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  I believe that the real differentiating factor in life—between overgrown adolescents and actual responsible adults—is that adults eat dinner at a real table. They don’t sit hunched over their coffee table shoveling heartburn-inducing food into their mouths as fast as possible like most recent college grads and the rest of the animal kingdom. How do the apes at the zoo eat bananas? Hunched over. The amoebas that emerged from primordial ooze? You couldn’t tell without a microscope, but they were absorbing nutrients hunched over too. For the first time in my life, my current apartment actually has a dinner table where I can sit and eat. Though it’s difficult, I resist the temptation to plop down and eat off the coffee table instead. I interpret this as a sign, albeit subtle, that I’m at least moving in the right direction.

  SPURNING THIRTY

  One of the scariest parts about turning thirty is looking back to see if you’ve accomplished anything notable—be it in your personal or professional life—while still in your twenties. I once met a woman a few years older than me at a bar, and we got to talking. She mentioned that before moving to where I live, West Hollywood, she had lived in Malibu for ten years. As she continued, I got distracted because, one, she had enormous fake breasts, and two, I realized that since high school I’ve never lived in the same state for five years, let alone the same city. In that respect, thirtysomethings today are marked by something our predecessors lacked: transience. We are always on the move, which makes it harder to fall into a rut. In other words, thirty isn’t as old as it used to be, so there’s no point in wallowing about spending your twenties half-drunk.

  Lately, I’ve noticed a perplexing trend: people assuming that I’m older than I am. When I ask people to guess, they often think I’m in my mid-thirties. I’d like to chalk it up to my precocious demeanor, but I think it’s just the fact that I rock perpetual stubble. Further complicating matters is that when I’m occasionally clean-shaven, people think I’m only about twenty-three. So basically I have a complex either way. Happy birthday to me.

  * * *

  FURTHER ENRICHMENT

  A woman’s age means surprisingly less to guys than most people think. At thirty, I get the same kick out of hooking up with a twenty-five-year-old as I do with a thirty-five-year-old. It’s not a woman’s actual age that matters to us, it’s the absolute value of the age difference. A twenty-five-year-old and a thirty-five-year-old hook-up are both five years apart from me and both have distinct but equally appealing attributes—the older chick is more experienced and exotic and the younger chick is more toned and pliable. It’s when the absolute value shrinks that I start to get disinterested. No guy wants to bang a girl exactly his own age. What’s the fun in that?

  * * *

  I discovered my first gray hair, nestled in my right sideburn, on August 18, 2005, and recorded the date for posterity. It was a difficult day, but thankfully there haven’t been many more sightings since. Not that I haven’t been looking. You know you’re thirty when you can point out the exact location of each of your gray hairs with your eyes closed.

  You also know you’re thirty when, for the first time in your life, you turn to your buddy and complain that the bar you’re in is “too loud.” You know you’re thirty when, every once in a while, you turn on Saturday Night Live and realize you’ve never even heard of the musical guest. And, painfully, you know you’re thirty when SportsCenter refers to LeBron James as a “veteran” and you realize he’s more than five years younger than you are.

  * * *

  YOUTH MOVEMENT

  I know a girl who, when she was twenty-six, was dating a guy still in college. It was weird because I thought most chicks figured out never to sleep at a frat house by the time they were sophomores. What made it even stranger was that, because women mature so much faster than guys do, it’s rare to see a young woman dating an even younger man. Guys, of course, are notorious for dating women many years their junior. I’ll never forget the time, when I was still living in New York, that my buddy asked me if the bar we were going to that night was checking IDs at the door. Turns out the girl he was seeing at the time was only twenty. I can’t chastise him too much, though. Frankly speaking, my wife may still be in high school.

  * * *

  Since I turned thirty, I’ve had good days and bad, but overall I’ve remained pretty optimistic. One way to think about it is that, after several years of being in my “late” twenties, I’m now in my “early” thirties. Early is better than late, right? Another way to think about it is to, well, not think about it. Whether you believe thirty is the new twenty, or thirty is the new death, there’s nothing you can really do about it. That’s why I’m spurning thirty and paying it no mind. People ask me all the time how long I can continue this way of life. Those people are usually sober and annoying. And my response is always the same: “Who the fuck are you?”

  THE PATH OF MOST RESISTANCE

  Shortly before my thirtieth birthday, I ran into a bunch of guys from my fraternity who were seniors when I was a freshman. I always looked up to these guys—I mean actually looked up to them, as I often lay passed out drunk on the floor of their off-campus apartment. Whenever I would see them after they had graduated, it would be like a glimpse three years into the future for me. When I was a sophomore, they were living in Manhattan and working on Wall Street, as I would later do. By the time I graduated and they were in their mid-twenties, they had started to pursue other interests and disperse across the country, as I would also later do. But now, most of them have moved back to New York, gotten married, and even had kids—none of which I’ll be doing in the near future. I’ll admit I got a little worried that I might have disrupted the space-time continuum or something. Especially since these guys are all enormously successful and have very hot wives. Then again, their fresh produce drawers are probably stocked with lettuce and shit, which is kinda lame. It dawned on me that diverging from their path may not be the conventional route, but it’s definitely the most fun.

