The Total Douchebag's Guide©: High School Reunions
(The Total Douchebag© is a certified master in the art of douchebaggery. He tours the world, giving lectures on how to be a complete douchebag in any and every possible situation.)
First of all, you ALWAYS go to your high school reunion. No matter how many - or how few - years it has been, you do not miss this valuable opportunity to show your old classmates how much of an awesome dude you have become.
Part One: Preparation
This isn't just another Friday night at the local Chili's bar trying to talk the underage hostesses into letting you buy them booze after their shift. This is your high school reunion, so you've gotta step it up a little! The most important thing is obviously your appearance. People need to be able to take one look at you and know, without a doubt, that you are rich, famous and classy. If you want to be treated like a celebrity, you've got to look and act like one. Which is why I suggest showing up in ripped jeans, an old Iron Maiden shirt, sunglasses, bathroom slippers and smoking a cigarette. You will look so ridiculous that your classmates will naturally assume that you're simply too important to give a fuck about looking like they do. Bring a date covered in piercings and tattoos that will draw as much attention as possible. People admire what they don't understand.
Part Two: Showing Up
If you can't afford a limousine rental, I suggest bringing an empty piece of luggage and taking a taxi, then explaining to everyone that you "just got off a plane from Cabo" and didn't have time to make proper traveling arrangements. If you can't afford a taxi, wait until you're pretty sure most people are already inside, then have your buddy drop you off. Be sure to sit in the back of the car, so if anyone sees you, they will just assume he is your chauffeur. Once you get inside, do not acknowledge ANYBODY. Not even your best friend or that chick that you always used to hang out with platonically even though you secretly wanted to nail her. You go straight to the bar and begin settling in. This will be your home for the next few hours. Familiarize with the surroundings, make friends with the bartenders. You will need them to help you drink as much as humanly possible, in order to get your mind where it needs to be for the braggery that will follow.
Part Three: So What Do You Do?
The whole night, the first question everyone will inevitably ask you is, "What have you been doing lately?" It's an unspoken measuring up process, by which the group identifies who are the winners, and who are the losers. The rest of the evening will be socially segregated accordingly, so your handling of this question is crucial to your success. Remember, you have the advantage of mystery on your side - they probably don't really know what you do (otherwise, why would they be asking?) - so embellish generously. You're a coffee gopher at a local TV station? No, you're a fucking producer. Waiter? Try hospitality consultant. Sit at home beating off to Internet porn all day? You're a dot-com entrepreneur. If you have literally nothing to show for the last few years of your life, just say you're a writer. No matter what you do, you constantly refer to it as "the industry", and you make it sound like the industry consumes every moment of your life.
Part Four: Your Glamorous Life
Even if you don't live in New York or LA, you say you do. These are the only acceptable places in the United States to live if you want make an impression at your reunion. Your classmates will all be talking about how rewarding marriage and family is, because that's all those suckers got. Therefore you must liberally point out to them how rewarding it is to finger some chick in the China Club bathroom at 4am on a Thursday night. You must make them understand how much cooler your life is than anything they could ever possibly fathom. Begin every story by saying something like, "So I'm getting high with Gary Busey the other night.." or "I was at this gallery opening with Bjork when...", and then you can pretty much just make something up. Also, be sure to spend at least half of every conversation bitching about how annoying it is living in LA or New York City (especially LA). This adds authenticity to your stories and will make your classmates envy you even more.
If you've done your job so far, you should have your old classmates worked into a desperate frenzy of jealousy and desire. Deep down, your words and actions will have challenged the very foundations upon which they've built their pitiful little suburban lives. Your savage rebellion is like a shining beacon of hope, and they will all want to live vicariously through you. So now is not the time to blow it. At exactly 11:00 pm, you inform your now sizeable congregation that you've got a prior engagement to attend at a nearby bar and therefore must part ways. They will all secretly want to accompany you, so you should casually say, as an afterthought, "I guess I could bring a few of you with me. Just chicks, though." Then you chug the remaining contents of your drink, pound the glass down on the bar, give the bartender a high five, grab a couple ex-cheerleaders by their ass cheeks and stroll out of that gymnasium like Nick motherfucking Nolte.