by Ben Karlin
5. There exists a certain type of busty Manhattan redhead that makes the girl from those classic Tex Avery cartoons—you know the one, the showgirl that causes the cartoon wolf to spin cartwheels, shoot steam out his ears, and flail helplessly as his animated eyeballs pop out and go rolling across the floor?—look less like a comical cartoon exaggeration than an example of the Italian cinematic school known as Neorealismo. No, I’m not making this up.
Things Negative
1. That intense desire you felt to be free of your long-term high school girlfriend can turn, overnight, into an unbearable eight-month fit of jealousy, rage, sobbing, and self-pity, just by finding out, post–high school, that she has been sleeping with the pot dealer from her dorm. Who knew?
2. Falling in love with someone every other guy on campus is also in love with can make you feel better about yourself than any antidepressant ever concocted by modern science. But, you’ll discover, it also has its disadvantages—like the fact that at any given moment there are twenty-thousand-odd guys waiting to go out with her the instant she dumps you. This is a situation she will feel no compunction about taking full advantage of with no warning, whenever the whim strikes her.
3. Punk-rock drummer chicks are considered wild and unpredictable for a reason. They can fall head over heels for you, but if you aren’t up to speed, they can just as easily—mere days after declaring they can’t stand to be without you—pull a complete 180 and get back together with their ex, even if said ex happens to be on really dangerous street drugs at the time.
4. Spending the night with a fantasy celebrity woman you’ve seen on TV and looking over and realizing the decidedly male items littering the nightstand on your side of the bed belong to the major movie star she is “still in the process of breaking up with” is far less glamorous, and much more stressful, than you’d think. And being told the following morning over breakfast, repeatedly, that she “can’t wait to see you next” doesn’t mean you’ll actually ever hear from her again—even if she continues to flirt with you every time you run into each other over the next several months. Far from being an ego boost, the experience can leave you as confused about the very fabric of reality as Philip K. Dick writing his fabled Exegesis—and like him, you will never be able to convince yourself you’d didn’t just hallucinate the whole thing.
5. As talented, funny, and fabulous as they may be, sometimes flabbergasting Manhattan redheads call you up at midnight and demand you take a cab from Brooklyn to Manhattan, so they can yell at you until four a.m. about how they need to break up with you because you’re too emotionally inaccessible to make a commitment. Even if you’ve only seen each other, like, twice. What’s more, though they’ve decided they despise you with every fiber of their being, this is somehow no guarantee the relationship will actually end there.
6. There is a saying in the entertainment industry: “Faster, better, cheaper—you can only have two.” Unfortunately, this same principle applies to romantic partners, with the corresponding categories of sexy, smart, and sane. The tendency of some (me) is to go for the first two and damn the torpedoes. The consequences of doing so, however, can be more emotionally nightmarish than an H.P. Lovecraft story, crossed with a Manson Family acid trip, and directed by David Lynch.
7. That last sentence may have come across as hyperbole. Actually, it was a drastic understatement.
Things Indeterminate
1. Strangely enough, after a surprisingly brief elapse of time, you will no longer give two shits about the high school girlfriend you were once so devastated about you dropped out of college. It may seem like a happy ending that it was no big deal after all—until you realize this means you dropped out of college for absolutely no reason, which is an even more depressing conclusion to live with for the rest of your life.
2. Just because hot college chicks are capable of dumping you on a whim doesn’t mean they aren’t capable of reuniting on a whim too. This feels great—until they dump you on a whim again. But hey—then they can take you back on yet another whim! This cycle can continue for not one, not two, but five years . . . until you have firmly established a love/hate codependency not dissimilar from the Miami economy’s relationship with cocaine.
3. There are, always, other punk-rock chicks, fantasy women, and brassy redheads (to say nothing of the actresses, lawyers, writers, and vegan PETA activists) out there that you haven’t even met yet. Waiting, somewhere in the darkness, for you to fall in love with one day. On the one hand, this is as good a reason as you’ll ever have to get down on your knees and thank God for His eternal benevolence. On the other, it is valid cause to rend your garments and curse His holy name. This is neither good nor bad; like most aspects of the human condition, it is both.
