The Secret Society of Cool Moms

Spoiler: we're all cool moms.

Image: Hulki Okan Tabak | Unsplash

This story was developed in conjunction with 2nd Story Chicago last fall, and has never been published or performed anywhere.

If there’s one immutable truth I’ve learned as a parent of a kindergartener, it’s that drop-off line at an elementary school is an absolute jungle. It’s a matter of trample or be trampled. At any moment, you could be swept up in a tide of sticky little bodies, never to emerge the same person. 

The first time I took my daughter to kindergarten, we walked a couple blocks from our house to that squat beige building where she’ll spend a handful of her formative years. Around us, kids scootered by at breakneck speed, streaming onto yards like day-glo-clad ants, lugging behind them overfull backpacks and all the last regrets of summer. Parents juggled strollers, wagons, and dog leashes, screaming inaudible words of caution or love — it’s hard to tell the difference at that decibel. The buses huffed and puffed cheerfully into the parking lot, little faces pressed to the germy windows, while lines of cars snaked down the street.

And me? I had forgotten my daughter’s mask, I was wearing the equivalent of pajama shorts, and desperately trying to remember whether peanut butter was allowed in her packed lunch. I suspected — nay, knew — I’d forgotten my deodorant. My sweat from the 90-degree morning pooled behind my ears, of all places. I was the hottest mess that ever walked that sidewalk. My daughter, however, was jaunty as can be in her rainbow-colored dress, running a little ahead of me as I tried to pull her back for one last hug. But then, before I had the chance to weep the ancestral weep of a thousand clingy parents-in-arms, she was gone, happily floating in a sea of kids on their way to discover the myriad joys and sorrows of institutionalized learning. 

On my way home, sans kiddo, I found myself walking next to someone who could only be described as Gwyneth Paltrow’s young sister. Her golden hair was brushed with sunlight and expensive conditioner, and tied in a neat ponytail atop her head. She carried nothing with her — a move that takes a certain amount of confidence after a certain age, because if I trip on a sidewalk crack and sprain my ankle, which actually happened this summer, who would I call? Everything from the tips of this woman’s white tennis shoes to her knowing smile just screamed wholesome capability. She beamed her attention at me.

“I’m Heather. How old is your kid?” she asked.

“Five. Too old,” I smiled. “Yours?” 

Her kids were in second grade and fifth grade, and she was a seasoned champ at the whole school shuffle. She told me all about the Fall Festival, a PTO event that would require the help of all the parents (said with a pointedness I accepted sheepishly). She mentioned the unspoken rules of drop-off — you have to move fast, like a gazelle spiriting across parched terrain. That you have to get a gift for the teacher on the first day (Starbucks is always a safe bet). That you have to pay fees online before the end of the first week or else you go to Parent Jail, a place where only the most degenerate souls find themselves, with nothing more than tap water and stale Goldfish crackers to sustain them. 

“There’s so much to remember,” I said helplessly. My flip-flop fell off while walking and landed beside someone’s monstrously tall sunflower bed. Heather stopped patiently to let me gather myself. 

“You’ll get the hang of it,” she said. "You seem like the type of mom who has her shit together."

I wasn’t certain whether I should feel reassured or condescended to. But I won’t lie — it felt good to hear.

“Probably,” she amended, after a moment of studying me. She gave me a blithe wave as we parted ways.

I’ve seen Heather occasionally since that first meeting, and she always reintroduces herself, having forgotten that we talked. But I remember her. You see, Heather is part of the Secret Society of Cool Moms. A subset of the moms in the drop-off line at gym class, ballet class, swim class (why am I paying so much for a five-year-old’s classes?), and enrichment kindergarten (yes, that’s a thing!) seem to belong to this Secret Society of Cool Moms. 

They are the apex predators of the Drop-Off Jungle, sleek cats of prey. Their sunglasses drip with dark mystery and they half-smile through a glossy coat of lipstick even in the indecent 8 a.m. hour when I may or may not have even had a chance to brush my teeth. These Cool Moms don’t walk, my friends. They glide; they stretch in the sun, languorously dangerous. At birth, they got a special roadmap that I didn’t: that of effortlessness. 

I’ve encountered a lot of Cool Girls over the years, but there’s one who sticks in my memory like a shovel in mud. 

---

Let me rewind you to a time long, long ago, when Boyz II Men dominated every graduation and prom mix, their deep crooning the dulcet echo of young hope and writhing hormones. Back then, our waistbands drooped to our butt cracks, our belly buttons danced with gems from Piercing Pagoda, and we were all slowly burning our brains out in tanning beds. The Honda Civics were tricked out with rims earned from extra shifts at Red Lobster, and the bleached highlights ran like skunk tails down our backs. It was a golden era in more ways than one. 

Does it surprise you to know that, even then, I wasn’t a cool kid? I had plenty of friends and a boyfriend with whom I had epic, soap-opera-level fights, but I didn’t party with the cheerleaders or hang at the Shell gas station with strung-out punks.

