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I had my first real taste of freedom the summer I turned 16. I’m not talking about driving. I did get my license that July, and it was awesome, but what happened in August was even better: I convinced my parents to let me stay home alone while they spent a long weekend at my aunt’s cabin in Michigan for a family reunion.

Their trip was planned for the week before my best friend, Acacia,* was leaving for boarding school, and it seemed far more important to spend EVERY WAKING SECOND having fun with her rather than to hang out with my (boring, grown-up) relatives. Fortunately, since my mom had once been a teenager, she understood, so with her help I put together an airtight argument to get my dad on board. Acacia would stay with me the whole time, so I wouldn’t be alone. We’d take care of the dog, so they didn’t have to hire a pet-sitter. We wouldn’t use the car or throw parties or have sex or do drugs or anything else that kids do in the movies when their parents are away. I was responsible and could be trusted. I had the straight As and the pristine babysitting record to prove it.

Of course, when my dad grudgingly agreed to this arrangement, the very first thing I did was call my friend Juliet and ask how much pot I could buy with my babysitting savings. Then I started spreading the word to my other friends to see who wanted to sleep over and smoke up in my bedroom, figuring with the incense burning and the windows wide open, the smell would be gone by the time my folks got home. I told my friend Matt to pick a night for his band to play, and we’d have a party. And this is where everything goes epically wrong, right?

Actually, no. During the stoned sleepovers, we ran around in the sprinklers in my backyard and made massive ice cream shakes in one gigantic bowl that we all drank from with straws. (For the next year, “Shake in a bowl!” was an inside joke that immediately generated giggles among my friends.) The night Matt’s band played, Acacia and I carefully rearranged all of the furniture, moved everything that might break, and even rolled up the rug so it wouldn’t get stained. We’d learned our lesson from seeing Jake Ryan’s house get trashed in Sixteen Candles.

Nothing got broken. No one got hurt. No one got sick. The cops were never called. The pot smell was successfully aired out. I just had an incredible, unsupervised long weekend, and my parents were none the wiser—except for the band. When I told my mom that I was writing this piece, she told me that the neighbors had reported that back to her. Apparently, the only reason I was granted this liberation was because she trusted them to watch over me. But she agreed that while I’d broken some rules—actually, almost all of them—my friends and I just had fun.

Pushing boundaries is a rite of passage, a really thrilling one when you manage to pull it off, and there are a million ways to do it that don’t even involve sex or drugs or potential Big Trouble. I spent the rest of my teen years testing the waters of freedom. Some of the things I did were relatively innocent but totally empowering—I lobbied for a later curfew, went to concerts in new neighborhoods all by myself, and made friends with strangers I met at the venue or talking about Riot Grrrl online. Some were not innocent, but they felt good enough to ignore the consequences—I had a secret boyfriend, one I snuck out of my house to meet and lied to my friends about, afraid that if they met him, they’d only see his drug problem and not his sweet, artistic soul.

Once I tasted freedom, I craved it, so I graduated high school a semester early and moved out on my own before I turned 18. I spent the six months between high school and college living with one of the girls I met online in Madison, Wisconsin, a city two hours away from my parents in Chicago. While I was in Madison, I started dating Simon, who was six years older than me and who could buy booze when I still couldn’t legally buy cigarettes. The very first night we met, he slept over in my bed. He just held me. Nothing else happened, not even a kiss, because I was too nervous. This was probably the first time I felt in my gut that I might be going too far. I worried it was a little dangerous to let a strange older man into my bed. But I ignored my instincts, because I was caught up in the thrill of the moment.

I started drinking cocktails when I went out with Simon and his friends. We spent two or three nights a week dancing in nightclubs that I was several years too young to get into. When I got to college, I started drinking cheap boxed wine in my dorm room with Kirsten, the girl who lived next door, on a nightly basis—and sometimes in the morning, too, when we didn’t feel like going to class or decided to bring Tequila Sunrises with us. Even though college was fun, the school I’d chosen didn’t quite live up to my expectations, so I dropped out after my first year and moved back to Madison to live with Simon, despite the fact that he was in love with another girl.

You may look at this and see a downward spiral, but I see an amusement park full of rides. There were ups and downs, moments where I’d never felt so exhilarated and uninhibited, and moments where I was in a sickening freefall. Sometimes I experienced both of those moments at the same time—like on the spring break trip that Kirsten and I took to New Orleans. We spent our days exploring the cemeteries and voodoo shops of a city that I instantly fell in love with, but we spent our nights in bars and goth clubs, drinking and doing drugs. One night, I let Kirsten go home with a stranger, and I returned to our skeezy hotel alone and had a panic attack, convinced that Kirsten was going to be murdered and that I was going to OD on a mixture of coke, booze, and sleeping pills. In retrospect, she and I were both extremely lucky. When I look back at my so-called adventures, I want to slap my former self, or at least shake her really hard. I was once a smart, responsible girl, the daughter of nurses, who knew that the substances I regularly mixed together were lethal, but I did it anyway. I didn’t have a death wish, I’d just lost the ability to rein myself in.