4. That whole Icarus-flying-too-near-the-sun-and-plummeting-out-of-the-sky thing? That’s real. Same with the Sirens who lure you to death with their irresistible song, and the odalisque so beautiful anyone who looks at her dies. And remember: as badass as Grendel was, Beowulf hadn’t seen anything until he went up against Grendel’s mother. I know, I know—I thought they were just myths too. But the fact is, sometimes, if you don’t want to meet with a tragic end, your only option is to avert your gaze, tie yourself to the mast with cotton in your ears, or ascend a little less close to the Vault of Heaven.
The sad fact is, there are more ways to get rejected than you ever dreamed. You can get rejected by women who don’t like you enough and by women who like you too much. You can get rejected by women you didn’t even know you were going out with in the first place. And you can even get rejected by women for not rejecting them. But remember, though it’s counterintuitive, basic logic dictates that any time a relationship that should and does end, it is always, by definition, a good thing . . . even if it make you feel like tearing off your own head and angrily hurling it into oncoming traffic.
It is also crucial to bear in mind that even after a lifetime of such learning experiences, you will never understand the first thing about women. Do not delude yourself about this. Guys who claim to understand everything about women are like Kansas school boards that claim to understand everything about the creation of the world—interesting from a sociological perspective maybe, but still, totally full of shit.
And of course, none of the above changes in any way the larger, overriding fact that women have always been, are, and will eternally remain the Official Most Awesome Entities Ever Bestowed Upon Undeserving Mankind. Thus, despite my vast experience getting dumped, the number of times I have dumped someone else is, as of this writing, holding steady at exactly zero. Being what is sometimes euphemistically referred to as “the sensitive type,” I guess I know how it feels too well to bring myself to do that to somebody else—even in cases where it clearly would have been not only the smartest course of action, but also the most humane.
I am showing improvement, however: my last two relationships ended mutually. It is truly wonderful to be me!
Lesson#37
Always Make Her Feel Like She’s #1
“Distracted? Oh, Come on—I was using the hands-free headset!”
Lesson#38
Dirty Girls Make Bad Friends
by A. J. Jacobs
As with every man in America—even Jake Gyllenhaal—I’ve had many unrequited crushes over the years. They’re painful. Horrible. But, worse still, I’ve also suffered repeated exposure to a special subset of unrequited crush. And it is, I believe, the cruelest variety. Namely, unrequited crushes on women who talk dirty. As in, women who are dreaded “just friends,” but who discuss with you in vivid detail their exploits with other men who are not “just friends.” Avoid this situation. It is hell in its purest form—a constant and excruciating reminder of that which you will never experience.
In college, there was Anya—a striking Sandra Bullock look-alike from Portland. Anya took a lot of classes on human sexuality and enjoyed telling me the content of those classes, including how they related to her life. I’d listen intently,
nod my head, then spend the next half hour digging my fingernails out of my leg. Anya eventually became a noted sex researcher and wrote a book on her year of living with the girls at the Mustang Ranch brothel in Nevada. (Fun Fact: If you want a threesome with a black and a white woman, just ask for the “Salt and Pepper Special.”)
Years later, as part of my job as an editor at Esquire magazine, I oversaw the sex column, which was written by another impossibly attractive woman. Every week or so, we’d have long, intense phone discussions about, for instance, why lesbians in porn movies seem to enjoy fellating dildos. Then I’d hang up and furiously edit an article on how to write a thank-you note or the world’s best golf umbrella—anything to calm down.
Those were tough, for sure. But my most agonizing experience with a bawdy girl was with my friend Chloe. We met in college, but started hanging out in earnest after graduation, when we were both living in New York and severely underemployed. She was hard to miss: Blond hair that was seriously blond, like the color of a smiley face sticker. She wore a massive silver Playboy pendant, cowboy hats, tiger-skin pants, enormous pink sunglasses—shirts and dresses all with plunging necklines. Her theory being if you look and act like a celebrity, you will eventually become one. She was basically an early version of Nicole Richie, but with a high IQ and no trust fund. And it worked—a little. She did start to hang out with the famous, or at least to inhabit the fringes of celebrity culture. You can spot her as one of the official “hot girls in the background” of the opening credits of early-nineties Saturday Night Live.
