The First Essay of the First(ish) Draft of a Collection

How I Wrote a Memoir: Part X

When I sat down to write a book, writing an essay collection was a logical choice, and starting with romantic missteps in high school seemed like the best place to start.

In January 2014, with a few essays written and workshopped—and one of them published in an anthology—I finally realized I was capable of writing a nonfiction book about my tragic—and hilarious—love life, the topic I was drawn to almost exclusively. Up until then, however, I had no particular plan for these lengthy, nonchronological essays about dumb boys and my broken heart. At forty years old, it had been eighteen years since I had written in a journal, “I just want to be a writer,” and now I was able to say aloud, “I’m a writer,” without adding an undermining caveat. My assuredness wasn’t high, but it was improving because of people like Shawna Kenney, whom I wrote about in the last entry.

When my self-confidence was in the basement in 2008, after standing in a long line waiting for David Sedaris to sign When You Are Engulfed in Flames, I said, “I’m a writer too, but I’m not as good as you.”

“You’re probably as good a writer as I was when I was thirty-five,” he said when he found out how old I was. I doubted this was true, but it was thoughtful of him to say. He drew a turtle in my book while fifty-plus more people waited to talk to him.

While doodling, he asked if I was a Pisces.

“Gemini,” I said. “My sister is a Pisces.”

“Close enough,” he said.

Where to Start

When I finally sat down to write a book, it made sense I would write an essay collection because I had already been compiling standalone nonfiction pieces, and that was still my go-to genre when choosing other people’s books to read, like Sedaris’s.

I heard from published author acquaintances, “Essay collections are hard to sell,” and “the memoir market is saturated,” but someone was publishing them because I read them all the time! I wasn’t deterred. (I was naïve about publishing.)

But where to begin. When I thought about starting at the beginning-beginning—in my childhood—I thought about how stable and uneventful it was. A book about my first fifteen years would be boring! I didn’t have a tumultuous upbringing—quite the opposite. My parents loved me, took care of me, had a sister, in part, for me, and although we had nowhere near the money of so many others in our upscale geographic area, we only ever had “first-world problems.” I wasn’t abused; no one in my family was an alcoholic—although, some of us have a penchant for falling in love with alcoholics; my parents were still married and didn’t fight; my sister and I got along well; and I had a substantial group of supportive friends. I was fortunate and grateful. The only “real” problem I had was anxiety. (There’s a whole book about that I have yet to write.)

“Sweet Seventeen, Barely Been Kissed”

External conflicts arose when I reached an age when romance was a factor—or should have been—so I decided to start there, writing what would be the first chapter in my essay collection: “Sweet Seventeen, Barely Been Kissed.”

Here’s the beginning of that essay:

“When I was eighteen, I named my nonexistent children with my sixteen-year-old first boyfriend Jake. We would have one boy and one girl: James and Tiffany. I didn’t envision a white picket fence, but the kids were a given, and I thought we’d always be together, starting with the night before my eighteenth birthday, the first time I stuck my hand down his shorts. We were sitting on the lifeguard tower closest to the Newport Beach pier on a breezy June evening right before I graduated from high school.

‘Don’t worry,’ he said. ‘It won’t bite.’

I was in love.”

(Note: I changed the names of the characters in my true stories from day one and have ever since, not including immediate family members.)

In that first essay, I describe previous opportunities for first kisses that never happened, sort of happened, and happened but maybe didn’t count. (I confirmed years later a major high school crush does count my first kiss with him, so that’s a plus. I promise I’ll explain.)

I start with an eighth-grade graduation party in which seemingly everyone from my class—except the one boy I wish was there—is crammed into my friend’s attic bedroom playing a kissing game:

“. . . when the deflating balloon they were batting around the room landed on me at the party, I said, ‘I’m not playing. I just want to watch.’ The response I got was, ‘You have to play if you’re going to watch. If not, you have to leave.’ It was a dilemma. I didn’t want to leave, but I didn’t want my first kiss to be part of a stupid party game. I also didn’t want to tell them I’d never kissed anyone before.

