The Sad, Strange Saga of Jill Smiley and Friends: Part 1
My late teens and early twenties were a zit filled and hormone fueled nightmare that I only recently emerged from.

I've always been something of a romantic, but more in my brain than in real life. I used to have fantasies of singing to women and giving them flowers and showering them with gifts. Luckily for the female population this never actually happened. Instead I just wrote the girls I pursued overly verbose emails. My life lacked the magic that I wanted it to have as a kid. I was nowhere near being the Indiana Jones figure I’d always dreamed of becoming.

It wasn't for a lack of putting myself out there. By the time community college rolled around I'd already had a few serious relationships under my belt. They had all ended in tears, sure, but I knew I was capable of getting a girl to kiss my face. That was big. It's like knowing you can take a punch. Or so I'm told. I haven't been punched yet, so that still scares me.

I was ready for something new and great.

There was one little problem: I didn't really know any girls that I could ask out. I didn't drink and the only place I stayed past 11pm was the Scott-shaped dent in the couch in front of my TV. My social life consisted of waiting in line for 12 hours to see Star Wars Episode I. School was the only pool of available women I had at my disposal. I decided to become obsessed with a girl from one of my film classes named Devon. She'd gone to my high school and always seemed to have a good attitude. She was a cheerleader, but not the stupid, bitchy kind. At least, she didn't look like she was. I had no idea what she was actually like. But she looked nice.

We were the perfect hypothetical couple. She was a gorgeous girl with fetching short hair and a crooked smile. I was a 19 year old boy on Accutane, a particularly harsh acne remedy that brutally burned a layer of skin off of my face for six months. How could it go wrong?

The quarter was winding down and summer was on the way. Time was running out. Action was needed. I decided I would be direct and just go up and ask her out. Why not? How else do people go out on dates? It all made perfect sense to me. I sat awake late into the night, my stomach in knots, as I went over my plan. Where we went didn’t matter. That was for later, after we agreed to go there together.

The day before the quarter ended, I made my move.

"Devon, can I talk to you?" I asked.

"Sure," she said.

I suddenly felt as if I was channeling Lloyd Dobler, the awkward and yet charming hero from the movie Say Anything. Lloyd moved his arms a lot and paused when he spoke at the perfect moment, especially while on the phone asking out Diane Court. I decided to go with the feeling.

"So, uh," I said, "I was wondering if, uh, you know," I was really waving my arms a lot and moving my head like George Clooney had on ER, "you wanted to, uh, go out some, you know, uh, time."

I was no Lloyd, and I quickly realized my major miscalculation: I wasn't on the phone, walking around my bathroom alone in kickboxing gear. I was me, in a classroom, with a face that was red and hair that was white and lips that were cracked because of medication I was taking for my bad skin. I must have looked like a half-splattered tomato with a wig made of straw that was parted down the middle.

I can't imagine what Devon was thinking, but her face didn't register any disgust. Maybe this was a normal thing, this asking out of people you hardly know. I was just new to the world, this adult place where people just randomly go out with anyone in their peripheral vision.

"Sure, that sounds great," she said.

I couldn't believe it. I had asked out a stranger and she said YES. "I'm in a hurry, though," she quickly added, "Can I give you my number tomorrow?"

A perfectly reasonable request. We all had classes or lunches or jobs to get to. I agreed and she left, melting into the crowd in the hall and out of sight.

I had never used drugs, but I felt positively high. I remember I ran into my friend Jeff as I walked to my car and announced that I had a date. I felt a thousand feet tall. I was grinning so wide that the sides of my mouth, broken from my meds, began to bleed. It hurt like hell. AND I DIDN’T CARE.

I drove home singing Phil Collins' version of "Two Hearts" with my window down. I had visions of myself dancing and singing to Devon on a bar like Ewan McGregor did to Cameron Diaz in A Life Less Ordinary. I could even see the white suit and the open collar. I'm not sure exactly how I pictured myself in those days, but it must have been 40 pounds lighter and with a completely different face and hair style. I didn't live anywhere near reality.

The next day I got to my film class early and sat down. I was excited. I had a date, although I had no idea where a former high school cheerleader would want to go with me. A movie? What else did people do? Maybe she had some ideas, I thought. This was going to be an amazing day. Our class got along really well, and our last session was going to be a wrap up of our time together. The capper was that we were going to be learning our grade, so I knew everyone was going to be there, even some of the cool kids that didn’t always bother to show up to class.

Familiar face after familiar face trickled in, but no Devon. Must have slept in, the lovely minx. I tried to imagine her getting ready, trying to decide on the perfect outfit to wear when she finally gave me her phone number after a night of excruciating build up.

Class started and there was still no sign of her. My heart sank a little. I hoped she was OK. Clearly there must have been some sort of accident, a car crash or something. Perhaps her father was like Diane Court’s, a criminal whose unsavory activities somehow kept her from attending school that day.

I was so worried for her safety that I couldn't concentrate on having a good time in the class or celebrate the fact that, unlike high school, I hadn’t earned a failing grade. I smiled the whole class, but it was accompanied with an intense pain in my stomach and lower body. I felt glued to the chair. I laughed and pretended to have a good time, but I was in a private hell. It was not a pleasant mix of feelings.

Fifteen minutes into our class discussion the door opened. I looked up with great hope, but it wasn't her, just some lost student who walked into the wrong room. I began to face the crushing truth: She was so desperate to avoid going out with me that she skipped class.

I was devastated, and it wasn't the brutal smack of being stung in a single moment, but a cancerous growth that intensified with every moment of the class period that she didn’t appear. I lingered around a bit after class, figuring that at the very least she'd pop in to find out her grade. Even then I held out some hope, but she never showed.

I saw her on campus the next year, but she didn't make eye contact. At first I hoped she saw me, but then I realized she probably didn’t even remember who I was.

I met a girl a few months later and dated her for about a year. After we broke up I once again got the silly idea that I just NEEDED a date, and it didn't matter with whom.

Which led to the most horrifying phone calls since Drew Barrymore was fucked around with at the beginning of Scream.

CONTINUED IN THE FOLLOWING EDITION