The cool kids were fascinating to me: close enough to watch, but never close enough to be. They wafted pretty privilege behind them like that ubiquitous Clinique Happy perfume that drenched every Dillard’s entrance. Obviously, like any self-respecting kid-on-the-margins, I pretended I was above it all. Who wanted to attend another debauched midnight dance party on the beach when I could be reading an Amish romance novel from the safety of my own bed? 

There was one cool girl in particular; let’s call her Chastity. Chastity dated the sweetest football player around. They walked the hallways with their hands in one another’s back pockets, if that tells you where they were on the hot-and-heavy meter. Chastity did not like me and the feeling was entirely mutual. 

In chemistry class, we sat across from one another, amidst mildewy textbooks and laminated charts of elements I failed to memorize. Her boyfriend, Luke, was my lab partner, and he was studious and careful in his measurements, while I sat next to him, pretending to take notes. Our chemistry teacher — later fired for inappropriate conduct — leaned over the table of cheerleaders in class, joking about setting their skirts on fire. 

Luke turned on the flame of the bunsen burner. It burned blue and orange, and I wondered why we were allowed to set fires inside of classrooms in the first place. 

He said to me, “See, it’s fine. You’ve gotta learn to do it yourself one of these days.” 

“Nope,” I grinned. “That’s why I have you for a lab partner.”         

He put his arm around my shoulders. “Lucky you.”

Did I mention that I adored Luke? Like: would have stepped in front of a moving bus for him (or shoved Chastity in front of it for him). Would have baked him his favorite cookies every day for a week, or at least bought them from the Publix bakery and pretended I had. Would have written Taylor Swift-style ballads about sitting on park benches with him. Platonically, of course.

Chastity glared at me, and I quickly turned back to my notebook. But it was too late, she’d narrowed in. I’d known her since we were ten, and she hadn’t gotten better with age, only crustier with righteousness and a streak of cruelty that I secretly recognized in myself. Mostly, I tried to escape Chastity’s notice, partly out of fear, and partly out of revulsion. 

She leaned over the aisle and asked very loudly, “Why are you crossing your legs like that?”

I don’t know, Chastity, because I’m an awkward kid who gets nervous in public spaces? Everyone stared, including Luke, and then I couldn’t stop crossing my legs, because that would draw even more attention to them. I was wearing a denim skort, even though most of the girls were wearing thick-trunked JNCO jeans back then, and it rode up on my legs. 

She batted her thick eyelashes and said, “Well, I heard that girls who cross their legs like that are secretly masturbating in public.” 

Mortified, I spluttered something unintelligible. She leaned back a little in her chair, a smug smile plastered on her face. When chemistry class ended, she and Luke strode into the hallway together, leaving me behind, burning with rage. 

---

What was it about the cool girls that simultaneously fascinated and repelled me? It would be easy enough to say I wanted to be popular, but that wasn’t quite it. I wanted the security of popularity, of knowing I would be liked without trying, of being able to say what I pleased without replaying every possible reaction in my head for days afterward. 

The best part of leaving high school, aside from never having to take a science class or see Chastity again, was knowing that I could leave it behind. Start fresh. I had this big notion that in the “real world,” cool wouldn’t matter. 

And, don’t get me wrong. I wasn’t a person that peaked in high school. I consider my peak to be that time I ate a whole pizza by myself one Thanksgiving after drunk-dialing a psychic. But the cliques don’t stop in high school. Chastities become Heathers and the Heathers one day become Blanches, or whoever the senior-citizen equivalent is. They look at us across a canyon; we stare back, envious but incapable of bridging the gap.

---

My daughter is five, and the absolutely amazing, endearing thing about five is that it’s too young to be overly self-conscious. She yells “Good morning!” to our neighbors, even the ones who pretend not to hear, and readily introduces herself to kids at the playground, a hand flapping wildly in welcome. Her pursuit of friendship is totally guileless. She doesn’t know cool from the back of her hand.

One morning at drop-off, she ran into another boy in her class.

“Hi, Elias!” she called, pigtails bouncing as she walked.

Elias ignored her. The teacher said, “Hey, Elias. Did you hear her say hi?” 

“I heard,” he muttered, turning his back on my daughter.

I felt every muscle in my body clench up. Elias, you little jerk, say hello to my daughter or Lord help me, I will snatch that Paw Patrol lunchbox right out of your hand and eat your Lunchable in front of you while you watch. Elias disappeared into the building and the teacher gave me an apologetic shrug. “Kids,” she seemed to be saying.

Meanwhile, my daughter just tripped along with her backpack, blowing me a kiss through the open door. She never mentioned anything about the unreciprocated greeting, though after school, I hedged around it. At home, she was sitting in her usual chair with a plate of animal crackers in front of her, her braids askew, baby hairs slicked in all directions on her forehead. The sight of her, so small, so fragile, broke a part of me open.

