What I Learned From Dating (and Not Dating) Bad Boys

For me, junior high was a time of great excitement and devastation, mostly involving my hair but also involving a particular boy — my first bad boy.

He Doesn’t Follow the Rules & I Heard He Shaves

Nate showed up in history class a week into my 8th grade year and, as luck would have it, the only open seat in class was next to me. At the time, I was a brunette with straight, shoulder-length hair. I also had braces AND freckles AND bad posture from carrying my backpack on one shoulder (because for some reason, carrying it on both shoulders as it was DESIGNED made you socially-repellant). If you’re imagining Quasimodo with rabbit teeth and blotchy skin — STOP IT!

Anyway, Nate looked like he was about 18. He was, in fact, 15. I don’t like to make jokes about IQ’s (liar), but I will say that Nate didn’t give me much to work with in order to defend his intellect. Though at the time, I didn’t care. In the relatively limited sea of fish that is junior high, the much older Nate was automatically hot. I should note here that “hot” is, of course, in the eye of the beholder and, in this case, it was a 13 year-old girl beholder whose definition of “hot” may or may not have been… Richard Grieco.*

*In my defense, I chose Richard over Johnny (Depp) for strategic reasons. I figured when I inevitably ran into Richard (at the mall?), unlike Johnny, who would be hounded by screaming fans, I’d have Richie all to myself. Though now, if I ran into either, I’d just…keep walking.

Some things are just too painful to draw.

Nate had transferred from a beach somewhere in southern California, so I now had an older boy with sun-bleached, shoulder-length hair and dark, tanned skin, sitting next to me. And he smelled like grown-up dude cologne.

With the fumes of Drakkar Noir tickling my nose, I stared at Nate’s biceps. Biceps were unheard of in 8th grade, they simply did not exist …or at least not on anyone besides the gym teacher (that woman was fucking terrifying).

As I sat there admiring his surfer muscles, Mrs. Neam, our history teacher, snapped at Nate, “Where’s your textbook?!?”

Nate draped a languid arm over the back of his chair, “Don’t have it.”

“And why not?” Mrs. Neam’s voice went up a full octave.

“Don’t need it.”

“Exxx-cuse me, young man?” She scowled. “If you hope to survive my class, you will most definitely need your textbook!”

And that’s when Nate — in an act of rebellion so unheard of, so brazen that it became the unofficial Fairview Junior High motto — said,


At that moment, my brain turned to marshmallow and I whispered low and soft, “Nate, will you marry me?”

Why There Are No Photos of Me Between the Ages of 12 and 14

Well, this whole “I-heart-Nate” crap went on for most of the year. I’d wake up every morning excited at the thought of seeing him and I’d arrive to class with my heart racing.

I have a vague recollection that, while sitting mere inches from my future husband, I tried my awkward hand at being sexy, except that my idea of sexy was based upon Meg Ryan’s character in When Harry Met Sally and included a pair of high-waisted jeans like Shannon Dougherty wore on the 90’s version of Beverly Hills 90210 (Google it yourselves guys, I can’t relive the horror).

Alright, fine. Happy now?

On the highlight reel of stupid things I did in junior high, this crush was directly responsible for the stupidest. I somehow got the idea that, since I was in love with a California surfer boy (think Red Hot Chili Peppers crossed with Keanu’s Johnny Utah, but with a mild case of acne), I should have blond hair like Madonna. So I bleached my hair. And curled it. This resulted in me having blond hair but not having Madonna’s face.

By assuming that a beach guy like Nate would be heavily into blondes I also assumed that he’d be into pale ones with freckles and braces. And though Nate never said that he loved me per se, he never punched me in the face either, so there was definitely something going on between us.

So much better.

What if Romeo Didn’t Really Feel the Same Way About Juliet and Had Trouble with Authority?

Every time Mrs. Neam got irritated with Nate for being late, for being unprepared and for generally not giving a shit (because when you’re 15 and in 8th grade, you probably don’t actually give a shit), I would grow concerned. But what could I do? Mrs. Neam would bark at Nate and, as became custom, he would stand up, say “Screw this” and leave.

By now you’re probably wondering, “So, when did he ask you to the school dance?!”

Well, one afternoon, toward the very end of the year, something unexpected happened.