They arbitrarily demanded I kiss Mark, a boy who’d been in my class since kindergarten. I’d never been into him. He had a giant fuzzy mole on his cheek. Since then, I have kissed more questionable men, but I was picky at fourteen. Thankfully my cute brunette friend from second grade squealed, ‘I’ll do it!’ She threw herself at him. They slobbered on each other. I watched, relieved and disgusted, holding the balloon.

I wouldn’t have another opportunity to make out with anyone else through the better part of high school because I was clueless about male advances and an off-putting chickenshit who was attracted to petrified boys. It proved torturous to be loyal to so few crushes throughout my teen years.”

High Expectations

I wanted my first kiss to be special. I wanted it to mean something. I had built it up in my head since elementary school. I had been the go-between for my junior high school friends, relaying messages back and forth from hormonal girls to their would-be boyfriends, unwittingly getting them together, then watching as they made out next to their lockers, but I was never the protagonist in this narrative. I was the innocent sidekick. Maybe I’d been a hopeless romantic and too selective, or maybe I was scared and never noticed when boys liked me—nor understood why anyone would, for some ridiculous reason—oblivious to flirting until college, always attracted to the “safe” boys who wouldn’t make a move or the “wrong” dudes who ignored me. Maybe I came out of the womb destined to have trouble with romantic love; maybe it was learned; maybe both played a role, but the main reason I was drawn to writing a book about love (and lust) was because I was trying to understand why I found myself single at forty with no children, when that’s the opposite of what I’d always wanted, assuming I’d have what my parents have without being proactive, not understanding it was a choice and that I have agency.

Technically my first kiss was with a good friend when I was sixteen. It was a quick peck while sitting around with other friends on a regular Friday night watching TV or making cookies, only so they could say, “See, now you’ve kissed someone.”

That Time I Blew My First Real Kiss

From the essay:

“My second first kiss was with a boy named Chase. It’s iffy to count my second first kiss though. I was seventeen. I had never been on a real date before, probably because I’d been wearing my friend Dean’s letterman jacket to school because I was cold, thereby warding off any possible suitors. Later, at my ten-year reunion, a male classmate asked, ‘Didn’t you date Dean in high school?’

‘No,’ I said. ‘We were just friends.’

‘Then why were you always wearing his letterman jacket?’

Oh fuck.

When Chase finally called after my junior year to ask me out, I said yes. He was a year younger and had recently gotten his license. I had been pining over him for almost two years, like I’d done with a different blond boy in junior high. We’d only acknowledged our mutual adolescent attraction once. When I was in tenth grade, we met and sat next to each other in biology. One day I lent him my Catching Up with Depeche Mode cassette tape. The ’80s version of texting, I inserted a note into the plastic cover that said, ‘I like you.’ It came back with a one-word response: ‘Likewise.’ Like was underlined. I had to check my dictionary to determine what ‘likewise’ meant. I was giddy, but neither of us mentioned it again the entire school year, until he wrote something vague in my yearbook: ‘I’m really sorry that I didn’t. I guess I wasn’t ready.’

Didn’t what exactly?

On our courageous night out to the movie theater more than a year later, I put my hair in a ponytail, threw on my black Doc Marten boots, a white Erasure T-shirt, and faded skinny jeans, and paced my driveway. I watched his white compact car roll down my street soon after a rare phone call. He stopped midway down the block, turned on his overhead light, stared into the rearview mirror, and rapidly combed his short blond hair. He didn’t know I was watching him primp. I chuckled. He wore jeans and a button-up shirt and smelled shower fresh.

We saw Presumed Innocent. I don’t remember the film because my mind was focused on the boy radiating heat two inches from me. I held my breath, waiting for him to make a move on my skinny ass. Chase, not Harrison Ford. Neither of them did.

Chase dropped me off at my house afterward, where his clutch went out. He was embarrassed. I said he could use our landline to call his mom. It was 1990 after all. Their phone conversation went something like this:

‘Hey, mom, we got back from the movies, but my car broke down.’

Pause.

