I’m in the 7th grade, I’m 4’ 10, I have a big Jewfro, I’m wearing braces, and more than wanting the Chicago Cubs to win the world series, I want to win the attention of Debbie Dakota… so did all my friends. So, my classmates and I are on an overnight school trip to  Camp Henry Horner in Northern Illinois; the leaves are turning all red and orange and yellow. And there are these team-building games with blindfolds and trustfalls. I don’t remember much of that.

But I’ll never forget my special time with Debbie Dakota. Debbie has really white teeth, and when she brushes against my arm, I completely lose track of what I’m saying. She has long brown hair that goes all the way down to her butt, and she’s really curvy. I know now that you’re not supposed to talk about people’s bodies, but gimme a break. At 13, I was obsessed! I was wanting things I couldn’t name or explain. 

My pal, Steve and I come well-prepared for the weekend. Steve brings a can of Silly String that can fire a line of neon green 20 yards that’d make Spiderman jealous. I go with Crazy Foam which oozes out of the can like whipped cream. I’d need to get really close to launch an attack.

During Twilight, the magical “unstructured time,” Debbie Dakota’s sitting by a campfire in an Adirondack chair. Of course I sneak up behind her and give her head a nice swirl of Crazy Foam… like she’s an ice cream sundae. I think it’s hysterical, but Debbie Dakota’s pissed. She whispers a command: “Follow me.” 

This might be a good time to mention that Debbie Dakota’s my English teacher. She’s in her early twenties; this is her first job out of college. In the privacy of her cabin, Debbie Dakota lets loose a barrage of words like “disappointed” and “livid” (I was going to have to look that word up). I was terrified she was going to call my parents and I’d get suspended. Maybe arrested. Then, Debbie Dakota marches into her bathroom and comes out wielding her brush. She sits in a chair, and calls me over… then demands I brush that Crazy Foam out of her hair, “even if it takes all night.” 

Really, you want me to brush your hair, like all the way down your back.” What is she thinking? I have to get really close to her, and she smells like… patchouli oil (I didn’t figure that out until I had a hippie girlfriend in college). Anyway, the Crazy Foam dissipates quickly like bubbles in a bathtub. When I’m all done, she makes me look her in the eye… and apologize. She makes it clear that she’s my teacher, not my friend. Got it!?

Well, a few years later, when I’m in high school, Steve’s parents head out of town; they don’t trust him to hold down the fort by himself, so they hire a house sitter to keep an eye on things. They hire Debbie Dakota.

In Steve’s house, I address my former teacher as “Debbie” instead of “Miss Dakota.” We play Hearts every night, eat pizza, talk about girls and books. I admit I’m not much of a reader, but I write down her recommendations. But she’d never know how inexperienced I am, based on the way I brag about my mad skills, right? While most adults merely tolerate me and the stupid stuff I say, Debbie treats me like an adult. She asks questions. She listens.

After Debbie’s house-sitting stint, we stay in touch and talk on the phone every few months. It’s a friendship that’s… easy and comfortable. During winter break– my sophomore year of college– I give Debbie a call. She tells me she’s gone through a rough break-up and moved back to Milwaukee Wisconsin, an hour’s drive from my parent’s home.

I do not expect what Debbie says next: “All right, Brill. You’re 19 years old now.  I’ve been hearing about your exploits for years. Time for you to put up or shut up. Why don’t you drive up to Milwaukee, spend the night. Let’s have some fun.”

So I say, “Well, uh, yeah, you know, um, so maybe, um…”

The truth is, I didn’t know what to do. And I never once considered if Debbie Dakota’s overture was inappropriate. I just really wanted to go to Milwaukee; I hear it’s a nice city. But… I didn’t go…  cause I was terrified. The Debbie Dakota in my imagination had been idealized over the past six years.  She was like a movie star in my mind’s eye. And the experienced, cocky college kid- he was mostly fiction too. Put the two together… and you have a perfect recipe for disaster. Some things are better left safely in the world of fantasy.