  * * *

  MANIFEST DESTINY’S CHILD

  The biggest variable in my path has undoubtedly been my move from New York to Los Angeles, where I now live far away from most of the people I’ve known the longest in my life. One of the oldest running jokes in Los Angeles is that no one is actually born here, they’ve just moved here from someplace else. I think that’s why at parties, when asked how long they’ve lived in LA, people will often tell you their exact anniversary, like they’re recovering alcoholics recounting how long they’ve been sober: “It’ll be twenty-six months next Thursday!”

  * * *

  Among the countless emails from female fans I’ve received over the years, many have thanked me for providing them with insight into the mind of the twentysomething male. This was never something I set out purposely to do and, quite frankly, if I represented the typical twentysomething male, our entire civilization is fucked. Nevertheless, I wonder if I will be able to duplicate those efforts in my thirties. One could argue that the twentysomething experience is relatively homogenous: move to the nearest big city, work in a cubicle, struggle to pay rent, try to get laid, get a raise, move to another big city, and repeat. At thirty and beyond, however, those parallel trajectories begin to be altered irrevocably. No two paths are the same, which makes it more difficult to generalize. I’m not too worried, though, because when it comes to the opposite sex, some things never change. As you get older, you may stand straighter and walk taller, but the ultimate goal is always to end up horizontal.

  CHAPTER 2

  AHEAD OF THE GAME

  All the world’s a stage,

  And all the men and women merely players.

  WILLIAM SHAKESPEARE

  Being in a serious relationship presents a frustrating paradox: you no longer have to work for sex, but you can also only have it with one person. On the other hand, being single means having to pound the pavement just to get some action, though the possible sources of that action are seemingly endless (depending on your standards an
d the acuity of your beer goggles). We bachelors have chosen to take our chances with the latter scenario. Luckily, we have also developed an arsenal of resources and strategies to help weaken the resolve of the women we encounter. Consequently, women have become adept at thwarting our advances. It’s essentially an arms race, with two adversaries stockpiling weapons despite calls from both sides to literally make love, not war. The entire courtship process—hitting on, being hit on, buying drinks, playing coy, lying, texting, thrusting, and parrying—is known collectively as “game.” And while I believe it’s possible that single men and women actually have an equal desire to hook up, it is the guys who most often act on these instincts, which usually casts us in the role of the aggressor. Our ploys are sophisticated, our angles many, and so the only way for a girl to keep her sanity—and her clothes on—is to stay ahead of the game.

  THE APPROACH

  Any guy will tell you that the hardest thing of all to do is pick up a completely random chick. Not a friend of a friend, not a girl you kind of know from camp. Just a complete stranger. Because we have absolutely nothing to go on. Which is why I’ve always wished that chicks had Citysearch reviews. I could spot a girl at a bar and then look her up on my BlackBerry to get the lowdown before approaching her. A review might read: “Michelle is ultra-hip and stylish. Attracts investment bankers with expense accounts. A tight squeeze but open late and accommodating to most requests.” I’d contemplate this and then say to my buddies, “I don’t know. I’m really looking for something a bit easier to get in to.”

  Of course, if I were actually able to ascertain any shred of intelligence about a girl in a bar before approaching her, it would be whether or not she’s single. The problem is, single guys broadcast their availability while women tend to conceal it. Ask me if I’m single and I’ll immediately say yes and then interrogate you about why you’re asking and who wants to know. Ask a girl if she’s single and she’ll invariably stammer, glance at her girl friends, giggle, mention something about some guy in Chicago she’s “sorta seeing,” and then finally confess she’s unattached.

  If you’re a girl in a bar who has a boyfriend, the law should require that, instead of “hello,” the first word out of your mouth be “boyfriend.” That would solve so many problems. Me: “Come here often?” You: “Boyfriend.” Me: “Let’s pretend this never happened.” The reason it needs to be the very first word she says is that, for some reason, whenever I’ve spent more than two minutes talking to a girl and then all of a sudden she mentions her significant other, my initial reaction is to start making fun of her boyfriend’s name, like somehow that will break them up on the spot. “Ben?You’re dating a guy named Ben? What kind of name is Ben? Sounds like a really cool guy. Ben? You’ve gotta be fucking kidding me.”

  * * *

  TERMINOLOGY

  Throughout this book, I will use the term “game” to refer generally to the art of hitting on a member of the opposite sex. In many parts of the country, kicking game to a chick is also called “macking.” However, upon moving to Los Angeles I learned that here the verb “to mack” actually means to physically hook up with someone, not merely flirt with them. So for a while, my boys in LA were under the impression that I was getting laid all the time, until they realized I was misusing the term. To avoid further confusion, I will refrain from using “mack” in any context, and hopefully stop my friends from making fun of me.