I was sitting on the large grassy hill in front of the school waiting for my dad to come pick me up after band practice (Oh, did I forget to mention that I played saxophone in the school band? Weird, I don’t know why I would have left that out). The school was nearly vacant so I just sat there with my giant saxophone case watching cars that were not my dad’s wiz past, when I heard Principal Stewart’s voice shouting in the distance. 
“That’s right, keep going!”

I looked up to see Nate, strolling defiantly across the lawn.

Principal Stewart was fifty feet behind him, shouting and pointing, “Get off my campus and don’t ever come back!”

As Nate walked by me, he smiled and waved. And he kept walking until he became a tiny dot that disappeared into the distance.

That was it, I never saw him again.

There’s More Than One Kind of Bad Boy

For a long while, I thought of Nate as my first bad boy. Of course he wasn’t actually mine because, other than planning our honeymoon to Disneyland and giving him understanding looks every time he grunted, we didn’t have much of a “relationship.” Though, I like to think if he hadn’t been kicked out of school, we would have made-out at least once.

For several years following my junior high crush, I continued to favor “bad boys” — guys with tattoos—who stood around wrapped in a permanent cloud of cigarette smoke and aloofness. They looked like a Hollywood stereotype, wearing their anti-authority like armor.

But sometimes they don’t quite look the part. For example, after college I dated a guy that was best described as a walking abyss of emotional destruction or, in lay terms: a big asshole. His insecurity, though heavily papered over with control, arrogance and Polo shirts, was painfully obvious — if you looked closely (which I don’t recommend because it’s a lot like staring at a solar eclipse too long: after 19 seconds, your retinas burst into flames… or you get swept into a vortex of psychological dysfunction).

Infographic of Psychological dysfunction.

Being around this guy was exhausting and it took a deep well of misplaced empathy for me to not tell him, “You suck… at all of this,” while waving my arms in a giant circular motion to demonstrate the all-encompassing sucking of his suckiness.

In hindsight, I should have at least sent him a text with a horrified emoji.

And frustratingly, he was and probably always will be, superficially, “successful” — which was somewhat owing to how he looked. At first glance, you wouldn’t think he was a bad boy. He didn’t fit the stereotype. He didn’t have a sleeve of angry tattoos or wear t-shirts that said “Eat the Rich,” because for him, such defiance would be <gasp> social cannibalism. He’d never qualify as misunderstood because he defines the &@*$&!! status quo. That’s gotta be a conflict of interest.

In fact, he was something far worse than a bad boy, he was a bad man. More specifically, an emotionally abusive person.

It’s this particular brand of “bad” — the guy (or gal) who hides behind a façade of shiny shoes, good job and seemingly acceptable behavior — that you have to keep an especially sharp eye out for. Because that wolf in sheep’s clothing will start out saying exactly what you want to hear and look oh-so neat and tidy while he (or she) says it.


Nate, on the other hand, wasn’t that sort of bad boy. To his apparent detriment, he wore his agitation like a perpetual wound, lashing out at those in charge who were trained to spot only one kind of troublemaker. And if the rumors were true, he was kicked out of school for smoking pot. As far as “scandals” go, meh, I wasn’t impressed.

Now if the story was more along the lines of:

He was smoking pot …AND plundered the retirement accounts of state employees, dumped toxic waste into the river that supplies the community drinking water and cut funding to vital social services while giving massive tax cuts to corporations that abuse workers, consumers and the environment…”

…well then, yeah, he clearly wasn’t Fairview Junior High material.

But knowing the school administrators (and societal attitudes) at the time, I have a feeling he was just smoking pot (I heard it’s a gateway drug to packaging subprime loans into collateralized debt obligations and torching the economy).

In fairness, I’ll never know what Nate was really up to, or going through, or why he couldn’t just bring his history textbook to class ONE DAMN TIME. I only know there’s a reason he was called a bad boy (hint: he was only 15).

And on a late Wednesday afternoon many years ago, he disappeared into the summer horizon and I couldn’t help but feel a little bit sorry for him…

Mostly because we never got to make out.

Note: Sherman, my husband, would like everyone to know that he’s a bad boy too (but in a good, socially responsible way). Also he vigorously objects to being called “Sherman” and would prefer to be known as “Dolph” or “Jason Statham.”

If you enjoyed reading this post or looking at the pictures… or preferred the white space surrounding the words and pictures, here’s some other stuff I made: