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The 6 Biggest Disappointments of My Disappointing Life

By:: Gladstone

April 30, 2011

Next week, I unveil the ninth and final installment of my series, Notes from the Internet Apocalypse. And even though it's so great that sexual scientists are calibrating its orgasm-inducing qualities right now, I know some people will be disappointed. It's inevitable because in books, like in life, we make certain assumptions about the way things are going to turn out. And sometimes the larger the assumption, the greater the disappointment. Here are sixof the biggest disappointments of my life spanning from pre-K to my first post-college job -- all of which came from flawed assumptions no one ever asked me to make.

Little Girls Suck Just As Much As Little Boys

The Assumption: Little Girls Are More Mature And, Therefore, Better Than Little BoysI'm not sure how this got into my head. After all, we're talking about when I was four, but I seem to recall hearing all through my early childhood that girls were more mature than boys. Maybe it was just a misquote intended to describe physical maturation. But to young Gladstone that meant little girls weren't petty or cruel. They were above childish playground taunts and silly cut-throat competition.

The Crushing Realization: Little Girls Are The DevilI remember some boys in pre-K who refused to play with little girls. Cooties or something. I was never quite sure on the details, but I swear I never had that phase. And one day during quiet reading time, I saw two of my classmates sharing a book that I also wanted to read. Undaunted by their lack of a penis, I asked to join in. Denied. And this is a quote: "No. You're a booooooooooooooooooooy." (That's pronounced "boy," but apparently little girls are capable of making that a four syllable word.)I soon came to realize that if testosterone is the hormone that turns boys to men who wage war on their brother, then latent supplies of estrogen are responsible for fashioning prepubescent girls into Satan's little helpers. I'm sure there are worse things in the world than ten-year-old girls, but thankfully I've yet to encounter them. Sure, Jeffrey Dahmer would drill holes into his victims' skulls in a failed attempt to convert them into sexual zombies, and then eat them, but only a ten-year-old she-beast would go up to a little girl on welfare to show off her $80 dollar shoes. Only a little girl would throw a party inviting everyone in the class except the one girl she hated. If little girls are more mature than little boys, then that means only they've more quickly acquired the shameful skills of adulthood.

I still can't believe Samantha doesn't know we fed her the remains of her cat in those brownies!

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Grown-Ups Cheat

The Assumption: Selfish Cheating Children Will Have To Grow Up One DayI remember being a kid and seeing kids cheat at games. I remember lies told to teachers about the extra Munchkins stolen from Dunkin' Donuts boxes. And I remember just a whole bunch of basically immature, shitty little kid behavior, flowing from thinking that went like this: "who cares about being fair? I want what's best for me." I'd shake my little prepubescent head (which I guess means my head before it sprouted a penis?) and comfort myself with thoughts that one day these kids would have to grow up. Maybe it's because my parents were pretty fair so I kind of assumed that's what grown ups were.The Disappointing Realization. Grown Ups Are Just Taller ChildrenI remember the exact day this assumption was shattered. I was about ten years old and in Hebrew School. For reasons that were not clear to me, some kid was throwing sharpened pencils at the back of my head during class. Obviously, because I'm incredibly cool, I didn't tell on him, but I did warn him to stop. He did not. And I did nothing because I didn't want to get in trouble during class. (I was cool and practical!) But when class was over, I walked out to the hall and promptly punched him as hard as I could in the stomach. I then walked to where my mom was supposed to pick me up. Well, before I got there, I was accosted by this kid's mom who was screaming at me for striking her son. I explained that I wasn't a bully. That her son was throwing pencils at my head. And then she said something I'll never forget: "I don't care what he was doing!" I was pretty stunned. If my mother found out I had first been picking on the kid who then kicked my ass, she would have smacked me herself. But not so with this mom. There was no acceptable reason for her son getting smacked, including him really earning it. I know. I'm bumming you out. Don't leave, I'm about to talk about sex.

The 6 Biggest Disappointments of My Disappointing Life

College Is Not Much Different Than High School

The Assumption: In College Everyone Will Get The Real Me I don't know about you, but I did not particularly enjoy high school. Not because I wasn't having tons of great sex with naughty cheerleaders and worldly visiting twenty nine-year-old English teachers from Holland - I totally was. But I thought most of my peers were shallow, sheltered, petty, suburbanite jerks. But come college? Look out! My peers would see the real me! I'd wear a long scarf for no apparent reason and ponder poetry in the windows of 200-year-old institutions, striking the fancy of some bisexual, bipolar girl who dared me to achieve orgasm on the front lawn of the Bursar's office. Or at the very least, no one would call me a fag for liking David Bowie.The Disappointing Realization: Those Jerks From High School Go To College Now.Y'know, you'd think I would have seen this coming having actually scored high enough to get into a University, but apparently, it did not occur to me that everyone I disliked was also going off to college too. And that the thick-headed, boring Bruce Springsteen fans of suburban New Jersey I was about to meet were not going to be very different than the thick-headed, boring Billy Joel fans of suburban Long Island I was leaving. (If those musical references are too antiquated, replace Springsteen and Joel with any two nouns in your room and turn my column into your own Mad Libs).So yeah, it was a depressing realization. But then, in the second half of my freshmen year, this dark, mysterious girl moved in across the hall from me. One day, we got to talking in her room about how cool David Bowie and Alice Cooper were. One thing led to another and suddenly she was making my face up with her mascara, eyeshadow, and lipstick. Y'see, besides being confident in my sexuality, I was pretty sure this was just foreplay. I quickly excused myself and went back to my room across the hall to get a condom. While I was gone, however, my sophomore transfer roommate had invited his gang of well-tailored Sigma Chi date rapists over. My appearance was difficult to explain, but considering these guys literally vomited on each other as part of initiation, I didn't feel I owed anyone an explanation. Anyway, the joke was on them because I totally got - actually I think it just ended up being second base. Maybe shortstop. Is that a thing? Anyway those first two years of college were super rough.