There’s a fine line between freedom and losing control, and I spent the five years between the ages of 16 and 21 slipping back and forth across it. Then, just as I’d had that gorgeous long weekend of freedom, I had the moment where I realized the ride was over. The rollercoaster I was on was now nothing but a series of stomach-churning drops.

One spring afternoon, a few months before my 21st birthday, I woke up in the apartment that Simon and I shared, head pounding, mouth dry, eyes crusted over with makeup after a night of dancing, drinking, and fighting with Simon. My cat, Sid, was outside the room meowing pitifully, and when I staggered out to him, I found him staring into the bathroom at his litter box, unable to get to it across the lake of puke. My puke. It was red, the color of the many, MANY drinks I’d had before driving home. Maybe it was the crying cat or the fact that I was sober, but when I realized that I’d driven home blind drunk, I was so horrified that I couldn’t ignore the this-is-very-very-bad voice any longer. Previously, all of my idiotic choices affected only me. If I had OD’d or went home with a stranger who turned out to be a serial killer, that was the result of a decision that I’d made—which isn’t to say that I deserved such misfortune, just that I was endangering myself. But I couldn’t remember anything about my drive home except hitting the curb and laughing, even though that curb could have been another car or a person. I could have KILLED SOMEONE. That thought looped in my brain, making me feel a new kind of sickness. And poor, helpless Sid, whom my parents had gifted to me on my 16th birthday…it dawned on me that it’s true what they say: with freedom comes responsibility. I was in charge of Sid’s life and my own.

So, after cleaning up my vomit, I took a long, hard look at my life in recent years. In the beginning, there was my Home Alone weekend, where I was able to pull off the kind of party that no one gets away with in the movies without going too far. I was testing limits: the ones my parents set for me. And in part, this gave me the confidence to make decisions that were scary and liberating, like graduating early and moving out. And I’d also had some pretty amazing, spontaneous adventures, like that New Orleans trip before it went downhill. My stomach had twisted when Kirsten suggested splitting up, and a voice started chirping in my ear, but I popped a pill to shut it up. At some point, the limits I was testing were my own. The only thing I had to keep me in line was my own intuition, and when I ignored it, I crossed the line. I lost control.

At 21, I had the kind of life that would have seemed awesome to me at 16. But my life wasn’t awesome, and I wasn’t happy, and I realized that I had to start trusting my gut again, and hope it would prevent me from making the kind of mess that might kill me or someone else. I needed to set goals, which I did by going back to college. I needed to abide by my own limits, and that was the hard part. My gut told me things that I really didn’t want to hear, like that my relationship with Simon was unhealthy and that if I didn’t cut myself off after three drinks, I almost always behaved in ways I would regret in the morning. It took me five more years to break up with Simon and curb my drinking. There was therapy involved and a lot of tearful, freaked-out journal-writing. But I finally got back to feeling the way I had that very first time my parents left me alone: I rediscovered freedom, but I had a new understanding of it this time.

Unlike in high school, where someone with authority was always stepping in to tell me what to do, I was in charge of my own destiny. If I wanted to drop out of college or end a relationship or move across the country (hell, across the world), I could. It was totally empowering. But it also meant that I was responsible for the consequences. Before, when I pushed boundaries, I was usually rebelling against someone—my parents, the guidance counselor, The Man—and for the most part, the worst that could happen was getting grounded or suspended. Now “getting in trouble” was different, and it wasn’t always trouble in the traditional sense. My years of drinking and my messy relationship with Simon led to the miserable feeling that I’d wasted precious time doing things I was ashamed of. That kind of regret wasn’t fun or freeing AT ALL, so I really had to think about what risks were worth taking. I was the ultimate authority.

Six months after breaking up with Simon, I moved to Los Angeles for a semester to study the adaptation of books into film. It was just me and three girlfriends, living in a brand new town. We went to famous nightclubs like the Viper Room, took a weekend trip to Vegas, and snuck into the pool at our rules-y apartment complex for a bit of nightswimming. But when I reached my threshold for feeling buzzed or my stomach knotted up in discomfort, I listened to the voice inside of my head rather than ignoring it. I didn’t have any regrets that semester. It was pure freedom, which isn’t always synonymous with fun. But in many ways, it’s better. ♦

* All names have been changed.