“So … is Elias nice to you at school?” I asked, trying for ill-fitting casualness. 

“Yup, he’s fine,” she told me. She was intent on separating the frosting from her animal crackers, a pursuit as messy as it was fruitless.

“Does anyone bully you?” I prodded.

She gave me a look of unveiled annoyance. “No, Mommy, everyone’s great.”  

“But who plays with you?”

“My friends!” she said, throwing her hands in the air, her justifiable annoyance bubbling over. 

In my most rational mind, I know that it’s totally OK for kids to ignore each other sometimes and to have bad days and not observe small courtesies. It doesn't have to mean anything bigger or more treacherous. It’s just that my heart is always a little taut, waiting for a moment of aggression that usually never comes. I wonder how many friends my daughter has, whether she plays in a group on the playground or swings by herself. I wonder if she speaks up or if her little voice gets drowned out by bolder kids. Mostly, I wonder if she is lonely without me. 

I hope she won’t often have to experience the pain of being on the periphery. Sometimes I find myself wondering if coolness could act as some kind of protection in her life, shielding her when I can’t.

---

Where is Chastity now, you wonder? She ended up befriending one of my best friends in college — more evidence of her treachery — and we eventually found ourselves sipping champagne in a pearl-colored ballroom at that mutual friend’s wedding in our mid-twenties. Chastity looked exactly the same and wore a blue satin dress that cut like a diamond across one shoulder. She still surrounded herself with a well-groomed and formidable group of friends. We ignored each other during the vows and cake slicing and interminable replays of Van Morrison. 

But then came the after-party at a very loud downtown club. The champagne (turned vodka, turned whatever appeared in our glasses) had gotten to us all. Everyone had their shoes kicked off, and the sweat slicked across our foreheads, the sheen of the night wiping away any historical animosity. There was a lot of 50 Cent playing and everything smelled like Hawaiian Ginger body mist. It was a geriatric millennial’s fever dream. 

Around the midnight hour, I ended up dancing on a table with Chastity, holding her hand as if we were inseparable soul sisters. Her hair hit me square in the mouth as she danced, but I didn’t care. High school me would have been appalled or impressed, I’m not sure which.

Through the din of the music, the laughter, the joy of manufactured spontaneity, Chastity shouted to me, “Oh my god, you are so fun!”

“No, you are!” I said, shamelessly. 

She was just so friendly. A stranger really. 

She said, “I fucking love you!”

“Love you too, girl!” I screamed back, not willing to remember how, just a few hours ago, I would have shredded her favorite pair of jeans without an ounce of guilt. 

She twirled me and yelled, “Why didn’t we ever do this before?” 

I could have named many reasons, the public masturbation innuendoes among them, but at the moment, I had nothing. I could only hear the beat of the music, the thump of my heart, the swirling togetherness we had all achieved through the urgent frenzy of mid-life fun. 

I snapped a selfie of us, which I found on my phone recently. The club’s lighting, combined with the flash, made it seem like we were covered in sparkles. Her arm was slung around my shoulder, the other arm raised in triumph towards the sky. We were dancing above it all. 

---

Sometime afterward, sitting in the cold and sober reality of an airport lounge during my early-morning flight home, I remembered that I hadn’t exactly been kind to Chastity in high school. Groaning, I recalled that I used to refer to her as That Rat Face, which was an entirely inappropriate nickname because she was lovely and had zero resemblance to a rodent. I gossiped behind her back, celebrated when she didn’t make homecoming court, high-fived Luke when they broke up. I could have probably spun some tale for myself about self-defense, but I was actually just a little asshole.

“Yeah,” a friend told me recently, “you were really harsh to those girls.” 

It was a pretty shameful thing to hear, but it wasn’t inaccurate. Maybe, for Chastity, I was the girl who tormented her. I was only the hero in my own story.

And cool, it turns out, isn’t something earned or bequeathed. It’s a label slapped on quickly, a cheap excuse not to get to know someone. I never saw Chastity again, but that night felt like a pivot. Like someone scribbled over the road map and sent me something enigmatic in return. 

I began to understand that maybe coolness, this thing I’ve obsessed over for decades, isn’t actually real. Like currency, its value depends on a system of acceptance. Maybe I’ll just crumple up the road map. Burn it all down. (Not literally; I’m still petrified of fire.) 

A quick, illicit peek at Chastity’s social media account tells me she is now a nurse. She looks exactly the same as she did at the age of 16, and again at age 25, though her smile is wider and more guileless. She’s a tireless advocate for vaccination and donates to causes I believe in. Her posts are well-reasoned, compassionate, and upbeat. If we were to meet in the pickup line at our kids’ school, maybe we’d strike up a conversation. Arrange a playdate. Talk about our shared high school trauma, tsking over the bullies of our youth. We’d start our own secret society of Moms Who Are Much More Than They Seem. And Heather can join too.