In middle school, I developed an enormous crush on a girl I initially met in my gym and “counseling” electives (the latter is a weird one – did other school have an actual class taught by the counselors about stuff like emotions, bodies, etc.? I know they often talk about that stuff with students one-on-one, but we had a twice-weekly, like, class). I was already a pretty well-known and liked guy in school, and this was my first major crush, so, of course, everyone became very invested in “who does Armando like?!”
Including, of course, the girl herself. And most of her best friends. And my best friends. And the overlapping besties.
So, cue about a year endless speculation and mild picking from everyone around me as I tried to work up the courage to say anything in what in retrospect was a painfully obvious and evident manner, but at the time, I was sure I was being very suave and debonair. Slowly over time, I crafted an inner circle of people who knew who the target of my affections was and would give me romantic advice. It was an interesting period in my life, fwiw; nightly getting onto AIM, ICQ, and MSN Messenger after dinner as everyone else from school with a computer did the same, juggling a dozen conversations for hours as we all talked about our days and dreams and tastes and thoughts and of course HOT GOSS. It was how I learned to talk to girls! I’d even end the night by calling one or two of them for another hour or three after all our parents kicked us off the internet. Amusingly, I actually developed a crush on a few of these people as well, but nevermind that!
Anyway, by Fall semester 7th grade, things are at fever pitch in the leadup to the big Beta Club (some academic honors type organization, I dunno) field trip to the state conference in the state’s capital. Huge hotel, taking buses, overnight trip, big dance at the end of the conference, the whole nine yards.
So, I decide that the best possible time to make my move is during this trip, specifically during the bus ride up. But, ugh, of course, actually saying anything to her was mortifying – I’ve been avoiding doing just that for a year by this point for a reason, goddammit! – so it would be best to set the stage with a virtual communication and then of course cement our perfect relationship forevermore on the bus ride and then the big conference and dance, duh!
So, I write a three-page long Word document love letter detailing, in excruciatingly specific terms, every single thing I liked about this girl, very creepily including very particular elements of her physical appearance in addition to countless tiny moments that, in retrospect, it was super weird to remember in crystal clear detail months later. And then I just dropped this Word doc into her email with zero preface or warning, shut down my computer, and went to bed looking forward to the consummation of my dream relationship at 6AM the next morning when we got on the buses.
Except, of course, uh, I actually had terrified this poor girl with my ludicrous obsessive behavior. She very politely emailed back that she was flattered but didn’t see me like that and then she was very careful to orchestrate things with her friends to make sure we wound up on different buses. Throughout the entire conference, every time we’d almost run into each other, her friends would circle up and provide a buffer zone/distraction. I finally managed to catch up with her at the dance, still sure I could salvage things if she’d just grant me the honor of a slow dance, which I asked for in a stumbling, half-teary-eyed slur of emotions.
She said no, oh, she’s quite tired and not up for dancing right now, then turned around, crossed half the big ballroom, and started dancing with an actually charming not-serial-killer-creepy guy she knew while I spent the rest of the night trying not to cry and walking around the dance floor picking up pieces of loose change people without pockets had dropped with the other too-nerdy-and-weird-to-dance-with dudes.
Best part of all of this is that weeks later when I’d finally come down from the resulting shametrain, I mentioned the crush I had one one of my longtime romance advice phone call partners throughout that whole escapade, who told me with a great deal of fury that she’d liked me that entire time but I was too busy obsessing over some dumb stuckup preppy girl who’d never realize how cool and dateable I was in a million years while she’d been there all along, patiently waiting to be noticed, and there was now no way in fuck (she may have used a gentler term; we were babies after all) she was interested in being my fucking backup plan.
Middle school was fun :)