‘No, it’s okay. I can get a ride home.’

Pause.

‘No, please, really, it’s okay. She can give me a ride home.’

Pause.

‘Geez, mom. It’s okay. Fine. Bye.’

He turned to me, exasperated.

‘She’s coming to pick me up.’

So much for my first real kiss, I thought. I’d been nervous about this moment all night. I was somewhat relieved but still bummed. There’s no way he’ll try to kiss me now, is there? I thought.

When his mom arrived, she politely waited in the car, but she left it running, adding to the anxiety of a quick, unromantic goodbye to accompany our transient, tense evening. We stood within her line of vision. I anticipated a hug. His face moved in. I wasn’t prepared and didn’t have a clue what I was doing. I closed my eyes and pushed out my puckered lips. His tongue hit my closed mouth and then immediately disappeared. I opened my eyes. He was scurrying away.

‘Bye,’ he called over his shoulder. I’d blown it. I hadn’t opened my mouth. He had licked my face. His breath smelled good. I was in heaven.”

Where Is This Collection Headed?

The rest of the essay covers the one time I went to Chase’s house, and while we watched MTV, I lay sprawled on his bed, and he stood leaning against his desk chair—far away from me. Next I go to the prom with Dean, which is a disaster that ends our friendship. Then I detail how I met Jake in typing class, and why I was attracted to someone so cocky—the opposite of Chase. The essay is 3,155 words, but the meaning of the piece—aside from showing how inexperienced I was in high school—comes at the end:

“I don’t recognize that innocent girl anymore: a girl who sidestepped a first kiss in eighth grade, found comfort in a boy licking her face, and daydreamed about the one guy who would love her fully and make babies with her. She’s a wholesome version of me cloaked in a tiny burgundy velvet prom dress. She has yet to be rejected or make faulty decisions, and while this hopeful teenager has been obscured, she and I still have one desire in common: We both want lasting romantic love, even if the definition has changed. The picture of love no longer needs to include wedding bells and a baby. It calls for experienced partners who’ve already loved and lost before. It involves passion, friendship, and commonalities. Perhaps it even includes older children who already have a mother. The best part, however, is the dream still necessitates a first kiss.”

I still like that paragraph, and the essay showcases my voice and humor, but it’s missing depth. One paragraph at the end doesn’t quite cover how the essay should speak to the other ones yet to come. Where am I going with this collection? Why am I writing it? For whom am I writing it? Why is it universal?

Writing the Book I Had to Write, So I Could Start Over

In 2014, during a six-month period, I write an entire first draft—editing as I go because that’s how I roll—attempting to answer these and other questions in 79,000 words; trying to recall the long-ago details of my life; struggling to sift through what’s important and what’s not; and not understanding that much of what will appear in later drafts hasn’t even occurred yet. I tweak the book for the next year and a half and initially call it done.

If I had known how much longer it would take to write and revise an alternate version; write and revise a nonfiction book proposal; research and query agents; and submit to independent presses, I may have given up before I started, but thank goodness I didn’t. (And you shouldn’t either!)

Next: more from that first(ish) draft of my essay collection—the book I had to write so I could start over and write a different book later.

Writing about Teaching

My friend and I planned a “writing day” at a private club on Sunset Boulevard. We’d be a brunch server’s nightmare: get there early; find the best booth for people-watching; grab fresh muffins off the bar; set up camp, complete with computers, iPhones, and notepads, and order food and wine leisurely for five hours while we chatted, wrote, and tallied celebrity sightings.

In our booth next to the staircase that led up from the front desk, my goal was to start an essay about how I’ve moved home with my parents four separate times: once after college when I returned to school for a teaching credential; once when I divorced; once when I moved back from Georgia, and once to chip away at debt. I wanted to say something meaningful about “home” and the accessibility of my parents, and how that could be both tremendous and a crutch, which may have led to broader comments about the economy and my generation overall. But no.

Normally I stick with an essay topic once I get going. On this day, however, the subject matter veered in an unexpected direction as I wrote about my short teaching career: I found myself focusing on specific students who haunted the dreams of my late 20s. An essay about moving home four times not only didn’t seem important anymore, it seemed way too broad a topic to cover in one piece.

