First Encounters

Charlie Sheen’s Teenage Dirtbag in ‘Ferris Bueller’s Day Off’ Set off My Lifelong Bad Boy Phase

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First Encounters is a series in which writers explore the media that inspired their first brush with their sexuality. Whether it was a book, a cartoon character, a film, or a painting, we all have one cultural artifact from our adolescence which informs how we think about our bodies and desires for the rest of our lives. Have a First Encounter you’d like to share? Send your story to .

My best friend from elementary school had an older brother with a motorcycle. The motorcycle isn’t at all relevant to this story, except to say that he was the first boy I ever met who had one. He also had a VHS cassette of Ferris Bueller’s Day Off.

We were little girls — way too young even to be watching a PG-13 movie by ourselves, but on the days when I would come to her house after school, my best friend’s mother didn’t give a shit what we stuck into the basement VCR as long as we didn’t bother her in the living room while she smoked cigarettes and drank pink wine during General Hospital.

It must have been dozens, but I honestly can’t remember how many times the two of us snuck down the stairs to watch her brother’s copy of Ferris Bueller’s Day Off, my first of many John Hughes movies that made Chicago seem like a faraway land where the luckiest kids in the world got to go to a magical place called high school.

My best friend was obsessed with Sloane Peterson. That was fine with me, because I always thought Sloane was kind of boring. I was obsessed with Jeanie Bueller. (All you misunderstood brats out there know exactly what I’m talking about.) I wanted to be constantly scowling and still look super cute. I wanted my own room where everything was mauve and I had my own telephone. I wanted pretty much everything about her life, but what I really wanted most of all — like, more than anything else in the world — was to make out with a teenage delinquent Charlie Sheen on a police station bench.

Holy shit. To this day, when the camera pans off Jeanie’s look over to “boy in the police station,” it still gives my insides a little flutter. It’s an easily overlooked moment in a movie already crammed full of ridiculous hijinks, but damn, Charlie Sheen’s minor character in Ferris Bueller’s Day Off quietly established the foundational archetype for my lifelong bad boy fantasy.

That scene made me feel things, and I don’t mean emotionally. I mean physiologically. My reaction was chemical, and wow did it feel good. There was nothing overtly sexual about their interaction, but something about Sheen’s posture, his leather jacket, his mussed up hair, his literally “too cool for school” attitude — I was instantly and for the very first time a warm gooey pile of boy crazy.

I got such a thrill when later in the movie they cut back to the two of them making out on the police station bench. At the time, I hadn’t kissed any boys. Hell, that wasn’t even a thing yet, but I totally understood why Jeanie was suddenly acting so smitten, and I knew I wanted to feel that for myself.

Even now as an adult, when I watch the way Jennifer Grey projects her character’s sheer infatuation by goofball giggle-snorting her exit down the stairs, I still want to feel that. Every once in a while, I still do, and of course, whenever I get giddy over a boy, the theme music that plays in my head is “Ooo Shawna.”

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