  * * *

  As I prepare for my approach, I pay careful attention to a woman’s hands. Because there I may find one of two red flags that will cause me to abort the mission: an engagement ring or a cigarette. Looking for a ring is a habit that only first became necessary in the latter half of my twenties. Perhaps it’s unconscious denial on my part, but most of the time I still forget to do it. And every time I kick myself, because married chicks won’t stop you for a while when you hit on them. I think it makes them feel like part of the action. Like they’re watching a game show and playing along for fun.

  Spying a girl fingering a cigarette runs a close second to spotting a wedding ring in terms of turning me off completely. Smokers are just making it that much harder for themselves, as a chick with a cigarette has to be twice as hot for me to even consider approaching her. I’ve even been told that I get an involuntary scowl on my face when people smoke nearby. My friend Holly once said, “Karo, I feel worse lighting up in front of you than I would in front of my mom.” Apparently I’m giving off the right vibe.

  THE NUMBERS GAME

  I’m a confident guy but still get nervous around really attractive women, especially when I’m sober. Recently I was in this lounge that I frequent a few blocks from my apartment when a ridiculous chick touched me on the arm and asked if I knew the name of the bar. I stared at her slack-jawed before finally muttering, “I have no idea.” Very slick. My buddy Jeff has a term for these girls who are way out of anyone’s league. He calls them “uncomfortably hot.” This is the rare girl who is so gorgeous, you actually feel awkward around her.

  The issue that has plagued men for millennia is how to properly gauge a woman’s attractiveness and, more importantly, convey that measurement to his drinking buddies in an efficient manner. Merely describing a girl as “hot” is insufficient. I mean, there’s a big difference between the hottest girl who went to my high school and the hottest girl from the last season of Entourage. Thus, rating systems were born: mechanisms passed down for generations that enable guys to assign a universally understood numerical value to a girl they see in a bar. The entire exercise is, of course, superficial and borderline offensive. Which is why I’d like to break down the four major schools of thought.

  * * *

  RATING SYSTEMS

  SYSTEM

  SCALE

  BENEFITS

  DRAWBACKS

  One-to-Ten (a.k.a. “The Classic”)

  Ten is hot, one is not; the higher the better.

  Most popular.

  Open to large degrees of interpretation.

  Area Code

  Three digits: each one to nine. First rates the girl’s face, second her body, and third overall.

  Most detailed.

  Most complicated; borders on doing math.

  Binary

  Two choices: zero or one. One means “go for it,” zero means “don’t.”

  Simplest.

  Only works if both parties have seen the girl in question. (You can’t call your buddy the next day and brag about banging a one.)

  Beer-Intake Scale

  How many beers it would take me to hook up with her; the lower the better.

  Combines alcohol with ogling.

  Drinking said amount of beers may render the possibility of hooking up moot.

  * * *

  It is considered uncouth for a guy to reveal to a woman her rating. But if a girl somehow comes across this delicate information, it’s important that she know which system is being used to rate her. For instance, if she overhears a guy telling his friends that she’s a three, she might get really upset. But that’s only bad if he’s rating her from one to ten. Instead, he may be using the Beer-Intake Scale. Under that methodology, three is pretty good. Unless the dude is a real lightweight, in which case she doesn’t want to be messing with him anyway.

  Unfortunately, the various systems are not really compatible. It’s sort of like Celsius and Fahrenheit. You can convert Area Code to Binary, but it’s a complicated formula and, quite frankly, who has the time? There are, however, many subtleties and nuances to a girl’s rating. For instance, an accent always adds at least one point (notwithstanding those from New York’s outer boroughs). I was out to dinner with the boys once and our waitress was British. We spent most of the meal giggling like schoolgirls whenever she spoke and then we left about a 45 percent tip. Shortly thereafter, I was at a wedding and met a girl with a really thick Southern accent. I couldn’t tell you what she looks like, but I do know that I love her.

  Another variable is geography. Some regions
of the country just have better-looking women. A nine in LA is much better than a nine in Minneapolis. A “true Miami eight” is essentially a 9.5 in Boston. This is the same reason why attractive women in smaller or cold weather cities get more attention—there’s less competition. Moral of the story: if you’re hot in Omaha, don’t move.

  TENS

  When bachelors on the prowl set their sights high, they’re looking for the Holy Grail of women—a perfect ten. At first I thought this was just a myth. A girl with a perfect body and perfect face couldn’t really exist this side of Megan Fox, could she? I’d performed stand-up in nearly every major American city, but still had not found this elusive bounty. And then I moved to Los Angeles. Bingo.

  I’ve been to fairly low-key bars in LA and still had trouble keeping track of how many “tens” were in the room. It’s absurd. I’m not saying I hook up with them, or even talk to them. In fact, I’m saying I don’t and I can’t. But I’m strangely comforted by the fact that someone must be. Recently I was at a party in Hollywood—hammered—and found myself talking to this ten I had no shot with. I stumbled to the bathroom and, when I returned, resumed the conversation. After a few minutes, I realized that this was actually a different girl. LA has got to be the only place on earth where you can be talking to a ten, and then turn around and start talking to another fucking ten! (And have them both hate you equally.)