Dry, offbeat, and mostly profane, How to Be Inappropriate glorifies all things TMI. Arguments, lists, barstool rants, queries, pedantic footnotes, play scripts, commonplace miscellany, profiles, and overly revealing memoir-ettes, How to Be Inappropriate adds up to the portrait of a 20-something-become-30-something, bachelor-become-husband, boy-man-about-town who bumbles through life obsessed with one thing: extreme impropriety.

In How to Be Inappropriate, Daniel Nester determines the boundary of acceptable behavior—mostly by disregarding it. As a here-to-cut-a-hipster-swathe-through-the-city man he looks for love with a Williamsburg abstract painter who has had her feet licked for money. As a teacher, he tries out curse words with Chinese students in ESL classes. Along the way, Nester provides a short cultural history on mooning and attempts to cast a spell on a neighbor who fails to curb his dog. He fields middle fingers from bratty NYU film students, explores the world of Christian parody bands, befriends exiled video game king Todd Rogers, re-imagines a conversation with NPR’s Terry Gross, and invents a robot version of Kiss bassist Gene Simmons.

For Daniel Nester, also known as Captain Embarrassment, to be inappropriate is a matter of worldview, a code of behavior. Every moment skews to the profane, inappropriate, and just plain wrong. No matter which misadventure catches your eye, How to Be Inappropriate will make you appreciate that someone else has experienced these embarrassing sides of life, so you won’t have to.

Daniel Nester's writing has appeared in The Best Creative Nonfiction, Open City, Nerve, The Daily Beast, The Best American Poetry, Time Out New York, The Morning News, The Bloomsbury Review, Poets & Writers, and Bookslut. He is the former Sestinas editor for McSweeney’s and teaches at The College of Saint Rose in Albany, New York. He lives in Upstate New York with his wife and daughter.

All my life I have acted wrongly, very wrongly.

Let my try again. The word I am looking for, I think, is inappropriate. All my life, dear reader, I have acted inappropriately, very inappropriately. I then regret the act; I confess it, talk about it, apologize. Sometimes I am forgiven for the inappropriate act. Then I act in an inappropriate manner again.
Any attempt at a specific definition of inappropriate leads to blind alleys. My father, for instance, offers the talk radio party line definition. “It’s a code word tied to political correctness,” he writes to me, a “typical usage of “semantics” as used by the leftist , bed-wetting control freaks.”

That’s part of it; but it’s more than that, of course.

Inappropriate dress, inappropriate acts, inappropriate words, settings, interactions, touches; abnormal, unsuitable, unbecoming, unfitting, unseemly, unbefitting, incongruous, ill-defined; to be out of place or keeping, inapt; the manner in which a clergyman touches a woman’s leg or the content of a congressman’s homoerotic text messages; an Australian opposition leader caught sniffing a woman’s chair; two more Australians, cadets this time, of Chinese descent, singled out by superiors to play-act Koreans in knife combat; among a group of New York State special education teachers, one of whom exposes her breasts, a second slaps other conventioneer’s buttocks, another calls students ‘Drool Machines,’ all deemed inappropriate; a viral video stars “Mr. Inappropriate,” who rubs his butt everywhere, eats a coworker’s sandwich, pees in the same urinal as someone else; on college campuses, inappropriate describes how fraternity brothers tamper and use fire equipment, roommates who leave rude notes on a dorm room door, resident assistants who taking another’s students laundry out of a washing or drying machine, stealing—then smoking—someone else’s pot; Headline: Drunken cricketer’s rampage leads to inappropriate racial rants; late night talk shop host Conan O’Brien’s skit, “Heavy Metal Guitar Legend Clive Clemmons’ Inappropriate Response Channel,” in which bawdy-dada comments punctuate somber situations; “not appropriate” is how Bill Clinton described his relationship with Monica Lewinsky, how a high school coach’s placed a “foreign substance” in a freshman’s Gatorade; remarks whispered over the Cultural Revolution in China are called inappropriate, remarks about another man’s tattoo of a woman that leads to a fistfight (the tattoo was of the man’s daughter); in Houston’s George Bush International Airport, a warning against making ‘inappropriate comments or jokes about security’ or else risk ejection from the premises; a professional soccer coach urinates on the head of a patron at a nightspot; a Russian Formalist critic points out a playwright’s disregard for logic, and offers as evidence how characters break into scenes with strange or “inappropriate remarks”; a Poughkeepsie judge compliments a criminal defense lawyer on her “nice butt,” which is then deemed “inappropriate” by a panel of his peers; a sleeping pill that causes “inappropriate or strange automatic behavior” such as hallucinations, painting the front door, binge-eating, and sleep-driving; a proposed new drug treats “inappropriate” levels of separation anxiety in dogs; and all this, through the bank-and-pile and torrent of manners and human custom, inappropriate has come to mean anything aberrant, odd, out-of-place.

As for myself, how does he define inappropriate?

The author answers: I can only tell you my inappropriate stories.

I tell these stories to explain why people stop liking me.