She was funny and smart and outrageous and let me tag along with her everywhere—to bars that were too hip for me, parties that were too hip for me, concerts that were too hip for me. We once went to the Catskills together, and when I was with her, it seemed the Catskills were too hip for me too.
I was smitten. She was not. But she was no prude. She was quite romantically adventurous with other men. And she liked to tell me about those romantic adventures.
She told me about how this indie film director was performing oral sex on her the night before and, while he was doing it, he made her call her mom and discuss Thanksgiving plans. It gave him some sort of perverse Freudian thrill. The sick bastard. The sick, lucky bastard.
She told me about how, when she was in Florence, Italy, she got drunk at a café, and at the next table was a famous network sports anchor who was even more hammered. They, of course, ended up messing around in the restaurant bathroom.
She also had a weakness for musicians. It killed me. How could she fall for that cliché? Why not a weakness for something more original . . . say, Boggle players? Or guys who’ve read every Hercule Poirot mystery? Or men with moles on their face? That’d give me a fighting chance. (And not just because I have a giant mole on my face and can quote Poirot chapter and verse.)
But no, she went ahead and had flings with guitarists and lead singers, probably a drummer or two. I’d never heard of any of the bands these guys were in, but apparently they were well known to people who read Paper magazine and rented walk-ups in Alphabet City.
So I’d listen to the stories of her escapades. And I’d pine. For those who’ve never endured this particular torture, how can I describe it? It’s like sitting at a restaurant while the waiter describes the mouthwatering specials—then returns to say they’re all no longer available. (Oh, and by the way, the restaurant is out of food altogether. And you have to go in the back and help with dishes. And you won’t get paid.) Or maybe it’s like the dot-com boom. This was the midnineties, after all. Every day I’d read about another twenty-two-year-old who sold his online turtle aquarium company for a quarter billion, while I scraped by on a journalist’s salary, sucking down the bitter cocktail of jealousy, longing, and regret.
I can’t say for sure why I kept coming back to the dirty gals. Partly, I think, bad luck. But partly, the maddening fact that these women all tended to be interesting and funny.
With Chloe, I tried this tactic: Whenever she’d talk about her boyfriend du jour, I’d try to come up with all the reasons she and I would make a terrible couple. She was a commitmentphobe. I could have been happily married at twenty-two. She’d stay out till four every night. I don’t like going outside, unless it is to evacuate a burning building. She loved going to earsplitting concerts. I got cranky when NPR was on too loud. A valiant attempt, but it didn’t work.
What made it worse was that everyone assumed we were a couple. Even my family. When I wasn’t dating anyone—which was not uncommon—I would take Chloe to family functions, which always resulted in a similar scene. We’d walk in—Chloe would be wearing, say, a cleavage-bearing baby T, a micro-miniskirt, and knee-high black leather boots—and she’d whisper to me, “Everyone’s staring at me.”
“Naaah,” I’d say.
Then I’d look around and, well, yes they were. In fact, they all would have their eyebrows raised like Spencer Tracy when Sidney Poitier entered the dining room. One time, my aunt gathered up enough courage to ask Chloe about her wardrobe. Chloe explained that she sees getting dressed every morning as a chance to put on a costume.
“Ohhhh, I understand,” said my aunt. It finally made sense to her: She is not an actual prostitute. She just puts on a costume that makes her look like one.
Chloe encouraged me to date other women, which was hard when she was around, since Chloe could be an intimidating, cleavage-bearing presence. One time, she prodded me into my first pickup attempt at a bar. Here’s the quick version: We spotted an attractive brunette drinking Dos Equis with a couple of friends. “Come on,” said Chloe. “Let’s go.” She would be my wingwoman.