Don't worry. When L was greeted by the Hitler Youth in my dorm room, I only looked 20% gayer than this.

Girls Like Jerks

The Assumption: Girls Want A Sensitive Guy Who Understands ThemI can't pinpoint who told me that girls liked nice guys. Maybe I made that up. But in my home and on TV and in school I was always raised to treat women with respect. Why would the whole world conspire against me to teach me something that would prevent me from getting laid? It just didn't make sense. So yeah, I wanted to be that guy who listened. Who understood. Not only was it the right thing to do, but everyone would agree I had a way with the ladies.The Disappointing Realization: That Douchebag Is Gonna Get More Tail Than YouWell it became pretty clear, pretty quick that my lady-killing techniques were more properly suited for a gay best friend than a ladies' man. Girls seemed to like jerks. Dumb guys. Bad boys. Whatever you want to call them. Basically, if you're the kind of dude Hollywood would cast as the jerk who loses the girl at the end of the sitcom episode, then you totally get to keep the girl in real life. I'd actually figured this out by the time I was 17. I even made this pronouncement in my health class during a discussion about feelings or something. My middle-aged ex-hippie health teacher was vaguely offended. "Really," she said. "Any of you ladies want to set him straight?" No one did. Isn't that amazing? A classroom of 17 year-old-girls sat silent and fessed up to liking jerks. But not just because it was true. They knew if they claimed to be seeking a sensitive guy with a great sense of humor, I'd ask them out at the end of class. Eeew.

Yes, his girlfriend thinks he's a D-bag. The girlfriend who has sex with him.

You Could Be Functionally Retarded And Still Be My Boss

The Assumption: Elders, Especially Elders in Power, Are WiseI know it's hard to believe, but for the longest time I just kind of assumed everyone who was older was smarter. Or maybe it wasn't older people. Maybe it was people in power. I was raised to believe in a merit system. That all you had to be was smart and hard-working and the rest just took care of itself. So when I finally entered the market place, I just kind of assumed anyone in a position of power had to have a skill set that justified their position.The Disappointing Realization: Most People Are Bad At Their Job And Some of Them Are Your Boss It's incredible how few people are good at their job. I mean, we all know the crappy waitress or drug store cashier, but it pretty much applies to everyone: doctors, lawyers, teachers, phone sex operators. And ultimately some of these people get promoted. Maybe they're related to the boss. Maybe the boss doesn't want someone too impressive directly below him/her for fear of being shown up. Maybe they're married to someone who can bring in business. The point is horrible talentless people get promoted all the time. And some of them are your boss or will be your boss. I know that's not a surprise to so many of you, but it was a pretty devastating realization to me. My first boss cleared in excess of $500,000 a year and, I promise you, he could not speak in full sentences. Know what's worse? He was smart enough to know he wasn't bright. And he knew it didn't matter. More than once he dangled his stupidity in front of me for the sole purpose of letting me know I couldn't do a thing about it.

My boss, Jack O'Brien, is neither the subject of this entry nor John Mayer.

Anal

The Assumption: The Dirtiest Greatest Thing EverTaboo sex. What's hotter than that? That's gotta be like the tightest, raunchiest, most amazing kind of sex there is, right?The Disappointing Realization: An Inferior OrificeMaybe it's just because I'm a huge fan and supporter of the vagina, but I have to go on record right now and say the anus is just an inferior orifice. I don't mean to offend anyone who spends a lot of time there. I mean, the anus truly is a miraculous place. Offer the right amount of stimulation and BAM, suddenly the whole thing just opens right up, doesn't it? And that's kind of the problem. Once you reach that magical moment, you transition from um, how to put this eloquently, forcing a hot dog into an erotically undersized bun to just kind of dropping it into a Big Gulp. In order to get that much transformation out of a vagina you usually have to push a baby through it.At the end of the day, I think it's really more of a psychologically rewarding accomplishment than physical sensation overload type thing. Don't get me wrong, I much prefer sodomy to let's say working for my first boss, but it was a disappointment nonetheless.

The Notes from the Internet Apocalypse finale is coming next week so catch up, starting here. You can also keep up with the latest Internet Apocalypse news on Facebook. And/or follow Gladstone on Twitter. And then there's his site and fan page.