. Wife certainly does.

You could also say that sincerity — footwear related or not — is an attractive feature in a man, because it shows genuine interest in the other person. You don't have to fake it.

My pitiful advice on skirt-chasing is not without a lesson in the realm of writing, that activity for which millions of loyal readers tune in to this space twice weekly. Sincerity is one of the hardest thing for me to convey in my writing, and at its worst, characters come off as plot devices or stand-ins for emotion or symbols.


Nice shoe, babe

You have have sincerity in your characters to make them whole, to make them believable. Readers can smell half-assed attempts at sincerity better than that really, really, beautiful redhead who nearly slapped me on the "L" when I said I thought her shoes were interesting. (Perhaps I shouldn't have called them "fuck me pumps.")

One of the main characters in my novel, the narrator's maternal grandfather, is a brilliant, deceitful, manic, petty, and downright evil tyrant who also happens to be one of the world's greatest cotton traders and a bowling aficionado, the intersection of which fuels much of the book's plot. My agent loves this character, who he calls "almost Biblical" (I took it as a compliment).

The easy part of the old codger are his tics and madness; with a few strokes, one can illustrate the grandfather's insanity. You show him having a breakdown, or committing a particularly cruel act upon his issue, or paying retail for that suit that my Uncle Izzy on the Lower East Side could have gotten him for wholesale! It's crazy to pay retail!

But the hard part, the stuff that makes me crazy, is creating a character sincere enough to be believable. The best characters have lives completely divorced from the page, independent of the person creating them. They laugh, they cry, they eat Sphincter McNuggets and spend long hours in the bathroom, etc. And that requires showing complete sides to characters, their good and bad, their tender and mean, their generous and avaricious.

You don't have to be a lit major to understand what I'm talking about when I say that it's about making characters three-dimensional. The classic example of a writer accused of "two-dimensional" characterization is Charles Dickens, though I would cut off my right one to write a book like "Great Expectations," even if Magwitch and Miss Havisham are as flat as a coffee filter.

Writing outrageous characters is easy; writing complex ones is hard.


Worth a nut

I think that's why you get dull, artless prose a la Raymond Carver or supercharged rocket fuel from someone like T. C. Boyle. Staking a middle ground means amping up the volume while keeping it below a level that will blow out the eardrums.

One of the few writing teachers I actually respect said to love all of your characters, even the ones readers hate. Which means I could never write a character based on myself.

Now I have to go back and write my latest effort, about a megamanical movie star belonging to a cult whose recent marriage produced a baby unseen by the world. Don't say I lack imagination.

Also, I hope that every horndog who Googled "how to pick up women" and landed here appreciates what I've done for them. I feel bad for you. After all, if you rely upon Bookfraud for pick up tips, you must be a wee bit desperate.