As I took a break from writing to sip a glass of red wine, I noticed John Mayer sitting at the table behind us. Later, my friend pointed out a Jonas brother standing at the bar in front of us. Last time we were here, we saw Joe; this time we saw Nick. How we knew the names of two-thirds of the Jonas Brothers, we weren’t sure, but we Googled them to confirm we weren’t making shit up.

At one point, my friend whispered, “Eric Bana,” and gestured toward the handsome man standing next to our table.

“Ohhhh, good one!” I said.

The expansive room, empty when we sat down, was now packed, and we had the best seat in the house. People were hovering. I wanted to invite Mr. Bana and his friends to join us; I could have been persuaded to skip “writing day” altogether. But I didn’t. Celebrities like this club because it’s camera-free, and no one acts like a fangirl.

Non-industry girls like me just squeal internally.

Soon after, I looked to my left and saw penetrating blue eyes peeking out from under an Eskimo-style fur hat that belonged to a skinny dude lurking in the corner.

I wanted to say, “You know you’re in Los Angeles, right? Not Siberia? What’s with the hat?”

Instead I whispered, “Jared Leto” in my friend’s direction.

We were surrounded. I felt like I was an outsider at an Oscar party, only I wasn’t invited. Instead, I wrote this:

Teaching Psychopaths

I was hired to teach freshmen, junior, and senior English the Friday before the first week of classes began in September 2000. At the first English department meeting, the department chair informed the group of the school’s plans for me. She spoke slowly, trying not to scare us. She prefaced it with a caveat: “We are going to help Chelsey.”

She paused.

“She’s teaching freshman college prep, junior college prep, and junior and senior intermediate.”

A collective gasp sucked the oxygen out of the room. Veteran writing and literature teachers stared at me as if I’d been given a death sentence, one that would be drawn-out and involve any number of medieval torture devices. That would turn out to be not far off.

“Oh my god, what are you trying to do to her?” one teacher asked.

My anxiety rose.

I learned the teacher who’d taught senior intermediate the year before had quit. She’d taught other classes for 20 magical years. I was 27 and looked 18. What would they do to me? What had I gotten myself into? I’d always wanted to be a writer, but that seemed lofty and unreachable in my 20s, so I blocked desire and aimed for what I thought I “should” do because that’s what I’d always done. Many years would pass before I’d begin to pursue my true passion.

Student teaching in the fall semester of 1999 had already been an ordeal. I cried daily, thankfully not in front of my students. I’d had one freshman student who ruined every class period of an otherwise gentle group of ninth graders, especially on days when he’d forgotten to take his meds. I would know those days immediately when he’d walk through the door; he’d be manic and mouthy.

He was diagnosed with ADHD, but I was more inclined to think he was a psychopath. I referred to him as “Columbine” with close friends outside of school. He had the qualities one hears bystanders describe on the news after a heinous tragedy involving angry loners. He reminded me of an Eric Harris without a Dylan Klebold. I doubt, however, his Individualized Education Program had a box to check for “psychopath.” He was disgusted with women, particularly his wishy-washy mother, whom he claimed was out every night drinking with friends. He declared this in front of the principal and other administrators. I was the only teacher who showed up for the meeting, and I wasn’t getting paid. I was naïve to care what happened to him, I thought, but I did. His mother denied his claims of neglect, but his words silenced the room, and she grew sheepish. It was hard not to believe him.

Sitting in that meeting I wondered if I’d made a grave mistake becoming a teacher. Why did I spend a semester putting together a book-sized portfolio about how I was going to nurture America’s youth when I had no clue what I was doing? This kid’s life appeared unfixable. I was helpless. I was starting to realize teaching requires a person to be a substitute parent, psychologist, cheerleader, and punching bag—and I still had trouble taking care of myself.