We approached, and Chloe engaged the woman in a conversation. After a minute—and I can’t remember how it came up—we learned that both the brunette and I were born in 1968. Now, 1968 happens to be pretty much the worst year in American history: the assassinations of Robert Kennedy and Martin Luther King, the Tet Offensive, and on and on. So whenever my birth year came up in conversation, I would comment, “Such a wonderful year, 1968. So proud I was born then.” At which point I’d list all the horrible things that happened. It’s not Noël Coward, but I’d usually get a mild chuckle. So I tried it out.
“Such a wonderful year, 1968. The assassination of Martin Luther King . . . ”
And then I stopped. I lost steam. I’m not 100 percent sure why. I think I realized the joke was iffy, so I bailed. It didn’t seem appropriate for the first couple of minutes of conversation. Unfortunately, it was much less appropriate to stop where I stopped. The brunette recoiled, repulsed and frightened. She shot me a look, “Please don’t kill me. Just go back to your Aryan Nation meeting.” She walked away without another word. (I think it goes without saying, I have since retired that joke . . . and have never again spoken to strange women in bars.)
Maybe I unconsciously torpedoed the pickup attempt because I was so infatuated with Chloe. Something had to give. So one summer night, I finally made a pass at Chloe. It was the worst-planned, poorest-executed pass of my life. She was sleeping over at my apartment, as she did whenever she didn’t want to schlep home. That very night I had been dumped by a mutual friend of ours. I thought the woman dumped me for another guy. But Chloe gently informed me that the other guy was gay, and my ex was bisexual, and they were at a gay club together as we were speaking. This is what happens when you go to a liberal arts college with no core requirements.
At the end of the night, we were watching TV, and I looked at Chloe and said, “I want to kiss you.’
“No. I don’t think that’s a good idea.”
“Why not?” Perhaps I could debate her into it.
“I don’t want to get involved in your love triangle. Or love square. Or love pentagon, or whatever it is.”
Then she paused. “Love pentagon. That’s almost an oxymoron.”
“What?”
“The Pentagon is all about war, not love.”
I was finally confessing my long-term crush, and she was doing
wordplay. And not even good wordplay. I think it was the third whiskey sour talking.
What was clear was that this was not an emotionally wrenching moment for her. Awkward, yes. But not wrenching. It was probably the only sexual encounter we never talked about again. On that night, I finally snapped out of denial. I realized she would never like me. Never see me the way I saw her. It was at once painful and so staggeringly obvious. I should have known. But the dirty girls keep you hanging on. Every dirty story. Every dirty detail. You think, “That could be me.”
Eventually, as could be scripted by Captain Obvious, Chloe ended up with a guitarist from an alternative band, and I married a woman who worked in magazines. We lost touch, partly because my wife and Chloe didn’t mesh. (See the preceding 1764 words for the reason why.) But I still think about Chloe often. I am reminded of her when I see a certain famous sportscaster or catch an old episode of Saturday Night Live, or even hear about the Pentagon. But not, thank God, when I call my mother to discuss our Thanksgiving plans.
Lesson#39
Being Awkward Can Be a Prophylactic Against Dry Humping
by Matt Goodman
That middle school is rough is a truism, but consider the pressures of the environment in this particular experiment: being a non-Jew in a school in full bloom bar mitzvah season, gold-foil-encrusted invitations and candle lightings at the Waldorf, me with my L.L.Bean tie and a bowl haircut, wishing for my nascent Jewish faith to awaken inside me; reading through Guitar World, learning the vernacular of licks and pick scrapes (“sizzling leads,” “shrieking wail,” “Malmsteen”), and then picking up my three-quarter-size acoustic guitar with the plinky nylon strings I find so embarrassing, piddling out a bare approximation of the intro to that Sublime song where he goes and shoots that esse; joining the soccer team and being the slowest, panting-est one there with the least spring in his kick, the one who is told “I’m going to fucking breeze by you, fatty” by members of the opposing team and then is fucking breezed by, wishing I could head the ball in from my penalty box, sending the orb across the entire pitch.