Plus, this kid was mean. He once whispered something horrific in a 14-year-old girl’s ear during class; her face dropped. I couldn’t imagine what he could have said that caused her to look so changed, and she refused to tell me, but the moment appeared to have pulled the innocence right out of her. She thought if she repeated his words, she’d get in trouble.

The next year, as a 10th grader, Columbine was expelled. Not only was he malicious, he was also technologically savvy and had somehow shut down the computer lab. It took the computer science teacher three days to restore the computers to working order. This tickled the perpetrator. I often wonder what became of him; when I Google him, I find nothing to suggest he ended up a serial killer, but I’m not convinced otherwise.

Later, at the school that hired me, I deemed a second student a psychopath. (Diagnosing mental disorders as a layman was a shaky process at best, but it’s possible I’m not wrong.) He was a chiseled, scary blond junior with dead blue eyes. The high school girls didn’t pick up on his lack of empathy and anger toward women. I did. Usually when I’d ask other teachers for suggestions about how to deal with troublesome students, they’d say things like, “Talk to his mom. Do this. Do that.” With Doll Eyes, they all said, “Get him out of your class NOW.”

On days when he was absent, the room felt lighter. Everyone was less tense. On days when he was in class, the mood shifted. Everything was heavy. One day when he was disruptive, I booted him into the hallway, where he sat on a blue plastic chair and glared at me through the thick glass window, unblinking. It was unnerving. His eyes conveyed, “I’m going to return to school with a gun to shoot you.”

I dreamed of black trench coats and piercing screams—when I was able sleep.

A week later, that same blue chair was still sitting outside my classroom door because I hadn’t bothered to move it back inside. I was too distracted and frazzled, and it was now “the chair” for disrespectful shitheads. I don’t know how I missed it: the permanent bold black marker. Someone had written on one of the metal legs, and it caught my eye as I scurried down the crowded hallway to seek temporary refuge in another teacher’s classroom. It read “Fuck you, Miss Drysdale.” It was a signpost for my short teaching career, and every student who’d walked the English halls for the entire week had seen it, meaning every student in the school.

Two thoughts went through my head when I saw it: a) Oh fuck, and b) I know exactly who did this.

But there was no way to prove it. The second I saw the chair, I hauled it down the stairs, across the quad, and into the administrators’ building. I slammed it down in the disciplinary office and said, “So-and-so did this,” even though I knew they couldn’t punish him for it. The VP shook his head. He’d seen it all. This didn’t faze him. I was new and rattled.

I had referrals to the vice principal pre-written in my roll book, ready to hand to Doll Eyes at a moment’s notice. The magic number was four referrals. On the fourth, students were removed from class with an F for the semester. I daydreamed about serving him with number four. The happy occasion would come on a rare test day when I used Scantron sheets, instead of assigning essays I’d have to pick apart for hours during my weekend free time.

Free time. As if I had any.

I loved Scantron tests, but they were no-nos for English teachers; it meant students weren’t writing. Sometimes it was a way to preserve my mental health, if only for a moment.

After I passed out the test, right away Doll Eyes began cheating off the girl in front of him. He’d peek over her shoulder without moving his head and bubble his sheet. Peek and bubble. Peek and bubble. She didn’t notice. I didn’t stop him. I waited and watched, grasping the edges of my podium, smiling. He was toast. I refrained from doing a happy dance.

He was cheating off the wrong girl. She missed class all the time in favor of Hollywood auditions. She didn’t do the work. She would surely fail the test. She was beautiful and smart, but uninformed.

After class, I rushed to the Scantron machine and ran his test and hers through the machine to confirm what I already knew. The same red marks lined the sides of their sheets. I went straight to the VP’s office (again) with both failed exams and a referral.

The VP was my friend. The students hated him, but he always had my back. Once, when I showed him the roster of one of my senior intermediate classes, he asked, “Why did they put all of these students together in ONE CLASS?”

He went down the list and provided one-line suggestions for how to deal with each of them; he knew them all. I remember a comment about a blonde girl who sat close to the front of the classroom:

“Oh god, just throw a blanket over her head,” he said.

I laughed because I knew what he meant: There wasn’t a damn thing we could do to make this girl a nice, well-behaved person, and it was frustrating. (Collectively, high school boys were awful. On occasion, individually, girls were worse. This girl was one of those.)

The intention second semester was for the school to shuffle students around so the disciplinary problems weren’t all in the same room, and I could regain some sanity, but as it turned out, each student they planned to move had a “conflict” in his or her schedule, which meant all the same students stayed with me again. Except one, and he wasn’t even a big problem. He decided I’d picked him out of the crowd and made an example of him.

“You hate me,” he said.

It wasn’t true, but I couldn’t convince him.

I only hated Doll Eyes, and thankfully his chair in my class was empty before the end of the first semester. I can’t Google Doll Eyes now to locate his rap sheet; he has the same name as a famous singer. (No, not John Mayer, but that would be funny under the circumstances.)

Columbine and Doll Eyes were the only students out of hundreds who had zero redeeming qualities. I liked plenty of the rest as humans-in-progress, but that didn’t keep me in the profession. Teaching was an astronomical amount of work, and a pervasive lack of respect did me in, as did state standards and helicopter parents. Plus, the kids drove better cars than I did.

What the hell, man?

It was a cheap thrill to bubble in the final grades at the end of semester; when someone who’d made my life hell also earned an F and an “unsatisfactory” in citizenship, I would cry out, “F U!” as I scribbled in his or her permanent grade. I was too debilitated to care how hateful that sounded.

Here are other “highlights” from my five-semester teaching career:

• On the first day of school, a different boy in all five classes raised his hand and asked, “Do you have a boyfriend?”
  

• Once, a senior boy climbed on the roof of our mildew-ridden portable during a lecture because he was “bored.”
  

• In that same class, one student in the back of the room held up a sign in May that said, “Give up.”
  
  “I haven’t given up yet, and I’m not about to start now,” I said.
  
  A snarky girl in front said, “Oh, you will.”
  

• A fellow newbie teacher and I codeveloped a unit for Lord of the Flies that involved the students creating their own islands. Unforeseen outcome: The students’ islands became debaucherous meccas for sex and drugs. I scrapped grades for the whole project.
  

• A curmudgeon-y substitute teacher made the tallest, bulkiest varsity football player cry, threatened his life, and took home a stack of essays I hadn’t graded yet and never returned them. I had to write a report so he’d never work in our district again.
  

• A fellow teacher tried to take me home after graduation when we were liquored up at a bar down the street: “Sober graduation,” we joked.
  
  When he propositioned me, I said, “Don’t you have a girlfriend?”
  
  “Don’t worry. She won’t be there,” he said.
  

• Once while reading Macbeth in class, I got fed up with all the interruptions.
  
  “Anyone who wants to learn something, come with me,” I said and walked out the door.
  
  My seniors were puzzled but intrigued. One by one, they followed me into the English department hallway, leaving only two students behind in the classroom to goof off. The rest of the class period was heaven. Everyone paid attention and participated. I thought maybe I should hold class on the floor outside the room every day, but we were a fire hazard, blocking the exit, and I received a weird look from another teacher who passed us during her off period.
  

• One of my students was stabbed in the neck at a park during a fight and was in the hospital. I told his friend to tell him I was “thinking about him” because I was worried he might die.
  
  “You don’t want me to tell him that,” he said.
  
  “Oh,” I said.

Teaching high school was beyond stressful. I’ve never worked so hard for so little reward, but I was reminded of my minor positive impact on the day of graduation that first year when a student’s parents searched a crowded football field to find and thank me for everything I’d done for their son. I was shocked I’d done anything right at all, and I cried with relief right there on the field in front of everyone.

So, it wasn’t all bad.

***

Writing in the middle of a bustling brunch crowd was a new experience for me. I tend to write in the privacy of my own home, hiding. I’m an “edit as I write” kind of person. On this day, surrounded by the creative people of Los Angeles, 1,600 words flew out of me with minor effort. The nitpicky perfectionist in my head was taking a leave of absence and would return back at home. I should plan public writing days flanked by recognizable personalities more often.